Editorial

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Open AccessEditorial

Flavonoid Functions in Plants and Their Interactions with Other Organisms

by Ulrike Mathesius

Plants 2018, 7(2), 30; https://doi.org/10.3390/plants7020030 - 03 Apr 2018

Cited by 149 | Viewed by 9719

Flavonoids are structurally diverse secondary metabolites in plants, with a multitude of functions. These span from functions in regulating plant development, pigmentation, and UV protection, to an array of roles in defence and signalling between plants and microorganisms. Because of their prevalence in [...] Read more.

Flavonoids are structurally diverse secondary metabolites in plants, with a multitude of functions. These span from functions in regulating plant development, pigmentation, and UV protection, to an array of roles in defence and signalling between plants and microorganisms. Because of their prevalence in the human diet, many flavonoids constitute important components of medicinal plants and are used in the control of inflammation and cancer prevention. Advances in the elucidation of flavonoid biosynthesis and its regulation have led to an increasing number of studies aimed at engineering the flavonoid pathway for enhancing nutritional value and plant defences against pathogens and herbivores, as well as modifying the feeding value of pastures. Many future opportunities await for the exploitation of this colourful pathway in crops, pastures, and medicinal plants. Full article

(This article belongs to the Special Issue Plant Flavonoids)

Research

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999 KiB

Open AccessArticle

The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity

by Andreas Douros, Dimitra Hadjipavlou-Litina, Konstantinos Nikolaou and Helen Skaltsa

Plants 2018, 7(1), 1; https://doi.org/10.3390/plants7010001 - 27 Dec 2017

Cited by 11 | Viewed by 5578

Abstract

The phytochemical analysis of the polar extracts of Cedrus brevifolia needles yielded 20 compounds, namely from the methanol extract we isolated three flavonoids (1–3), one hydrolysable tannin (4), eleven phenolic derivatives (5–15) and [...] Read more.

The phytochemical analysis of the polar extracts of Cedrus brevifolia needles yielded 20 compounds, namely from the methanol extract we isolated three flavonoids (1–3), one hydrolysable tannin (4), eleven phenolic derivatives (5–15) and one apocarotenoid (16), while from the methanol: water (5:1) extract we isolated four flavonoids (17–20). Chemical structures of all isolated compounds were determined by 1D, 2D-NMR (1 Dimension, 2 Dimensions Nuclear Magnetic Resonance) and UV-Vis (Ultraviolet-Visible) spectroscopy. Furthermore, the antioxidant potentials and the anti-inflammatory activities of both crude extracts and isolates were evaluated through DPPH radical scavenging capability, linoleic acid lipid peroxidation inhibition, and soybean LOX inhibition assays. This is the first report on the chemical profile of C. brevifolia needles. Catechin was the main compound derived from the methanol extract. According to our results, 4-O-β-d-glucopyranyl trans-p-coumaric acid and taxifolin were the most active ingredients. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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2390 KiB

Open AccessArticle

Flavonoids and Ellagitannins Characterization, Antioxidant and Cytotoxic Activities of Phyllanthus acuminatus Vahl

by Mirtha Navarro, Ileana Moreira, Elizabeth Arnaez, Silvia Quesada, Gabriela Azofeifa, Felipe Vargas, Diego Alvarado and Pei Chen

Plants 2017, 6(4), 62; https://doi.org/10.3390/plants6040062 - 15 Dec 2017

Cited by 23 | Viewed by 6161

Abstract

The phenolic composition of leaves from Phyllanthus acuminatus L., a plant commonly used in Costa Rica as traditional medicine, was studied using UPLC-ESI-MS on an enriched phenolic extract. A total of 20 phenolic compounds were identified, comprising eight flavonoids (two flavanones—pinocembrin isomers and [...] Read more.

The phenolic composition of leaves from Phyllanthus acuminatus L., a plant commonly used in Costa Rica as traditional medicine, was studied using UPLC-ESI-MS on an enriched phenolic extract. A total of 20 phenolic compounds were identified, comprising eight flavonoids (two flavanones—pinocembrin isomers and six derivatives from apigenin, chrysin, quercetin, and kaempferol); seven ellagitannins, two flavan-3-ols (prodelphinidin B dimer and (epi)gallocatechin); and three phenolic acids (ellagic acid, trimethylellagic acid, and ferulic acid). All of these compounds are reported for the first time in P. acuminatus, while previously reported in the genus Phyllanthus. Antioxidant evaluation was performed for P. acuminatus phenolic extract obtaining DPPH results with a remarkably low IC₅₀ value of 0.15 μg/mL. Also, cytotoxicity on gastric AGS and colon SW20 adenocarcinoma cell lines was evaluated, and highly promising results were obtained, with IC₅₀ values of 11.3 μg/mL and 10.5 μg/mL, respectively. Furthermore, selectivity index values obtained when comparing cytotoxicity on normal Vero cells was SI > 20 for both cancer cell lines, indicating a particularly high selectivity. Additionally, Justicidin B, a metabolite extensively studied for its antitumoral activity, was isolated from a non-polar extract of P. acuminatus, and comparatively evaluated for both bioactivities. The DPPH value obtained for Justicidin B was moderate (IC₅₀ = 14.28 μg/mL), while cytotoxicity values for both AGS (IC₅₀ = 19.5 μg/mL) and SW620 (IC₅₀ = 24.8 μg/mL) cell lines, as well as selectivity when compared with normal Vero cells (SI = 5.4 and 4.2 respectively), was good, but lower than P. acuminatus extract. These preliminary results suggest that P. acuminatus enriched phenolic extract containing flavonoids, ellagitannins, flavan-3-ols, and phenolic acids, reported for the first time in this plant, could be of interest for further cancer cytotoxicity studies to elucidate structure–bioactivity relationships, and the molecular mechanisms and pathways. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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761 KiB

Open AccessArticle

Phenylphenalenones Accumulate in Plant Tissues of Two Banana Cultivars in Response to Herbivory by the Banana Weevil and Banana Stem Weevil

by Dirk Hölscher, Andreas Buerkert and Bernd Schneider

Plants 2016, 5(3), 34; https://doi.org/10.3390/plants5030034 - 25 Aug 2016

Cited by 11 | Viewed by 6354

Abstract

Phenylphenalenone-type compounds accumulated in the tissues of two banana cultivars—Musa acuminata cv. “Grande Naine” (AAA) and Musa acuminata × balbisiana Colla cv. “Bluggoe” (ABB)—when these were fed on by the banana weevil (Cosmopolites sordidus (Germ.) (Coleoptera: Curculionidae)) and the banana stem [...] Read more.

Phenylphenalenone-type compounds accumulated in the tissues of two banana cultivars—Musa acuminata cv. “Grande Naine” (AAA) and Musa acuminata × balbisiana Colla cv. “Bluggoe” (ABB)—when these were fed on by the banana weevil (Cosmopolites sordidus (Germ.) (Coleoptera: Curculionidae)) and the banana stem weevil (Odoiporus longicollis (Oliver) (Coleoptera: Curculionidae)). The chemical constituents of the banana material were separated by means of chromatographic techniques and identified by NMR spectroscopy. One new compound, 2-methoxy-4-phenylphenalen-1-one, was found exclusively in the corm material of “Bluggoe” that had been fed on by the weevils. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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2267 KiB

Open AccessArticle

The Occurrence of Flavonoids and Related Compounds in Flower Sections of Papaver nudicaule

by Bettina Dudek, Anne-Christin Warskulat and Bernd Schneider

Plants 2016, 5(2), 28; https://doi.org/10.3390/plants5020028 - 22 Jun 2016

Cited by 34 | Viewed by 7981

Abstract

Flavonoids play an important role in the pigmentation of flowers; in addition, they protect petals and other flower parts from UV irradiation and oxidative stress. Nudicaulins, flavonoid-derived indole alkaloids, along with pelargonidin, kaempferol, and gossypetin glycosides, are responsible for the color of white, [...] Read more.

Flavonoids play an important role in the pigmentation of flowers; in addition, they protect petals and other flower parts from UV irradiation and oxidative stress. Nudicaulins, flavonoid-derived indole alkaloids, along with pelargonidin, kaempferol, and gossypetin glycosides, are responsible for the color of white, red, orange, and yellow petals of different Papaver nudicaule cultivars. The color of the petals is essential to attract pollinators. We investigated the occurrence of flavonoids in basal and apical petal areas, stamens, and capsules of four differently colored P. nudicaule cultivars by means of chromatographic and spectroscopic methods. The results reveal the specific occurrence of gossypetin glycosides in the basal spot of all cultivars and demonstrate that kaempferol glycosides are the major secondary metabolites in the capsules. Unlike previous reports, the yellow-colored stamens of all four P. nudicaule cultivars are shown to contain not nudicaulins but carotenoids. In addition, the presence of nudicaulins, pelargonidin, and kaempferol glycosides in the apical petal area was confirmed. The flavonoids and related compounds in the investigated flower parts and cultivars of P. nudicaule are profiled, and their potential ecological role is discussed. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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Review

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609 KiB

Open AccessReview

Flavonoids and Phenolic Acids from Oregano: Occurrence, Biological Activity and Health Benefits

by Erick P. Gutiérrez-Grijalva, Manuel A. Picos-Salas, Nayely Leyva-López, Marilyn S. Criollo-Mendoza, Gabriela Vazquez-Olivo and J. Basilio Heredia

Plants 2018, 7(1), 2; https://doi.org/10.3390/plants7010002 - 26 Dec 2017

Cited by 165 | Viewed by 24711

Abstract

Several herb species classified as oregano have been widely used in folk medicine to alleviate inflammation-related diseases, respiratory and digestive disorders, headaches, rheumatism, diabetes and others. These potential health benefits are partially attributed to the phytochemical compounds in oregano such as flavonoids (FL) [...] Read more.

Several herb species classified as oregano have been widely used in folk medicine to alleviate inflammation-related diseases, respiratory and digestive disorders, headaches, rheumatism, diabetes and others. These potential health benefits are partially attributed to the phytochemical compounds in oregano such as flavonoids (FL) and phenolic acids (PA). Flavonoids and phenolic acids are among the most abundant and most studied phytochemicals in oregano species. Epidemiological, in vitro and in vivo experiments have related long-term consumption of dietary FL and PA with a decreased risk of incidence of chronic diseases. The aim of this manuscript is to summarize the latest studies on the identification and distribution of flavonoids and phenolic compounds from oregano species and their potential antioxidant, anti-inflammatory and anti-cancer health benefits. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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2917 KiB

Open AccessReview

TRANSPARENT TESTA GLABRA 1-Dependent Regulation of Flavonoid Biosynthesis

by Bipei Zhang and Andrea Schrader

Plants 2017, 6(4), 65; https://doi.org/10.3390/plants6040065 - 20 Dec 2017

Cited by 55 | Viewed by 7749

Abstract

The flavonoid composition of various tissues throughout plant development is of biological relevance and particular interest for breeding. Arabidopsis thaliana TRANSPARENT TESTA GLABRA 1 (AtTTG1) is an essential regulator of late structural genes in flavonoid biosynthesis. Here, we provide a review of the [...] Read more.

The flavonoid composition of various tissues throughout plant development is of biological relevance and particular interest for breeding. Arabidopsis thaliana TRANSPARENT TESTA GLABRA 1 (AtTTG1) is an essential regulator of late structural genes in flavonoid biosynthesis. Here, we provide a review of the regulation of the pathway’s core enzymes through AtTTG1-containing R2R3-MYELOBLASTOSIS-basic HELIX-LOOP-HELIX-WD40 repeat (MBW(AtTTG1)) complexes embedded in an evolutionary context. We present a comprehensive collection of A. thaliana ttg1 mutants and AtTTG1 orthologs. A plethora of MBW(AtTTG1) mechanisms in regulating the five major TTG1-dependent traits is highlighted. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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663 KiB

Open AccessFeature PaperReview

Flavonoid Profile of the Cotton Plant, Gossypium hirsutum: A Review

by Aaron Nix, Cate Paull and Michelle Colgrave

Plants 2017, 6(4), 43; https://doi.org/10.3390/plants6040043 - 25 Sep 2017

Cited by 54 | Viewed by 8887

Abstract

Cotton, Gossypium hirsutum L., is a plant fibre of significant economic importance, with seeds providing an additional source of protein in human and animal nutrition. Flavonoids play a vital role in maintaining plant health and function and much research has investigated the role [...] Read more.

Cotton, Gossypium hirsutum L., is a plant fibre of significant economic importance, with seeds providing an additional source of protein in human and animal nutrition. Flavonoids play a vital role in maintaining plant health and function and much research has investigated the role of flavonoids in plant defence and plant vigour and the influence these have on cotton production. As part of ongoing research into host plant/invertebrate pest interactions, we investigated the flavonoid profile of cotton reported in published, peer-reviewed literature. Here we report 52 flavonoids representing seven classes and their reported distribution within the cotton plant. We briefly discuss the historical research of flavonoids in cotton production and propose research areas that warrant further investigation. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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993 KiB

Open AccessReview

The Role of Flavonoids in Nodulation Host-Range Specificity: An Update

by Cheng-Wu Liu and Jeremy D. Murray

Plants 2016, 5(3), 33; https://doi.org/10.3390/plants5030033 - 11 Aug 2016

Cited by 200 | Viewed by 11668

Abstract

Flavonoids are crucial signaling molecules in the symbiosis between legumes and their nitrogen-fixing symbionts, the rhizobia. The primary function of flavonoids in the interaction is to induce transcription of the genes for biosynthesis of the rhizobial signaling molecules called Nod factors, which are [...] Read more.

Flavonoids are crucial signaling molecules in the symbiosis between legumes and their nitrogen-fixing symbionts, the rhizobia. The primary function of flavonoids in the interaction is to induce transcription of the genes for biosynthesis of the rhizobial signaling molecules called Nod factors, which are perceived by the plant to allow symbiotic infection of the root. Many legumes produce specific flavonoids that only induce Nod factor production in homologous rhizobia, and therefore act as important determinants of host range. Despite a wealth of evidence on legume flavonoids, relatively few have proven roles in rhizobial infection. Recent studies suggest that production of key “infection” flavonoids is highly localized at infection sites. Furthermore, some of the flavonoids being produced at infection sites are phytoalexins and may have a role in the selection of compatible symbionts during infection. The molecular details of how flavonoid production in plants is regulated during nodulation have not yet been clarified, but nitrogen availability has been shown to play a role. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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1914 KiB

Open AccessReview

Flavones: From Biosynthesis to Health Benefits

by Nan Jiang, Andrea I. Doseff and Erich Grotewold

Plants 2016, 5(2), 27; https://doi.org/10.3390/plants5020027 - 21 Jun 2016

Cited by 214 | Viewed by 19648

Abstract

Flavones correspond to a flavonoid subgroup that is widely distributed in the plants, and which can be synthesized by different pathways, depending on whether they contain C- or O-glycosylation and hydroxylated B-ring. Flavones are emerging as very important specialized metabolites involved [...] Read more.

Flavones correspond to a flavonoid subgroup that is widely distributed in the plants, and which can be synthesized by different pathways, depending on whether they contain C- or O-glycosylation and hydroxylated B-ring. Flavones are emerging as very important specialized metabolites involved in plant signaling and defense, as well as key ingredients of the human diet, with significant health benefits. Here, we appraise flavone formation in plants, emphasizing the emerging theme that biosynthesis pathway determines flavone chemistry. Additionally, we briefly review the biological activities of flavones, both from the perspective of the functions that they play in biotic and abiotic plant interactions, as well as their roles as nutraceutical components of the human and animal diet. Full article

(This article belongs to the Special Issue Plant Flavonoids)

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