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Phenolic Composition, Antioxidant Potential and Bioactive Potential of Natural Products

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 October 2022) | Viewed by 44224

Special Issue Editors


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Guest Editor
Department of Physical and Analytical Chemistry, Faculty of Experimental Sciences, University of Jaén, Campus Las Lagunillas, 23071 Jaén, Spain
Interests: spectroscopy; luminescence; automation; chlorophylls; phenolics; natural compounds; natural colorants; food analysis; HPLC-MS; nanomaterials; antioxidant; in vitro digestion; analytical methods for the determination of colorants
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Department of Biology, Science Faculty, Selcuk University, Selcuk 42130, Turkey
Interests: antioxidant capacity; natural products; enzyme inhibition; phenolics
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Edible fruits, herbs and vegetables usually present high levels of polyphenols, which have high antioxidant activity and are useful against stress conditions in the human body, therefore presenting important health benefits. However, not only edible plants are useful from this point of view, but also non-edible plant materials. In the last decade, interest has grown around natural plant extracts for different applications, mainly for the development of novel food products (food supplements and nutraceuticals) and pharmaceutical products. Many of the protecting effects of natural products are derived from plant secondary metabolites, mainly phenolic compounds. Phenolic compounds are well-known for their wide array of remarkable biochemical and pharmacological properties, including antioxidant, antiviral, anticancer, and anti-inflammatory activities. They are also widely studied due to their enzyme inhibitory properties. Most usual assays involve key enzymes relevant in metabolic disorders. Consequently, phenolic compounds can be functional in the prevention of many diseases as well as in health maintenance. This Special Issue will thus cover a wide range of research areas concerning natural products. Research or review articles are welcomed, including but not limited to identification of novel natural products, determination of phenolic composition, antioxidant activity and bioactivity of novel plant species, advances in sample treatment for the extraction of phenolics from natural products, improvements in analytical methods for quantitation and quality control purposes, theoretical and experimental studies on the (bio)chemical properties of natural products, and potential industrial applications of new natural products based on their bioactivity.

Dr. Eulogio J. Llorent-Martínez
Dr. Gokhan Zengin
Guest Editors

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Keywords

  • natural products
  • plants
  • phenolic compounds
  • antioxidant activity
  • bioactivity
  • enzyme inhibitory properties
  • sample treatment
  • industrial applications

Published Papers (18 papers)

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18 pages, 3060 KiB  
Article
Unveiling the Antioxidant, Clinical Enzyme Inhibitory Properties and Cytotoxic Potential of Tambourissa peltata Baker—An Understudied Endemic Plant
by Shanoo Suroowan, Eulogio J. Llorent-Martínez, Gokhan Zengin, Kalaivani Buskaran, Sharida Fakurazi, Ashraf N. Abdalla, Asaad Khalid, Bao Le Van and Mohamad Fawzi Mahomoodally
Molecules 2023, 28(2), 599; https://doi.org/10.3390/molecules28020599 - 6 Jan 2023
Cited by 7 | Viewed by 1542
Abstract
This study documents for the first time the phytochemical composition and biological activities of Tambourissa peltata Baker, an endemic plant from Mauritius. Phytochemical extraction was performed using ethyl acetate, methanol and distilled water as solvents. The phytochemical composition was determined through HPLC-MS and [...] Read more.
This study documents for the first time the phytochemical composition and biological activities of Tambourissa peltata Baker, an endemic plant from Mauritius. Phytochemical extraction was performed using ethyl acetate, methanol and distilled water as solvents. The phytochemical composition was determined through HPLC-MS and other standard assays. The DPPH, ABTS, FRAP, CUPRAC and phosphomolybdenum assays were employed for the determination of the antioxidant potential, whereas cell viability assays were used to determine the cytotoxicity. The highest phenolic and phenolic acid contents were obtained in the aqueous extract (179.91 ± 0.67 gallic acid equivalents/g and 55.74 ± 1.43 caffeic acid equivalents/g). The highest quantity of flavonoids was obtained in the ethyl acetate extract (28.97 ± 0.46 rutin equivalents/g). The methanolic extract was the highest source of flavonols (33.71 ± 0.13 mg catechin equivalents/g). A total of 34 phytochemicals were identified, mainly proanthocyanidins and flavonoid glycosides. The highest antioxidant activity in DPPH (973.40 ± 5.65 mg TE (Trolox equivalents)/g), ABTS (2030.37 ± 40.83 mg TE/g), FRAP (1461.39 ± 5.95 mg TE/g), CUPRAC (1940.99 ± 20.95 mg TE/g) and phosphomolybdenum (8.37 ± 0.23 mmol TE/g) assays was recorded for the aqueous extract. The ethyl acetate extract was the most active metal chelator. The highest acetylcholinesterase inhibitor was the methanolic extract, whereas the ethyl acetate extract was the most active against BChE. The tyrosinase enzyme was most inhibited by the methanolic extract. Alpha-amylase and glucosidase were most inhibited by the aqueous extract. The methanolic extract was capable of inducing cell cytotoxicity to the human colorectal carcinoma without damaging normal cells. T. peltata warrants further attention from the scientific community given its multifaceted biological properties. Full article
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23 pages, 2193 KiB  
Article
New Biological and Chemical Evidences of Two Lamiaceae Species (Thymbra capitata and Thymus sipyleus subsp. rosulans): In Vitro, In Silico and Ex Vivo Approaches
by Eulogio J. Llorent-Martínez, Antonio Ruiz-Medina, Gokhan Zengin, Gunes Ak, Sharmeen Jugreet, Mohamad Fawzi Mahomoodally, Gizem Emre, Giustino Orlando, Maria Loreta Libero, Nilofar, Alessandra Acquaviva, Simonetta Cristina Di Simone, Luigi Menghini, Claudio Ferrante, Luigi Brunetti, Lucia Recinella, Sheila Leone, Mohamad Ali Shariati, Abdullahi Ibrahim Uba and Annalisa Chiavaroli
Molecules 2022, 27(24), 9029; https://doi.org/10.3390/molecules27249029 - 18 Dec 2022
Cited by 18 | Viewed by 1761
Abstract
In this study, the methanolic and infusion extracts of two species, Thymbra capitata and Thymus sipyleus subsp. rosulans, were tested for their chemical composition and biological abilities (antioxidant, enzyme inhibitory and anti-inflammatory effects). The extracts yielded total phenolic and flavonoid contents in [...] Read more.
In this study, the methanolic and infusion extracts of two species, Thymbra capitata and Thymus sipyleus subsp. rosulans, were tested for their chemical composition and biological abilities (antioxidant, enzyme inhibitory and anti-inflammatory effects). The extracts yielded total phenolic and flavonoid contents in the range of 83.43–127.52 mg GAE/g and 9.41–46.34 mg RE/g, respectively. HPLC analysis revealed rosmarinic acid to be a major component of the studied extracts (15.85–26.43%). The best ABTS radical scavenging ability was observed in the methanol extract of T. capitata with 379.11 mg TE/g, followed by in the methanol extract of T. sipylus (360.93 mg TE/g). In the CUPRAC assay, the highest reducing ability was also found in the methanol extract of T. capitata with 802.22 mg TE/g. The phosphomolybdenum ability ranged from 2.39 to 3.61 mmol TE/g. In terms of tyrosinase inhibitory effects, the tested methanol extracts (83.18–89.66 mg KAE/g) were higher than the tested water extracts (18.74–19.11 mg KAE/g). Regarding the BChE inhibitory effects, the methanol extracts were active on the enzyme while the water extracts showed no inhibitory effect on it. Overall, the methanolic extracts showed better enzyme inhibition compared to the infusion extracts. Molecular docking also showed the selected exhibited potential binding affinities with all enzymes, with a preference for cholinesterases. Additionally, the extracts were effective in attenuating the LPS-induced increase in COX-2 and IL-6 gene expression in isolated colon, thus indicating promising anti-inflammatory effects. The preliminary results of this study suggest that these species are good natural sources of antioxidants and also provide some scope as enzyme inhibitors, most likely due to their bioactive contents such as phenolic acids, and thus can be exploited for different applications related to health promotion and disease prevention. Full article
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21 pages, 2560 KiB  
Article
Comparative Investigation of Chemical Constituents of Kernels, Leaves, Husk, and Bark of Juglans regia L., Using HPLC-DAD-ESI-MS/MS Analysis and Evaluation of Their Antioxidant, Antidiabetic, and Anti-Inflammatory Activities
by Ilhame Bourais, Salma Elmarrkechy, Douae Taha, Bouabid Badaoui, Yassine Mourabit, Najoua Salhi, Mohammed Merae Alshahrani, Ahmed Abdullah Al Awadh, Abdelhakim Bouyahya, Khang Wen Goh, Ching Siang Tan, Souad El Hajjaji, Nadia Dakka and Naima Iba
Molecules 2022, 27(24), 8989; https://doi.org/10.3390/molecules27248989 - 16 Dec 2022
Cited by 13 | Viewed by 2148
Abstract
Leaves, husk, kernels, and bark methanolic extracts of Juglans regia L. were tested for their in vitro antidiabetic, anti-inflammatory, and antioxidant activities. For these purposes, α-amylase and α-glucosidase were used as the main enzymes to evaluate antidiabetic activities. Moreover, lipoxidase and tyrosinase activities [...] Read more.
Leaves, husk, kernels, and bark methanolic extracts of Juglans regia L. were tested for their in vitro antidiabetic, anti-inflammatory, and antioxidant activities. For these purposes, α-amylase and α-glucosidase were used as the main enzymes to evaluate antidiabetic activities. Moreover, lipoxidase and tyrosinase activities were tested to estimate anti-inflammatory properties. Antioxidant properties of Juglans regia L., extracts were determined using three different assays. Leaves extract has an important radical scavenging activity and a-amylase inhibition. Similarly, husk extracts showed high total phenolic content (306.36 ± 4.74 mg gallic acid equivalent/g dry extract) with an important α-amylase inhibition (IC50 = 75.42 ± 0.99 µg/mL). Kernels exhibit significant tyrosinase (IC50 = 51.38 ± 0.81 µg/mL) correlated with antioxidant activities (p < 0.05). Husk and bark extracts also showed strong anti-lipoxidase activities with IC50 equal to 29.48 ± 0.28 and 28.58 ± 0.35 µg/mL, respectively. HPLC-DAD-ESI-MS/MS analysis highlights the phenolic profile of methanolic extracts of Juglans regia L. plant parts. The identified polyphenols were known for their antioxidant, antidiabetic (dicaffeoyl-quinic acid glycoside in kernels), and anti-inflammatory (3,4-dihydroxybenzoic acid in leaves) activities. Further investigations are needed to determine molecular mechanisms involved in these effects as well as to study the properties of the main identified compounds. Full article
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18 pages, 6212 KiB  
Article
Characterization of Polyphenolic Compounds from Bacopa procumbens and Their Effects on Wound-Healing Process
by Adriana Martínez-Cuazitl, María del Consuelo Gómez-García, Oriana Hidalgo-Alegria, Olivia Medel Flores, José Alberto Núñez-Gastélum, Eduardo San Martín Martínez, Ada María Ríos-Cortés, Mario Garcia-Solis and David Guillermo Pérez-Ishiwara
Molecules 2022, 27(19), 6521; https://doi.org/10.3390/molecules27196521 - 2 Oct 2022
Cited by 5 | Viewed by 2100
Abstract
Wounds represent a medical problem that contributes importantly to patient morbidity and to healthcare costs in several pathologies. In Hidalgo, Mexico, the Bacopa procumbens plant has been traditionally used for wound-healing care for several generations; in vitro and in vivo experiments were designed [...] Read more.
Wounds represent a medical problem that contributes importantly to patient morbidity and to healthcare costs in several pathologies. In Hidalgo, Mexico, the Bacopa procumbens plant has been traditionally used for wound-healing care for several generations; in vitro and in vivo experiments were designed to evaluate the effects of bioactive compounds obtained from a B. procumbens aqueous fraction and to determine the key pathways involved in wound regeneration. Bioactive compounds were characterized by HPLC/QTOF-MS, and proliferation, migration, adhesion, and differentiation studies were conducted on NIH/3T3 fibroblasts. Polyphenolic compounds from Bacopa procumbens (PB) regulated proliferation and cell adhesion; enhanced migration, reducing the artificial scratch area; and modulated cell differentiation. PB compounds were included in a hydrogel for topical administration in a rat excision wound model. Histological, histochemical, and mechanical analyses showed that PB treatment accelerates wound closure in at least 48 h and reduces inflammation, increasing cell proliferation and deposition and organization of collagen at earlier times. These changes resulted in the formation of a scar with better tensile properties. Immunohistochemistry and RT-PCR molecular analyses demonstrated that treatment induces (i) overexpression of transforming growth factor beta (TGF-β) and (ii) the phosphorylation of Smad2/3 and ERK1/2, suggesting the central role of some PB compounds to enhance wound healing, modulating TGF-β activation. Full article
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17 pages, 3528 KiB  
Article
Phenolic Profile, Antioxidant and Enzyme Inhibitory Activities of Leaves from Two Cassia and Two Senna Species
by Haifa A. A. Omer, Giovanni Caprioli, Doaa Abouelenein, Ahmed M. Mustafa, Abdullahi Ibrahim Uba, Gunes Ak, Refiye Beyza Ozturk, Gokhan Zengin and Sakina Yagi
Molecules 2022, 27(17), 5590; https://doi.org/10.3390/molecules27175590 - 30 Aug 2022
Cited by 21 | Viewed by 2702
Abstract
Several species within the genera Cassia or Senna have a treasure of traditional medicines worldwide and can be a promising source of bioactive molecules. The objective of the present study was to evaluate the phenolic content and antioxidant and enzyme inhibition activities of [...] Read more.
Several species within the genera Cassia or Senna have a treasure of traditional medicines worldwide and can be a promising source of bioactive molecules. The objective of the present study was to evaluate the phenolic content and antioxidant and enzyme inhibition activities of leaf methanolic extracts of C. fistula L., C. grandis L., S. alexandrina Mill., and S. italica Mill. The two Cassia spp. contained higher total polyphenolic content (42.23–49.75 mg GAE/g) than the two Senna spp., and C. fistula had significantly (p ˂ 0.05) the highest concentration. On the other hand, the Senna spp. showed higher total flavonoid content (41.47–59.24 mg rutin equivalent per g of extract) than that found in the two Cassia spp., and S. alexandrina significantly (p ˂ 0.05) accumulated the highest amount. HPLC–MS/MS analysis of 38 selected bioactive compounds showed that the majority of compounds were identified in the four species, but with sharp variations in their concentrations. C. fistula was dominated by epicatechin (8928.75 µg/g), C. grandis by kaempferol-3-glucoside (47,360.04 µg/g), while rutin was the major compound in S. italica (17,285.02 µg/g) and S. alexandrina (6381.85). The methanolic extracts of the two Cassia species exerted significantly (p ˂ 0.05) higher antiradical activity, metal reducing capacity, and total antioxidant activity than that recorded from the two Senna species’ methanolic extracts, and C. fistula displayed significantly (p ˂ 0.05) the highest values. C. grandis significantly (p ˂ 0.05) exhibited the highest metal chelating power. The results of the enzyme inhibition activity showed that the four species possessed anti-AChE activity, and the highest value, but not significantly (p ≥ 0.05) different from those obtained by the two Cassia spp., was exerted by S. alexandrina. The Cassia spp. exhibited significantly (p ˂ 0.05) higher anti-BChE and anti-Tyr properties than the Senna spp., and C. grandise revealed significantly (p ˂ 0.05) the highest values. C. grandise revealed significantly (p ˂ 0.05) the highest α- amylase inhibition, while the four species had more or less the same effect against the α-glucosidase enzyme. Multivariate analysis and in silico studies showed that many of the identified phenols may play key roles as antioxidant and enzyme inhibitory properties. Thus, these Cassia and Senna species could be a promising source of natural bioactive agents with beneficial effects for human health. Full article
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19 pages, 1957 KiB  
Article
Polyphenolic Profiling, Antioxidant, and Antimicrobial Activities Revealed the Quality and Adaptive Behavior of Viola Species, a Dietary Spice in the Himalayas
by Rishabh Kaundal, Manish Kumar, Subhash Kumar, Dharam Singh and Dinesh Kumar
Molecules 2022, 27(12), 3867; https://doi.org/10.3390/molecules27123867 - 16 Jun 2022
Cited by 13 | Viewed by 2612
Abstract
Background: Himalayan Viola species (Banksha) are traditionally important herbs with versatile therapeutic benefits such as antitussive, analgesic, antipyretic, antimalarial, anti-inflammatory, and anticancerous ones. The current investigation was focused on exploring polyphenolic profiles, antioxidant, and antimicrobial potentials of wild viola species at 15 gradient [...] Read more.
Background: Himalayan Viola species (Banksha) are traditionally important herbs with versatile therapeutic benefits such as antitussive, analgesic, antipyretic, antimalarial, anti-inflammatory, and anticancerous ones. The current investigation was focused on exploring polyphenolic profiles, antioxidant, and antimicrobial potentials of wild viola species at 15 gradient locations (375–1829 m). Methods: Morphological, physiochemical, and proximate analyses were carried out as per WHO guidelines for plant drug standardization. Total polyphenolic and flavonoid content were carried out using gallic acid and rutin equivalent. UPLC-DAD was used to profile the targeted polyphenols (gallic acid, vanillic acid, syringic acid, p-coumaric acid, ferulic acid, rutin, quercetin, luteolin, caffeic acid, and epicatechin). Similarly, all samples were screened for antioxidant and antimicrobial activity. Statistical analysis was used to correlate polyphenolic and targeted activities to assess Viola species adaptation behavior patterns. Results: Viola canescens (V. canescens) and Viola pilosa (V. pilosa) were found abundantly at their respective sites. Among flowers and leaves, flowers of V. canescens and V. pilosa showed higher total polyphenolic and flavonoid content (51.4 ± 1.13 mg GAE/g and 65.05 ± 0.85 mg RE/g, and 33.26 ± 0.62 mg GAE/g and 36.10 ± 1.41 mg RE/g, respectively). Furthermore, UPLC-DAD showed the uppermost content of p-coumaric acid in flowers and ferulic acid in leaves, while rutin was significant in both the tissues. Conclusions: The adaptive behavior of Viola species showed variability in morphological characters with the altitudes, while targeted polyphenols and activities were significant at mid-altitudes. This research helps in the selection of right chemotype for agrotechnological interventions and the development of nutraceutical products. Full article
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24 pages, 4656 KiB  
Article
Towards the Pharmacological Validation and Phytochemical Profiling of the Decoction and Maceration of Bruguiera gymnorhiza (L.) Lam.—A Traditionally Used Medicinal Halophyte
by Nabeelah Bibi Sadeer, Kouadio Ibrahime Sinan, Zoltán Cziáky, József Jekő, Gokhan Zengin, Rajesh Jeewon, Hassan H. Abdallah, Yusra AlDhaheri, Ali H. Eid and Mohamad Fawzi Mahomoodally
Molecules 2022, 27(6), 2000; https://doi.org/10.3390/molecules27062000 - 20 Mar 2022
Cited by 13 | Viewed by 2338
Abstract
Decoctions (leaves and roots) of Bruguiera gymnorhiza (L.) Lam. are traditionally used against diabetes in many countries, including Mauritius. This study endeavoured to evaluate the inhibitory potential of leaves, roots, twigs and fruits extracts (decoction and maceration) of B. gymnorhiza against key enzymes [...] Read more.
Decoctions (leaves and roots) of Bruguiera gymnorhiza (L.) Lam. are traditionally used against diabetes in many countries, including Mauritius. This study endeavoured to evaluate the inhibitory potential of leaves, roots, twigs and fruits extracts (decoction and maceration) of B. gymnorhiza against key enzymes relevant to diabetes. Considering complications related to diabetes, other clinical enzymes, namely, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), tyrosinase, elastase and pancreatic lipase, were used. Identification of compounds was carried out using ultra-high-performance liquid chromatography/electrospray ionization tandem mass spectrometry (UHPLC-ESI-MS/MS). Antioxidant capacities were assessed using DPPH, ABTS, FRAP, CUPRAC, phosphomolybdenum, metal chelating. The relationship between mode of extraction, plant parts and biological activities was determined using multivariate analysis. Macerated fruits, rich in phytochemicals (phenolic, flavanol, tannin, and triterpenoid), exhibited substantially high antioxidant capacities related to radical scavenging (DPPH: 547.75 ± 10.99 and ABTS: 439.59 ± 19.13 mg TE/g, respectively) and reducing potential (CUPRAC: 956.04 ± 11.90 and FRAP: 577.26 ± 4.55 mg TE/g, respectively). Additionally, the same extract significantly depressed AChE and BChE (3.75 ± 0.03 and 2.19 ± 0.13 mg GALAE/g, respectively), tyrosinase (147.01 ± 0.78 mg KAE/g), elastase (3.14 ± 0.08 mg OE/g) and amylase (1.22 ± 0.01 mmol ACAE/g) enzymatic activities. Phytochemical results confirmed the presence of 119 compounds in all maceration and 163 compounds in all decoction samples. The screening also revealed important compounds in the extracts, namely, quinic acid, brugierol, bruguierol A, epigallocatechin, chlorogenic acid, to name a few. Multivariate analysis reported that the plant parts of B. gymnorhiza greatly influenced the observed biological activities in contrast to the types of extraction methods employed. Docking calculations have supported the findings of the experimental part through the high binding affinity and strong interactions of some compounds against tyrosinase, AChE, BChE and elastase enzymes. The decocted root and leaf of B. gymnorhiza showed low to moderate antidiabetic activity, thereby partially supporting its traditional uses in the management of diabetes. However, the fruit, the most active organ, can be used as a diet supplement to reduce the risk of diabetes complications after evaluating its cytotoxic effects. Full article
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11 pages, 1468 KiB  
Article
Characterization of the Phenolic Profile and Antioxidant Activity of Cathissa reverchonii (Lange) Speta
by Eulogio J. Llorent-Martínez, Ana I. Gordo-Moreno, María Luisa Fernández-de Córdova, Carlos Salazar-Mendías and Amanda Tercero-Araque
Molecules 2022, 27(6), 1979; https://doi.org/10.3390/molecules27061979 - 18 Mar 2022
Cited by 2 | Viewed by 1221
Abstract
Cathissa reverchonii (formerly Ornithogalum reverchonii) is a threatened species, constituting an endemism present in the south of Spain and northern Morocco. In Spain, it is only found in two disjoint populations in the region of Andalusia. The determination of its chemical composition [...] Read more.
Cathissa reverchonii (formerly Ornithogalum reverchonii) is a threatened species, constituting an endemism present in the south of Spain and northern Morocco. In Spain, it is only found in two disjoint populations in the region of Andalusia. The determination of its chemical composition and the influence that environmental factors have on it can contribute significantly to the development of appropriate protection and conservation plans. However, there are no previous reports about this species to date. Consequently, this research aimed to study the phenolic composition and antioxidant activity of C. reverchonii and to assess the influence of environmental factors on the phenolic profile and bioactivity. The vegetal material was collected in seven places inhabited by the two separate populations in Spain. The phenolic composition of methanolic extracts of the species was determined by HPLC-ESI-Q-TOF-MS, and the antioxidant activity was assessed by DPPH and ABTS assays. Fifteen compounds were characterized in the extracts of the aerial parts of C. reverchonii, revealing differences in the phytochemical profile between both populations analyzed, mainly in the saponin fraction. The main phenolics were flavone di-C-glucoside (lucenin-2), followed by a quercetin-di-C-glucoside. The composition of the extracts of C. reverchonii and their radical scavenging power were compared with those of other species of the genus Ornithogalum L., revealing significant differences between the latter and the genus Cathissa. Full article
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17 pages, 2143 KiB  
Article
Comparative Evaluation of the Phytochemical Profiles and Antioxidant Potentials of Olive Leaves from 32 Cultivars Grown in China
by Chengcheng Zhang, Xiaoting Xin, Jianming Zhang, Shenlong Zhu, Erli Niu, Zhongjing Zhou and Daqun Liu
Molecules 2022, 27(4), 1292; https://doi.org/10.3390/molecules27041292 - 15 Feb 2022
Cited by 19 | Viewed by 2240
Abstract
Olives (Olea europaea L.) are a significant part of the agroindustry in China. Olive leaves, the most abundant by-products of the olive and olive oil industry, contain bioactive compounds that are beneficial to human health. The purpose of this study was to [...] Read more.
Olives (Olea europaea L.) are a significant part of the agroindustry in China. Olive leaves, the most abundant by-products of the olive and olive oil industry, contain bioactive compounds that are beneficial to human health. The purpose of this study was to evaluate the phytochemical profiles and antioxidant capacities of olive leaves from 32 cultivars grown in China. A total of 32 phytochemical compounds were identified using high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry, including 17 flavonoids, five iridoids, two hydroxycinnamic acids, six triterpenic acids, one simple phenol, and one coumarin. Specifically, olive leaves were found to be excellent sources of flavonoids (4.92–18.29 mg/g dw), iridoids (5.75–33.73 mg/g dw), and triterpenic acids (15.72–35.75 mg/g dw), and considerable variations in phytochemical content were detected among the different cultivars. All tested cultivars were classified into three categories according to their oil contents for further comparative phytochemicals assessment. Principal component analysis indicated that the investigated olive cultivars could be distinguished based upon their phytochemical profiles and antioxidant capacities. The olive leaves obtained from the low-oil-content (<16%) cultivars exhibited higher levels of glycosylated flavonoids and iridoids, while those obtained from high-oil-content (>20%) cultivars contained mainly triterpenic acids in their compositions. Correspondingly, the low-oil-content cultivars (OL3, Frantoio selection and OL14, Huaou 5) exhibited the highest ABTS antioxidant activities (758.01 ± 16.54 and 710.64 ± 14.58 mg TE/g dw, respectively), and OL9 (Olea europaea subsp. Cuspidata isolate Yunnan) and OL3 exhibited the highest ferric reducing/antioxidant power assay values (1228.29 ± 23.95 mg TE/g dw and 1099.99 ± 14.30 mg TE/g dw, respectively). The results from this study may be beneficial to the comprehensive evaluation and utilization of bioactive compounds in olive leaves. Full article
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13 pages, 1089 KiB  
Article
The Content of Phenolic Compounds and Organic Acids in Two Tagetes patula Cultivars Flowers and Its Dependence on Light Colour and Substrate
by Agnieszka Krzymińska, Barbara Frąszczak, Monika Gąsecka, Zuzanna Magdziak and Tomasz Kleiber
Molecules 2022, 27(2), 527; https://doi.org/10.3390/molecules27020527 - 14 Jan 2022
Cited by 4 | Viewed by 1463
Abstract
The main focus of the study was to determine the content of phenolic acids, flavonoids, and organic acids in the flowers of Tagetes patula ‘Petite Gold’ and ‘Petite Orange’. The growth of the plants was assessed depending on the cultivation conditions. The above [...] Read more.
The main focus of the study was to determine the content of phenolic acids, flavonoids, and organic acids in the flowers of Tagetes patula ‘Petite Gold’ and ‘Petite Orange’. The growth of the plants was assessed depending on the cultivation conditions. The above plants were illuminated with white light, whereas the ‘Petite Gold’ ones with white light enhanced with blue or red light. Both cultivars grew in a two-level-mineral compounds organic substrate. The research showed that the French marigold flowers were rich in phenolic compounds and organic acids. The ‘Petite Gold’ flowers had more bioactive compounds compared with the ‘Petite Orange’ flowers. Three flavonoids, 10 phenolic acids and seven organic acids were found in the ‘Petite Gold’ flowers. The artificial lighting used during the cultivation of the plants showed diversified influence on the content of organic compounds in their flowers. The measurements of the plants’ morphological traits and the number of inflorescences showed that illumination with red light resulted in a better effect. Large plants with numerous inflorescences grew in the substrate with a lower content of nutrients. Full article
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15 pages, 1692 KiB  
Article
Different Fruit-Specific Promoters Drive AtMYB12 Expression to Improve Phenylpropanoid Accumulation in Tomato
by Xiangyu Ding, Ziyi Yin, Shaoli Wang, Haoqi Liu, Xiaomeng Chu, Jiazong Liu, Haipeng Zhao, Xinyu Wang, Yang Li and Xinhua Ding
Molecules 2022, 27(1), 317; https://doi.org/10.3390/molecules27010317 - 5 Jan 2022
Cited by 7 | Viewed by 2503
Abstract
Tomato is an economically crucial vegetable/fruit crop globally. Tomato is rich in nutrition and plays an essential role in a healthy human diet. Phenylpropanoid, a critical compound in tomatoes, reduces common degenerative and chronic diseases risk caused by oxidative stress. As an MYB [...] Read more.
Tomato is an economically crucial vegetable/fruit crop globally. Tomato is rich in nutrition and plays an essential role in a healthy human diet. Phenylpropanoid, a critical compound in tomatoes, reduces common degenerative and chronic diseases risk caused by oxidative stress. As an MYB transcription factor, ATMYB12 can increase phenylpropanoid content by activating phenylpropanoid synthesis related genes, such as PAL, C4H, 4CL, CHS. However, the heterologous expression of AtMYB12 in tomatoes can be altered through transgenic technologies, such as unstable expression vectors and promoters with different efficiency. In the current study, the efficiency of other fruit-specific promoters, namely E8S, 2A12, E4, and PG, were compared and screened, and we determined that the expression efficiency of AtMYB12 was driven by the E8S promoter was the highest. As a result, the expression of phenylpropanoid synthesis related genes was regulated by AtMYB12, and the phenylpropanoid accumulation in transgenic tomato fruits increased 16 times. Additionally, the total antioxidant capacity of fruits was measured through Trolox equivalent antioxidant capacity (TEAC) assay, which was increased by 2.4 times in E8S transgenic lines. TEAC was positively correlated with phenylpropanoid content. Since phenylpropanoid plays a crucial role in the human diet, expressing AtMYB12 with stable and effective fruit-specific promoter E8S could improve tomato’s phenylpropanoid and nutrition content and quality. Our results can provide genetic resources for the subsequent improvement of tomato varieties and quality, which is significant for human health. Full article
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16 pages, 3147 KiB  
Article
Supplementary Far-Red and Blue Lights Influence the Biomass and Phytochemical Profiles of Two Lettuce Cultivars in Plant Factory
by Yamin Li, Linyuan Wu, Haozhao Jiang, Rui He, Shiwei Song, Wei Su and Houcheng Liu
Molecules 2021, 26(23), 7405; https://doi.org/10.3390/molecules26237405 - 6 Dec 2021
Cited by 18 | Viewed by 3191
Abstract
Three different LED spectra (W: White light; WFR: W + far-red light; WB: W + blue light) with similar photosynthetic photon flux density (PPFD) were designed to explore the effects of supplementary far-red and blue lights on leaf color, biomass and phytochemicals of [...] Read more.
Three different LED spectra (W: White light; WFR: W + far-red light; WB: W + blue light) with similar photosynthetic photon flux density (PPFD) were designed to explore the effects of supplementary far-red and blue lights on leaf color, biomass and phytochemicals of two cultivars of red-leaf lettuce (“Yanzhi” and “Red Butter”) in an artificial lighting plant factory. Lettuce plants under WB had redder leaf color and significantly higher contents of pigments, such as chlorophyll a, chlorophyll b, chlorophyll (a + b) and anthocyanins. The accumulation of health-promoting compounds, such as vitamin C, vitamin A, total phenolic compounds, total flavonoids and anthocyanins in the two lettuce cultivars were obviously enhanced by WB. Lettuce under WFR showed remarkable increase in fresh weight and dry weight; meanwhile, significant decreases of pigments, total phenolic compounds, total flavonoids and vitamin C were found. Thus, in the plant factory system, the application of WB can improve the coloration and quality of red leaf lettuce while WFR was encouraged for the purpose of elevating the yield of lettuce. Full article
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13 pages, 315 KiB  
Article
Antioxidant and Starch-Hydrolyzing Enzymes Inhibitory Properties of Striga-Resistant Yellow-Orange Maize Hybrids
by Abdulazeez Olamilekan Elemosho, Emmanuel Anyachukwu Irondi, Emmanuel Oladeji Alamu, Emmanuel Oladipo Ajani, Abebe Menkir and Busie Maziya-Dixon
Molecules 2021, 26(22), 6874; https://doi.org/10.3390/molecules26226874 - 15 Nov 2021
Cited by 6 | Viewed by 2062
Abstract
Most of the health benefits derived from cereals are attributed to their bioactive compounds. This study evaluated the levels of the bioactive compounds, and the antioxidant and starch-hydrolyzing enzymes inhibitory properties of six pipeline Striga-resistant yellow-orange maize hybrids (coded AS1828-1, 4, 6, [...] Read more.
Most of the health benefits derived from cereals are attributed to their bioactive compounds. This study evaluated the levels of the bioactive compounds, and the antioxidant and starch-hydrolyzing enzymes inhibitory properties of six pipeline Striga-resistant yellow-orange maize hybrids (coded AS1828-1, 4, 6, 8, 9, 11) in vitro. The maize hybrids were grown at the International Institute of Tropical Agriculture (IITA), Nigeria. The bioactive compounds (total phenolics, tannins, flavonoids, and phytate) levels, antioxidant (DPPH and ABTS•+ scavenging capacity and reducing power) and starch-hydrolyzing enzymes (α-amylase and α-glucosidase) inhibitory activities of the maize hybrids were determined by spectrophotometry. At the same time, carotenoids were quantified using a reverse-phase HPLC system. The ranges of the bioactive compounds were: 11.25–14.14 mg GAE/g (total phenolics), 3.62–4.67 mg QE/g (total flavonoids), 3.63–6.29 mg/g (tannins), 3.66–4.31% (phytate), 8.92–12.11 µg/g (total xanthophylls), 2.42–2.89 µg/g (total β-carotene), and 3.17–3.77 µg/g (total provitamin A carotenoids). Extracts of the maize hybrids scavenged DPPH (SC50: 9.07–26.35 mg/mL) and ABTS•+ (2.65–7.68 TEAC mmol/g), reduced Fe3+ to Fe2+ (0.25 ± 0.64–0.43 ± 0.01 mg GAE/g), and inhibited α-amylase and α-glucosidase, with IC50 ranges of 26.28–52.55 mg/mL and 47.72–63.98 mg/mL, respectively. Among the six clones of the maize hybrids, AS1828-9 had the highest (p < 0.05) levels of tannins and phytate and the strongest antioxidant and starch-hydrolyzing enzymes inhibitory activities. Significant correlations were observed between total phenolics and the following: ABTS•+ (p < 0.01, r = 0.757), DPPH SC50 (p < 0.01, r = −0.867), reducing power (p < 0.05, r = 0.633), α-amylase IC50 (p < 0.01, r = −0.836) and α-glucosidase IC50 (p < 0.05, r = −0.582). Hence, the Striga-resistant yellow-orange maize hybrids (especially AS1828-9) may be beneficial for alleviating oxidative stress and postprandial hyperglycemia. Full article
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20 pages, 10760 KiB  
Article
Phytochemical Screening and Antioxidant Activity of Seven Native Species Growing in the Forests of Southern Chilean Patagonia
by Merly de Armas-Ricard, Francisco Quinán-Cárdenas, Harold Sanhueza, Rodrigo Pérez-Vidal, Cristina Mayorga-Lobos and Oney Ramírez-Rodríguez
Molecules 2021, 26(21), 6722; https://doi.org/10.3390/molecules26216722 - 6 Nov 2021
Cited by 2 | Viewed by 2364
Abstract
The genus Nothofagus is one of the most abundant in the subantarctic Patagonian forests. Five species inhabit these ecosystems, three evergreen (Nothofagus betuloides, Nothofagus dombeyi, and Nothofagus nitida) and two deciduous (Nothofagus pumilio and Nothofagus antarctica). This [...] Read more.
The genus Nothofagus is one of the most abundant in the subantarctic Patagonian forests. Five species inhabit these ecosystems, three evergreen (Nothofagus betuloides, Nothofagus dombeyi, and Nothofagus nitida) and two deciduous (Nothofagus pumilio and Nothofagus antarctica). This is the first report on the levels of secondary metabolites and the antioxidant capacity of Patagonian tree species growing in natural environments. The aim of this work was to carry out a phytochemical screening, to determine the antioxidant capacity, the sun protection factor, and the α-glucosidase and tyrosinase inhibitory activity of foliar extracts of the five previous species. Besides, Aristotelia chilensis and Berberis microphylla, two species of Patagonian shrubs growing in the same forests, were used as reference. N. dombeyi was the Nothofagus with the best antioxidant capacity. B. microphylla differed from all studied species. Moreover, the Nothofagus was split into two groups. N. betuloides and N. dombeyi are the most similar species to A. chilensis. The α-glucosidase was completely inhibited by all studied extracts. Furthermore, N. antarctica, N.pumilio, and N. nitida inhibited about 70% of the tyrosinase activity. All the results found in this study for the species of the genus Nothofagus support further research on their potential beneficial properties for human health. Full article
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12 pages, 5347 KiB  
Article
Untargeted Metabolomics Combined with Bioassay Reveals the Change in Critical Bioactive Compounds during the Processing of Qingzhuan Tea
by Peng-Cheng Zheng, Chun-Yin Qin, Pan-Pan Liu, Lin Feng, Tie-Jun Ling, Jing-Ming Ning, Liang Zhang and Xiao-Chun Wan
Molecules 2021, 26(21), 6718; https://doi.org/10.3390/molecules26216718 - 6 Nov 2021
Cited by 12 | Viewed by 2564
Abstract
Qingzhuan tea (QZT) is a typical Chinese dark tea that has a long-time manufacturing process. In the present study, liquid chromatography coupled with tandem mass spectrometry was used to study the chemical changes of tea samples during QZT processing. Untargeted metabolomics analysis revealed [...] Read more.
Qingzhuan tea (QZT) is a typical Chinese dark tea that has a long-time manufacturing process. In the present study, liquid chromatography coupled with tandem mass spectrometry was used to study the chemical changes of tea samples during QZT processing. Untargeted metabolomics analysis revealed that the pile-fermentation and turnover (post-fermentation, FT) was the crucial stage in transforming the main compounds of QZT, whose contents of flavan-3-ols and flavonoids glycosides were decreased significantly. The bioactivities, including the antioxidant capacities and inhibitory effects on α-amylase and α-glucosidase, were also reduced after the FT process. It was suggested that although the QZT sensory properties improved following pile-fermentation and aging, the bioactivities remained restrained. Correlation analysis indicated that the main galloylated catechins and flavonoid glycosides were highly related to their antioxidant capacity and inhibitory effects on α-amylase and α-glucosidase. Full article
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16 pages, 711 KiB  
Article
Influence of In Vitro Human Digestion Simulation on the Phenolics Contents and Biological Activities of the Aqueous Extracts from Turkish Cistus Species
by Yiğit İnan, Selin Akyüz, Inci Kurt-Celep, Engin Celep and Erdem Yesilada
Molecules 2021, 26(17), 5322; https://doi.org/10.3390/molecules26175322 - 1 Sep 2021
Cited by 8 | Viewed by 2754
Abstract
Oxidative stress is one of the significant precursors of various metabolic diseases such as diabetes, Parkinson’s disease, cardiovascular diseases, cancer, etc. Various scientific reports have indicated that secondary plant metabolites play an important role in preventing oxidative stress and its harmful effects. In [...] Read more.
Oxidative stress is one of the significant precursors of various metabolic diseases such as diabetes, Parkinson’s disease, cardiovascular diseases, cancer, etc. Various scientific reports have indicated that secondary plant metabolites play an important role in preventing oxidative stress and its harmful effects. In this respect, this study was planned to investigate the phenolic profile and antioxidant and antidiabetic potentials of the aqueous extracts from Turkish Cistus species by employing in vitro methods. In vitro digestion simulation procedure was applied to all extracts to estimate the bioavailability of their phenolic contents. Total phenolic, flavonoid, phenolic acid and proanthocyanidin contents were determined for all phases of digestion. In addition, changes in the quantity of the assigned marker flavonoids (tiliroside, hyperoside and quercitrin) were monitored by High-Performance Thin Layer Chromatography (HPTLC) analysis. The antioxidant activity potentials of the extracts were studied by various methods to reveal their detailed activity profiles. On the other hand, in vitro α-amylase and α-glucosidase enzymes and advanced-glycation end product (AGE) inhibitory activities of the extracts were determined to evaluate the antidiabetic potentials of extracts. The results showed that aqueous extracts obtained from the aerial parts of Turkish Cistus species have rich phenolic contents and potential antioxidant and antidiabetic activities; however, their bioactivity profiles and marker flavonoid concentrations might significantly be affected by human digestion. The results exhibited that total phenolic contents, antioxidant activities and diabetes-related enzyme inhibitions of the bioavailable samples were lower than non-digested samples in all extracts. Full article
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20 pages, 4427 KiB  
Article
Unravelling the Phytochemical Composition and the Pharmacological Properties of an Optimized Extract from the Fruit from Prunus mahaleb L.: From Traditional Liqueur Market to the Pharmacy Shelf
by Giustino Orlando, Annalisa Chiavaroli, Sabrina Adorisio, Domenico V. Delfino, Luigi Brunetti, Lucia Recinella, Sheila Leone, Gokhan Zengin, Alessandra Acquaviva, Paola Angelini, Giancarlo Angeles Flores, Roberto Venanzoni, Simonetta Cristina Di Simone, Francesca Di Corpo, Andrei Mocan, Luigi Menghini and Claudio Ferrante
Molecules 2021, 26(15), 4422; https://doi.org/10.3390/molecules26154422 - 22 Jul 2021
Cited by 14 | Viewed by 3664
Abstract
Prunus mahaleb L. fruit has long been used in the production of traditional liqueurs. The fruit also displayed scavenging and reducing activity, in vitro. The present study focused on unravelling peripheral and central protective effects, antimicrobial but also anti-COVID-19 properties exerted by the [...] Read more.
Prunus mahaleb L. fruit has long been used in the production of traditional liqueurs. The fruit also displayed scavenging and reducing activity, in vitro. The present study focused on unravelling peripheral and central protective effects, antimicrobial but also anti-COVID-19 properties exerted by the water extract of P. mahaleb. Anti-inflammatory effects were studied in isolated mouse colons exposed to lipopolysaccharide. Neuroprotection, measured as a blunting effect on hydrogen-peroxide-induced dopamine turnover, was investigated in hypothalamic HypoE22 cells. Antimicrobial effects were tested against different Gram+ and Gram- bacterial strains. Whereas anti-COVID-19 activity was studied in lung adenocarcinoma H1299 cells, where the gene expression of ACE2 and TMPRSS2 was measured after extract treatment. The bacteriostatic effects induced on Gram+ and Gram- strains, together with the inhibition of COX-2, TNFα, HIF1α, and VEGFA in the colon, suggest the potential of P. mahaleb water extract in contrasting the clinical symptoms related to ulcerative colitis. The inhibition of the hydrogen peroxide-induced DOPAC/DA ratio indicates promising neuroprotective effects. Finally, the downregulation of the gene expression of ACE2 and TMPRSS2 in H1299 cells, suggests the potential to inhibit SARS-CoV-2 virus entry in the human host. Overall, the results support the valorization of the local cultivation of P. mahaleb. Full article
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Review

Jump to: Research

10 pages, 6050 KiB  
Review
Gelsemium elegans Benth: Chemical Components, Pharmacological Effects, and Toxicity Mechanisms
by Hailing Lin, Hongqiang Qiu, Yu Cheng, Maobai Liu, Maohua Chen, Youxiong Que and Wancai Que
Molecules 2021, 26(23), 7145; https://doi.org/10.3390/molecules26237145 - 25 Nov 2021
Cited by 27 | Viewed by 3302
Abstract
Gelsemium elegans Benth (GEB), also known as heartbreak grass, is a highly poisonous plant belonging to the family Loganiaceae and genus Gelsemium that has broad application prospects in medicine. This article reviews its chemical components, pharmacological effects, toxicity mechanisms, and research progress in [...] Read more.
Gelsemium elegans Benth (GEB), also known as heartbreak grass, is a highly poisonous plant belonging to the family Loganiaceae and genus Gelsemium that has broad application prospects in medicine. This article reviews its chemical components, pharmacological effects, toxicity mechanisms, and research progress in clinical applications in recent years. Indole alkaloids are the main active components of GEB and have a variety of pharmacological and biological functions. They have anti-tumor, anti-inflammatory, analgesic, and immunomodulation properties, with the therapeutic dose being close to the toxic dose. Application of small-dose indole alkaloids fails to work effectively, while high-dose usage is prone to poisoning, aggravating the patient’s conditions. Special caution is needed, especially to observe the changes in the disease condition of the patients in clinical practice. In-depth research on the chemical components and mechanisms of GEB is essential to the development of promising lead compounds and lays the foundation for extensive clinical application and safe usage of GEB in the future. Full article
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