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Flavonoids: From Structure to Health Issues II

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

Deadline for manuscript submissions: closed (15 November 2019) | Viewed by 57069

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Dr. Celestino Santos-Buelga

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Department of “Nutrición y Bromatología” (Food Science and Nutrition), Facultad de Farmacia, Universidad de Salamanca (Spain), Campus Miguel de Unamuno, E37007 Salamanca, Spain
Interests: food; phenolic compounds; anthocyanins; flavonoids; metabolites; biological activity; health implication
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Ana M. González-Paramás

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Grupo de Investigación en Polifenoles (GIP-USAL), Campus Miguel de Unamuno, Facultad de Farmacia, Universidad de Salamanca, E-37007 Salamanca, Spain
Interests: polyphenols; flavonoids; products of the hive (honey and bee-pollen); health implications; biological activity; C. elegans

Special Issue Information

Dear colleagues,

Owing to the great success of the Molecules Special Issue on "Flavonoids: from Structure to Health Issues" (https://www.mdpi.com/journal/molecules/special_issues/flavonoids) with 31 published articles over 2017 accumulating more than 300 citations, a second edition is now being prepared.

As for the previous edition, a wide scope of hot topics in current flavonoid research is intended to be covered, from the physico-chemical to biological properties. The main but not exclusive subjects that will be addressed are advanced extraction and analysis, structural characterization, synthesis, influence on the technological and sensory properties of food, interest as nutraceuticals and functional food ingredients, dietary intake or health implications. Particular focus will be placed on novel methodological approaches in the study of the bioavailability, metabolism and molecular mechanisms involved in the biological effects of flavonoids, such as omics techniques, assays in model organisms, and interactions with the intestinal microbiota.

We invite you to participate in this new Special Issue by submitting a contribution from your field of expertise regarding flavonoids, in the form of either an original research article, a short communication or a specialized critical review, although in this latter case the subject must be previously agreed, to prevent possible overlapping topics.

We thank you in advance for your interest and cooperation and look forward to hearing from you.

Kindest regards,

Prof. Celestino Santos-Buelga
Prof. Ana M. González-Paramás
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

Advanced extraction and analysis
Structural characterization
Synthesis of flavonoids and metabolites
Sensory properties
Nutraceuticals and functional foods
Dietary intake
Health implications
Bioavailability and metabolism
Molecular mechanisms of activity
Omics approaches
Model organisms
Interactions with the intestinal microbiota.

Related Special Issue

Flavonoids: From Structure to Health Issues in Molecules (41 articles)

Published Papers (10 papers)

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Research

Jump to: Review

17 pages, 1716 KiB

Open AccessArticle

Adsorption and Desorption Properties of Total Flavonoids from Oil Palm (Elaeis guineensis Jacq.) Mature Leaf on Macroporous Adsorption Resins

by Mohamad Shazeli Che Zain , Soo Yee Lee, Chian Ying Teo and Khozirah Shaari

Molecules 2020, 25(4), 778; https://doi.org/10.3390/molecules25040778 - 11 Feb 2020

Cited by 43 | Viewed by 5662

Abstract

Three different macroporous resins (XAD7HP, DAX-8, and XAD4) were evaluated for their adsorption and desorption properties in preparing flavonoid-enriched oil palm (Elaeis guineensis Jacq.) leaf extract. The influences of initial concentration, solution pH, contact time, and desorption solvent (ethanol) concentration were determined by static sorption/desorption methods. The optimal condition for adsorption of flavonoids was achieved when the solution of the extract was adjusted to pH 7, reaching equilibrium after 1440 min at 298 K. The adsorption process was well described by a pseudo-second-order kinetics model, while the adsorption isotherm data fitted well with a Freundlich model. The adsorption by each resin was via an exothermic and physical adsorption process. Based on the static experiment results, XAD7HP was found to be the most appropriate adsorbent, while 80% ethanol was the best solvent for desorbent. Further evaluation of its dynamic adsorption and desorption characteristics on a packed glass column showed that XAD7HP could enrich the OPL total flavonoid content by a 3.57-fold increment. Moreover, UHPLC–UV/PDA and UHPLC–MS/MS analysis revealed that apigenin and luteolin derivatives were selectively adsorbed by XAD7HP. Additionally, both the crude OPL extract and the flavonoid-enriched fraction have good DPPH and NO free radical scavenging activities. Multiple interactions between the flavonoids and cross-linked polymeric XAD7HP resin through van der Waals forces and hydrogen bonding described the sorption processes. Therefore, by utilizing this method, the flavonoid-enriched fraction from crude OPL extract could be used as a potential bioactive ingredient in nutraceutical and pharmaceutical applications at minimum cost with optimum efficiency. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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14 pages, 14877 KiB

Open AccessArticle

Study on Structure Activity Relationship of Natural Flavonoids against Thrombin by Molecular Docking Virtual Screening Combined with Activity Evaluation In Vitro

by Xiaoyan Wang, Zhen Yang, Feifei Su, Jin Li, Evans Owusu Boadi, Yan-xu Chang and Hui Wang

Molecules 2020, 25(2), 422; https://doi.org/10.3390/molecules25020422 - 20 Jan 2020

Cited by 23 | Viewed by 6181

Abstract

Thrombin, a key enzyme of the serine protease superfamily, plays an integral role in the blood coagulation cascade and thrombotic diseases. In view of this, it is worthwhile to establish a method to screen thrombin inhibitors (such as natural flavonoid-type inhibitors) as well as investigate their structure activity relationships. Virtual screening using molecular docking technique was used to screen 103 flavonoids. Out of this number, 42 target compounds were selected, and their inhibitory effects on thrombin assayed by chromogenic substrate method. The results indicated that the carbon-carbon double bond group at the C2, C3 sites and the carbonyl group at the C4 sites of flavones were essential for thrombin inhibition, whereas the methoxy and O-glycosyl groups reduced thrombin inhibition. Noteworthy, introduction of OH groups at different positions on flavonoids either decreased or increased anti-thrombin potential. Myricetin exhibited the highest inhibitory potential against thrombin with an IC₅₀ value of 56 μM. Purposively, the established molecular docking virtual screening method is not limited to exploring flavonoid structure activity relationships to anti-thrombin activity but also usefully discovering other natural active constituents. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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17 pages, 3306 KiB

Open AccessArticle

Polyphenol Extracts from Three Colombian Passifloras (Passion Fruits) Prevent Inflammation-Induced Barrier Dysfunction of Caco-2 Cells

by Juan Carlos Carmona-Hernandez, Gonzalo Taborda-Ocampo, Jonathan C. Valdez, Bradley W. Bolling and Clara Helena González-Correa

Molecules 2019, 24(24), 4614; https://doi.org/10.3390/molecules24244614 - 17 Dec 2019

Cited by 30 | Viewed by 4643

Abstract

Chronic intestinal inflammation is associated with pathophysiology of obesity and inflammatory bowel diseases. Gastrointestinal inflammation increases barrier dysfunction exacerbating the immune response and perpetuating chronic inflammation. Anti-inflammatory flavonoids may prevent this intestinal barrier dysfunction. The purpose of this study was to evaluate the polyphenol composition of Colombian Passiflora edulis var. Flavicarpa (Maracuyá), Passiflora edulis var. Sims (Gulupa), and Passiflora ligularis var. Juss (Granadilla) (passion fruits) and to evaluate their ability to inhibit disruption of intestinal barrier dysfunction of Caco-2 (colorectal adenocarcinoma) cells by an inflammatory cocktail (IC). Polyphenols (flavan-3-ols, phenolic acids, flavonols), xanthenes, and a terpene were identified in passion fruits. Cyanidin 3-rutinoside, (+)-catechin and ferulic acid were the most abundant phenolics in P. edulis var. Flavicarpa, P. edulis var. Sims, and P. ligularis var. Juss, respectively. Fruit extracts prevented loss of transepithelial electrical resistance in Caco-2 cells treated with the IC. Among the extracts, P. ligularis var. Juss was most effective at maintaining Caco-2 transepithelial electrical resistance (TEER) with ~73% relative to the IC-treated cells with about 43% of initial TEER values. This fruit had cyanidin-3-rutinoside, (+)-catechin, (−)-epicatechin, and ferulic acid in its phenolic profile. Results of this work support the hypothesis that consumption of passion fruit extracts could benefit intestinal health. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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24 pages, 5249 KiB

Open AccessArticle

Grape Berry Flavonoid Responses to High Bunch Temperatures Post Véraison: Effect of Intensity and Duration of Exposure

by Julia C. Gouot, Jason P. Smith, Bruno P. Holzapfel and Celia Barril

Molecules 2019, 24(23), 4341; https://doi.org/10.3390/molecules24234341 - 27 Nov 2019

Cited by 11 | Viewed by 3863

Abstract

Climate models predict an increase in the frequency and duration of heatwaves with an increase in intensity already strongly evident worldwide. The aim of this work was to evaluate the effect of two heatwave-related parameters (intensity and duration) during berry ripening and identify a threshold for berry survival and flavonoid accumulation. A Doehlert experimental design was used to test three temperature intensities (maxima of 35, 46, and 54 °C) and five durations (3 to 39 h), with treatments applied at the bunch level shortly after véraison. Berry skin and seeds were analysed by liquid chromatography-triple quadrupole-mass spectrometry (LC-QqQ-MS) for flavonoids (flavonols, anthocyanins, free flavan-3-ols, and tannins). Berries exposed to 46 °C showed little difference compared to 35 °C. However, berries reaching temperatures around 54 °C were completely desiccated, and all flavonoids were significantly decreased except for skin flavonols on a per berry basis and seed tannins in most cases. Some compounds, such as dihydroxylated flavonoids and galloylated flavan-3-ols (free and polymerised), were in higher proportion in damaged berries suggesting they were less degraded or more synthesised upon heating. Overall, irreversible berry damages and substantial compositional changes were observed and the berry survival threshold was estimated at around 50–53 °C for mid-ripe Shiraz berries, regardless of the duration of exposure. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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17 pages, 1950 KiB

Open AccessArticle

Novel Flavonoid Glycosides of Quercetin from Leaves and Flowers of Gaiadendron punctatum G.Don. (Violeta de Campo), used by the Saraguro Community in Southern Ecuador, Inhibit α-Glucosidase Enzyme

by Héctor Cedeño, Sandra Espinosa, José Miguel Andrade, Luis Cartuche and Omar Malagón

Molecules 2019, 24(23), 4267; https://doi.org/10.3390/molecules24234267 - 22 Nov 2019

Cited by 15 | Viewed by 4383

Abstract

Gaiadandendron punctatum G.Don. (violeta de campo) is a plant used in traditional medicine by the Saraguro people, an ancient indigenous group that lives in southern Ecuador. From samples collected in the region, six glycoside flavonoids, five with quercetin and one with kaempferol as aglycon, were isolated and characterized from hydroalcoholic extracts of leaves and flowers. Rutin (2) was found in flowers and leaves, nicotiflorin (1) was found in flowers, artabotryside A (3) was found in leaves, and three novel quercetin flavonoid glycosides were isolated, elucidated, and characterized via 1D and 2D NMR experiments (¹H, ¹³C, COSY, DEPT, HMBC, HSQC, TOCSY, NOESY, ROESY), acid hydrolysis–derivatization–GC-MS analysis, HPLC-MS, IR, UV, and optical rotation. The new quercetin flavonoid glycosides were named hecpatrin (4) (isolated from leaves), gaiadendrin (5) (isolated from leaves), and puchikrin (6) (isolated from flowers). The hydroalcoholic extracts of the leaves presented antimicrobial activity against Micrococcus luteus, Staphylococcus aureus, and Enterococcus faecalis and the hydroalcoholic extract of the flowers was active against Micrococcus luteus. However, glycoside flavonoids presented scarce antimicrobial activity against bacteria. Hydroalcoholic extracts from leaves and flowers and their secondary metabolites showed inhibition against the α-glucosidase enzyme at different concentrations. Rutin, gaiadendrin, and nicotiflorin showed competitive α-glucosidase inhibition, while hecpatrin presented non-competitive inhibition. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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12 pages, 2232 KiB

Open AccessArticle

Antibacterial Activity and Molecular Docking Studies of a Selected Series of Hydroxy-3-arylcoumarins

by Maria Barbara Pisano, Amit Kumar, Rosaria Medda, Gianluca Gatto, Rajesh Pal, Antonella Fais, Benedetta Era, Sofia Cosentino, Eugenio Uriarte, Lourdes Santana, Francesca Pintus and Maria João Matos

Molecules 2019, 24(15), 2815; https://doi.org/10.3390/molecules24152815 - 01 Aug 2019

Cited by 61 | Viewed by 8937

Abstract

Antibiotic resistance is one of the main public health concerns of this century. This resistance is also associated with oxidative stress, which could contribute to the selection of resistant bacterial strains. Bearing this in mind, and considering that flavonoid compounds are well known for displaying both activities, we investigated a series of hydroxy-3-arylcoumarins with structural features of flavonoids for their antibacterial activity against different bacterial strains. Active compounds showed selectivity against the studied Gram-positive bacteria compared to Gram-negative bacteria. 5,7-Dihydroxy-3-phenylcoumarin (compound 8) displayed the best antibacterial activity against Staphylococcus aureus and Bacillus cereus with minimum inhibitory concentrations (MICs) of 11 μg/mL, followed by Staphylococcus aureus (MRSA strain) and Listeria monocytogenes with MICs of 22 and 44 μg/mL, respectively. Moreover, molecular docking studies performed on the most active compounds against Staphylococcus aureus tyrosyl-tRNA synthetase and topoisomerase II DNA gyrase revealed the potential binding mode of the ligands to the site of the appropriate targets. Preliminary structure–activity relationship studies showed that the antibacterial activity can be modulated by the presence of the 3-phenyl ring and by the position of the hydroxyl groups at the coumarin scaffold. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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12 pages, 2824 KiB

Open AccessArticle

Analysis of Flavonoid Metabolites in Citrus Peels (Citrus reticulata “Dahongpao”) Using UPLC-ESI-MS/MS

by Fu Wang, Lin Chen, Hongping Chen, Shiwei Chen and Youping Liu

Molecules 2019, 24(15), 2680; https://doi.org/10.3390/molecules24152680 - 24 Jul 2019

Cited by 101 | Viewed by 8273

Abstract

Flavonoids are a kind of essential substance for the human body because of their antioxidant properties and extremely high medicinal value. Citrus reticulata “Dahongpao” (DHP) is a special citrus variety that is rich in flavonoids, however little is known about its systematic flavonoids profile. In the present study, the presence of flavonoids in five important citrus varieties, including DHP, Citrus grandis Tomentosa (HZY), Citrus ichangensis Swingle (YCC), Citrus sinensis (L.) Osbeck (TC), and Citrus reticulata ‘Buzhihuo’ (BZH), was determined using a UPLC-ESI-MS/MS-based, widely targeted metabolome. Results showed that a total of 254 flavonoid metabolites (including 147 flavone, 39 flavonol, 21 flavanone, 24 anthocyanins, 8 isoflavone, and 15 polyphenol) were identified. The total flavonoid content of peels from DHP was the highest. DHP could be clearly separated from other samples through clustering analysis and principal component analysis (PCA). Further, 169 different flavonoid metabolites were observed between DHP peels and the other four citrus peels, and 26 down-regulated differential metabolites displayed important biological activities in DHP. At the same time, a unique flavonoid component, tricin 4′-O-syringyl alcohol, was only found in DHP, which could be used as a marker to distinguish between other varieties. This work might facilitate a better understanding of flavonoid metabolites between DHP peels and the other four citrus peels and provide a reference for its sufficient utilization in the future. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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12 pages, 2328 KiB

Open AccessArticle

Velutin, an Aglycone Extracted from Korean Mistletoe, with Improved Inhibitory Activity against Melanin Biosynthesis

by Se-Hui Jung, Jaehyun Kim, Juneyong Eum, Jung Won Choe, Hak Hyun Kim, Yun Kee and Kooyeon Lee

Molecules 2019, 24(14), 2549; https://doi.org/10.3390/molecules24142549 - 12 Jul 2019

Cited by 12 | Viewed by 3728

Abstract

The abnormal regulation of melanin synthesis leads to a wide range of pigmentary disorders. Although various melanin biosynthesis inhibitors have been developed, their efficacy and long-term safety needs to be further improved, and thus the goal of this study is to develop promising natural compound inhibitors of melanin biosynthesis. Here, we obtained aglycone flavonoid extract through the microwave-assisted hydrolysis of glycoside extract from Korean mistletoe in acidic condition. The aglycone extract inhibited tyrosinase activity more efficiently with better antioxidant activity than glycoside extract in vitro. The microwave-assisted aglycone extract of mistletoe was further analyzed for in vivo activity, and the results showed the aglycone extract inhibited both early melanocyte development and melanin synthesis more efficiently in zebrafish embryo in a dose-dependent manner. Our in vivo toxicity assay quantitatively measured cell death in zebrafish embryos and showed that the microwave-assisted aglycone extract of mistletoe had no significant effect on cell death (p < 0.001), indicating that aglycone extract is more biocompatible than glycoside extract. Furthermore, our in vitro and in vivo analyses successfully identified and characterized velutin, an aglycone of a homoflavoyadorinin B glycoside, as a major inhibitory component in the microwave-assisted mistletoe extract. Ultimately, this study showed that the novel natural compound inhibitor velutin, which was generated through microwave-assisted extraction from mistletoe, improved the efficacy of melanin biosynthesis inhibition with little toxicity. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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14 pages, 1008 KiB

Open AccessArticle

Flavonoid Composition of Salacia senegalensis (Lam.) DC. Leaves, Evaluation of Antidermatophytic Effects, and Potential Amelioration of the Associated Inflammatory Response

by Nelson G. M. Gomes, Andreia P. Oliveira, Diana Cunha, David M. Pereira, Patrícia Valentão, Eugénia Pinto, Luísa Araújo and Paula B. Andrade

Molecules 2019, 24(14), 2530; https://doi.org/10.3390/molecules24142530 - 10 Jul 2019

Cited by 15 | Viewed by 3974

Abstract

Predominantly spread in West Tropical Africa, the shrub Salacia senegalensis (Lam.) DC. is known because of its medicinal properties, the leaves being used in the treatment of skin diseases. Prompted by the ethnomedicinal use, a hydroethanolic extract obtained from the leaves of the plant was screened against a panel of microbial strains, the majority of which involved in superficial infections. The extract was found to be active against the dermatophytes Trichophyton rubrum and Epidermophyton floccosum. Notable results were also recorded regarding the attenuation of the inflammatory response, namely the inhibitory effects observed against soybean 5-lipoxygenase (IC₅₀ = 71.14 μg mL⁻¹), no interference being recorded in the cellular viability of RAW 264.7 macrophages and NO levels. Relevantly, the extract did not lead to detrimental effects against the keratinocyte cell line HaCaT, at concentrations displaying antidermatophytic and anti-inflammatory effects. Flavonoid profiling of S. senegalensis leaves was achieved for the first time, allowing the identification and quantitation of myricitrin, three 3-O-substituted quercetin derivatives, and three other flavonoid derivatives, which may contribute, at least partially, to the observed antidermatophytic and anti-inflammatory effects. In the current study, the plant S. senegalensis is assessed concerning its antidermatophytic and anti-inflammatory properties. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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Review

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18 pages, 4723 KiB

Open AccessReview

Influence of Saccharomyces and non-Saccharomyces Yeasts in the Formation of Pyranoanthocyanins and Polymeric Pigments during Red Wine Making

by Antonio Morata, Carlos Escott, Iris Loira, Juan Manuel Del Fresno, Carmen González and Jose Antonio Suárez-Lepe

Molecules 2019, 24(24), 4490; https://doi.org/10.3390/molecules24244490 - 08 Dec 2019

Cited by 36 | Viewed by 6813

Abstract

Yeast are able to modulate many sensory parameters of wines during red must fermentation. The effect on color and on the formation of derived pigments during fermentation has been studied thoroughly since the 90s. Yeast can increase grape anthocyanin’s color by acidification by hyperchromic effect (increase of flavylium molecules). Recent studies with non-Saccharomyces species, as Lachancea thermotolerans, described the intense effect of some strains on anthocyanin’s color, and subsequent, stability, by strongly reducing wine’s pH during fermentation. Moreover, selected yeast strains of Saccharomyces have been shown to release metabolites such as pyruvic acid or acetaldehyde that promote the formation of vitisin A and B pyranoanthocyanins during must fermentation. Schizosaccharomyces pombe, because of its specific metabolism, can produce higher concentrations of pyruvate, which enhances the formation of vitisin A-type derivatives. The hydroxycinnamate decarboxylase activity that some Saccharomyces strains express during fermentation also promotes the formation of vinylphenolic derivatives. Some non-Saccharomyces species, such as S. pombe or P. guilliermondii can also improve the production of these derivatives compared to selected strains of Saccharomyces cerevisiae. Lastly, some yeasts are also able to modulate the formations of polymeric pigments between grape anthocyanins and flavonoids, such as catechins and procyanidins. Full article

(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues II)

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