2022

Jump to: 2021, 2020, 2019, 2018

19 pages, 1170 KiB

Open AccessArticle

Phenolic Compounds as Phytochemical Tracers of Varietal Origin of Some Autochthonous Apple Cultivars Grown in Serbia

by Nikola Horvacki, Filip Andrić, Uroš Gašić, Dejan Đurović, Živoslav Tešić, Milica Fotirić Akšić and Dušanka Milojković-Opsenica

Molecules 2022, 27(21), 7651; https://doi.org/10.3390/molecules27217651 - 07 Nov 2022

Cited by 3 | Viewed by 1365

Abstract

Domesticated international (standard) apple cultivars, together with resistant apple cultivars are the core of the Serbian apple production. Furthermore, autochthonous cultivars are characterized by a good adaptability to the local environmental conditions and represent a valuable source of genetic variability, as well as [...] Read more.

Domesticated international (standard) apple cultivars, together with resistant apple cultivars are the core of the Serbian apple production. Furthermore, autochthonous cultivars are characterized by a good adaptability to the local environmental conditions and represent a valuable source of genetic variability, as well as an important source of the gene pool for further breeding programs. Additionally, they show a higher phenolic content and a stronger antioxidant activity, in comparison to commercial cultivars. Therefore, they are more likely to be used as a functional food. The subjects of this study were seventeen samples of fruits and leaves from autochthonous apple cultivars, five international standard cultivars, and six resistant apple cultivars. The phenolic profile was determined using ultra-high performance liquid chromatography (UHPLC), coupled with a diode array detector and a TSQ Quantum Access Max triple-quadrupole mass spectrometer. A total of twenty compounds were quantified in the samples. Most of the analyzed phenolics were detected in higher amounts in the peel, compared to the mesocarp. The results of the multivariate analysis of variance (MANOVA) indicate that 5-O-caffeoylquinic acid is present in the highest amount in the mesocarp, while in the peel and leaves, quercetin-glycosides were detected in the highest amount. According to the MANOVA: phloretin, phlorizin, 5-O-caffeoylquinic acid, kaempferol, and p-coumaric acid are present in significantly higher levels in the autochthonous cultivars, compared to the standard and resistant ones (in both fruits and leaves). Therefore, these compounds can be used as chemical tracers of the apple varietal origin. Full article

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11 pages, 11760 KiB

Open AccessArticle

Euphormins A and B, New Pyranocoumarin Derivatives from Euphorbia formosana Hayata, and Their Anti-Inflammatory Activity

by Yu-Hsuan Lan, I-Hsiao Chen, Hsin-Hung Lu, Ting-Jing Guo, Tsong-Long Hwang and Yann-Lii Leu

Molecules 2022, 27(6), 1885; https://doi.org/10.3390/molecules27061885 - 14 Mar 2022

Cited by 2 | Viewed by 1838

Abstract

Euphormin-A (1) and euphormin-B (2), two new pyranocoumarin derivatives, and forty known compounds (3–42) were isolated from Euphorbia formosana Hayata (Euphorbiaceae). The chemical structures of all compounds were established based on spectroscopic analyses. Several isolates [...] Read more.

Euphormin-A (1) and euphormin-B (2), two new pyranocoumarin derivatives, and forty known compounds (3–42) were isolated from Euphorbia formosana Hayata (Euphorbiaceae). The chemical structures of all compounds were established based on spectroscopic analyses. Several isolates were evaluated for their anti-inflammatory activity. Compounds 1, 2, 10, 18, 25, and 33 significantly inhibited against superoxide anion generation and elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Furthermore, compounds 25 and 33 displayed the most potent effects with IC₅₀ values of 0.68 ± 0.18 and 1.39 ± 0.12 µM, respectively, against superoxide anion generation when compared with the positive control (2.01 ± 0.06 µM). Full article

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15 pages, 2975 KiB

Open AccessArticle

Extraction and Study of Hypoglycemic Constituents from Myrica rubra Pomace

by Guoli Chang, Chenggang Cai, Yannan Xiang, Xiangjun Fang and Hailong Yang

Molecules 2022, 27(3), 846; https://doi.org/10.3390/molecules27030846 - 27 Jan 2022

Cited by 4 | Viewed by 2106

Abstract

Myrica rubra pomace accounts for 20% of the fruit’s weight that is not utilized when it is juiced. The pomace contains bioactive phenolic substances such as anthocyanins and flavonoids. To improve the utilization value of Myrica rubra pomace, an optimized extraction method for [...] Read more.

Myrica rubra pomace accounts for 20% of the fruit’s weight that is not utilized when it is juiced. The pomace contains bioactive phenolic substances such as anthocyanins and flavonoids. To improve the utilization value of Myrica rubra pomace, an optimized extraction method for the residual polyphenols was developed using response surface methodology (RSM). The resulting extract was analyzed by high performance liquid chromatography (HPLC), and the in vitro hypoglycemic activity and antioxidant activity of the polyphenolic compounds obtained were also investigated. The optimum extraction conditions (yielding 24.37 mg·g⁻¹ total polyphenols content) were: extraction temperature 60 °C, ultrasonic power 270 W, ethanol concentration 53%, extraction time 57 min, and solid to liquid ratio 1:34. Four polyphenolic compounds were identified in the pomace extract by HPLC: myricitrin, cyanidin-O-glucoside, hyperoside, and quercitrin. DPPH and hydroxyl radical scavenging tests showed that the Myrica rubra polyphenols extract had strong antioxidant abilities. It is evident that the residual polyphenols present in Myrica rubra pomace have strong hypoglycemic activity and the juiced fruits can be further exploited for medicinal purposes. Full article

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2021

Jump to: 2022, 2020, 2019, 2018

20 pages, 4703 KiB

Open AccessArticle

Acacetin Inhibits the Growth of STAT3-Activated DU145 Prostate Cancer Cells by Directly Binding to Signal Transducer and Activator of Transcription 3 (STAT3)

by Sun Yun, Yu-Jin Lee, Jiyeon Choi, Nam Doo Kim, Dong Cho Han and Byoung-Mog Kwon

Molecules 2021, 26(20), 6204; https://doi.org/10.3390/molecules26206204 - 14 Oct 2021

Cited by 14 | Viewed by 3073

Abstract

Signal transducer and activator of transcription 3 (STAT3) plays a critical role in the formation and growth of human cancer. Therefore, STAT3 is a therapeutic target for cancer drug discovery. Acacetin, a flavone present in various plants, inhibits constitutive and inducible STAT3 activation [...] Read more.

Signal transducer and activator of transcription 3 (STAT3) plays a critical role in the formation and growth of human cancer. Therefore, STAT3 is a therapeutic target for cancer drug discovery. Acacetin, a flavone present in various plants, inhibits constitutive and inducible STAT3 activation in STAT3-activated DU145 prostate cancer cells. Acacetin inhibits STAT3 activity by directly binding to STAT3, which we confirmed by a pull-down assay with a biotinylated compound and two level-free methods, namely, a drug affinity responsive target stability (DARTS) experiment and a cellular thermal shift assay (CETSA). Acacetin inhibits STAT3 phosphorylation at the tyrosine 705 residue and nuclear translocation in DU145 cells, which leads to the downregulation of STAT3 target genes. Acacetin then induces apoptosis in a time-dependent manner. Interestingly, acacetin induces the production of reactive oxygen species (ROS) that are not involved in the acacetin-induced inhibition of STAT3 activation because the suppressed p-STAT3 level is not rescued by treatment with GSH or NAC, which are general ROS inhibitors. We also found that acacetin inhibits tumor growth in xenografted nude mice. These results suggest that acacetin, as a STAT3 inhibitor, could be a possible drug candidate for targeting STAT3 for the treatment of cancer in humans. Full article

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14 pages, 1301 KiB

Open AccessArticle

Phenolic Extract from Aralia nudicaulis L. Rhizomes Inhibits Cellular Oxidative Stresses

by Quentin Lion, Andre Pichette, Mouadh Mihoub, Vakhtang Mshvildadze and Jean Legault

Molecules 2021, 26(15), 4458; https://doi.org/10.3390/molecules26154458 - 23 Jul 2021

Cited by 3 | Viewed by 2226

Abstract

UV-B and IR-A radiation are important inducers of biological changes in skin involving ROS generation. The overloading of antioxidant defense mechanisms by ROS production could lead to photoaging and photocarcinogenesis processes. Various traditional usages are reported for Aralia nudicaulis L. extracts, including treatment [...] Read more.

UV-B and IR-A radiation are important inducers of biological changes in skin involving ROS generation. The overloading of antioxidant defense mechanisms by ROS production could lead to photoaging and photocarcinogenesis processes. Various traditional usages are reported for Aralia nudicaulis L. extracts, including treatment of dermatological disorders. Antioxidant and anti-inflammatory properties have already been reported for other Aralia species possibly due to the presence of phenolic compounds. However, the phenolic composition and the potential activity of A. nudicaulis rhizomes extract against oxidative stress and UV/IR damages have not been investigated. The main aims of this study were to prepare a fraction enriched in phenolic compounds (FEPC) from A. nudicaulis rhizomes, to identify its major phenolic compounds and to assess its potential for protective effects against oxidative stress induced by UV-B, IR-A or inflammation. A quantitative LC-MS study of FEPC shows that chlorogenic, caffeic and protocatechuic acids are the main phenolic compounds present, with concentrations of 15.6%, 15.3% and 4.8% of the total composition, respectively. With a validated analytical method, those compounds were quantified over different stages of the growing period. As for biological potential, first this extract demonstrates antioxidant and anti-inflammatory activities. Furthermore, ROS generation induced by IR-A and UV-B were strongly inhibited by A. nudicaulis extract, suggesting that Aralia nudicaulis L. rhizome extract could protect dermal cells against oxidative stress induced by UV-B and IR-A. Full article

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13 pages, 17257 KiB

Open AccessArticle

Ferroptosis-Inhibitory Difference between Chebulagic Acid and Chebulinic Acid Indicates Beneficial Role of HHDP

by Lin Yang, Yangping Liu, Wenhui Zhang, Yujie Hua, Ban Chen, Quanzhou Wu, Dongfeng Chen, Shuqin Liu and Xican Li

Molecules 2021, 26(14), 4300; https://doi.org/10.3390/molecules26144300 - 15 Jul 2021

Cited by 7 | Viewed by 2950

Abstract

The search for a safe and effective inhibitor of ferroptosis, a recently described cell death pathway, has attracted increasing interest from scientists. Two hydrolyzable tannins, chebulagic acid and chebulinic acid, were selected for the study. Their optimized conformations were calculated using computational chemistry [...] Read more.

The search for a safe and effective inhibitor of ferroptosis, a recently described cell death pathway, has attracted increasing interest from scientists. Two hydrolyzable tannins, chebulagic acid and chebulinic acid, were selected for the study. Their optimized conformations were calculated using computational chemistry at the B3LYP-D3(BJ)/6-31G and B3LYP-D3(BJ)/6-311 + G(d,p) levels. The results suggested that (1) chebulagic acid presented a chair conformation, while chebulinic acid presented a skew-boat conformation; (2) the formation of chebulagic acid requires 762.1729 kcal/mol more molecular energy than chebulinic acid; and (3) the 3,6-HHDP (hexahydroxydiphenoyl) moiety was shown to be in an (R)- absolute stereoconfiguration. Subsequently, the ferroptosis inhibition of both tannins was determined using a erastin-treated bone marrow-derived mesenchymal stem cells (bmMSCs) model and compared to that of ferrostatin-1 (Fer-1). The relative inhibitory levels decreased in the following order: Fer-1 > chebulagic acid > chebulinic acid, as also revealed by the in vitro antioxidant assays. The UHPLC–ESI-Q-TOF-MS analysis suggested that, when treated with 16-(2-(14-carboxytetradecyl)-2-ethyl-4,4-dimethyl-3-oxazolidinyloxy free radicals, Fer-1 generated dimeric products, whereas the two acids did not. In conclusion, two hydrolyzable tannins, chebulagic acid and chebulinic acid, can act as natural ferroptosis inhibitors. Their ferroptosis inhibition is mediated by regular antioxidant pathways (ROS scavenging and iron chelation), rather than the redox-based catalytic recycling pathway exhibited by Fer-1. Through antioxidant pathways, the HHDP moiety in chebulagic acid enables ferroptosis-inhibitory action of hydrolyzable tannins. Full article

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11 pages, 812 KiB

Open AccessArticle

Structural Characterization and Assessment of Anti-Inflammatory and Anti-Tyrosinase Activities of Polyphenols from Melastoma normale

by Rui-Jie He, Jun Li, Yong-Lin Huang, Ya-Feng Wang, Bing-Yuan Yang, Zhang-Bin Liu, Li Ge, Ke-Di Yang and Dian-Peng Li

Molecules 2021, 26(13), 3913; https://doi.org/10.3390/molecules26133913 - 26 Jun 2021

Cited by 4 | Viewed by 2001

Abstract

Polyphenols, widely distributed in the genus Melastoma plants, possess extensive cellular protective effects such as anti-inflammatory, anti-tyrosinase, and anti-obesity, which makes it a potential anti-inflammatory drug or enzyme inhibitor. Therefore, the aim of this study is to screen for the anti-inflammatory and enzyme [...] Read more.

Polyphenols, widely distributed in the genus Melastoma plants, possess extensive cellular protective effects such as anti-inflammatory, anti-tyrosinase, and anti-obesity, which makes it a potential anti-inflammatory drug or enzyme inhibitor. Therefore, the aim of this study is to screen for the anti-inflammatory and enzyme inhibitory activities of compounds from title plant. Using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, the extract of Melastoma normale roots was separated. Four new ellagitannins, Whiskey tannin C (1), 1-O-(4-methoxygalloyl)-6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (2), 1-O-galloyl-6-O-(3-methoxygalloyl)-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (3), and 1-O-galloyl-6-O-vanilloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (4), along with eight known polyphenols were firstly obtained from this plant. The structures of all isolates were elucidated by HRMS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW2 64.7 cells, we investigated the anti-inflammatory activities of compounds 1–4, unfortunately, none of them exhibit inhibit nitric oxide (NO) production, their IC₅₀ values are all > 50 μM. Anti-tyrosinase activity assays was done by tyrosinase inhibition activity screening model. Compound 1 showed weak tyrosinase inhibitory activity with IC₅₀ values of 426.02 ± 11.31 μM. Compounds 2–4 displayed moderate tyrosinase inhibitory activities with IC₅₀ values in the range of 124.74 ± 3.12–241.41 ± 6.23 μM. The structure–activity relationships indicate that hydroxylation at C-3′, C-4′, and C-3 in the flavones were key to their anti-tyrosinase activities. The successful isolation and structure identification of ellagitannin provide materials for the screening of anti-inflammatory drugs and enzyme inhibitors, and also contribute to the development and utilization of M. normale. Full article

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14 pages, 3802 KiB

Open AccessArticle

Effect of Pyrolysis Temperature on the Characterisation of Dissolved Organic Matter from Pyroligneous Acid

by Genmao Guo, Qingqing Wang, Qing Huang, Qionglin Fu, Yin Liu, Junfeng Wang, Shan Hu, Ondřej Mašek, Luya Wang and Ju Zhang

Molecules 2021, 26(11), 3416; https://doi.org/10.3390/molecules26113416 - 04 Jun 2021

Cited by 8 | Viewed by 3026

Abstract

Dissolved organic matter (DOM) greatly influences the transformation of nutrients and pollutants in the environment. To investigate the effects of pyrolysis temperatures on the composition and evolution of pyroligneous acid (PA)-derived DOM, DOM solutions extracted from a series of PA derived from eucalyptus [...] Read more.

Dissolved organic matter (DOM) greatly influences the transformation of nutrients and pollutants in the environment. To investigate the effects of pyrolysis temperatures on the composition and evolution of pyroligneous acid (PA)-derived DOM, DOM solutions extracted from a series of PA derived from eucalyptus at five pyrolysis temperature ranges (240–420 °C) were analysed with Fourier transform infrared spectroscopy, gas chromatography–mass spectroscopy, and fluorescence spectroscopy. Results showed that the dissolved organic carbon content sharply increased (p < 0.05) with an increase in pyrolysis temperature. Analysis of the dissolved organic matter composition showed that humic-acid-like substances (71.34–100%) dominated and other fluorescent components (i.e., fulvic-acid-like, soluble microbial by-products, and proteinlike substances) disappeared at high temperatures (>370 °C). The results of two-dimensional correlation spectroscopic analysis suggested that with increasing pyrolysis temperatures, the humic-acid-like substances became more sensitive than other fluorescent components. This study provides valuable information on the characteristic evolution of PA-derived DOM. Full article

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16 pages, 4632 KiB

Open AccessArticle

Viburnum stellato-tomentosum Extract Suppresses Obesity and Hyperglycemia through Regulation of Lipid Metabolism in High-Fat Diet-Fed Mice

by Seona Cho, Hwa Lee, Jisu Han, Haneul Lee, Rosales Ovares Kattia, Zamora Villalobos Nelson, Sangho Choi, Soo-Yong Kim, Ho-Yong Park, Hye Gwang Jeong and Tae-Sook Jeong

Molecules 2021, 26(4), 1052; https://doi.org/10.3390/molecules26041052 - 17 Feb 2021

Cited by 10 | Viewed by 3142

Abstract

The potential biological activities of Viburnum stellato-tomentosum (VS), a plant mainly found in Costa Rica, have yet to be reported. Supplementation of VS extract for 17 weeks significantly decreased body weight gain, fat weight, fasting glucose, insulin, homeostasis model assessment of insulin resistance [...] Read more.

The potential biological activities of Viburnum stellato-tomentosum (VS), a plant mainly found in Costa Rica, have yet to be reported. Supplementation of VS extract for 17 weeks significantly decreased body weight gain, fat weight, fasting glucose, insulin, homeostasis model assessment of insulin resistance (HOMA-IR), and triglyceride levels in high-fat diet (HFD)-fed C57BL/6J mice. The molecular mechanisms underlying the anti-obesity and glucose-lowering effects of VS extract were investigated. VS extract suppressed adipocyte hypertrophy by regulating lipogenesis-related CCAAT/enhancer-binding protein α (C/EBPα) and insulin sensitivity-related peroxisome proliferator-activated receptor γ (Pparg) expression in adipose tissue (AT) and hepatic steatosis by inhibiting C/EBPα and lipid transport-related fatty acid binding protein 4 (FABP4) expression. VS extract enhanced muscular fatty acid β-oxidation-related AMP-activated protein kinase (AMPK) and PPARα expression with increasing Pparg levels. Furthermore, VS extract contained a much higher content of amentoflavone (AMF) (29.4 mg/g extract) compared to that in other Viburnum species. AMF administration decreased Cebpa and Fabp4 levels in the AT and liver, as well as improved insulin signaling-related insulin receptor substrate 1 (Irs1) and glucose transporter 1 (Glut1) levels in the muscle of HFD-fed mice. This study elucidated the in vivo molecular mechanisms of AMF for the first time. Therefore, VS extract effectively diminished obesity and hyperglycemia by suppressing C/EBPα-mediated lipogenesis in the AT and liver, enhancing PPARα-mediated fatty acid β-oxidation in muscle, and PPARγ-mediated insulin sensitivity in AT and muscle. Full article

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2020

Jump to: 2022, 2021, 2019, 2018

15 pages, 17739 KiB

Open AccessFeature PaperArticle

Potato By-Products as a Source of Natural Chlorogenic Acids and Phenolic Compounds: Extraction, Characterization, and Antioxidant Capacity

by Nicolas Joly, Kaies Souidi, David Depraetere, Daniel Wils and Patrick Martin

Molecules 2021, 26(1), 177; https://doi.org/10.3390/molecules26010177 - 31 Dec 2020

Cited by 19 | Viewed by 3761

Abstract

Total phenolic compounds (TPC) and the chlorogenic acids content of potato by-product extracts of two hydro alcoholic solvents (methanol, ethanol) and two extraction methods (maceration and heating-assisted extraction) were studied. The content of TPC in the extracts was determined spectrometrically according to the [...] Read more.

Total phenolic compounds (TPC) and the chlorogenic acids content of potato by-product extracts of two hydro alcoholic solvents (methanol, ethanol) and two extraction methods (maceration and heating-assisted extraction) were studied. The content of TPC in the extracts was determined spectrometrically according to the Folin–Ciocalteu procedure and calculated as chlorogenic acid equivalents. Soluble phenolic acids, especially the chlorogenic acids, were performed by HPLC. The antioxidant activity of potato by-product extracts was determined by using the total oxygen radical absorbance capacity (ORAC) method. The highest content of TPC was found in raw and lyophilized red waters when using ethanol as a solvent around 57 mg/g fresh weight. Heating-assisted extraction enhances this quantitative increasing. At the given operating conditions, unpeeled potato samples exhibit a higher TPC than peeled ones, showing that TPC are accumulated in skin tissue. The greatest amount of chlorogenic acid (Caffeoyl-Quinic Acids, 3, 4, 5 CQA), mainly the 5-CQA (870 ± 39.66 µg/g WM for wet matter versus DM dry matter), was obtained in the pellets and lyophilized fresh peels (skin vs. flesh). In addition, the greatest amounts of chlorogenic acids were found when potato peels were extracted with methanol. Heating-assisted extraction improved the chlorogenic acid concentration of the potato peel extracts. The total ORAC amounts recorded in the different potato fractions varied between 1500 and 1650 µM TE/g. They were higher than those of some fruits, vegetables, nuts, cereals, and sweet potato cultivar. The good correlation coefficient found between TPC, chlorogenic acids determination, and the ORAC capacity indicates that the TPC can be used as a good indicator of the antioxidant capacity of potato by-products. Full article

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17 pages, 3338 KiB

Open AccessArticle

Catechin Photolysis Suppression by Aluminum Chloride under Alkaline Conditions and Assessment with Liquid Chromatography–Mass Spectrometry

by Meei-Ju Yang, Shwu-Yuan Lee, Chieh-I Liu, Shih-Hsuan Chen, Iou-Zen Chen, Tsung-Chen Su, Jeu-Ming P. Yuann, Chien-Wei Cheng, Shiuh-Tsuen Huang and Ji-Yuan Liang

Molecules 2020, 25(24), 5985; https://doi.org/10.3390/molecules25245985 - 17 Dec 2020

Cited by 3 | Viewed by 2423

Abstract

Tea is rich in catechins and aluminum. In this study, the process of catechin photolysis was applied as a model for examining the effects of aluminum chloride (AlCl₃) on the structural changes of catechin and the alteration of aluminum complexes under [...] Read more.

Tea is rich in catechins and aluminum. In this study, the process of catechin photolysis was applied as a model for examining the effects of aluminum chloride (AlCl₃) on the structural changes of catechin and the alteration of aluminum complexes under blue light irradiation (BLI) at pH 8 using liquid chromatography and mass spectrometry techniques. Additionally, the effects of anions on catechin upon the addition of AlCl₃ and treatment with BLI were also studied. In this study, when 1 mM catechin was treated with BLI, a superoxide anion radical (

O_{2}^{• -}

) was generated in an air-saturated aqueous solution, in addition to forming a dimeric catechin (proanthocyanidin) via a photon-induced redox reaction. The relative percentage of catechin was found to be 59.0 and 95.7 for catechin treated with BLI and catechin upon the addition of 1 mM AlCl₃ treated with BLI, respectively. It suggested that catechin treated with BLI could be suppressed by AlCl₃, while AlCl₃ did not form a complex with catechin in the photolytic system. However, under the same conditions, it was also found that the addition of AlCl₃ inhibited the photolytic formation of

O_{2}^{• -},

and reduced the generation of proanthocyanidin, suggesting that the disconnection of proanthocyanidin was achieved by AlCl₃ acting as a catalyst under treatment with BLI. The influence of 1 mM fluoride (

F^{-}

) and 1 mM oxalate (

C_{2} O_{4}^{2 -}

) ions on the photolysis of 1 mM catechin upon the addition of 1 mM AlCl₃ and treatment with BLI was found to be insignificant, implying that, during the photolysis of catechin, the Al species were either neutral or negatively charged and the aluminum species did not form a complex with anions in the photolytic system. Therefore, aluminum, which is an amphoteric species, has an inherent potential to stabilize the photolysis of catechin in an alkaline conditions, while suppressing the

O_{2}^{• -}

and proanthocyanidin generation via aluminum ion catalysis in the catechin/Al system under treatment with BLI. Full article

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15 pages, 603 KiB

Open AccessArticle

Phenolic Composition and Biological Properties of Wild and Commercial Dog Rose Fruits and Leaves

by Milena Polumackanycz, Mateusz Kaszuba, Agnieszka Konopacka, Urszula Marzec-Wróblewska, Marek Wesolowski, Krzysztof Waleron, Adam Buciński and Agnieszka Viapiana

Molecules 2020, 25(22), 5272; https://doi.org/10.3390/molecules25225272 - 12 Nov 2020

Cited by 20 | Viewed by 2547

Abstract

Rosa canina L. (dog rose) is a rich source of phenolic compounds that offer great hope for the prevention of chronic human diseases. Herein, wild and commercial samples of dog rose were chemically characterized with respect to their phenolic composition by liquid chromatography [...] Read more.

Rosa canina L. (dog rose) is a rich source of phenolic compounds that offer great hope for the prevention of chronic human diseases. Herein, wild and commercial samples of dog rose were chemically characterized with respect to their phenolic composition by liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (LC-DAD-ESI/MS). Furthermore, in vitro antioxidant properties and antibacterial activity of dog rose fruits and leaves hydromethanolic extracts and infusions were also evaluated. The results revealed that wild and commercial fruits of dog rose are similar in terms of l(+)-ascorbic acid, total phenolics (TPC), total flavonoids (TFC) and total phenolic acids (TPAC) content, individual phenolic constituents and antioxidant activity. Moreover, the fruits had lower levels of phenolic compounds and also revealed lower biological activity than the leaves. On the other hands, the highest content of TPC, TFC, TPAC, individual phenolic constituents, DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging activity and FRAP (ferric reducing antioxidant power) were found in the leaf’s infusions. They were also the only ones to show antibacterial activity. Overall, these finding confirmed usefulness of R. canina L. leaves and fruits as a rich source of bioactive phenolic compounds with potential use in food, pharmaceutical, and cosmetic industries. Full article

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10 pages, 2046 KiB

Open AccessArticle

Elicitor-Induced Production of Biomass and Pharmaceutical Phenolic Compounds in Cell Suspension Culture of Date Palm (Phoenix dactylifera L.)

by Jameel Mohammed Al-Khayri and Poornananda Madhava Naik

Molecules 2020, 25(20), 4669; https://doi.org/10.3390/molecules25204669 - 13 Oct 2020

Cited by 29 | Viewed by 3088

Abstract

Plants that synthesize bioactive compounds that have high antioxidant value and elicitation offer a reliable in vitro technique to produce important nutraceutical compounds. The objective of this study is to promote the biosynthesis of these phenolic compounds on a large scale using elicitors [...] Read more.

Plants that synthesize bioactive compounds that have high antioxidant value and elicitation offer a reliable in vitro technique to produce important nutraceutical compounds. The objective of this study is to promote the biosynthesis of these phenolic compounds on a large scale using elicitors in date palm cell suspension culture. Elicitors such as pectin, yeast extract (YE), salicylic acid (SA), cadmium chloride (CdCl₂), and silver nitrate (AgNO₃) at 50, 100, and 200 mg/L concentrations are used. The effects of elicitors on cell culture were determined in terms of biomass [packed cell volume (PCV), fresh and dry weight], antioxidant activity, and phenolic compounds (catechin, caffeic acid, kaempferol, apigenin) were determined using high-performance liquid chromatography (HPLC). Results revealed that enhanced PCV (12.3%), total phenolic content [317.9 ± 28.7 mg gallic acid equivalents (GAE)/100 g of dry weight (DW)], and radical scavenging activity (86.0 ± 4.5%) were obtained in the 50 mg/L SA treated cell culture of Murashige and Skoog (MS) medium. The accumulation of optimum catechin (26.6 ± 1.3 µg/g DW), caffeic acid (31.4 ± 3.8 µg/g DW), and kaempferol (13.6 ± 1.6 µg/g DW) was found in the 50 mg/L SA-treated culture when compared to the control. These outcomes could be of great importance in the nutraceutical and agronomic industries. Full article

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18 pages, 1962 KiB

Open AccessArticle

Phenolic Profile of Herbal Infusion and Polyphenol-Rich Extract from Leaves of the Medicinal Plant Antirhea borbonica: Toxicity Assay Determination in Zebrafish Embryos and Larvae

by Bryan Veeren, Batoul Ghaddar, Matthieu Bringart, Shaymaa Khazaal, Marie-Paule Gonthier, Olivier Meilhac, Nicolas Diotel and Jean-Loup Bascands

Molecules 2020, 25(19), 4482; https://doi.org/10.3390/molecules25194482 - 29 Sep 2020

Cited by 12 | Viewed by 3695

Abstract

Antirhea borbonica (A. borbonica) is an endemic plant from the Mascarene archipelago in the Indian Ocean commonly used in traditional medicine for its health benefits. This study aims (1) at exploring polyphenols profiles from two types of extracts—aqueous (herbal infusion) and [...] Read more.

Antirhea borbonica (A. borbonica) is an endemic plant from the Mascarene archipelago in the Indian Ocean commonly used in traditional medicine for its health benefits. This study aims (1) at exploring polyphenols profiles from two types of extracts—aqueous (herbal infusion) and acetonic (polyphenol rich) extracts from A. borbonica leaves—and (2) at evaluating their potential toxicity in vivo for the first time. We first demonstrated that, whatever type of extraction is used, both extracts displayed significant antioxidant properties and acid phenolic and flavonoid contents. By using selective liquid chromatography–tandem mass spectrometry, we performed polyphenol identification and quantification. Among the 19 identified polyphenols, we reported that the main ones were caffeic acid derivatives and quercetin-3-O-rutinoside. Then, we performed a Fish Embryo Acute Toxicity test to assess the toxicity of both extracts following the Organisation for Economic Cooperation and Development (OECD) guidelines. In both zebrafish embryos and larvae, the polyphenols-rich extract obtained by acetonic extraction followed by evaporation and resuspension in water exhibits a higher toxic effect with a median lethal concentration (LC₅₀: 5.6 g/L) compared to the aqueous extract (LC₅₀: 20.3 g/L). Our data also reveal that at non-lethal concentrations of 2.3 and 7.2 g/L for the polyphenol-rich extract and herbal infusion, respectively, morphological malformations such as spinal curvature, pericardial edema, and developmental delay may occur. In conclusion, our study strongly suggests that the evaluation of the toxicity of medicinal plants should be systematically carried out and considered when studying therapeutic effects on living organisms. Full article

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16 pages, 2516 KiB

Open AccessArticle

Partition Coefficients (logP) of Hydrolysable Tannins

by Valtteri Virtanen and Maarit Karonen

Molecules 2020, 25(16), 3691; https://doi.org/10.3390/molecules25163691 - 13 Aug 2020

Cited by 18 | Viewed by 4385

Abstract

The partition coefficients (logP) between n-octanol and water of 47 purified and characterized hydrolysable tannins were measured with the shake flask method utilizing UPLC and HPLC with UV detection. Results show that galloyl glucoses and gallotannins are clearly more hydrophobic [...] Read more.

The partition coefficients (logP) between n-octanol and water of 47 purified and characterized hydrolysable tannins were measured with the shake flask method utilizing UPLC and HPLC with UV detection. Results show that galloyl glucoses and gallotannins are clearly more hydrophobic than ellagitannins but the differences in hydrophobicity within ellagitannins are more varied than within galloyl glucoses or gallotannins. Most notable structural features that were found to influence the hydrophobicity of ellagitannins were the number of free galloyl groups, acyclic versus cyclic polyol, substitution of the anomeric position of glucose and ⁴C₁ versus ¹C₄ conformation of the glucopyranose core. Full article

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26 pages, 5309 KiB

Open AccessReview

Flavonoids and Stilbenoids of the Genera Dracaena and Sansevieria: Structures and Bioactivities

by Zaw Min Thu, Ko Ko Myo, Hnin Thanda Aung, Chabaco Armijos and Giovanni Vidari

Molecules 2020, 25(11), 2608; https://doi.org/10.3390/molecules25112608 - 03 Jun 2020

Cited by 23 | Viewed by 7407

Abstract

The genera Dracaena and Sansevieria (Asparagaceae, Nolinoideae) are still poorly resolved phylogenetically. Plants of these genera are commonly distributed in Africa, China, Southeast Asia, and America. Most of them are cultivated for ornamental and medicinal purposes and are used in various traditional medicines [...] Read more.

The genera Dracaena and Sansevieria (Asparagaceae, Nolinoideae) are still poorly resolved phylogenetically. Plants of these genera are commonly distributed in Africa, China, Southeast Asia, and America. Most of them are cultivated for ornamental and medicinal purposes and are used in various traditional medicines due to the wide range of ethnopharmacological properties. Extensive in vivo and in vitro tests have been carried out to prove the ethnopharmacological claims and other bioactivities. These investigations have been accompanied by the isolation and identification of hundreds of phytochemical constituents. The most characteristic metabolites are steroids, flavonoids, stilbenes, and saponins; many of them exhibit potent analgesic, anti-inflammatory, antimicrobial, antioxidant, antiproliferative, and cytotoxic activities. This review highlights the structures and bioactivities of flavonoids and stilbenoids isolated from Dracaena and Sansevieria. Full article

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16 pages, 968 KiB

Open AccessArticle

Identification and Characterization of α-Glucosidase Inhibition Flavonol Glycosides from Jack Bean (Canavalia ensiformis (L.) DC

by Anita M. Sutedja, Emiko Yanase, Irmanida Batubara, Dedi Fardiaz and Hanifah N. Lioe

Molecules 2020, 25(11), 2481; https://doi.org/10.3390/molecules25112481 - 27 May 2020

Cited by 7 | Viewed by 3006

Abstract

Although the intake of jack bean (Canavalia ensiformis (L.) DC.), an underutilized tropical legume, can potentially decrease the risk of several chronic diseases, not much effort has been directed at profiling the polyphenolics contained therein. Hence, this work aimed to identify and [...] Read more.

Although the intake of jack bean (Canavalia ensiformis (L.) DC.), an underutilized tropical legume, can potentially decrease the risk of several chronic diseases, not much effort has been directed at profiling the polyphenolics contained therein. Hence, this work aimed to identify and quantify the dominant jack bean polyphenolics, which are believed to have antioxidant and other bioactivities. Four major compounds were detected and identified as kaempferol glycosides with three or four glycoside units. Their structures were established based on UV-visible, 1D, 2D NMR, and HR-ESI-MS analyses. Specifically, kaempferol 3-O-α-l-rhamnopyranosyl (1→6)- β-d-glucopyranosyl (1→2)-β-d-galactopyranosyl-7-O-[3-O-o-anisoyl]-α-l-rhamnopyranoside was detected for the first time, while the other three compounds have already been described in plants other than jack bean. This new compound was found to have a higher α-glucosidase inhibition activity compared to acarbose. Full article

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11 pages, 536 KiB

Open AccessArticle

Chemical Diversity of Bastard Balm (Melittis melisophyllum L.) as Affected by Plant Development

by Izabela Szymborska-Sandhu, Jarosław L. Przybył, Olga Kosakowska, Katarzyna Bączek and Zenon Węglarz

Molecules 2020, 25(10), 2421; https://doi.org/10.3390/molecules25102421 - 22 May 2020

Cited by 4 | Viewed by 2330

Abstract

The phytochemical diversity of Melittis melissophyllum was investigated in terms of seasonal changes and age of plants including plant organs diversity. The content of phenolics, namely: coumarin; 3,4-dihydroxycoumarin; o-coumaric acid 2-O-glucoside; verbascoside; apiin; luteolin-7-O-glucoside; and o-coumaric; p [...] Read more.

The phytochemical diversity of Melittis melissophyllum was investigated in terms of seasonal changes and age of plants including plant organs diversity. The content of phenolics, namely: coumarin; 3,4-dihydroxycoumarin; o-coumaric acid 2-O-glucoside; verbascoside; apiin; luteolin-7-O-glucoside; and o-coumaric; p-coumaric; chlorogenic; caffeic; ferulic; cichoric acids, was determined using HPLC-DAD. Among these, luteolin-7-O-glucoside, verbascoside, chlorogenic acid, and coumarin were the dominants. The highest content of flavonoids and phenolic acids was observed in 2-year-old plants, while coumarin in 4-year-old plants (272.06 mg 100 g^–1 DW). When considering seasonal changes, the highest content of luteolin-7-O-glucoside was observed at the full flowering, whereas verbascoside and chlorogenic acid were observed at the seed-setting stage. Among plant organs, the content of coumarin and phenolic acids was the highest in leaves, whereas verbascoside and luteolin-7-O-glucoside were observed in flowers. The composition of essential oil was determined using GC-MS/GC-FID. In the essential oil from leaves, the dominant was 1-octen-3-ol, whilst from flowers, the dominant was α-pinene. Full article

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17 pages, 17032 KiB

Open AccessArticle

Evaluation of the Cytotoxic Activity of the Usnea barbata (L.) F. H. Wigg Dry Extract

by Violeta Popovici, Laura Adriana Bucur, Verginica Schröder, Daniela Gherghel, Cosmin Teodor Mihai, Aureliana Caraiane, Florin Ciprian Badea, Gabriela Vochița and Victoria Badea

Molecules 2020, 25(8), 1865; https://doi.org/10.3390/molecules25081865 - 17 Apr 2020

Cited by 15 | Viewed by 4916

Abstract

The secondary metabolites of lichens have proven to be promising sources of anticancer drugs; one of the most important of these is usnic acid, which is a phenolic compound with dibenzofuran structure that is responsible for the numerous biological actions of lichens of [...] Read more.

The secondary metabolites of lichens have proven to be promising sources of anticancer drugs; one of the most important of these is usnic acid, which is a phenolic compound with dibenzofuran structure that is responsible for the numerous biological actions of lichens of genus Usnea. As a result, in this study, we related to this phenolic secondary metabolite. The aim of the present study is the evaluation of the cytotoxic activity of Usnea barbata (L.) F. H. Wigg dry acetone extract (UBE). In advance, the usnic acid content was determined in various extracts of Usnea barbata (L.) F. H. Wigg: the liquid extracts were found in water, ethanol, acetone, and the dry acetone extract; the highest usnic acid quantity was found in the dry acetone extract. First, the cytotoxic action of UBE was assessed using Brine Shrimp Lethality (BSL) test; a significant lethal effect was obtained after 24 h of treatment at high used concentrations of UBE, and it was quantified by the high mortality rate of the Artemia salina (L.) larvae. Secondly, in vitro cytotoxicity of UBE was evaluated on human tongue squamous cells carcinoma, using CAL 27 (ATCC^® CRL-2095™) cell line. The most intense cytotoxic effect of UBE on CAL 27 cells was registered after 24 h; this response is directly proportional with the tested UBE concentrations. The obtained results have been reported regarding usnic acid content of UBE, and the data show that CAL 27 cells death was induced by apoptosis and high oxidative stress. Full article

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19 pages, 3515 KiB

Open AccessArticle

Ultrasound-Assisted Extraction of Taxifolin, Diosmin, and Quercetin from Abies nephrolepis (Trautv.) Maxim: Kinetic and Thermodynamic Characteristics

by Mengxia Wei, Ru Zhao, Xiaojin Peng, Chunte Feng, Huiyan Gu and Lei Yang

Molecules 2020, 25(6), 1401; https://doi.org/10.3390/molecules25061401 - 19 Mar 2020

Cited by 12 | Viewed by 3048

Abstract

Extraction behaviors of the 3 flavonoids taxifolin, diosmin, and quercetin have been investigated in Abies nephrolepis leaves and bark. The following operation parameters—ethanol volume fraction, liquid–solid ratio, temperature, ultrasound irradiation power and time, and ultrasound frequency—were varied to study their effect on the [...] Read more.

Extraction behaviors of the 3 flavonoids taxifolin, diosmin, and quercetin have been investigated in Abies nephrolepis leaves and bark. The following operation parameters—ethanol volume fraction, liquid–solid ratio, temperature, ultrasound irradiation power and time, and ultrasound frequency—were varied to study their effect on the yield of the 3 flavonoids during extraction. The results showed that a low extraction efficiency occurred at 293.15 K due to slow kinetics, while the situation was significantly improved at 333.15 K. The kinetic data for the extraction yields of the 3 flavonoids achieved good fits by the first-order kinetic model. From the thermodynamic analysis results, we realized that the ultrasound-assisted extraction of taxifolin, diosmin, and quercetin from the leaves and bark of A. nephrolepis was a spontaneous and endothermic process in which the disorder increased (ΔG⁰ < 0, ΔH⁰ > 0, and ΔS⁰ > 0). According to the response surface methodology (RSM) analysis, under the optimal operation conditions (ethanol concentration of 50%, liquid–solid ratio of 20 mL/g, frequency of 45 kHz, extraction time of 39.25 min, ultrasound irradiation power of 160 W and temperature of 332.19 K), the total yield of the 3 flavonoids were 100.93 ± 4.01 mg/g from the leaves of A. nephrolepis (with 31.03 ± 1.51 mg/g, 0.31 ± 0.01 mg/g, 69.59 ± 2.57 mg/g for taxifolin, diosmin, and quercetin, respectively), and under the optimal operation conditions (ethanol concentration of 50%, liquid–solid ratio of 20 mL/g, frequency of 45 kHz, extraction time of 36.80 min, ultrasound irradiation power of 150 W and temperature of 328.78 K), 16.05 mg/g ± 0.38 mg/g were obtained from the bark of A. nephrolepis (with 1.44 ± 0.05 mg/g, 0.47 ± 0.01 mg/g, 14.14 ± 0.38 mg/g for taxifolin, diosmin, and quercetin, respectively), which were close to the prediction values. Full article

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19 pages, 5796 KiB

Open AccessArticle

Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) In Vitro

by Katharina Schueller, Joachim Hans, Stefanie Pfeiffer, Jessica Walker, Jakob P. Ley and Veronika Somoza

Molecules 2020, 25(6), 1382; https://doi.org/10.3390/molecules25061382 - 18 Mar 2020

Cited by 4 | Viewed by 3309

Abstract

Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with [...] Read more.

Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 µM to 100 µM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 2′,4,4′,6′-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 µM and 100 µM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products. Full article

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10 pages, 960 KiB

Open AccessArticle

Phenolic Compounds, Antioxidant Activities, and Inhibitory Effects on Digestive Enzymes of Different Cultivars of Okra (Abelmoschus esculentus)

by Ding-Tao Wu, Xi-Rui Nie, Dan-Dan Shen, Hong-Yi Li, Li Zhao, Qing Zhang, De-Rong Lin and Wen Qin

Molecules 2020, 25(6), 1276; https://doi.org/10.3390/molecules25061276 - 11 Mar 2020

Cited by 26 | Viewed by 4333

Abstract

In this study, the phenolic profiles and bioactivities of five representative cultivars of okra collected in China were investigated. Noticeable variations of phenolic compounds and their bioactivities were observed among these different cultivars of okra. The contents of total flavonoids (TFC) in “Shuiguo”, [...] Read more.

In this study, the phenolic profiles and bioactivities of five representative cultivars of okra collected in China were investigated. Noticeable variations of phenolic compounds and their bioactivities were observed among these different cultivars of okra. The contents of total flavonoids (TFC) in “Shuiguo”, “Kalong 8”, “Kalong 3”, “Wufu”, and “Royal red” ranged from 1.75 to 3.39 mg RE/g DW, of which “Shuiguo” showed the highest TFC. Moreover, five individual phenolic compounds were found in okra by high performance liquid chromatography analysis, including isoquercitrin, protocatechuic acid, quercetin-3-O-gentiobioside, quercetin, and rutin, while isoquercitrin and quercetin-3-O-gentiobioside were detected as the main phenolic compounds in okra. Moreover, all tested okra exhibited significant antioxidant activities (2,2-diphenyl-1-picrylhydrazyl radical scavenging capacity, 2,2’-azino-bis (3-ethylenzthiazoline-6-sulphonic acid) radical scavenging capacity, and ferric reducing antioxidant power) and inhibitory effects on digestive enzymes (lipase, α-glucosidase, and α-amylase). Indeed, “Shuiguo” exhibited much better antioxidant activities and inhibitory activities on digestive enzymes, which might be attributed to its high TFC. Results suggested that okra, especially “Shuiguo”, could be developed as natural antioxidants and inhibitors against hyperlipidemia and hyperglycemia in the fields of functional foods and pharmaceuticals, which could meet the increasing demand for high-quality okra with health-promoting properties in China. Full article

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18 pages, 2145 KiB

Open AccessArticle

Seasonal and Diurnal Variation in Leaf Phenolics of Three Medicinal Mediterranean Wild Species: What Is the Best Harvesting Moment to Obtain the Richest and the Most Antioxidant Extracts?

by Antonella Gori, Luana Beatriz Nascimento, Francesco Ferrini, Mauro Centritto and Cecilia Brunetti

Molecules 2020, 25(4), 956; https://doi.org/10.3390/molecules25040956 - 20 Feb 2020

Cited by 27 | Viewed by 3669

Abstract

Mediterranean plants biosynthesize high amounts of polyphenols, which are important health-promoting compounds. Leaf polyphenolic composition changes according to environmental conditions. Therefore, it is crucial to know the temporal variation in their production. This study aimed to: i) evaluate the monthly and daily changes [...] Read more.

Mediterranean plants biosynthesize high amounts of polyphenols, which are important health-promoting compounds. Leaf polyphenolic composition changes according to environmental conditions. Therefore, it is crucial to know the temporal variation in their production. This study aimed to: i) evaluate the monthly and daily changes in polyphenols of Phyllirea latifolia, Cistus incanus, and Pistacia lentiscus to identify their best harvesting moment, ii) verify the possible correlations between phenolic production and temperature and irradiation, iii) evaluate their antioxidant capacity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hydroxyl radical (OH)scavenging assays. The extracts of leaves harvested at 8:00, 13:00 and 18:00, in May, July, and October for two years were analysed by HPLC-DAD. Both “month” and “time of the day” affected the polyphenolic content in all species. July at 13:00 was the best harvesting moment for all polyphenolic classes of P. latifolia and only for some classes of C. incanus and P. lentiscus. Environmental parameters positively correlated with the polyphenols of C. incanus and P. latifolia, while the antioxidant capacity only varied in this last species, reaching the highest value in July. Results of the study allow to determine the balsamic time for each species. Moreover, the relationship between polyphenols and environmental data can be useful for the cultivation of these plants under controlled conditions. Full article

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18 pages, 2560 KiB

Open AccessArticle

The Effect of Polyphenols on Pomegranate Fruit Susceptibility to Pilidiella granati Provides Insights into Disease Tolerance Mechanisms

by Annamaria Mincuzzi, Antonio Ippolito, Virginia Brighenti, Lucia Marchetti, Stefania Benvenuti, Angela Ligorio, Federica Pellati and Simona Marianna Sanzani

Molecules 2020, 25(3), 515; https://doi.org/10.3390/molecules25030515 - 24 Jan 2020

Cited by 7 | Viewed by 3039

Abstract

Pilidiella granati, also known as Coniella granati, is the etiological agent of pomegranate fruit dry rot. This fungal pathogen is also well-known as responsible for both plant collar rot and leaf spot. Because of its aggressiveness and the worldwide diffusion of [...] Read more.

Pilidiella granati, also known as Coniella granati, is the etiological agent of pomegranate fruit dry rot. This fungal pathogen is also well-known as responsible for both plant collar rot and leaf spot. Because of its aggressiveness and the worldwide diffusion of pomegranate crops, the selection of cultivars less susceptible to this pathogen might represent an interesting preventive control measure. In the present investigation, the role of polyphenols in the susceptibility to P. granati of the two royalties-free pomegranate cultivars Wonderful and Mollar de Elche was compared. Pomegranate fruit were artificially inoculated and lesion diameters were monitored. Furthermore, pathogen DNA was quantified at 12–72 h post-inoculation within fruit rind by a real time PCR assay setup herein, and host total RNA was used in expression assays of genes involved in host-pathogen interaction. Similarly, protein extracts were employed to assess the specific activity of enzymes implicated in defense mechanisms. Pomegranate phenolic compounds were evaluated by HPLC-ESI-MS and MS². All these data highlighted ‘Wonderful’ as less susceptible to P. granati than ‘Mollar de Elche’. In the first cultivar, the fungal growth seemed controlled by the activation of the phenylpropanoid pathway, the production of ROS, and the alteration of fungal cell wall. Furthermore, antifungal compounds seemed to accumulate in ‘Wonderful’ fruit following inoculation. These data suggest that pomegranate polyphenols have a protective effect against P. granati infection and their content might represent a relevant parameter in the selection of the most suitable cultivars to reduce the economic losses caused by this pathogen. Full article

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2019

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17 pages, 4565 KiB

Open AccessArticle

In Vitro Anti-Inflammatory Effects of Phenolic Compounds from Moraiolo Virgin Olive Oil (MVOO) in Brain Cells via Regulating the TLR4/NLRP3 Axis

by Agnese Taticchi, Stefania Urbani, Elisabetta Albi, Maurizio Servili, Michela Codini, Giovanna Traina, Stefania Balloni, Federica Filomena Patria, Luana Perioli, Tommaso Beccari and Carmela Conte

Molecules 2019, 24(24), 4523; https://doi.org/10.3390/molecules24244523 - 10 Dec 2019

Cited by 29 | Viewed by 4155

Abstract

Neuroinflammation is a feature of many classic neurodegenerative diseases. In the healthy brain, microglia cells are distributed throughout the brain and are constantly surveilling the central nervous system (CNS). In response to CNS injury, microglia quickly react by secreting a wide array of [...] Read more.

Neuroinflammation is a feature of many classic neurodegenerative diseases. In the healthy brain, microglia cells are distributed throughout the brain and are constantly surveilling the central nervous system (CNS). In response to CNS injury, microglia quickly react by secreting a wide array of apoptotic molecules. Virgin olive oil (VOO) is universally recognized as a symbol of the Mediterranean diet. In the current study, using lipopolysaccharide (LPS)-stimulated BV2 microglia, the anti-inflammatory effects of VOO phenolic extracts from Moraiolo cultivar (MVOO-PE) were investigated. The results showed that low concentration of MVOO-PE prevented microglia cell death and attenuated the LPS-induced activation of toll-like receptor 4 (TLR4)/NOD-like receptor pyrin domain-containing-3 (NLRP3) signaling cascade. The levels of TLR4 and NF-kB were diminished, as well as NLRP3 inflammasome and interleukin-1β (IL-1β) production. Cyclooxygenase-2 (COX-2) isoenzyme and ionized calcium binding adaptor molecule 1 (Iba-1) inflammatory mediator were also reduced. By modulating the TLR4/NLRP3 axis, MVOO-PE pretreatment was able to significantly down-regulate the mRNA expression of inflammatory mediators and suppress the cytokine secretion. Finally, we showed protective effect of MVOO-PE in a transwell neuron–microglia co-culture system. In conclusion, these results suggest that MVOO-PE could exerts anti-inflammatory activity on brain cells and become a promising candidate for preventing several neuroinflammatory diseases. Full article

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16 pages, 4099 KiB

Open AccessArticle

Evaluation of Antifungal Phenolics from Helianthus tuberosus L. Leaves against Phytophthora capsici Leonian by Chemometric Analysis

by Fu-Jia Chen, Xiao-Hua Long and En-Zhong Li

Molecules 2019, 24(23), 4300; https://doi.org/10.3390/molecules24234300 - 25 Nov 2019

Cited by 11 | Viewed by 3061

Abstract

Phytophthora capsici Leonian causes destructive economical losses in pepper production, and a promising source of natural fungicides- Helianthus tuberosus leaves was reported. The antifungal activities of different extracts and compounds from H. tuberosus leaves against the phytopathogen, P. capsici Leonian, were examined by [...] Read more.

Phytophthora capsici Leonian causes destructive economical losses in pepper production, and a promising source of natural fungicides- Helianthus tuberosus leaves was reported. The antifungal activities of different extracts and compounds from H. tuberosus leaves against the phytopathogen, P. capsici Leonian, were examined by chemometric analysis, including HPLC-MS/MS and multivariate data analyses. Principal component analysis and orthogonal partial least squares-discriminate analysis were applied to examine the four groups of H. tuberosus leaves samples, including crude extracts obtained by different methods, including refluxing, macerating, and refluxing under vacuum; four fractions, namely, petroleum ether (PE), chloroform (Chl), ethyl acetate (EA), and n-butanol (NB) fractions; the samples of three H. tuberosus cultivars; and the samples at three growth stages of cultivar Nan Yu. The phenolics contents were categorized based on 3,5-Dicaffeoylquinic acid (3,5-DiCQA), 1,5-Dicaffeoylquinic acid (1,5-DiCQA), 3-O-Caffeoylquinic acid (3-CQA), and 4,5-Dicaffeoylquinic acid (4,5-DiCQA), which were predominant in all the samples. Antifungal activity assay revealed that Chl and NB fractions were more active against P. capsici Leonian with lower IC₅₀(half of maximal inhibitory concentration) values, whereas partial least squares-discriminate analysis suggested caffeoylquinic acid isomer(4-CQA), methyl-quercetin glycoside(MQG), and caffeic acid(CA) might be the main active components in H. tuberosus leaves against P. capsici Leonian. Furthermore, microscopic evaluation demonstrated structural deformities in P. capsici Leonian treated with Chl and NB fractions, indicating the antifungal effects of H. tuberosus leaves. These results imply that H. tuberosus leaves with a high concentration of phenolics might be a promising source of natural fungicides. Full article

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15 pages, 2531 KiB

Open AccessArticle

Antioxidant Activity of Blueberry (Vaccinium spp.) Cultivar Leaves: Differences across the Vegetative Stage and the Application of Near Infrared Spectroscopy

by Ricardo N.M.J. Páscoa, Maria João Gomes and Clara Sousa

Molecules 2019, 24(21), 3900; https://doi.org/10.3390/molecules24213900 - 29 Oct 2019

Cited by 6 | Viewed by 3337

Abstract

Blueberries production has increased in the last few years boosted somehow by the World Health Organization (WHO) recommendations for a healthier nutrition and their recognized potential to treat several diseases. The production increase lead to high amounts of discarded leaves that could be [...] Read more.

Blueberries production has increased in the last few years boosted somehow by the World Health Organization (WHO) recommendations for a healthier nutrition and their recognized potential to treat several diseases. The production increase lead to high amounts of discarded leaves that could be very valuable. In this context, the antioxidant activity of Vaccinium spp. leaves, by means of the total phenolic (TPC) and flavonoid (TFC) content and total antioxidant capacity (TAC) was determined. Adult leaves of twenty-seven Vaccinium cultivars collected in three geographic regions and three seasons of the year were included. The antioxidant activity was additionally estimated with near infrared (NIR) spectroscopy and data transferability across the regions and seasons was evaluated. The TPC, TFC and TAC ranged from 39.6–272.8 mg gallic acid, 41.2–269.1 mg catechin and 22.6–124.8 mM Trolox per g of dry leaf, respectively. Globally through the seasons, the higher values of the three parameters were obtained in December. Regarding the geographic region, region A provided the cultivars with the higher antioxidant content. Titan was the cultivar with higher TPC and TAC and Misty the one with the higher TFC. NIR spectroscopy combined with the partial least squares analysis was able to successfully predict the antioxidant activity with coefficients of determination and range error ratios ranging from 0.84–0.99 and 11.2–26.8. Despite some identified limitations on data transferability, NIR spectroscopy proved to be a reliable, low cost and quick method to predict the antioxidant activity of the considered cultivar leaves. Full article

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13 pages, 1699 KiB

Open AccessCommunication

Heat-Dependent Desorption of Proanthocyanidins from Grape-Derived Cell Wall Material under Variable Ethanol Concentrations in Model Wine Systems

by Jordan W. Beaver, Konrad V. Miller, Cristina Medina-Plaza, Nicolas Dokoozlian, Ravi Ponangi, Thomas Blair, David Block and Anita Oberholster

Molecules 2019, 24(19), 3561; https://doi.org/10.3390/molecules24193561 - 01 Oct 2019

Cited by 10 | Viewed by 2861

Abstract

Desorption of proanthocyanidins (PA) from grape cell wall material (CWM) was investigated in solutions of varying ethanol concentrations and increasing temperature. The results reveal the reversibility of PA-CWM interactions and the role that temperature and ethanol concentration play in the extent of PA [...] Read more.

Desorption of proanthocyanidins (PA) from grape cell wall material (CWM) was investigated in solutions of varying ethanol concentrations and increasing temperature. The results reveal the reversibility of PA-CWM interactions and the role that temperature and ethanol concentration play in the extent of PA desorption. Sequentially raising temperature from 15 to 35 °C resulted in desorption of up to 48% of the initial adsorbed PA. A comparison to a phenolic extraction model showed significant differences between the predicted and actual amount of PA that desorbed from the CWM. This suggests that the initial conditions of temperature and ethanol concentration must be considered when estimating PA extraction in red wine production. Under typical winemaking conditions, a significant amount of PA may be irreversibly adsorbed if exposed to CWM at low temperature (i.e., cold soak). A compositional analysis suggests the selective desorption of large molecular weight PA from CWM under all experimental conditions. Additionally, a preferential desorption of skin-derived PA over seed-derived PA was noted in the absence of ethanol. Full article

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14 pages, 5768 KiB

Open AccessArticle

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity between Viniferin Enantiomers

by Luce M. Mattio, Mauro Marengo, Chiara Parravicini, Ivano Eberini, Sabrina Dallavalle, Francesco Bonomi, Stefania Iametti and Andrea Pinto

Molecules 2019, 24(18), 3225; https://doi.org/10.3390/molecules24183225 - 05 Sep 2019

Cited by 26 | Viewed by 4031

Abstract

To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents [...] Read more.

To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies. Full article

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21 pages, 4817 KiB

Open AccessReview

Neuroprotective Potential of Secondary Metabolites from Melicope lunu-ankenda (Rutaceae)

by Zeinab Abdulwanis Mohamed, Enas Mohamed Eliaser, Emanuela Mazzon, Patrick Rollin, Gwendoline Cheng Lian Ee and Ahmad Faizal Abdull Razis

Molecules 2019, 24(17), 3109; https://doi.org/10.3390/molecules24173109 - 27 Aug 2019

Cited by 13 | Viewed by 3383

Abstract

Plant natural compounds have great potential as alternative medicines for preventing and treating diseases. Melicope lunu-ankenda is one Melicope species (family Rutaceae), which is widely used in traditional medicine, consumed as a salad and a food seasoning. Consumption of different parts of [...] Read more.

Plant natural compounds have great potential as alternative medicines for preventing and treating diseases. Melicope lunu-ankenda is one Melicope species (family Rutaceae), which is widely used in traditional medicine, consumed as a salad and a food seasoning. Consumption of different parts of this plant has been reported to exert different biological activities such as antioxidant and anti-inflammatory qualities, resulting in a protective effect against several health disorders including neurodegenerative diseases. Various secondary metabolites such as phenolic acid derivatives, flavonoids, coumarins and alkaloids, isolated from the M. lunu-ankenda plant, were demonstrated to have neuroprotective activities and also exert many other beneficial biological effects. A number of studies have revealed different neuroprotective mechanisms for these secondary metabolites. This review summarizes the most significant and recent studies for neuroprotective activity of M. lunu-ankenda major secondary metabolites in neurodegenerative diseases. Full article

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8 pages, 249 KiB

Open AccessArticle

Influence of Olive Extracts on the Expression of Genes Involved in Lipid Metabolism in Medaka Fish

by Luis Torró-Montell, Ernesto Cortés-Castell, Elia Sirvent-Segura, Carmen Veciana-Galindo, Vicente Gil-Guillén and Mercedes Rizo-Baeza

Molecules 2019, 24(17), 3068; https://doi.org/10.3390/molecules24173068 - 23 Aug 2019

Cited by 6 | Viewed by 2450

Abstract

Aims. To assess the possible effect of polyphenol-rich olive extracts on lipid metabolism in medaka fish by quantifying the expression of lipogenic and lipolytic genes. Materials and methods. Adult medaka fish were maintained in tanks for five days with five extracts [...] Read more.

Aims. To assess the possible effect of polyphenol-rich olive extracts on lipid metabolism in medaka fish by quantifying the expression of lipogenic and lipolytic genes. Materials and methods. Adult medaka fish were maintained in tanks for five days with five extracts at 0.01% in water, causing obesity through a diet rich in carbohydrates, with a control group maintained in water with a normal diet. The extracts contained polyphenols ranging between 7 and 116 mg/g (oleuropein, hydroxytyrosol) with an antioxidant power of 2–13 mmol of 2,4,6-tri(2-pyridyl)-1,3,5-triazine/100 g. After five days, the fish were sacrificed and the hepatic mRNA and its complementary DNA were extracted by reverse transcription. Complementary DNAs were quantified for three lipolytic and three lipogenic genes by real-time PCR. The relative gene expression was calculated from the amplification curves in reference to the control group. Results. The expression of genes involved in lipolysis, including peroxisome proliferator-activated receptor-±, acyl-CoA oxidase 1, and carnitine palmitoyltransferase 1, were clearly decreased in fish subjected to an obesogenic diet, and this situation could not be reversed in fish maintained with polyphenol-rich extracts. In contrast, lipogenic fatty acid synthase, acetyl-CoA carboxylase 1, and sterol regulatory element-binding protein 1 genes increased considerably with the obesogenic diet and reverted to the normal state with the olive extracts. The effect was not dependent on the total polyphenol content, the specific oleuropein or hydroxytyrosol concentration, or the antioxidant power, suggesting a synergistic effect. Conclusion. Olive polyphenols, acting as anti-lipogenic agents, have a positive effect on lipid metabolism, but their mechanism in each gene is different according to the extract, which supports synergistic mechanisms with the different proportions of polyphenols and accompanying phytochemicals in each extract. Full article

14 pages, 1043 KiB

Open AccessArticle

An Original HPLC Method with Coulometric Detection to Monitor Hydroxyl Radical Generation via Fenton Chemistry

by Maria Carmen Catapano, Michele Protti, Tommaso Fontana, Roberto Mandrioli, Přemysl Mladěnka and Laura Mercolini

Molecules 2019, 24(17), 3066; https://doi.org/10.3390/molecules24173066 - 23 Aug 2019

Cited by 17 | Viewed by 4882

Abstract

Hydroxyl radicals (•OH) can be generated via Fenton chemistry catalyzed by transition metals. An in vitro Fenton system was developed to test both the inhibition and stimulation of •OH formation, by monitoring salicylate aromatic hydroxylation derivatives as markers of •OH production. The reaction [...] Read more.

Hydroxyl radicals (•OH) can be generated via Fenton chemistry catalyzed by transition metals. An in vitro Fenton system was developed to test both the inhibition and stimulation of •OH formation, by monitoring salicylate aromatic hydroxylation derivatives as markers of •OH production. The reaction was optimized with either iron or copper, and target analytes were determined by means of an original HPLC method coupled to coulometric detection. The method granted good sensitivity and precision, while method applicability was tested on antioxidant compounds with and without chelating properties in different substance to metal ratios. This analytical approach shows how Fenton’s reaction can be monitored by HPLC coupled to coulometric detection, as a powerful tool for studying molecules′ redox behavior. Full article

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17 pages, 898 KiB

Open AccessArticle

Terpenoids and Phytocannabinoids Co-Produced in Cannabis Sativa Strains Show Specific Interaction for Cell Cytotoxic Activity

by Dvora Namdar, Hillary Voet, Vinayaka Ajjampura, Stalin Nadarajan, Einav Mayzlish-Gati, Moran Mazuz, Nurit Shalev and Hinanit Koltai

Molecules 2019, 24(17), 3031; https://doi.org/10.3390/molecules24173031 - 21 Aug 2019

Cited by 70 | Viewed by 9270

Abstract

Mixtures of different Cannabis sativa phytocannabinoids are more active biologically than single phytocannabinoids. However, cannabis terpenoids as potential instigators of phytocannabinoid activity have not yet been explored in detail. Terpenoid groups were statistically co-related to certain cannabis strains rich in Δ⁹-tetrahydrocannabinolic [...] Read more.

Mixtures of different Cannabis sativa phytocannabinoids are more active biologically than single phytocannabinoids. However, cannabis terpenoids as potential instigators of phytocannabinoid activity have not yet been explored in detail. Terpenoid groups were statistically co-related to certain cannabis strains rich in Δ⁹-tetrahydrocannabinolic acid (THCA) or cannabidiolic acid (CBDA), and their ability to enhance the activity of decarboxylase phytocannabinoids (i.e., THC or CBD) was determined. Analytical HPLC and GC/MS were used to identify and quantify the secondary metabolites in 17 strains of C. sativa, and correlations between cannabinoids and terpenoids in each strain were determined. Column separation was used to separate and collect the compounds, and cell viability assay was used to assess biological activity. We found that in “high THC” or “high CBD” strains, phytocannabinoids are produced alongside certain sets of terpenoids. Only co-related terpenoids enhanced the cytotoxic activity of phytocannabinoids on MDA-MB-231 and HCT-116 cell lines. This was found to be most effective in natural ratios found in extracts of cannabis inflorescence. The correlation in a particular strain between THCA or CBDA and a certain set of terpenoids, and the partial specificity in interaction may have influenced the cultivation of cannabis and may have implications for therapeutic treatments. Full article

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35 pages, 4135 KiB

Open AccessReview

Veronica Plants—Drifting from Farm to Traditional Healing, Food Application, and Phytopharmacology

by Bahare Salehi, Mangalpady Shivaprasad Shetty, Nanjangud V. Anil Kumar, Jelena Živković, Daniela Calina, Anca Oana Docea, Simin Emamzadeh-Yazdi, Ceyda Sibel Kılıç, Tamar Goloshvili, Silvana Nicola, Giuseppe Pignata, Farukh Sharopov, María del Mar Contreras, William C. Cho, Natália Martins and Javad Sharifi-Rad

Molecules 2019, 24(13), 2454; https://doi.org/10.3390/molecules24132454 - 04 Jul 2019

Cited by 62 | Viewed by 8347

Abstract

The Veronica genus, with more than 200 species, belongs to the Plantaginaceae family and is distributed over most of the Northern Hemisphere and in many parts of Southern Hemisphere. These plants are traditionally used in medicine for wound healing, in the treatment of [...] Read more.

The Veronica genus, with more than 200 species, belongs to the Plantaginaceae family and is distributed over most of the Northern Hemisphere and in many parts of Southern Hemisphere. These plants are traditionally used in medicine for wound healing, in the treatment of rheumatism, and in different human diseases. This paper reviews the chemical composition of some valuable Veronica species, the possibilities Veronica extracts have in food preservation and as food ingredients, and their functional properties. Veronica species represent a valuable source of biological active secondary metabolites, including iridoid glycosides and phenolic compounds. In particular, due to presence of these phytochemicals, Veronica species exhibit a wide spectrum of biological activities, including antimicrobial and antioxidant. In fact, some studies suggest that some Veronica extracts can inhibit foodborne pathogens, such as Listeria monocytogenes, but only a few of them were performed in food systems. Moreover, anticancer, anti-inflammatory, and other bioactivities were reported in vitro and in vivo. The bioactivity of Veronica plants was demonstrated, but further studies in food systems and in humans are required. Full article

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33 pages, 974 KiB

Open AccessReview

Symphytum Species: A Comprehensive Review on Chemical Composition, Food Applications and Phytopharmacology

by Bahare Salehi, Farukh Sharopov, Tugba Boyunegmez Tumer, Adem Ozleyen, Celia Rodríguez-Pérez, Shahira M. Ezzat, Elena Azzini, Tahereh Hosseinabadi, Monica Butnariu, Ioan Sarac, Cristian Bostan, Krishnendu Acharya, Surjit Sen, Kadriye Nur Kasapoglu, Ceren Daşkaya-Dikmen, Beraat Özçelik, Navid Baghalpour, Javad Sharifi-Rad, Patrick Valere Tsouh Fokou, William C. Cho and Natália Martins Show full author list Hide full author list

Molecules 2019, 24(12), 2272; https://doi.org/10.3390/molecules24122272 - 18 Jun 2019

Cited by 53 | Viewed by 9829

Abstract

Symphytum species belongs to the Boraginaceae family and have been used for centuries for bone breakages, sprains and rheumatism, liver problems, gastritis, ulcers, skin problems, joint pain and contusions, wounds, gout, hematomas and thrombophlebitis. Considering the innumerable potentialities of the Symphytum species and [...] Read more.

Symphytum species belongs to the Boraginaceae family and have been used for centuries for bone breakages, sprains and rheumatism, liver problems, gastritis, ulcers, skin problems, joint pain and contusions, wounds, gout, hematomas and thrombophlebitis. Considering the innumerable potentialities of the Symphytum species and their widespread use in the world, it is extremely important to provide data compiling the available literature to identify the areas of intense research and the main gaps in order to design future studies. The present review aims at summarizing the main data on the therapeutic indications of the Symphytum species based on the current evidence, also emphasizing data on both the efficacy and adverse effects. The present review was carried out by consulting PubMed (Medline), Web of Science, Embase, Scopus, Cochrane Database, Science Direct and Google Scholar (as a search engine) databases to retrieve the most updated articles on this topic. All articles were carefully analyzed by the authors to assess their strengths and weaknesses, and to select the most useful ones for the purpose of review, prioritizing articles published from 1956 to 2018. The pharmacological effects of the Symphytum species are attributed to several chemical compounds, among them allantoin, phenolic compounds, glycopeptides, polysaccharides and some toxic pyrrolizidine alkaloids. Not less important to highlight are the risks associated with its use. In fact, there is increasing consumption of over-the-counter drugs, which when associated with conventional drugs can cause serious and even fatal adverse events. Although clinical trials sustain the folk topical application of Symphytum species in musculoskeletal and blunt injuries, with minor adverse effects, its antimicrobial potency was still poorly investigated. Further studies are needed to assess the antimicrobial spectrum of Symphytum species and to characterize the active molecules both in vitro and in vivo. Full article

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40 pages, 1383 KiB

Open AccessReview

A Comparative Review on the Extraction, Antioxidant Content and Antioxidant Potential of Different Parts of Walnut (Juglans regia L.) Fruit and Tree

by Ali Jahanban-Esfahlan, Alireza Ostadrahimi, Mahnaz Tabibiazar and Ryszard Amarowicz

Molecules 2019, 24(11), 2133; https://doi.org/10.3390/molecules24112133 - 05 Jun 2019

Cited by 111 | Viewed by 11583

Abstract

As a valuable tree nut, walnut is a well-known member of the Juglandaceae family. The fruit is made up of an outer green shell cover or husk, the middle shell which must be cracked to release the kernel, a thin layer known as [...] Read more.

As a valuable tree nut, walnut is a well-known member of the Juglandaceae family. The fruit is made up of an outer green shell cover or husk, the middle shell which must be cracked to release the kernel, a thin layer known as skin or the seed coat, and finally, the kernel or meat. The nutritional importance of walnut fruit is ascribed to its kernel. The shell and husk are burned as fuel or discarded away as waste products. In the past two decades, the evaluation of the phenolic content and antioxidant activity of different parts of walnut has received great interest. In this contribution, the recent reports on the extraction and quantification of phenolic content from each part of the walnut tree and fruit using different solvents were highlighted and comparatively reviewed. The current review paper also tries to describe the antioxidant content of phenolic extracts obtained from different parts of the walnut tree and fruit. Additionally, the antioxidant and antiradical activities of the prepared extracts have also been discussed. Full article

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15 pages, 1544 KiB

Open AccessArticle

Comparison of Multiple Bioactive Constituents in the Flower and the Caulis of Lonicera japonica Based on UFLC-QTRAP-MS/MS Combined with Multivariate Statistical Analysis

by Zhichen Cai, Chengcheng Wang, Lisi Zou, Xunhong Liu, Jiali Chen, Mengxia Tan, Yuqi Mei and Lifang Wei

Molecules 2019, 24(10), 1936; https://doi.org/10.3390/molecules24101936 - 20 May 2019

Cited by 35 | Viewed by 3161

Abstract

Lonicerae japonicae flos (LJF) and Lonicerae japonicae caulis (LJC) are derived from different parts of Lonicera japonica Thunb. (Caprifoliaceae), and have been used as herbal remedies to treat various diseases for thousands of years with confirmed curative effects. However, little attention has been [...] Read more.

Lonicerae japonicae flos (LJF) and Lonicerae japonicae caulis (LJC) are derived from different parts of Lonicera japonica Thunb. (Caprifoliaceae), and have been used as herbal remedies to treat various diseases for thousands of years with confirmed curative effects. However, little attention has been paid to illustrating the differences in efficacy from the perspective of phytochemistry. In the present study, a simultaneous determination of 47 bioactive constituents, including 12 organic acids, 12 flavonoids, six iridoids, 13 amino acids and four nucleosides in 44 batches of LJF and LJC samples from different habitats and commercial herbs was established based on ultra-fast liquid chromatography tandem triple quadrupole mass spectrometry (UFLC-QTRAP-MS/MS). Moreover, principal component analysis (PCA), partial least squares discriminant analysis (PLS-DA) and t-test were then performed to classify and reveal the differential compositions of LJF and LJC according to the content of the tested constituents. The results demonstrated that the types and contents of chemical components (e.g., isochlorogenic acid A, chlorogenic acid, neochlorogenic acid, quinic acid, secologanic acid, luteoloside, loganin, secoxyloganin, morroniside and L-isoleucine) were significantly different, which may lead to the classification and the differences in efficacy of LJF and LJC. Our findings not only provide a basis for the comprehensive evaluation and intrinsic quality control of LJF and LJC, but also pave the way for discovering the material basis contributing to the different properties and efficacies of the two medicinal materials at the phytochemical level. Full article

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24 pages, 2134 KiB

Open AccessArticle

Assessment of Diversity in the Accessions of Setaria italica L. Based on Phytochemical and Morphological Traits and ISSR Markers

by Bimal Kumar Ghimire, Chang Yeon Yu, Seung-Hyun Kim and Ill-Min Chung

Molecules 2019, 24(8), 1486; https://doi.org/10.3390/molecules24081486 - 15 Apr 2019

Cited by 10 | Viewed by 3641

Abstract

This study was carried out to evaluate genetic diversity, phenolic compound composition, and biological activity of Setaria italica L. collected from different parts of South Korea. Antioxidant potential of seeds was estimated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and antimicrobial activity was [...] Read more.

This study was carried out to evaluate genetic diversity, phenolic compound composition, and biological activity of Setaria italica L. collected from different parts of South Korea. Antioxidant potential of seeds was estimated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and antimicrobial activity was determined by evaluating the minimum inhibitory concentration (MIC). Eight phenolic acids and 3 flavonoids were identified and quantified, among which myricetin and salicylic acid were the most dominant phytochemical compounds detected in the majority of accessions. The antioxidant potential of the leaf extracts of all the accessions was significantly higher (ranging from 32.33 ± 1.53 µg mL⁻¹ in SI-03 to 87.87 ± 1.63 µg mL⁻¹) in SI-10 than that of the root, stem, or seeds. Among the 15 accessions, methanolic extracts of the SI-15 accession strongly suppressed the growth of Escherichia coli (250 µg mL⁻¹). Accessions SI-14 and SI-15 showed positive antimicrobial activity against all gram-positive bacteria. Interestingly, extracts of all accessions were more sensitive towards E. coli and Staphylococcus aureus, with MICs ranging from 250 to 1000 µg mL⁻¹. Three phenolic acids, namely chlorogenic acid, catechin, caffeic acid, naringin, hesperetin, and myricetin, were found to be moderately positively correlated with antioxidant activities. A wide range of diversity was observed in morphological traits, namely plant height (99.33 to 201.33 cm), culm length (67.10 to 160.00 cm), spike length (12.80 to 24.00 cm), 1000 seeds weight 1.44 to 2.91 g), bloom beginning (93.67 to 128.00 days), and full bloom (99.67 to 135 days). A dendogram generated from unweighted pair group method with arithmetic mean clustering (UPGMA) cluster analysis based on the morphological traits and inter simple sequence repeat (ISSR) marker data revealed three major groups. However, no clear correlation between these two different approaches was found. The average Shannon’s information index value (I) was 0.492, and it ranged from 0 to 0.693. The average expected heterozygosity (He) was 0.335, and it ranged from 0 to 0.499. The substantial variation in the morphological traits, bioactive properties, and genetic diversity among the accessions may provide useful information for breeding programs attempting to obtain S. italica with improved bioactive properties. Full article

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15 pages, 2312 KiB

Open AccessArticle

Micropropagation of Chaenomeles japonica: A Step towards Production of Polyphenol-rich Extracts Showing Antioxidant and Antimicrobial Activities

by Małgorzata Kikowska, Agata Włodarczyk, Monika Rewers, Elwira Sliwinska, Elżbieta Studzińska-Sroka, Ewa Witkowska-Banaszczak, Anna Stochmal, Jerzy Żuchowski, Jolanta Dlugaszewska and Barbara Thiem

Molecules 2019, 24(7), 1314; https://doi.org/10.3390/molecules24071314 - 03 Apr 2019

Cited by 18 | Viewed by 3302

Abstract

A protocol for C. japonica micropropagation with a confirmation of genome size stability of the in vitro-propagated plantlets was developed. The highest number of shoots multiplied in vitro was obtained on Murashige & Skoog medium (MS) with 1.0 mg L⁻¹ N6-benzyladenine plus [...] Read more.

A protocol for C. japonica micropropagation with a confirmation of genome size stability of the in vitro-propagated plantlets was developed. The highest number of shoots multiplied in vitro was obtained on Murashige & Skoog medium (MS) with 1.0 mg L⁻¹ N6-benzyladenine plus 1.0 mg L⁻¹ indole-3-acetic acid. The highest number of roots was observed for the shoots on MS with 15 g L⁻¹ sucrose plus 1.0 mg L⁻¹ indole-3-acetic acid. The acclimatization rate was significantly high. The qualitative HPLC analyses confirmed the presence of phenolic acids and flavonoids in the extracts. The extracts from both shoot cultures and the leaves from field-grown plants revealed antioxidant activity and they exhibited moderate antimicrobial activity. The conducted research confirmed the regeneration potential of genetically-stable plants of C. japonica under in vitro conditions, the ability of the plantlets to produce polyphenols as those present in field-grown plants, as well as their antioxidant potential. Full article

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15 pages, 2010 KiB

Open AccessArticle

Metabolomic Profiling of the Desiccation-Tolerant Medicinal Shrub Myrothamnus flabellifolia Indicates Phenolic Variability Across Its Natural Habitat: Implications for Tea and Cosmetics Production

by Joanne Bentley, John P. Moore and Jill M. Farrant

Molecules 2019, 24(7), 1240; https://doi.org/10.3390/molecules24071240 - 29 Mar 2019

Cited by 21 | Viewed by 4289

Abstract

The leaves and twigs of the desiccation-tolerant medicinal shrub Myrothamnus flabellifolia are harvested for use in traditional and commercial teas and cosmetics due to their phenolic properties. The antioxidant and pharmacological value of this plant has been widely confirmed; however, previous studies typically [...] Read more.

The leaves and twigs of the desiccation-tolerant medicinal shrub Myrothamnus flabellifolia are harvested for use in traditional and commercial teas and cosmetics due to their phenolic properties. The antioxidant and pharmacological value of this plant has been widely confirmed; however, previous studies typically based their findings on material collected from a single region. The existence of phenolic variability between plants from different geographical regions experiencing different rainfall regimes has thus not been sufficiently evaluated. Furthermore, the anthocyanins present in this plant have not been assessed. The present study thus used an untargeted liquid chromatography-tandem-mass spectrometry approach to profile phenolics in M. flabellifolia material collected from three climatically distinct (high, moderate, and low rainfall) regions representing the western, southern, and eastern extent of the species range in southern Africa. Forty-one putative phenolic compounds, primarily flavonoids, were detected, nine of which are anthocyanins. Several of these compounds are previously unknown from M. flabellifolia. Using multivariate statistics, samples from different regions could be distinguished by their phenolic profiles, supporting the existence of regional phenolic variability. This study indicates that significant phenolic variability exists across the range of M. flabellifolia, which should inform both commercial and traditional cultivation and harvesting strategies. Full article

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13 pages, 297 KiB

Open AccessArticle

Evaluation of the Behavior of Phenolic Compounds and Steviol Glycosides of Sonicated Strawberry Juice Sweetened with Stevia (Stevia rebaudiana Bertoni)

by Jana Šic Žlabur, Nadica Dobričević, Mladen Brnčić, Francisco J. Barba, Jose M. Lorenzo, Daniel Franco, Atanas G. Atanasov, Sandra Voća and Suzana Rimac Brnčić

Molecules 2019, 24(7), 1202; https://doi.org/10.3390/molecules24071202 - 27 Mar 2019

Cited by 17 | Viewed by 2906

Abstract

In this study, the influence of stevia addition and sonication processing parameters on the phenolic content and profile as well as the steviol glycosides of strawberry juice-based samples was investigated. For this purpose, three matrices—control samples of strawberry juices without green stevia powder [...] Read more.

In this study, the influence of stevia addition and sonication processing parameters on the phenolic content and profile as well as the steviol glycosides of strawberry juice-based samples was investigated. For this purpose, three matrices—control samples of strawberry juices without green stevia powder (CS), strawberry juices with green stevia powder (JGSP), and sonicated juices with green stevia powder (SJGSP)—were prepared. For sonication purposes, different conditions regarding probe diameters (7 mm and 22 mm), amplitudes (50%, 75%, and 100%), and time (15 min, 20 min, and 25 min) were tested. The results that were obtained upon the measurement of the total phenolic content, total flavonoids, steviol glycosides, and antioxidant capacity showed significant differences according to the matrices evaluated, obtaining overall higher values in the samples with stevia added. Moreover, when sonication was evaluated, it was found that a higher amplitude (100%), a larger probe diameter (22 mm), and a longer sonication period (25 min) led to higher values. Flavones such as luteolin and apigenin were identified and quantified in JGSP and SJGSP, while they were not found in CS. Besides these phenolic compounds, kaempferol, quercetin, pyrogallic acid, 4-methylcatechol, and 4-methoxybenzoic acid were also identified and quantified. Similarly to the total phenolic compounds, total flavonoids, and total antioxidant capacity, an increased amount of these compounds was found in SJGSP, especially after using the most intense sonication conditions. Therefore, the use of sonication together with stevia added could be a useful tool to preserve strawberry juices, increasing at the same time the sweetness and the antioxidant value of the beverages. Full article

18 pages, 749 KiB

Open AccessReview

A Critical Review of Phenolic Compounds Extracted from the Bark of Woody Vascular Plants and Their Potential Biological Activity

by Corneliu Tanase, Sanda Coșarcă and Daniela-Lucia Muntean

Molecules 2019, 24(6), 1182; https://doi.org/10.3390/molecules24061182 - 26 Mar 2019

Cited by 176 | Viewed by 8931

Abstract

Polyphenols are one of the largest and most widespread groups of secondary metabolites in the plants world. These compounds are of particular interest due to their occurrence and the properties they possess. The main sources of phenolic compounds are fruits and vegetables, but [...] Read more.

Polyphenols are one of the largest and most widespread groups of secondary metabolites in the plants world. These compounds are of particular interest due to their occurrence and the properties they possess. The main sources of phenolic compounds are fruits and vegetables, but lately, more and more studies refer to woody vascular plants, especially to bark, as an important source of phenolic compounds with a potential biological effect. This study aims to bring together information on the phenolic compounds present in the bark of woody vascular plants by discussing extraction methods, the chemical composition of the extracts and potential biological effects. The literature data used in this paper were collected via PubMed (2004–2019). Search terms were: bark, rhytidome, woody vascular plant, polyphenols, phenolic compounds, biologic activity, antioxidant, immunostimulatory, antimutagenic, antibacterial, anti-inflammatory, and antitumoral. This paper intends to highlight the fact that the polyphenolic extracts obtained from the bark of woody vascular plants represent sources of bioactive compounds with antioxidant, immunostimulatory, antimutagenic, antibacterial properties, etc. Future research directions should be directed towards identification and isolation of bioactive compounds. Consequently, biologically active compounds obtained from the bark of woody plants could be exploited on an industrial scale. Full article

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12 pages, 937 KiB

Open AccessArticle

Phenylalkanoid Glycosides (Non-Salicinoids) from Wood Chips of Salix triandra × dasyclados Hybrid Willow

by Clarice Noleto-Dias, Yanqi Wu, Alice Bellisai, William Macalpine, Michael H. Beale and Jane L. Ward

Molecules 2019, 24(6), 1152; https://doi.org/10.3390/molecules24061152 - 23 Mar 2019

Cited by 14 | Viewed by 3595

Abstract

Salix triandra (almond leaved willow) is an established crop, grown in coppicing regimes for basket-making materials. It is known as a source of non-salicinoid phenolic glycosides, such as triandrin and salidroside. A spontaneous natural hybrid of S. triandra and S. dasyclados was subjected [...] Read more.

Salix triandra (almond leaved willow) is an established crop, grown in coppicing regimes for basket-making materials. It is known as a source of non-salicinoid phenolic glycosides, such as triandrin and salidroside. A spontaneous natural hybrid of S. triandra and S. dasyclados was subjected to metabolite profiling by high resolution LC-MS, and 22 phenolic glycosides, including 18 that are new to the Salicaceae, were identified. Structures were determined by HPLC isolation and NMR methods. The hybridisation process has introduced novel chemistry into the Salix phenolic glycoside palette, in particular, the ability to generate disaccharide conjugates where the glycosyl group is further extended by a range of sugars, including apiose, rhamnose, xylose, and arabinose. Also of note is the appearance of chavicol derivatives, also not previously seen in Salix spp. The work demonstrates the plasticity of the phenolic glycoside biosynthetic pathway, and the potential to improve established crops such as S. triandra and S. dasyclados, via high-value metabolites, for both basketry and bioenergy markets. Full article

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18 pages, 1323 KiB

Open AccessFeature PaperArticle

Onion (Allium cepa L.) Skin: A Rich Resource of Biomolecules for the Sustainable Production of Colored Biofunctional Textiles

by Lucia Pucciarini, Federica Ianni, Valentina Petesse, Federica Pellati, Virginia Brighenti, Claudia Volpi, Marco Gargaro, Benedetto Natalini, Catia Clementi and Roccaldo Sardella

Molecules 2019, 24(3), 634; https://doi.org/10.3390/molecules24030634 - 11 Feb 2019

Cited by 35 | Viewed by 8008

Abstract

The aqueous extract of dry onion skin waste from the ‘Dorata di Parma’ cultivar was tested as a new source of biomolecules for the production of colored and biofunctional wool yarns, through environmentally friendly dyeing procedures. Specific attention was paid to the antioxidant [...] Read more.

The aqueous extract of dry onion skin waste from the ‘Dorata di Parma’ cultivar was tested as a new source of biomolecules for the production of colored and biofunctional wool yarns, through environmentally friendly dyeing procedures. Specific attention was paid to the antioxidant and UV protection properties of the resulting textiles. On the basis of spectrophotometric and mass spectrometry analyses, the obtained deep red-brown color was assigned to quercetin and its glycoside derivatives. The Folin–Ciocalteu method revealed good phenol uptakes on the wool fiber (higher than 27% for the textile after the first dyeing cycle), with respect to the original total content estimated in the water extract (78.50 ± 2.49 mg equivalent gallic acid/g onion skin). The manufactured materials showed remarkable antioxidant activity and ability to protect human skin against lipid peroxidation following UV radiation: 7.65 ± 1.43 (FRAP assay) and 13.60 (ORAC assay) mg equivalent trolox/g textile; lipid peroxidation inhibition up to 89.37%. This photoprotective and antioxidant activity were therefore ascribed to the polyphenol pool contained in the outer dried gold skins of onion. It is worth noting that citofluorimetric analysis demonstrated that the aqueous extract does not have a significative influence on cell viability, neither is capable of inducing a proapoptotic effect. Full article

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17 pages, 2147 KiB

Open AccessArticle

Comparison of Bioactive Compounds and Antioxidant Activities of Maclura tricuspidata Fruit Extracts at Different Maturity Stages

by Dae-Woon Kim, Won-Jae Lee, Yoseph Asmelash Gebru, Han-Seok Choi, Soo-Hwan Yeo, Young-Jae Jeong, Seung Kim, Young-Hoi Kim and Myung-Kon Kim

Molecules 2019, 24(3), 567; https://doi.org/10.3390/molecules24030567 - 04 Feb 2019

Cited by 22 | Viewed by 4416

Abstract

Maclura tricuspidata fruit contains various bioactive compounds and has traditionally been used in folk medicine and as valuable food material in Korea. The composition and contents of bioactive compounds in the fruit can be influenced by its maturity stages. In this study, total [...] Read more.

Maclura tricuspidata fruit contains various bioactive compounds and has traditionally been used in folk medicine and as valuable food material in Korea. The composition and contents of bioactive compounds in the fruit can be influenced by its maturity stages. In this study, total phenol, total flavonoid, individual polyphenolic compounds, total carotenoids and antioxidant activities at four maturity stages of the fruit were determined. Polyphenolic compounds were analyzed using high-pressure liquid chromatography-quadrupole time-of-flight mass spectrometry (HPLC-QTOF-MS) and HPLC. Among 18 polyphenolic compounds identified in this study, five parishin derivatives (gastrodin, parishin A, B, C, E) were positively identified for the first time in this plant. These compounds were also validated and quantified using authentic standards. Parishin A was the most abundant component, followed by chlorogenic acid, gastrodin, eriodictyol glucoside, parishin C, parishin E and parishin B. The contents of all the polyphenolic compounds were higher at the immature and premature stages than at fully mature and overmature stages, while total carotenoid was found to be higher in the mature and overmature stages. Overall antioxidant activities by three different assays (DPPH, ABTS, FRAP) decreased as maturation progressed. Antioxidant properties of the fruit extract are suggested to be attributed to the polyphenols. Full article

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16 pages, 2114 KiB

Open AccessArticle

Ripe and Raw Pu-Erh Tea: LC-MS Profiling, Antioxidant Capacity and Enzyme Inhibition Activities of Aqueous and Hydro-Alcoholic Extracts

by Gabriella Roda, Cristina Marinello, Anita Grassi, Claudia Picozzi, Giancarlo Aldini, Marina Carini and Luca Regazzoni

Molecules 2019, 24(3), 473; https://doi.org/10.3390/molecules24030473 - 29 Jan 2019

Cited by 19 | Viewed by 5175

Abstract

Herein, we reported a detailed profiling of soluble components of two fermented varieties of Chinese green tea, namely raw and ripe pu-erh. The identification and quantification of the main components was carried out by means of mass spectrometry and UV spectroscopy, after chromatographic [...] Read more.

Herein, we reported a detailed profiling of soluble components of two fermented varieties of Chinese green tea, namely raw and ripe pu-erh. The identification and quantification of the main components was carried out by means of mass spectrometry and UV spectroscopy, after chromatographic separation. The antioxidant capacity towards different radical species, the anti-microbial and the enzyme inhibition activities of the extracts were then correlated to their main constituents. Despite a superimposable qualitative composition, a similar caffeine content, and similar enzyme inhibition and antimicrobial activities, raw pu-erh tea extract had a better antioxidant capacity owing to its higher polyphenol content. However, the activity of raw pu-erh tea seems not to justify its higher production costs and ripe variety appears to be a valid and low-cost alternative for the preparation of products with antioxidant or antimicrobial properties. Full article

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9 pages, 946 KiB

Open AccessArticle

Preparation and Characterization of Protocatechuic Acid Sulfates

by Sofia M. Gutierrez-Zetina, Susana Gonzalez-Manzano, Jose J. Perez-Alonso, Ana M. Gonzalez-Paramas and Celestino Santos-Buelga

Molecules 2019, 24(2), 307; https://doi.org/10.3390/molecules24020307 - 16 Jan 2019

Cited by 11 | Viewed by 4230

Abstract

Protocatechuic acid (3,4-dihydroxybenzoic acid; PCA) is a phenolic acid present in plants as a secondary metabolite and is also produced in the human organism as a metabolite from the degradation of polyphenols by the intestinal microbiota, particularly of flavonoids. However, PCA, like most [...] Read more.

Protocatechuic acid (3,4-dihydroxybenzoic acid; PCA) is a phenolic acid present in plants as a secondary metabolite and is also produced in the human organism as a metabolite from the degradation of polyphenols by the intestinal microbiota, particularly of flavonoids. However, PCA, like most polyphenols, is biotransformed in the human body to different conjugates as sulfates, which are found circulating in blood and could be involved in the bioactivity of the original compound. This paper describes a simple process for the preparation of PCA monosulfates with satisfactory yields. Two compounds were obtained that were identified as PCA-3-sulfate and PCA-4-sulfate by mass spectrometry and ¹H and ¹³C nuclear magnetic resonance using one- and two-dimensional techniques (heteronuclear single-quantum coherence and heteronuclear multiple-bond correlation). Differential MS fragmentation behavior and UV spectra were observed for each compound, which could be used for their identification in samples of unknown composition. The described procedure can be used for the preparation of these polyphenol metabolites in view of their use in in vivo and in vitro studies, as well as standards for their analysis in biological fluids, to contribute to the elucidation of biological effects of dietary polyphenols. Full article

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18 pages, 658 KiB

Open AccessArticle

Polyphenolic Profile and Antioxidant Activity of Leaf Purified Hydroalcoholic Extracts from Seven Mexican Persea americana Cultivars

by Cecilia Castro-López, Israel Bautista-Hernández, María D. González-Hernández, Guillermo C. G. Martínez-Ávila, Romeo Rojas, Adriana Gutiérrez-Díez, Nancy Medina-Herrera and Víctor E. Aguirre-Arzola

Molecules 2019, 24(1), 173; https://doi.org/10.3390/molecules24010173 - 04 Jan 2019

Cited by 31 | Viewed by 6732

Abstract

Persea americana (avocado) is a fruit consumed worldwide; however, since avocado leaves are apparently a natural ingredient that can be used as a traditional medicine, they can be a potential source of bioactive compounds. This study aimed to analyze the antioxidant activity of [...] Read more.

Persea americana (avocado) is a fruit consumed worldwide; however, since avocado leaves are apparently a natural ingredient that can be used as a traditional medicine, they can be a potential source of bioactive compounds. This study aimed to analyze the antioxidant activity of seven Mexican avocado leaf extracts by DPPH^•, ABTS^•+, and lipid peroxidation (LPO), and to identify the compound profile by liquid chromatography coupled to mass spectrometry/electron spray ionization. The highest free radical-scavenging activity was observed for Platano Delgado and Criollo 6 avocado cultivars havin IC₅₀ values of 271.86 ± 13.69 and 269.56 ± 6.53 for DPPH^• and ABTS^•+ radicals, respectively, while the best result for lipid oxidation inhibition was registered in Criollo 6 cultivar extract. In this study forty-one compounds were detected in avocado leaves of the the seven cultivars analyzed, and of these compounds, eighteen phenolics were identified for first time in such plant material. The present study demonstrated that Mexican cultivars of Persea americana possess diverse polyphenolic compounds with strong antioxidant activity, which might be useful in the food and pharmaceutical industries. Full article

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2018

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12 pages, 2019 KiB

Open AccessArticle

A New Polyoxygenated Flavonol Gossypetin-3-O-β-d-Robinobioside from Caesalpinia gilliesii (Hook.) D. Dietr. and In Vivo Hepatoprotective, Anti-Inflammatory, and Anti-Ulcer Activities of the Leaf Methanol Extract

by Mahmoud Emam, Mohamed A. El Raey, Alaadin E. El-Haddad, Sally A. El Awdan, Abdel-Gawad M. Rabie, Mohamed A. El-Ansari, Mansour Sobeh, Samir M. Osman and Michael Wink

Molecules 2019, 24(1), 138; https://doi.org/10.3390/molecules24010138 - 31 Dec 2018

Cited by 16 | Viewed by 4189

Abstract

A hitherto unknown polyoxygenated flavonol robinobioside (gossypetin-3-O-β-d-robinobioside) was isolated from the leaves of Caesalpinia gilliesii along with thirteen known phenolic secondary metabolites. The isolated compounds were characterized using spectroscopic analysis, including 1D and 2D NMR and mass [...] Read more.

A hitherto unknown polyoxygenated flavonol robinobioside (gossypetin-3-O-β-d-robinobioside) was isolated from the leaves of Caesalpinia gilliesii along with thirteen known phenolic secondary metabolites. The isolated compounds were characterized using spectroscopic analysis, including 1D and 2D NMR and mass spectrometry (MS) analyses. The extract reduced the level of liver damage in CCl₄-induced liver injury in rats. A decrease of the liver biomarkers—aspartate aminotransferase (AST) and alanine aminotransferase (ALT) and an increase of total antioxidant capacity (TAC) levels—were observed similar to the liver protecting drug silymarin. In addition, the extract showed promising activity against carrageenan-induced paw edema in rats and protected their stomachs against ethanol-induced gastric ulcers in a concentration dependent fashion. The observed activities could be attributed to the high content of antioxidant polyphenols. Our results suggest that the C. gilliesii has the capacity to scavenge free radicals and can protect against oxidative stress, and liver and stomach injury. Full article

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10 pages, 1285 KiB

Open AccessArticle

Characterization of Purified Red Cabbage Anthocyanins: Improvement in HPLC Separation and Protective Effect against H₂O₂-Induced Oxidative Stress in HepG2 Cells

by Sheng Fang, Fubin Lin, Daofeng Qu, Xianrui Liang and Liping Wang

Molecules 2019, 24(1), 124; https://doi.org/10.3390/molecules24010124 - 31 Dec 2018

Cited by 22 | Viewed by 5494

Abstract

In this study, the chemical profiles and antioxidant activities of red cabbage anthocyanin (RCA)-enriched extract are evaluated. The effects of column temperature on the HPLC resolution of the RCAs are studied. The HPLC resolutions became better as the column temperature increased from 20 [...] Read more.

In this study, the chemical profiles and antioxidant activities of red cabbage anthocyanin (RCA)-enriched extract are evaluated. The effects of column temperature on the HPLC resolution of the RCAs are studied. The HPLC resolutions became better as the column temperature increased from 20 °C–45 °C. An optimized HPLC condition was achieved at 45 °C and used for the quantification and qualification of the RCAs. The anthocyanins in the enriched powder are all derivatives of cyanidin (268 ± 2 μg/mg), mainly with 19% nonacylated, 51% monoacylated, and 31% diacylated structures with ferulic, sinapic, p-coumaric, and caffeic acids characterized by HPLC-MS. The RCA extracts markedly reduced intracellular oxidative stress production by H₂O₂ on HepG2 cells and consequently ameliorated cell apoptosis and improved viability. The analytical method and cellular antioxidant activity demonstration of the RCAs will greatly facilitate their functional applications. Full article

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9 pages, 2466 KiB

Open AccessArticle

Influence of Bovine Serum Albumin-Flavonoid Interaction on the Antioxidant Activity of Dietary Flavonoids: New Evidence from Electrochemical Quantification

by Rui Geng, Lei Ma, Liangliang Liu and Yixi Xie

Molecules 2019, 24(1), 70; https://doi.org/10.3390/molecules24010070 - 25 Dec 2018

Cited by 14 | Viewed by 3776

Abstract

Interaction between dietary flavonoids and albumins plays an important role in the bioavailability and bioactivity of flavonoids. Therefore, the influence of this interaction on the antioxidant activity of flavonoid has attracted much interest. In this study, a ceric reducing/antioxidant capacity assay (CRAC) was [...] Read more.

Interaction between dietary flavonoids and albumins plays an important role in the bioavailability and bioactivity of flavonoids. Therefore, the influence of this interaction on the antioxidant activity of flavonoid has attracted much interest. In this study, a ceric reducing/antioxidant capacity assay (CRAC) was employed to investigate the effects of albumin-flavonoid interaction on the antioxidant activity of seven common flavonoids. The results obtained from the CRAC assay were also compared separately with the results from the spectrophotometric methods including 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays. All the flavonoids show a decreasing in the antioxidant activity detected by CRAC assay, indicting a “masking effect” of bovine serum albumin (BSA)-flavonoid interaction. However, the results from DPPH and FRAP assays were conflicting, which may be attributed to the influence of solvent systems. Full article

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8 pages, 1202 KiB

Open AccessArticle

Four New Depsides Isolated from Salvia miltiorrhiza and Their Significant Nerve-Protective Activities

by Qinghao Jin, Xinyi Hu, Yanping Deng, Jinjun Hou, Min Lei, Hongjian Ji, Jing Zhou, Hua Qu, Wanying Wu and Dean Guo

Molecules 2018, 23(12), 3274; https://doi.org/10.3390/molecules23123274 - 11 Dec 2018

Cited by 5 | Viewed by 2795

Abstract

By investigating of the roots of Salvia miltiorrhiza, which is one of the most widely used Chinese herbs, we used phytochemical methods successfully to obtain twelve depsides: four depsides (1–4) that were previously undescribed, along with eight known [...] Read more.

By investigating of the roots of Salvia miltiorrhiza, which is one of the most widely used Chinese herbs, we used phytochemical methods successfully to obtain twelve depsides: four depsides (1–4) that were previously undescribed, along with eight known ones (5–12). Their structure characteristics were assessed by HR-ESIMS, CD, NMR (¹H, ¹³C, HSQC, HMBC) data analyses. These four newly isolated compounds (1–4), as well as the other eight compounds (5–12), show extraordinary protective effects on hydrogen peroxide-induced apoptosis in HS-SY5Y cells. Among them, depside 4 and depside 6 displayed more obviously protective effects than others. Full article

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