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12 pages, 1254 KiB

Open AccessArticle

Phytochemical Investigation and Antioxidant Activity of Globularia alypum L.

by Fadoua Asraoui, Ayoub Kounnoun, Hafssa El Cadi, Francesco Cacciola, Yassine Oulad El Majdoub, Filippo Alibrando, Filippo Mandolfino, Paola Dugo, Luigi Mondello and Adnane Louajri

Molecules 2021, 26(3), 759; https://doi.org/10.3390/molecules26030759 - 02 Feb 2021

Cited by 30 | Viewed by 5336

Abstract

The Moroccan flora is rich in medicinal plants that are commonly used in folk medicine for the treatment of various diseases. The present study was designed to investigate the total phenolic and flavonoid contents, as well as the antioxidant properties of leaves extracts [...] Read more.

The Moroccan flora is rich in medicinal plants that are commonly used in folk medicine for the treatment of various diseases. The present study was designed to investigate the total phenolic and flavonoid contents, as well as the antioxidant properties of leaves extracts from Globularia alypum L. colected from the Taza region in northeast Morocco. Additionally, the individual phenolics and volatiles of the extracts were also evaluated. The organic extracts of this plant were obtained by Soxhlet extraction using two different solvents, namely ethyl acetate and chloroform. The antioxidant capacity of leaves extracts was measured using DPPH, ABTS and FRAP assays; the phenolic profile was determined by HPLC-DAD/ESI-MS analysis, whereas the volatile composition was elucidated by GC-MS. The ethyl acetate extract analysis showed a total of 20 phenolic compounds and the determination of phenolic contents showed a significant value of 56.5 ± 0.61 µg GAE/mg of extract in comparison with the chloroform extract (18.9 ± 0.48 µg GAE/mg of extract). Also, the determination of the flavonoid contents revealed that the ethyl acetate extract contained the highest value (30.2 ± 0.55 µg CE/mg of extract) in comparison with the chloroform extract (18.0 ± 0.36 µg CE/mg of extract). Concerning the antioxidant properties, interesting values were attained for the ethyl acetate extract which exhibited higher antioxidant activity, namely IC₅₀ = 12.3 ± 3.83 µg/mL and IC50 = 37.0 ± 2.45 µg/mL for the DPPH and ABTS assays, respectively, whereas a value of 531.1 ± 17.08 (mg AAE/g DW) was obtained for the FRAP assay. Concerning the volatile profile, a total of 73 compounds were positively detected and among them n-hexadecanoic acid (13.5%) was the most abundant one. The results achieved confirm the important role of this plant as a source of natural antioxidants. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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21 pages, 5205 KiB

Open AccessArticle

Phenolic Constituents of Lamium album L. subsp. album Flowers: Anatomical, Histochemical, and Phytochemical Study

by Aneta Sulborska, Agata Konarska, Anna Matysik-Woźniak, Marta Dmitruk, Elżbieta Weryszko-Chmielewska, Agnieszka Skalska-Kamińska and Robert Rejdak

Molecules 2020, 25(24), 6025; https://doi.org/10.3390/molecules25246025 - 19 Dec 2020

Cited by 14 | Viewed by 3086

Abstract

Flos Lamii albi has a high biological activity and is widely used in herbal medicine. The aim of the study was to characterize the secretory structures present in Lamium album subsp. album corolla and the location of phenolic compounds. Additionally, we carried out [...] Read more.

Flos Lamii albi has a high biological activity and is widely used in herbal medicine. The aim of the study was to characterize the secretory structures present in Lamium album subsp. album corolla and the location of phenolic compounds. Additionally, we carried out qualitative phytochemical analyses of flavonoids and phenolic acids. Light, fluorescence, and scanning electron microscopy were used to analyze the structure of the floral organs. The main classes of phenolic compounds and their localization were determined histochemically. Phytochemical analyses were performed with high-performance thin-layer chromatography (HPTLC) and high-performance liquid chromatography (HPLC). Six types of glandular trichomes were found which contained flavonoids, phenolic acids, and tannins. The phytochemical studies demonstrated the presence of caffeic, chlorogenic, ferulic, gallic, p-coumaric, protocatechuic, syringic, gentisic, and vanillic phenolic acids as well as rutoside, isoquercetin, and quercetin flavonoids. The corolla in L. album subsp. album has antioxidant properties due to the presence of various polyphenols, as shown by the histo- and phytochemical analyses. The distribution and morphology of trichomes and the content of phenolic compounds in the corolla have taxonomic, pharmacognostic, and practical importance, facilitating the identification of the raw material. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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16 pages, 2306 KiB

Open AccessArticle

Ethylene Induction of Non-Enzymatic Metabolic Antioxidants in Matricaria chamomilla

by Veronika Petrulova, Maria Vilkova, Zuzana Kovalikova, Matus Sajko and Miroslav Repcak

Molecules 2020, 25(23), 5720; https://doi.org/10.3390/molecules25235720 - 03 Dec 2020

Cited by 7 | Viewed by 1902

Abstract

Phytochemical investigations of Matricaria chamomilla L. (Asteraceae) stated the presence of several compounds with an established therapeutic and antioxidant potential. The chamomile non-enzymatic antioxidant system includes low molecular mass compounds, mainly polyphenols such as cinnamic, hydroxybenzoic and chlorogenic acids, flavonoids and coumarins. The [...] Read more.

Phytochemical investigations of Matricaria chamomilla L. (Asteraceae) stated the presence of several compounds with an established therapeutic and antioxidant potential. The chamomile non-enzymatic antioxidant system includes low molecular mass compounds, mainly polyphenols such as cinnamic, hydroxybenzoic and chlorogenic acids, flavonoids and coumarins. The objective of this work was to evaluate the role of the non-enzymatic antioxidant system after stimulation by ethylene in tetraploid chamomile plants. Seven days of ethylene treatment significantly increased the activity of phenylalanine ammonia-lyase, which influenced the biosynthesis of protective polyphenols in the first step of their biosynthetic pathway. Subsequently, considerable enhanced levels of phenolic metabolites with a substantial antioxidant effect (syringic, vanillic and caffeic acid, 1,5-dicaffeoylquinic acid, quercetin, luteolin, daphnin, and herniarin) were determined by HPLC-DAD-MS. The minimal information on the chlorogenic acids function in chamomile led to the isolation and identification of 5-O-feruloylquinic acid. It is accumulated during normal conditions, but after the excessive effect of abiotic stress, its level significantly decreases and levels of other caffeoylquinic acids enhance. Our results suggest that ethephon may act as a stimulant of the production of pharmaceutically important non-enzymatic antioxidants in chamomile leaves and thus, lead to an overall change in phytochemical content and therapeutic effects of chamomile plants, as well. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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14 pages, 2318 KiB

Open AccessArticle

Evaluation of the Cytotoxicity of Ayahuasca Beverages

by Ana Y. Simão, Joana Gonçalves, Ana Gradillas, Antonia García, José Restolho, Nicolás Fernández, Jesus M. Rodilla, Mário Barroso, Ana Paula Duarte, Ana C. Cristóvão and Eugenia Gallardo

Molecules 2020, 25(23), 5594; https://doi.org/10.3390/molecules25235594 - 28 Nov 2020

Cited by 12 | Viewed by 3193 | Correction

Abstract

Ayahuasca is a beverage consumed at shamanic ceremonies and currently has gained popularity on recreational scenarios. It contains beta-carboline alkaloids and N,N-dimethyltryptamine, which possesses hallucinogenic effects. Only a few studies have elicited the psychoactive effects and the dose of such [...] Read more.

Ayahuasca is a beverage consumed at shamanic ceremonies and currently has gained popularity on recreational scenarios. It contains beta-carboline alkaloids and N,N-dimethyltryptamine, which possesses hallucinogenic effects. Only a few studies have elicited the psychoactive effects and the dose of such compounds on neurological dopaminergic cells or animals. In this work, we aimed to study the cytotoxic effects of these compounds present in ayahuasca beverages and on five different teas (Banisteriopsis caapi, Psychotria viridis, Peganum harmala, Mimosa tenuiflora and Dc Ab (commercial name)) preparations on dopaminergic immortalized cell lines. Moreover, a characterization of the derivative alkaloids was also performed. All the extracts were characterized by chromatographic systems and the effect of those compounds in cell viability and total protein levels were analyzed in N27 dopaminergic neurons cell line. This is the first article where cytotoxicity of ayahuasca tea is studied on neurological dopaminergic cells. Overall, results showed that both cell viability and protein contents decreased when cells were exposed to the individual compounds, as well as to the teas and to the two mixtures based on the traditional ayahuasca beverages. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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17 pages, 2448 KiB

Open AccessArticle

Comparative Study of the Chemical Compositions and Antioxidant Activities of Fresh Juices from Romanian Cucurbitaceae Varieties

by Anna Cazanevscaia Busuioc, Andreea-Veronica Dediu Botezatu, Bianca Furdui, Costel Vinatoru, Filippo Maggi, Giovanni Caprioli and Rodica-Mihaela Dinica

Molecules 2020, 25(22), 5468; https://doi.org/10.3390/molecules25225468 - 23 Nov 2020

Cited by 32 | Viewed by 3574

Abstract

Cucurbitaceae is a family of health-promoting plants due to their compounds with beneficial effects. The aim of this study was to analyze, for the first time, the chemical composition, the antioxidant activity and the metal chelating properties of fruit juices obtained from four [...] Read more.

Cucurbitaceae is a family of health-promoting plants due to their compounds with beneficial effects. The aim of this study was to analyze, for the first time, the chemical composition, the antioxidant activity and the metal chelating properties of fruit juices obtained from four different species of the Cucurbitaceae family cultivated in Romania, namely Momordica charantia, Cucumis metuliferus, Benincasa hispida and Trichosanthes cucumerina. The samples of juice were analyzed by high-performance liquid chromatography (HPLC) and all the four species displayed high levels of the two triterpenes, oleanolic and ursolic acids, and also in phenolic compounds, including catechin, (−)-epicatechin and gallic acid. The juices demonstrated significant antioxidant activity against the free radical 2,2-diphenyl-1-picrylhydrazyl (ranging from 20 to 95%,), a good iron binding ability (ranging from 7.45 ± 0.28% to 86.95 ± 0.97%) and also promising antioxidant potential against the ABTS radical (ranging from 4.97 to 32.60 μETx/mL juice). Our findings raise interesting questions for further research on Cucurbitaceae fruit juices and, consequently, their very good antioxidant potential suggests these fruits should be further explored for their protective effect against oxidative damage. This is the first time the chemical composition and antioxidant activities of fruit juices from these four Romanian Cucurbitaceae varieties have been investigated. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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25 pages, 2042 KiB

Open AccessArticle

Chemical Characterization of Three Accessions of Brassica juncea L. Extracts from Different Plant Tissues

by Yassine Oulad El Majdoub, Filippo Alibrando, Francesco Cacciola, Katia Arena, Eleonora Pagnotta, Roberto Matteo, Giuseppe Micalizzi, Laura Dugo, Paola Dugo and Luigi Mondello

Molecules 2020, 25(22), 5421; https://doi.org/10.3390/molecules25225421 - 19 Nov 2020

Cited by 13 | Viewed by 2915

Abstract

Indian mustard or Brassica juncea (B. juncea) is an oilseed plant used in many types of food (as mustard or IV range salad). It also has non-food uses (e.g., as green manure), and is a good model for phytoremediation of metals [...] Read more.

Indian mustard or Brassica juncea (B. juncea) is an oilseed plant used in many types of food (as mustard or IV range salad). It also has non-food uses (e.g., as green manure), and is a good model for phytoremediation of metals and pesticides. In recent years, it gained special attention due to its biological compounds and potential beneficial effects on human health. In this study, different tissues, namely leaves, stems, roots, and flowers of three accessions of B. juncea: ISCI 99 (Sample A), ISCI Top (Sample B), and “Broad-leaf” (Sample C) were analyzed by HPLC-PDA/ESI-MS/MS. Most polyphenols identified were bound to sugars and phenolic acids. Among the three cultivars, Sample A flowers turned were the richest ones, and the most abundant bioactive identified was represented by Isorhamnetin 3,7-diglucoside (683.62 µg/100 mg dry weight (DW) in Sample A, 433.65 µg/100 mg DW in Sample B, and 644.43 µg/100 mg DW in Sample C). In addition, the most complex samples, viz. leaves were analyzed by GC-FID/MS. The major volatile constituents of B. juncea L. leaves extract in the three cultivars were benzenepropanenitrile (34.94% in Sample B, 8.16% in Sample A, 6.24% in Sample C), followed by benzofuranone (8.54% in Sample A, 6.32% in Sample C, 3.64% in Sample B), and phytone (3.77% in Sample B, 2.85% in Sample A, 1.01% in Sample C). The overall evaluation of different tissues from three B. juncea accessions, through chemical analysis of the volatile and non-volatile compounds, can be advantageously taken into consideration for future use as dietary supplements and nutraceuticals in food matrices. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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17 pages, 800 KiB

Open AccessArticle

Health-Promoting Capacities of In Vitro and Cultivated Goji (Lycium chinense Mill.) Fruit and Leaves; Polyphenols, Antimicrobial Activity, Macro- and Microelements and Heavy Metals

by Arleta Kruczek, Marcelina Krupa-Małkiewicz, Sabina Lachowicz, Jan Oszmiański and Ireneusz Ochmian

Molecules 2020, 25(22), 5314; https://doi.org/10.3390/molecules25225314 - 14 Nov 2020

Cited by 16 | Viewed by 2716

Abstract

There is a growing interest among the public in fruit with a positive impact on human health. Two goji berry cultivars (‘No. 1’ and ‘New Big’) were propagated in vitro, grown in an orchard and then evaluated for macro- and microelements and [...] Read more.

There is a growing interest among the public in fruit with a positive impact on human health. Two goji berry cultivars (‘No. 1’ and ‘New Big’) were propagated in vitro, grown in an orchard and then evaluated for macro- and microelements and harmful heavy metals (i.e., Pb, Ni, and Cd). The leaves and fruit were also assessed for nutritional value, polyphenols and the antimicrobial activity of the leaves. ‘New Big’ was characterized by a higher content of macro elements in the leaves (in vitro and orchard) and a higher content of microelements in the fruit. The harmful substances content was below the minimum value. Furthermore, neither the fruit nor the leaves contained cadmium. This study also indicated that leaves had a higher content of polyphenols compared to the fruit. The fruits were characterized by their health-promoting capacities, while the leaves were characterized by their antibacterial activity. Among the Gram-positive bacteria, the most sensitive strain was Bacillus subtilis, and among the Gram-negative bacteria, it was Proteus vulgaris. Taking into consideration the Recommended Daily Allowance (RDA) for minerals, goji berries can be declared to be a source of Cu, Fe, Mn, Zn and P. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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17 pages, 1157 KiB

Open AccessArticle

Physico-Chemical and Phytochemical Characterization of Moroccan Wild Jujube “Zizyphus lotus (L.)” Fruit Crude Extract and Fractions

by Hafssa El Cadi, Hajar EL Bouzidi, Ginane Selama, Asmae El Cadi, Btissam Ramdan, Yassine Oulad El Majdoub, Filippo Alibrando, Paola Dugo, Luigi Mondello, Asmae Fakih Lanjri, Jamal Brigui and Francesco Cacciola

Molecules 2020, 25(22), 5237; https://doi.org/10.3390/molecules25225237 - 10 Nov 2020

Cited by 17 | Viewed by 4808

Abstract

Wild jujube “Ziziphus lotus (L.) Desf.” belongs to the Rhamnaceae family and is a traditionally herbaceous medicinal plant. It is very common in arid and semi-arid regions and is currently used for its antidiabetic, sedative, analgesic, anti-inflammatory and hypoglycemic activities. The [...] Read more.

Wild jujube “Ziziphus lotus (L.) Desf.” belongs to the Rhamnaceae family and is a traditionally herbaceous medicinal plant. It is very common in arid and semi-arid regions and is currently used for its antidiabetic, sedative, analgesic, anti-inflammatory and hypoglycemic activities. The aim of the present work was to characterize the physico-chemical properties and the phytochemical profile of wild jujube sample collected from the Guercif region, in order to determine the polyphenolic compounds and the antioxidant ability Analyses were carried out directly after the harvest for the determination of pH, refractive index, total soluble solid (°Brix), dry matter, sugar/acidity, total sugars, reducing sugars, as well as lipid and protein content. Results showed that the investigated fruit is acidic (pH 4.9 ± 0.23) and rich in sugars (80.2 g/100 g ± 3.81). The GC-MS analysis of the fruit revealed a number of volatile compounds, as many as 97, belonging to different chemical classes. The HPLC-DAD-ESI/MS analysis showed the presence of a total of 20 polyphenolic compounds in both EtOAc and MeOH-water extracts. Among them, p-Hydroxybenzoic acid was the most abundant in the EtOAc extract (185.68 µg/100 mg ± 0.5) whereas Quercetin 3-O-rhamnoside-7-O-glucoside was found in higher amounts in the MeOH-water extract (25.40 µg/100 mg ± 0.5). These components have medical interest, notably for human nutrition, as well as health benefits and therapeutic effects. Therefore, Moroccan jujube “Zizyphus lotus (L.)” fruit may have potential industrial applications for food formulations. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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20 pages, 2906 KiB

Open AccessFeature PaperArticle

Botanical and Genetic Identification Followed by Investigation of Chemical Composition and Biological Activities on the Scabiosa atropurpurea L. Stem from Tunisian Flora

by Soukaina Hrichi, Raja Chaabane-Banaoues, Sihem Bayar, Guido Flamini, Yassine Oulad El Majdoub, Domenica Mangraviti, Luigi Mondello, Ridha El Mzoughi, Hamouda Babba, Zine Mighri and Francesco Cacciola

Molecules 2020, 25(21), 5032; https://doi.org/10.3390/molecules25215032 - 29 Oct 2020

Cited by 16 | Viewed by 2256

Abstract

Scarce information about the phenolic composition of Scabiosa atropurpurea L. is available, and no carotenoid compounds have been reported thus far. In this study the phenolic and carotenoid composition of this plant was both investigated and associated bioactivities were evaluated. Aiming to obtain [...] Read more.

Scarce information about the phenolic composition of Scabiosa atropurpurea L. is available, and no carotenoid compounds have been reported thus far. In this study the phenolic and carotenoid composition of this plant was both investigated and associated bioactivities were evaluated. Aiming to obtain extracts and volatile fractions of known medicinal plants to valorize them in the pharmaceutical or food industries, two techniques of extraction and five solvents were used to determine the biologically active compounds. Gas chromatography coupled to flame ionization and mass spectrometry and liquid chromatography coupled to photodiode array and atmospheric pressure chemical ionization/electrospray ionization mass spectrometry highlighted the presence of 15 volatiles, 19 phenolics, and 24 natural pigments in Scabiosa atropurpurea L. stem samples; among them, the most abundant were 1,8-cineole, chlorogenic acid, cynaroside, and lutein. Bioactivity was assessed by a set of in vitro tests checking for antioxidant, antibacterial, antifungal, and allelopathic (against Brassica oleracea L. and Lens culinaris Medik) effects. Scabiosa atropurpurea L. stem extracts presented a considerable antioxidant, antibacterial, and allelopathic potential, with less antifungal effectiveness. These results indicate that the volatile fractions and extracts from S. atropurpurea L. stem could be considered as a good source of bioactive agents, with possible applications in food-related, agriculture, and pharmaceutical fields. Genetic investigations showed 97% of similarity with Scabiosa tschiliensis, also called Japanese Scabiosa. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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13 pages, 6469 KiB

Open AccessArticle

Ultrasensitive Electrochemical Sensor for Luteolin Based on Zirconium Metal-Organic Framework UiO-66/Reduced Graphene Oxide Composite Modified Glass Carbon Electrode

by Qian Wang, Chunmeng Gu, Yafen Fu, Liangliang Liu and Yixi Xie

Molecules 2020, 25(19), 4557; https://doi.org/10.3390/molecules25194557 - 05 Oct 2020

Cited by 27 | Viewed by 3130

Abstract

Luteolin is a kind of natural flavonoid with many bioactivities purified from a variety of natural herbs, fruits and vegetables. Electrochemical sensing has become an outstanding technology for the detection of luteolin in low concentration due to its fast response, easy operation and [...] Read more.

Luteolin is a kind of natural flavonoid with many bioactivities purified from a variety of natural herbs, fruits and vegetables. Electrochemical sensing has become an outstanding technology for the detection of luteolin in low concentration due to its fast response, easy operation and low cost. In this study, electroreduced graphene oxide (ErGO) and UiO-66 were successively modified onto a glassy carbon electrode (UiO-66/ErGO/GCE) and applied to the detection of luteolin. A combination of UiO-66 and ErGO showed the highest promotion in the oxidation peak current for luteolin compared with those of a single component. The factors affecting the electrochemical behavior of UiO-66/ErGO/GCE were evaluated and optimized including pH, accumulation potential, accumulation time and scan rate. Under optimum conditions, UiO-66/ErGO/GCE showed satisfactory linearity (from 0.001 μM to 20 μM), reproducibility and storage stability. The detection limit of UiO-66/ErGO/GCE reached 0.75 nM of luteolin and was suitable for testing real samples. Stable detection could be provided at least eight times by one modified electrode, which guaranteed the practicability of the proposed sensor. The fabricated UiO-66/ErGO/GCE showed a rapid electrochemical response and low consumption of materials in the detection of luteolin. It also showed satisfactory accuracy for real samples with good recovery. In conclusion, the modification using MOFs and graphene materials made the electrode advanced property in electrochemical sensing of natural active compounds. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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13 pages, 1473 KiB

Open AccessArticle

Profiling Anticancer and Antioxidant Activities of Phenolic Compounds Present in Black Walnuts (Juglans nigra) Using a High-Throughput Screening Approach

by Khanh-Van Ho, Anuradha Roy, Sarah Foote, Phuc H. Vo, Namrita Lall and Chung-Ho Lin

Molecules 2020, 25(19), 4516; https://doi.org/10.3390/molecules25194516 - 02 Oct 2020

Cited by 15 | Viewed by 3882

Abstract

Our recent studies have demonstrated multiple health-promoting benefits from black walnut kernels. These biological functions of black walnuts are likely associated with their bioactive constituents. Characterization of phenolic compounds found in black walnut could point out underexplored bioactive activities of black walnut extracts [...] Read more.

Our recent studies have demonstrated multiple health-promoting benefits from black walnut kernels. These biological functions of black walnuts are likely associated with their bioactive constituents. Characterization of phenolic compounds found in black walnut could point out underexplored bioactive activities of black walnut extracts and promote the development of novel applications of black walnut and its by-products. In the present study, we assessed bioactivity profiles of phenolic compounds identified in the kernels of black walnuts using a high-throughput screening (HTS) approach. Black walnut phenolic compounds were evaluated in terms of their total antioxidant capacity, antioxidant response element (ARE) induction, and anticancer activities. The anticancer activities were identified by evaluating the effects of the phenolic compounds on the growth of the tumorigenic alveolar epithelial cells (A549) and non-tumorigenic lung fibroblast cells (MRC-5). Out of 16 phenolic compounds tested, several compounds (penta-O-galloyl-β-d-glucose, epicatechin gallate, quercetin, (–)-epicatechin, rutin, quercetin 3-β-d-glucoside, gallic acid, (+)-catechin, ferulic acid, syringic acid) exerted antioxidant activities that were significantly higher compared to Trolox, which was used as a control. Two phenolic compounds, penta-O-galloyl-β-d-glucose and quercetin 3-β-d-glucoside, exhibited antiproliferative activities against both the tumorigenic alveolar epithelial cells (A549) and non-tumorigenic lung fibroblast cells (MRC-5). The antioxidant activity of black walnut is likely driven not only by penta-O-galloyl-β-d-glucose but also by a combination of multiple phenolic compounds. Our findings suggested that black walnut extracts possibly possess anticancer activities and supported that penta-O-galloyl-β-d-glucose could be a potential bioactive agent for the cosmetic and pharmaceutical industries. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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12 pages, 3193 KiB

Open AccessArticle

Structure and Physical Properties of Cardamonin: A Spectroscopic and Computational Approach

by Iwona Budziak, Marta Arczewska and Daniel M. Kamiński

Molecules 2020, 25(18), 4070; https://doi.org/10.3390/molecules25184070 - 06 Sep 2020

Cited by 4 | Viewed by 2664

Abstract

This is the first study of the crystal structure of cardamonin (CA) confirmed using single-crystal XRD analysis. In the crystal lattice of CA, two symmetry independent molecules are linked by hydrogen bonds within the layers and by the π···π stacking interactions in the [...] Read more.

This is the first study of the crystal structure of cardamonin (CA) confirmed using single-crystal XRD analysis. In the crystal lattice of CA, two symmetry independent molecules are linked by hydrogen bonds within the layers and by the π···π stacking interactions in the columns which lead to the occurrence of two types of conformations among the CA molecules in the crystal structure. To better understand the stability of these arrangements in both crystals and the gaseous phase, seven different CA dimers were theoretically calculated. The molecular structures were optimized using density functional theory (DFT) at the B3LYP/6–311G+(d,p) level and the spectroscopic results were compared. It was found that the calculated configurations of dimer I and III were almost identical to the ones found in the CA crystal lattice. The calculated UV-Vis spectra for the CA monomer and dimer I were perfectly consistent with the experimental spectroscopic data. Furthermore, enhanced emissions induced by aggregated CA molecules were registered in the aqueous solution with the increase of water fractions. The obtained results will help to further understand the relation between a variety of conformations and the biological properties of CA, and the results are also promising in terms of the applicability of CA as a bioimaging probe to monitor biological processes. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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17 pages, 1441 KiB

Open AccessArticle

Coupling Ultrafiltration-Based Processes to Concentrate Phenolic Compounds from Aqueous Goji Berry Extracts

by Carmela Conidi, Enrico Drioli and Alfredo Cassano

Molecules 2020, 25(16), 3761; https://doi.org/10.3390/molecules25163761 - 18 Aug 2020

Cited by 6 | Viewed by 2687

Abstract

In this work, a membrane-based process for the purification and concentration of antioxidant compounds from aqueous Goji (Lycium barbarum L.) berry extracts was investigated. The aqueous extract was previously clarified with hollow fiber ultrafiltration (UF) membranes in order to remove suspended solids [...] Read more.

In this work, a membrane-based process for the purification and concentration of antioxidant compounds from aqueous Goji (Lycium barbarum L.) berry extracts was investigated. The aqueous extract was previously clarified with hollow fiber ultrafiltration (UF) membranes in order to remove suspended solids and β-carotene and to produce a clarified extract enriched in phenolic compounds. Then, three UF flat sheet polyamide membranes with a molecular weight cut-off (MWCO) in the range 1000–3500 Da were tested to purify and concentrate phenolic compounds from the clarified extract. The effect of MWCO and transmembrane pressure (TMP) on the performance of selected membranes in terms of productivity and selectivity towards total dissolved solids (TDS), total phenolic compounds (TPC), total carbohydrates (TC) and total antioxidant activity (TAA) was evaluated. Experimental results indicated that the 2500 Da membrane exhibited a lower fouling index, higher cleaning efficiency, lower rejection towards carbohydrates (lower than 30%) and higher rejection towards phenolic compounds (higher than 50%) in comparison to the other investigated membranes. The inclusion of a diafiltration process in the treatment of the clarified extract with this membrane in a spiral-wound configuration improved the concentration of sugar compounds in the permeate stream and increased the purification of phenolic compounds in the retentate fraction. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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21 pages, 5479 KiB

Open AccessArticle

Bioactive Compounds, Antioxidant Activity, and Antinutritional Content of Legumes: A Comparison between Four Phaseolus Species

by Montserrat Alcázar-Valle, Eugenia Lugo-Cervantes, Luis Mojica, Norma Morales-Hernández, Heidy Reyes-Ramírez, Jhony Navat Enríquez-Vara and Soledad García-Morales

Molecules 2020, 25(15), 3528; https://doi.org/10.3390/molecules25153528 - 01 Aug 2020

Cited by 36 | Viewed by 4622

Abstract

Beans (Phaseolus spp.) are one of the most important legumes for their nutritional value and health benefits in many world regions. In addition to Phaseolus vulgaris, there are four additional species that are cultivated in many regions of the world and [...] Read more.

Beans (Phaseolus spp.) are one of the most important legumes for their nutritional value and health benefits in many world regions. In addition to Phaseolus vulgaris, there are four additional species that are cultivated in many regions of the world and are a source of food for human consumption: P. lunatus, P. coccineus, P. polyanthus, and P. acutifolius. In this work, phenolic compounds, antioxidant activity, and anti-nutritional compounds of 18 bean accessions, corresponding to four different species of the genus Phaseolus, were analyzed. In addition, their physical characteristics, proximate composition, and amino acid content were determined in order to compare their phytochemical composition and nutritional value. The species closest to each other in terms of essential amino acid content were P. polyanthus with P. vulgaris and P. lunatus with P. coccineus. Furthermore, there was a strong positive correlation between antioxidant activity and flavonoids, anthocyanins, and lectins with all the accessions collected. Significant differences in the content of phenolic compounds were found among the bean species studied. Therefore, in addition to P. vulgaris, other species such as P. coccineus and P. lunatus have high biological and antioxidant potential that could be beneficial to human health when consumed as nutraceutical foods. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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12 pages, 745 KiB

Open AccessArticle

Variability of Major Phenyletanes and Phenylpropanoids in 16-Year-Old Rhodiola rosea L. Clones in Norway

by Abdelhameed Elameen, Vera M. Kosman, Mette Thomsen, Olga N. Pozharitskaya and Alexander N. Shikov

Molecules 2020, 25(15), 3463; https://doi.org/10.3390/molecules25153463 - 30 Jul 2020

Cited by 14 | Viewed by 2553

Abstract

Rhodiola rosea L. (roseroot) is an adaptogen plant belonging to the Crassulaceae family. The broad spectrum of biological activity of R. rosea is attributed to its major phenyletanes and phenylpropanoids: rosavin, salidroside, rosin, cinnamyl alcohol, and tyrosol. In this study, we compared the [...] Read more.

Rhodiola rosea L. (roseroot) is an adaptogen plant belonging to the Crassulaceae family. The broad spectrum of biological activity of R. rosea is attributed to its major phenyletanes and phenylpropanoids: rosavin, salidroside, rosin, cinnamyl alcohol, and tyrosol. In this study, we compared the content of phenyletanes and phenylpropanoids in rhizomes of R. rosea from the Norwegian germplasm collection collected in 2004 and in 2017. In general, the content of these bioactive compounds in 2017 was significantly higher than that observed in 2004. The freeze-drying method increased the concentration of all phenyletanes and phenylpropanoids in rhizomes compared with conventional drying at 70 °C. As far as we know, the content of salidroside (51.0 mg g⁻¹) observed in this study is the highest ever detected in Rhodiola spp. Long-term vegetative propagation and high genetic diversity of R. rosea together with the freeze-drying method may have led to the high content of the bioactive compounds observed in the current study. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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14 pages, 3747 KiB

Open AccessFeature PaperArticle

Differential Modulation of the Phospholipidome of Proinflammatory Human Macrophages by the Flavonoids Quercetin, Naringin and Naringenin

by Tiago A. Conde, Luís Mendes, Vítor M. Gaspar, João F. Mano, Tânia Melo, M. Rosário Domingues and Iola F. Duarte

Molecules 2020, 25(15), 3460; https://doi.org/10.3390/molecules25153460 - 29 Jul 2020

Cited by 8 | Viewed by 2796

Abstract

The immunomodulatory activity of flavonoids is increasingly appreciated. Macrophage phospholipids (PLs) play crucial roles in cell-mediated inflammatory responses. However, little is known on how these PLs are affected upon flavonoid treatment. In this work, we have used mass-spectrometry-based lipidomics to characterize the changes [...] Read more.

The immunomodulatory activity of flavonoids is increasingly appreciated. Macrophage phospholipids (PLs) play crucial roles in cell-mediated inflammatory responses. However, little is known on how these PLs are affected upon flavonoid treatment. In this work, we have used mass-spectrometry-based lipidomics to characterize the changes in the phospholipidome of proinflammatory human-macrophage-like cells (THP-1-derived and LPS+IFN-γ-stimulated) incubated with non-cytotoxic concentrations of three flavonoids: quercetin, naringin and naringenin. One hundred forty-seven PL species belonging to various classes were identified, and their relative abundances were determined. Each flavonoid displayed its own unique signature of induced effects. Quercetin produced the strongest impact, acting both on constitutive PLs (phosphatidylcholines, phosphatidylethanolamines and sphingomyelins) and on minor signaling lipids, such as phosphatidylinositol (PI) and phosphatidylserine (PS) species. Conversely, naringin hardly affected structural PLs, producing changes in signaling molecules that were opposite to those seen in quercetin-treated macrophages. In turn, albeit sharing some effects with quercetin, naringenin did not change PI and PS levels and interfered with a set of phosphatidylcholines distinct from those modulated by quercetin. These results demonstrate that flavonoids bioactivity involves profound and specific remodeling of macrophage phospholipidome, paving the way to future studies on the role of cellular phospholipids in flavonoid-mediated immunomodulatory effects. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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15 pages, 1800 KiB

Open AccessArticle

Combined MS/MS-NMR Annotation Guided Discovery of Iris lactea var. chinensis Seed as a Source of Viral Neuraminidase Inhibitory Polyphenols

by Hyun Woo Kim, Soo Sung Kim, Kyo Bin Kang, Byeol Ryu, Eunjin Park, Jungmoo Huh, Won Kyung Jeon, Hee-Sung Chae, Won Keun Oh, Jinwoong Kim, Sang Hyun Sung and Young-Won Chin

Molecules 2020, 25(15), 3383; https://doi.org/10.3390/molecules25153383 - 26 Jul 2020

Cited by 6 | Viewed by 2579

Abstract

In this study, the chemical diversity of polyphenols in Iris lactea var. chinensis seeds was identified by combined MS/MS-NMR analysis. Based on the annotated chemical profile, the isolation of stilbene oligomers was conducted, and consequently, stilbene oligomers (1-10) [...] Read more.

In this study, the chemical diversity of polyphenols in Iris lactea var. chinensis seeds was identified by combined MS/MS-NMR analysis. Based on the annotated chemical profile, the isolation of stilbene oligomers was conducted, and consequently, stilbene oligomers (1-10) were characterized. Of these, compounds 1 and 2 are previously undescribed stilbene dimer glycoside (1) and tetramer glycoside (2), respectively. Besides, to evaluate this plant seed as a rich source of stilbene oligomers, we quantified three stilbene oligomers of I. lactea var. chinensis seeds. The contents of three major stilbene oligomers—trans-ε-viniferin (3), vitisin A (6), and vitisin B (9)—in I. lactea var. chinensis seeds were quantified as 2.32 (3), 4.95 (6), and 1.64 (9) mg/g dry weight (DW). All the isolated compounds were tested for their inhibitory activities against influenza neuraminidase. Compound 10 was found to be active with the half maximal inhibitory concentration (IC₅₀) values at 4.76 μM. Taken together, it is concluded that I. lactea var. chinensis seed is a valuable source of stilbene oligomers with a human health benefit. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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16 pages, 3519 KiB

Open AccessArticle

Aronia melanocarpa Fruits as a Rich Dietary Source of Chlorogenic Acids and Anthocyanins: ¹H-NMR, HPLC-DAD, and Chemometric Studies

by Agnieszka Zielińska, Paweł Siudem, Katarzyna Paradowska, Małgorzata Gralec, Sławomir Kaźmierski and Iwona Wawer

Molecules 2020, 25(14), 3234; https://doi.org/10.3390/molecules25143234 - 15 Jul 2020

Cited by 21 | Viewed by 4157

Abstract

Aronia melanocarpa (Michx.) Elliott’s (chokeberry) besides anthocyanins contains significant amounts of hydroxycinnamic acids: Chlorogenic and its isomer neochlorogenic acid. They exhibit antioxidant, anti-inflammatory, antidiabetic, and antibacterial activities, thus they can have a significant impact on the health-promoting properties of Aronia. The aim [...] Read more.

Aronia melanocarpa (Michx.) Elliott’s (chokeberry) besides anthocyanins contains significant amounts of hydroxycinnamic acids: Chlorogenic and its isomer neochlorogenic acid. They exhibit antioxidant, anti-inflammatory, antidiabetic, and antibacterial activities, thus they can have a significant impact on the health-promoting properties of Aronia. The aim of our research was to determine the changes in the content of chlorogenic acids (CGAs) and anthocyanins during fruit development and ripening, with a particular emphasis on acids. Aronia fruit samples were collected from July to October on two organic farms in Poland. The chemical composition of the extracts was determined by NMR spectroscopy and HPLC-DAD. ¹H-NMR and HPLC data were analyzed using chemometric analysis and multivariate statistics (PCA). The results showed that the content of chlorogenic acids and anthocyanins changes during ripening and depends on the time of harvest and the region of cultivation. A correlation between the time of CGAs reduction and the appearance of anthocyanins was also noticed. The result of our research was also a database in the form of NMR parameters, which allows analysis of the metabolite profile and tracking of its changes. The ¹H-NMR spectrum showing anthocyanin and CGA resonance can be considered the Aronia berry fingerprint. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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27 pages, 1864 KiB

Open AccessArticle

Anti-Inflammatory and Antioxidant Activities of Terpene- and Polyphenol-Rich Premna odorata Leaves on Alcohol-Inflamed Female Wistar Albino Rat Liver

by Abeer H. Elmaidomy, Hani A. Alhadrami, Elham Amin, Hanan F. Aly, Asmaa M. Othman, Mostafa E. Rateb, Mona H. Hetta, Usama Ramadan Abdelmohsen and Hossam M. Hassan

Molecules 2020, 25(14), 3116; https://doi.org/10.3390/molecules25143116 - 08 Jul 2020

Cited by 16 | Viewed by 3629

Abstract

Premna odorata Blanco (Lamiaceae) is an ethnomedicinal plant native to different tropical regions. Although some reports addressed their anti-inflammatory, cytotoxic, and antituberculotic effects, their hepatoprotective potential is yet to be discovered. Accordingly, this study investigated the crude extract and different fractions of the [...] Read more.

Premna odorata Blanco (Lamiaceae) is an ethnomedicinal plant native to different tropical regions. Although some reports addressed their anti-inflammatory, cytotoxic, and antituberculotic effects, their hepatoprotective potential is yet to be discovered. Accordingly, this study investigated the crude extract and different fractions of the plant leaves; metabolic profiling using liquid chromatography/high-resolution electrospray ionization mass spectroscopy (LC–HRESIMS) analysis, in silico absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties for the dereplicated metabolite via online PreADMET program, ROS scavenger activity on the Hep G2 human liver cancer cell line, and the possible hepatic cellular treatment effects in alcohol-inflamed liver female Wistar albino rats. Metabolic profiling dereplicated a total of 28 metabolites from the crude extract and its various fractions. In silico ADMET and ROS scavenger activity screening suggested plant metabolites are of potential bioactivity. In vivo hepatic treatment with crude, defatted crude, and n-hexane leave extracts suggested all extracts significantly improved liver damage, which was indicated by the reduction of elevated serum levels of bilirubin, AST, ALT, ALP, CRP, TNF-α, ICAM-1, VCAM-1, and MDA. The reduced levels of GSH and TAC were normalized during the study. Histological examinations of liver tissue showed collagen fiber distribution nearly back to its normal pattern. The anti-inflammatory and antioxidant potentials of Premna odorata extracts could be partly related to the combined effects of these phytochemicals or their synergistic interactions. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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16 pages, 5734 KiB

Open AccessArticle

Sustainable Micro-Scale Extraction of Bioactive Phenolic Compounds from Vitis vinifera Leaves with Ionic Liquid-Based Surfactants

by Giulia Mastellone, Idaira Pacheco-Fernández, Patrizia Rubiolo, Verónica Pino and Cecilia Cagliero

Molecules 2020, 25(13), 3072; https://doi.org/10.3390/molecules25133072 - 06 Jul 2020

Cited by 7 | Viewed by 3067

Abstract

This paper proposes a new sustainable and simple strategy for the micro-scale extraction of phenolic compounds from grapevine leaves with analytical purpose. The method is based on a microwave-assisted solid-liquid extraction approach (MA-SLE), using an aqueous solution of an ionic liquid (IL)-based surfactant [...] Read more.

This paper proposes a new sustainable and simple strategy for the micro-scale extraction of phenolic compounds from grapevine leaves with analytical purpose. The method is based on a microwave-assisted solid-liquid extraction approach (MA-SLE), using an aqueous solution of an ionic liquid (IL)-based surfactant as extraction phase. The method does not require organic solvents, nor any clean-up step, apart from filtration prior to the injection in the analytical system. Two IL-based surfactants were evaluated, and the method was optimized by using experimental designs, resulting in the use of small amounts of sample (100 mg) and extraction phase (2.25 mL), low concentrations of the selected 1-hexadecyl-3-butyl imidazolium bromide IL (0.1 mM), and 30 min of extraction time. The proposed methodology was applied for the determination of the polyphenolic pattern of six different varieties of Vitis vinifera leaves from the Canary Islands, using high-performance liquid chromatography and photodiode array detection for the quantification of the compounds. The proposed MA-SLE approach was greener, simpler, and more effective than other methods, while the results from the analysis of the leaves samples demonstrate that these by-products can be exploited as a source of natural compounds for many applications. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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11 pages, 1232 KiB

Open AccessArticle

(Poly)phenolic Content and Profile and Antioxidant Capacity of Whole-Grain Cookies are Better Estimated by Simulated Digestion than Chemical Extraction

by Francesca Danesi, Luca Calani, Veronica Valli, Letizia Bresciani, Daniele Del Rio and Alessandra Bordoni

Molecules 2020, 25(12), 2792; https://doi.org/10.3390/molecules25122792 - 17 Jun 2020

Cited by 6 | Viewed by 2084

Abstract

It is widely recognized that the biological effects of phytochemicals cannot be attributed to the native compounds present in foods but rather to their metabolites endogenously released after intake. Bioavailability depends on bioaccessibility, which is the amount of the food constituent that is [...] Read more.

It is widely recognized that the biological effects of phytochemicals cannot be attributed to the native compounds present in foods but rather to their metabolites endogenously released after intake. Bioavailability depends on bioaccessibility, which is the amount of the food constituent that is released from the matrix in the gastrointestinal tract. The use of chemical extraction to evaluate the content and profile of phytochemicals does not mirror the physiological situation in vivo, and their bioaccessibility should be considered while assessing their nutritional significance in human health. The current study was designed to compare the (poly)phenolic profile and content and antioxidant capacity of whole-grain (WG) cookies using chemical extraction and a more physiological approach based on simulated digestion. Three types of organic WG cookies (made with durum, Italian khorasan, or KAMUT^® khorasan wheat) were considered, either fermented by Saccharomyces Cerevisiae or sourdough. Although the flour type and the fermentation process influenced the release of phytochemicals from the cookie matrix, in almost all samples, the simulated digestion appeared the most efficient procedure. Our results indicate that the use of chemical extraction for evaluation of the phytochemicals content and antioxidant capacity of food could lead to underestimation and underline the need for more physiological extraction methods. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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16 pages, 4229 KiB

Open AccessArticle

Targeted UHPLC–HRMS (Orbitrap) Polyphenolic and Capsaicinoid Profiling for the Chemometric Characterization and Classification of Paprika with Protected Designation of Origin (PDO) Attributes

by Sergio Barbosa, Javier Saurina, Lluís Puignou and Oscar Núñez

Molecules 2020, 25(7), 1623; https://doi.org/10.3390/molecules25071623 - 01 Apr 2020

Cited by 13 | Viewed by 3178

Abstract

Society’s interest in the quality of food products with certain attributes has increased, the attribute of a Protected Designation of Origin (PDO) being an effective tool to guarantee the quality and geographical origin of a given food product. In Spain, two paprika production [...] Read more.

Society’s interest in the quality of food products with certain attributes has increased, the attribute of a Protected Designation of Origin (PDO) being an effective tool to guarantee the quality and geographical origin of a given food product. In Spain, two paprika production areas with PDO (La Vera and Murcia) are recognized. In the present work, targeted UHPLC-HRMS polyphenolic and capsaicinoid profiling through the TraceFinder^TM screening software, using homemade accurate mass databases, was proposed as a source of chemical descriptors, to address the characterization, classification, and authentication of paprika. A total of 126 paprika samples from different production regions—Spain (La Vera PDO and Murcia PDO) and the Czech Republic, each including different flavor varieties, were analyzed. UHPLC-HRMS polyphenolic profiles showed to be good chemical descriptors to achieve paprika classification and authentication, based on the production region, through principal component analysis and partial least squares regression-discriminant analysis, with classification rates of 82%, 86%, and 100% for La Vera PDO, Murcia PDO, and the Czech Republic, respectively. In addition, a perfect classification was also accomplished among the flavor varieties for the Murcia PDO and Czech Republic samples. By employing the UHPLC-HRMS polyphenolic and capsaicinoid profiles as chemical descriptors, acceptable discrimination among La Vera PDO flavor varieties was also achieved. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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16 pages, 1290 KiB

Open AccessArticle

Brassica incana Ten. (Brassicaceae): Phenolic Constituents, Antioxidant and Cytotoxic Properties of the Leaf and Flowering Top Extracts

by Natalizia Miceli, Emilia Cavò, Monica Ragusa, Francesco Cacciola, Luigi Mondello, Laura Dugo, Rosaria Acquaviva, Giuseppe Antonio Malfa, Andreana Marino, Manuela D’Arrigo and Maria Fernanda Taviano

Molecules 2020, 25(6), 1461; https://doi.org/10.3390/molecules25061461 - 24 Mar 2020

Cited by 25 | Viewed by 4188

Abstract

Brassica incana Ten. is an edible plant belonging to the Brassicaceae family. In this work, the phenolic composition and the antioxidant and cytotoxic properties of the hydroalcoholic extracts obtained from the leaves and the flowering tops of B. incana grown wild in Sicily [...] Read more.

Brassica incana Ten. is an edible plant belonging to the Brassicaceae family. In this work, the phenolic composition and the antioxidant and cytotoxic properties of the hydroalcoholic extracts obtained from the leaves and the flowering tops of B. incana grown wild in Sicily (Italy) were studied for the first time. A total of 17 and 20 polyphenolic compounds were identified in the leaf and in the flowering top extracts, respectively, by HPLC-PDA-ESI-MS analysis. Brassica incana extracts showed in vitro antioxidant properties; the leaf extract displayed greater radical scavenging activity in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test than the flowering top extract (IC₅₀ = 1.306 ± 0.049 mg/mL and 2.077 ± 0.011 mg/mL), which in turn had a stronger ferrous ion chelating ability than the other (IC₅₀ = 0.232 ± 0.002 mg/mL and 1.147 ± 0.016 mg/mL). The cytotoxicity of the extracts against human colorectal adenocarcinoma (CaCo-2) and breast cancer (MCF-7) cell lines was evaluated through the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and the lactic dehydrogenase (LDH) release determination. The extracts showed cytotoxic efficacy against Caco-2 cells, with the flowering top extract being the most effective (about 90% activity at the highest concentration tested). In the brine shrimp lethality bioassay, the extracts exhibited no toxicity, indicating their potential safety. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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18 pages, 3910 KiB

Open AccessFeature PaperArticle

Effects of Exogenous Abscisic Acid on Bioactive Components and Antioxidant Capacity of Postharvest Tomato during Ripening

by Xiaoya Tao, Qiong Wu, Halah Aalim, Li Li, Linchun Mao, Zisheng Luo and Tiejin Ying

Molecules 2020, 25(6), 1346; https://doi.org/10.3390/molecules25061346 - 16 Mar 2020

Cited by 33 | Viewed by 3597

Abstract

Abscisic acid (ABA) is a phytohormone which is involved in the regulation of tomato ripening. In this research, the effects of exogenous ABA on the bioactive components and antioxidant capacity of the tomato during postharvest ripening were evaluated. Mature green cherry tomatoes were [...] Read more.

Abscisic acid (ABA) is a phytohormone which is involved in the regulation of tomato ripening. In this research, the effects of exogenous ABA on the bioactive components and antioxidant capacity of the tomato during postharvest ripening were evaluated. Mature green cherry tomatoes were infiltrated with either ABA (1.0 mM) or deionized water (control) and stored in the dark for 15 days at 20 °C with 90% relative humidity. Fruit colour, firmness, total phenolic and flavonoid contents, phenolic compounds, lycopene, ascorbic acid, enzymatic activities, and antioxidant capacity, as well as the expression of major genes related to phenolic compounds, were periodically monitored. The results revealed that exogenous ABA accelerated the accumulations of total phenolic and flavonoid contents; mostly increased the contents of detected phenolic compounds; enhanced FRAP and DPPH activity; and promoted the activities of PAL, POD, PPO, CAT, and APX during tomato ripening. Meanwhile, the expressions of the major genes (PAL1, C4H, 4CL2, CHS2, F3H, and FLS) involved in the phenylpropanoid pathway were up-regulated (1.13- to 26.95-fold) in the tomato during the first seven days after treatment. These findings indicated that ABA promoted the accumulation of bioactive components and the antioxidant capacity via the regulation of gene expression during tomato ripening. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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23 pages, 956 KiB

Open AccessArticle

Effects of Different Drying Methods on Untargeted Phenolic Metabolites, and Antioxidant Activity in Chinese Cabbage (Brassica rapa L. subsp. chinensis) and Nightshade (Solanum retroflexum Dun.)

by Millicent G. Managa, Yasmina Sultanbawa and Dharini Sivakumar

Molecules 2020, 25(6), 1326; https://doi.org/10.3390/molecules25061326 - 13 Mar 2020

Cited by 41 | Viewed by 5693

Abstract

Chinese cabbage (Brassica rapa L. subsp. chinensis) and Nightshade (Solanum retroflexum are popular traditional leafy vegetables consumed predominantly by rural Africans. Sun drying is adopted as a traditional method of postharvest preservation to store theses leaves during off seasons. The influence [...] Read more.

Chinese cabbage (Brassica rapa L. subsp. chinensis) and Nightshade (Solanum retroflexum are popular traditional leafy vegetables consumed predominantly by rural Africans. Sun drying is adopted as a traditional method of postharvest preservation to store theses leaves during off seasons. The influence of different types of postharvest processing treatments, such as conventional oven drying, solar cabinet drying, sun drying and freeze drying, on the changes on colour properties and antioxidant components were investigated. Freeze-drying retained the ascorbic acid content, antioxidant activities, total chlorophyll content, green colour by reducing the colour difference (∆E). With regard to Chinese cabbage and Nightshade leaves, sun and microwave drying respectively had the most negative impact on all the identified phenolic compounds. The OPLS-DA and the UPLC–QTOF/MS and chemometric approach showed kaempferol-3-O-sophoroside, kaempferol-3-sophorotrioside-7-glucoside and hydroxyoctadecenedioic acid as the markers responsible for the separation of sun-dried samples from the other drying treatments in Chinese cabbage. Sinapoyl malate was not detected in sun-dried samples. Caffeoylmalic acid was identified as the marker compound to separate the other drying treatments from the microwave dried samples of Nightshade leaves. Trihydroxyoctadecadiene derivative and hydroxyoctadecanedioic acid were detected in microwaved samples. Due to the cost effectiveness, solar dryer cabinet treatment was recommended for drying both vegetables. The proximate analysis of solar dried functional powder of Chinese cabbage and Nightshade vegetables demonstrated higher contents of protein and dietary fibre. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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14 pages, 1164 KiB

Open AccessArticle

A Targeted Approach by High Resolution Mass Spectrometry to Reveal New Compounds in Raisins

by Danilo Escobar-Avello, Alexandra Olmo-Cunillera, Julián Lozano-Castellón, María Marhuenda-Muñoz and Anna Vallverdú-Queralt

Molecules 2020, 25(6), 1281; https://doi.org/10.3390/molecules25061281 - 12 Mar 2020

Cited by 8 | Viewed by 2778

Abstract

Raisins are dried grapes mostly obtained from cultivars of Vitis vinifera L. and are extensively consumed worldwide. They are rich in bioactive compounds such as polyphenols, which are associated with a broad range of health benefits. The aim of the present study was [...] Read more.

Raisins are dried grapes mostly obtained from cultivars of Vitis vinifera L. and are extensively consumed worldwide. They are rich in bioactive compounds such as polyphenols, which are associated with a broad range of health benefits. The aim of the present study was to compare the phenolic profiles of three different raisin varieties (Thompson seedless, Muscat, and sultanas). Total polyphenols (TPs) were evaluated by the Folin–Ciocalteu (F–C) assay and significant differences were observed among all raisin varieties. Furthermore, liquid chromatography coupled with electrospray ionization hybrid linear ion trap quadrupole-Orbitrap-mass spectrometry (LC/ESI-LTQ-Orbitrap-MS) was employed for the comprehensive identification of phenolic constituents. A total of 45 compounds were identified, including hydroxybenzoic and hydroxycinnamic acids, flavanoids, flavonoids, flavonols, flavones, and stilbenoids. The three varieties of raisins showed a similar phenolic profile, although the highest number of phenolic compounds was identified in Muscat raisins owing to the proanthocyanidins extracted from their seeds, while stilbenoids were not detected in the Thompson variety. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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11 pages, 997 KiB

Open AccessCommunication

Opuntia Fruits as Food Enriching Ingredient, the First Step towards New Functional Food Products

by Anna Oniszczuk, Agnieszka Wójtowicz, Tomasz Oniszczuk, Arkadiusz Matwijczuk, Ahlem Dib and Ewa Markut-Miotła

Molecules 2020, 25(4), 916; https://doi.org/10.3390/molecules25040916 - 18 Feb 2020

Cited by 26 | Viewed by 3689

Abstract

Prickly pear (Opuntia ficus indica (L.) Mill.) is a rich source of vitamins C, B₁, B₂, A, and E, minerals such as calcium, potassium, magnesium, iron, and phosphorus, as well as bioactive substances, i.e., carotenoids, betalains, and phenolic [...] Read more.

Prickly pear (Opuntia ficus indica (L.) Mill.) is a rich source of vitamins C, B₁, B₂, A, and E, minerals such as calcium, potassium, magnesium, iron, and phosphorus, as well as bioactive substances, i.e., carotenoids, betalains, and phenolic compounds. Of these, the phenolic acids, betalains, and flavonoids are notable in that they are largely responsible for the health-promoting properties of this plant. The purpose of the presented research was to first determine the antioxidant properties and the content of polyphenolic compounds (including individual phenolic acids) in prickly pear fruit, then to produce an innovative gluten-free pasta from rice-field bean flour enriched with various amounts of pear prickly fruit. The content of free phenolic acids, the sum of polyphenols and antioxidant properties of pasta were subsequently determined in the supplemented pasta. Chromatographic analysis (HPLC-ESI-MS/MS) showed a wide variety of phenolic acids. In the fruit sample, 14 acids were detected, whereas in the pasta sample without additives, 9. The dominant acid was isoferulic. The total content of free phenolic acids and the sum of polyphenols increased with increasing content of the functional additive. Moreover, the content of individual acids generally increased as the Opuntia fruit was added. The antioxidant activity was also positively correlated with the addition of fruit, with the content of free phenolic acids and the sum of polyphenols. Our research has shown that our innovative pasta with the addition of prickly fruit can become a source of the free phenolic acids indispensable for human health. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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21 pages, 3033 KiB

Open AccessArticle

Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes

by Mark A. M. Simões, Diana C. G. A. Pinto, Bruno M. R. Neves and Artur M. S. Silva

Molecules 2020, 25(4), 812; https://doi.org/10.3390/molecules25040812 - 13 Feb 2020

Cited by 14 | Viewed by 3155

Abstract

Ethnopharmacological surveys on Portuguese flora reveal that Genista tridentata L. is a shrub used in traditional medicine for the treatment of various inflammation-related health problems, although scientific support of its benefits is still necessary. In order to establish the anti-inflammatory potential of G. [...] Read more.

Ethnopharmacological surveys on Portuguese flora reveal that Genista tridentata L. is a shrub used in traditional medicine for the treatment of various inflammation-related health problems, although scientific support of its benefits is still necessary. In order to establish the anti-inflammatory potential of G. tridentata and support its traditional use, ethanolic extracts of three sections of the plant (root, stem, and leaves) were subjected to in vitro evaluation of anti-inflammatory activity using lipopolysaccharide (LPS)-stimulates macrophages as an inflammation model. Simultaneously, we also aimed to establish the extracts’ flavonoids profile. The ethanolic extracts, obtained by Soxhlet extraction, profile of the three sections confirmed their richness in flavonoids, being three prenylated flavonoids isolated and characterized in the root, including a new natural compound, the 3-methoxymundulin. The extracts from the three plant sections showed strong antioxidant activity at the cellular level and significantly inhibit the LPS-triggered NO production by downregulating Nos2 gene transcription and consequently iNOS expression. Additionally, root and stem extracts also decreased the LPS-induced transcription of the pro-inflammatory genes Il1b, Il6, and Ptgs2. Thus, the results support the anti-inflammatory properties attributed to G. tridentate preparations. Relevantly, the roots of the shrub, plant part not used, is an unexplored source of compounds with pharmacological and nutraceutical value. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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14 pages, 2635 KiB

Open AccessArticle

Phenolic Profiling of Flax Highlights Contrasting Patterns in Winter and Spring Varieties

by Job Tchoumtchoua, David Mathiron, Nicole Pontarin, David Gagneul, Anne-Isaline van Bohemen, Elvis Otogo N’nang, François Mesnard, Emmanuel Petit, Jean-Xavier Fontaine, Roland Molinié and Anthony Quéro

Molecules 2019, 24(23), 4303; https://doi.org/10.3390/molecules24234303 - 26 Nov 2019

Cited by 17 | Viewed by 3901

Abstract

Flax (Linum usitatissimum) is a plant grown in temperate regions either for its fiber or for its seeds, which are rich in the essential fatty acid omega-3. It is also well known as a source of medicinal compounds. The chemical composition [...] Read more.

Flax (Linum usitatissimum) is a plant grown in temperate regions either for its fiber or for its seeds, which are rich in the essential fatty acid omega-3. It is also well known as a source of medicinal compounds. The chemical composition of its leaves is currently poorly described. In order to fill this gap, we have conducted a comprehensive analysis of flax leaf metabolome. The exploration of the metabolome allowed the characterization of compounds isolated for the first time in flax leaves. These molecules were isolated by preparative HPLC and then characterized by NMR, LC-MS and standard analysis. This work extended our picture of C-glycosyl-flavonoids and coniferyl alcohol derivatives accumulated in flax. The follow-up of the content of these different metabolites via UPLC-MS revealed significant accumulation differences in spring and winter flax leaves. In particular, two methylated C-glycosylflavonoids (swertisin and swertiajaponin) were the most abundant phenolic compounds in winter flax whereas they were not detected in spring flax. This result suggests that these 2 compounds are involved in cold stress tolerance in flax. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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14 pages, 507 KiB

Open AccessArticle

Phenolic Characterization, Antioxidant Activity, and Enzyme Inhibitory Properties of Berberis thunbergii DC. Leaves: A Valuable Source of Phenolic Acids

by María del Pilar Fernández-Poyatos, Antonio Ruiz-Medina, Gokhan Zengin and Eulogio J. Llorent-Martínez

Molecules 2019, 24(22), 4171; https://doi.org/10.3390/molecules24224171 - 17 Nov 2019

Cited by 43 | Viewed by 3356

Abstract

Berberis species are known for their use in traditional medicine. Here, we report the phenolic composition and bioactivity of methanolic and aqueous extracts of Berberis thunbergii DC. leaves. The phenolic profiling and the quantitation of the main compounds were performed by high-performance liquid [...] Read more.

Berberis species are known for their use in traditional medicine. Here, we report the phenolic composition and bioactivity of methanolic and aqueous extracts of Berberis thunbergii DC. leaves. The phenolic profiling and the quantitation of the main compounds were performed by high-performance liquid chromatography with diode array and mass spectrometry detections. The most abundant compounds in both extracts were caffeoylquinic acids (chlorogenic acid, particularly, with a concentration of 90.1–101.3 mg g⁻¹ dried extract), followed by caffeoylglucaric acids and quercetin glycosides. Antioxidant and radical scavenging assays (phosphomolybdenum, DPPH, ABTS, CUPRAC, FRAP, metal chelating activity), as well as enzyme inhibitory assays (acetylcholinesterase, butyrylcholinesterase, tyrosinase, amylase, glucosidase, and lipase), were carried out to evaluate the potential bioactivity of B. thunbergii. The methanolic extract presented the highest antioxidant and radical scavenging values, in agreement with its higher phenolic content. Regarding enzyme inhibitory potential, the methanolic extract was also more potent than the aqueous one. Hence, B. thunbergii leaves represent a suitable candidate for the preparation of pharmaceutical or nutraceutical products. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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17 pages, 1422 KiB

Open AccessArticle

The Contribution of Carotenoids, Phenolic Compounds, and Flavonoids to the Antioxidative Properties of Marine Microalgae Isolated from Mediterranean Morocco

by Imane Haoujar, Francesco Cacciola, Jamal Abrini, Domenica Mangraviti, Daniele Giuffrida, Yassine Oulad El Majdoub, Ayoub Kounnoun, Natalizia Miceli, Maria Fernanda Taviano, Luigi Mondello, Francesca Rigano and Nadia Skali Senhaji

Molecules 2019, 24(22), 4037; https://doi.org/10.3390/molecules24224037 - 07 Nov 2019

Cited by 88 | Viewed by 5131

Abstract

This study aimed to investigate the potential of four sea water microalgae, isolated and cultivated at M′diq Bay in Morocco, as a new source of natural antioxidants. These microalgae belong to different classes, including Phaedactylium tricornitum (Bacillariophyceae), Nannochloropsis gaditana (Eustigmatophyceae), Nannochloris sp (Trebouxiophyceae), [...] Read more.

This study aimed to investigate the potential of four sea water microalgae, isolated and cultivated at M′diq Bay in Morocco, as a new source of natural antioxidants. These microalgae belong to different classes, including Phaedactylium tricornitum (Bacillariophyceae), Nannochloropsis gaditana (Eustigmatophyceae), Nannochloris sp (Trebouxiophyceae), and Tetraselmis suecica (Chlorodendrophycea). The antioxidant properties were screened by the use of in vitro assays, namely 2,2-difenil-1-picrylhydrazyl, Ferric reducing antioxidant power, and Ferrous ions chelating activity, and compoundidentification was carried out in methanol and acetone extracts of both dried and fresh microalgae biomass by HPLC–PDA–MS analysis. Among the investigated microalgae, Phaedactylium tricornutum was the richest one regarding its carotenoid (especially all-E-fucoxanthin) and phenolic (especially protocatechuic acid) contents, as well as antioxidant activity (65.5%), followed by Nannochloris sp, Tetraselmis suicica, and Nannochloropsis gaditana, with antioxidant activity of 56.8%, 54.9%, and 51.1%, respectively. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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17 pages, 1945 KiB

Open AccessArticle

Anti-Platelet Properties of Phenolic Extracts from the Leaves and Twigs of Elaeagnus rhamnoides (L.) A. Nelson

by Bartosz Skalski, Bogdan Kontek, Agata Rolnik, Beata Olas, Anna Stochmal and Jerzy Żuchowski

Molecules 2019, 24(19), 3620; https://doi.org/10.3390/molecules24193620 - 08 Oct 2019

Cited by 10 | Viewed by 3075

Abstract

Sea buckthorn (Elaeagnus rhamnoides (L.) A. Nelson) is a small tree or bush. It belongs to the Elaeagnaceae family, and has been used for many years in traditional medicine in both Europe and Asia. However, there is no data on the effect [...] Read more.

Sea buckthorn (Elaeagnus rhamnoides (L.) A. Nelson) is a small tree or bush. It belongs to the Elaeagnaceae family, and has been used for many years in traditional medicine in both Europe and Asia. However, there is no data on the effect of sea buckthorn leaves and twigs on the properties of blood platelets. The aim of the study was to analyze the biological activity of phenolic extracts from leaves and twigs of sea buckthorn in blood platelets in vitro. Two sets of extracts were used: (1) phenolic compounds from twigs and (2) phenolic compounds from leaves. Their biological effects on human blood platelets were studied by blood platelet adhesion, platelet aggregation, arachidonic acid metabolism and the generation of superoxide anion. Cytotoxicity was also evaluated against platelets. The action of extracts from sea buckthorn twigs and leaves was compared to activities of the phenolic extract (a commercial product from the berries of Aronia melanocarpa (Aronox^®) with antioxidative and antiplatelet properties. This study is the first to demonstrate that extracts from sea buckthorn leaves and twigs are a source of bioactive compounds which may be used for the prophylaxis and treatment of cardiovascular pathologies associated with blood platelet hyperactivity. Both leaf and twig extracts were found to display anti-platelet activity in vitro. Moreover, the twig extract (rich in proanthocyanidins) displayed better anti-platelet potential than the leaf extract or aronia extract. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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13 pages, 1359 KiB

Open AccessArticle

Characterization and Quantification of Major Flavonol Glycosides in Ramps (Allium tricoccum)

by Wijdan M. Dabeek, Nik Kovinich, Callee Walsh and Melissa Ventura Marra

Molecules 2019, 24(18), 3281; https://doi.org/10.3390/molecules24183281 - 09 Sep 2019

Cited by 13 | Viewed by 4040

Abstract

The ramp (Allium tricoccum) is a traditional plant in the eastern Appalachian Mountains. Ramps have been used in traditional medicine for their health-promoting roles in lowering blood pressure and cholesterol. Information on the chemical composition of the potentially bioactive components in [...] Read more.

The ramp (Allium tricoccum) is a traditional plant in the eastern Appalachian Mountains. Ramps have been used in traditional medicine for their health-promoting roles in lowering blood pressure and cholesterol. Information on the chemical composition of the potentially bioactive components in ramps is limited. Therefore, the aim of this work was to characterize and quantify major flavonols in ramps. Flavonoids were extracted in 50% methanol and 3% acetic acid. Characterization was conducted using UHPLC-PDA-MS and MS/MS, and quantification was performed using UHPLC-PDA detection. The major flavonol glycosides were kaempferol sophoroside glucuronide, quercetin sophoroside glucuronide, kaempferol rutinoside glucuronide, quercetin hexoside glucuronide, quercetin sophoroside, and kaempferol sophoroside. All conjugates were detected in leaves. Quercetin and kaempferol sophoroside glucuronide conjugates were detected in the stem, but no flavonol glycosides were detected in the bulb. The total amounts of the identified quercetin and kaempferol conjugates in whole ramps were 0.5972 ± 0.235 and 0.3792 ± 0.130 mg/g dry weight, respectively. Flavonol conjugates were concentrated in the leaves. To our knowledge, this work is the first to identify and quantify the major flavonol glycosides in ramps. Our findings suggest that specifically the leaves may harbor the potentially bioactive flavonols components of the plant. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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Review

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19 pages, 939 KiB

Open AccessReview

Sephadex^® LH-20, Isolation, and Purification of Flavonoids from Plant Species: A Comprehensive Review

by Javad Mottaghipisheh and Marcello Iriti

Molecules 2020, 25(18), 4146; https://doi.org/10.3390/molecules25184146 - 10 Sep 2020

Cited by 24 | Viewed by 8434

Abstract

Flavonoids are considered one of the most diverse phenolic compounds possessing several valuable health benefits. The present study aimed at gathering all correlated reports, in which Sephadex^® LH-20 (SLH) has been utilized as the final step to isolate or purify of flavonoid [...] Read more.

Flavonoids are considered one of the most diverse phenolic compounds possessing several valuable health benefits. The present study aimed at gathering all correlated reports, in which Sephadex^® LH-20 (SLH) has been utilized as the final step to isolate or purify of flavonoid derivatives among all plant families. Overall, 189 flavonoids have been documented, while the majority were identified from the Asteraceae, Moraceae, and Poaceae families. Application of SLH has led to isolate 79 flavonols, 63 flavones, and 18 flavanones. Homoisoflavanoids, and proanthocyanidins have only been isolated from the Asparagaceae and Lauraceae families, respectively, while the Asteraceae was the richest in flavones possessing 22 derivatives. Six flavones, four flavonols, three homoisoflavonoids, one flavanone, a flavanol, and an isoflavanol have been isolated as the new secondary metabolites. This technique has been able to isolate quercetin from 19 plant species, along with its 31 derivatives. Pure methanol and in combination with water, chloroform, and dichloromethane have generally been used as eluents. This comprehensive review provides significant information regarding to remarkably use of SLH in isolation and purification of flavonoids from all the plant families; thus, it might be considered an appreciable guideline for further phytochemical investigation of these compounds. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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18 pages, 1001 KiB

Open AccessReview

A Review of Bark-Extract-Mediated Green Synthesis of Metallic Nanoparticles and Their Applications

by Ema Burlacu, Corneliu Tanase, Năstaca-Alina Coman and Lavinia Berta

Molecules 2019, 24(23), 4354; https://doi.org/10.3390/molecules24234354 - 28 Nov 2019

Cited by 59 | Viewed by 5028

Abstract

Nanoparticles are intensely studied because of their importance in diverse fields of biotechnology, especially in medicine. This paper highlights that waste bark can be a cheap source of biocompounds, with high recovery and functionalization potential in nanoparticle synthesis. Due to their biocompatibility and [...] Read more.

Nanoparticles are intensely studied because of their importance in diverse fields of biotechnology, especially in medicine. This paper highlights that waste bark can be a cheap source of biocompounds, with high recovery and functionalization potential in nanoparticle synthesis. Due to their biocompatibility and activity as antioxidant, antimicrobial, and anticancer agents, the green synthesis of metallic nanoparticles is of great importance. This review aims to bring together the diversity of synthesized metallic nanoparticles mediated by bark extracts obtained from different woody vascular plants, the phytoconstituents responsible for the reduction of metal salts, and the activity of metallic nanoparticles as diverse agents in combating the microbial, oxidant, and cancer activity. The literature data highlight the fact that metallic nanoparticles obtained from natural compounds are proven reducing agents with multiple activities. Thus, the activity of natural components in environmental protection and human health is confirmed. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds)

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