Biosynthesis of flavonoids

Heller, Werner; Forkmann, G.

doi:10.1007/978-1-4899-2911-2_11

Cited by 136 publications

(121 citation statements)

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“…Aloysia gratissima was collected from the same location as B. prismatica and V. menthifolia (Table 1), where they are sympatric; therefore, they are exposed to the same environmental conditions. This suggests that the clearly different phenolic profiles (Figure 1) are the result of genetic specific differences, which command a species-specific sequential order in the phenolic biosynthesis, as Heller and Forkmann (1994) pointed out.…”

Section: )mentioning

confidence: 58%

Foliar phenolic compounds of ten wild species of Verbenacea as antioxidants and specific chemomarkers

et al. 2017

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The family Verbenaceae hosts important species used in traditional medicine of many countries. The taxonomic controversies concerning the specific delimitation of several of its species make it difficult to guarantee the botanical origin of herbal preparations based on species of this family. To contribute to the development of both specific chemomarkers and a quality control tool to authenticate the botanical origin of herbal preparations of Verbenacea species, we determined the foliar HPLC-DAD phenolic profiles and the antioxidant properties of 10 wild species of this family occurring in Mexico. The contents of phenols and flavonoids varied significantly among species. Priva mexicana showed the highest levels of total phenolics (53.4 mg g -1 dry tissue) and Verbena carolina had the highest levels of flavonoids (17.89 mg g -1 dry tissue). Relevant antioxidant properties revealed by antiradical and reducing power were found for the analyzed species. These properties varied significantly in a species-dependent manner. The phenolic compounds accumulated were flavones and phenolic acids. Flavones were the only type of flavonoids found. The results of a cluster analysis showed that the compounds were accumulated in species-specific profiles. The phenolic profiles are proposed as valuable chemomarkers that can become a useful tool for the quality control concerning the botanical origin of herbal medicinal preparations based on the species analyzed. In addition, phenolic profiles could contribute importantly to solve the taxonomic controversies concerning species delimitation in the family Verbenaceae.Keywords: Verbenacea, antioxidant activity, chemomarkers, flavones, phenolic profiles. Compostos fenólicos das folhas de dez especies selvagem de Verbenaceae como antioxidantes e quimiomarcadores específicos ResumoA família Verbenaceae compreende importantes espécies utilizadas na medicina popular de muitos países. As dificuldades taxonômicas relativas à delimitação específica de muitas das suas espécies face difícil a verificar a origem botânico das preparações herbales baseadas nas espécies desta família. Para fazer uma contribuição ao desenvolvimento de indicadores taxonômicos e dum método de controle de qualidade para verificar a origem botânico de preparações herbales das espécies de Verbenaceae, os perfis fenólicos, obtidos pares HPLC-DAD, e as atividades antioxidantes das folhas de 10 espécies selvagens Mexicanas desta família foram determinados. Os conteúdos dos compostos fenólicos totais e dos flavonoides foram significativamente diferentes entre as espécies. Priva mexicana apresentou a maior quantidade de compostos fenólicos totais (53.4 mg g -1 amostra seca) e Verbena carolina apresentou a maior quantidade de flavonoides (17.89 mg g -1 amostra seca). Verifica-se importantes propriedades antioxidantes, como os resultados dos ensaios da capacidade antiradical e do poder redutor indicaram. As propriedades antioxidantes foram significativamente diferentes entre as espécies. Verificou-se que os compostos fe...

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confidence: 58%

Foliar phenolic compounds of ten wild species of Verbenacea as antioxidants and specific chemomarkers

et al. 2017

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“…22: 2856-2871, August 2010, www.plantcell.org 2010 American Society of Plant Biologists et al, 2003. Importantly, the bioactivities of these compounds are greatly modulated by their glycon structures (Jü rgenliemk et al, 2003;Soundararajan et al, 2008).Glycosylation of flavonoids in plant cells usually takes place in a regio-(or position-)specific manner after the completion of aglycon biosynthesis (Heller and Forkmann, 1994), providing a basis for the structural diversification of these important metabolites. Glycosylation is catalyzed by glycosyltransferases (UGTs), which generally catalyze transfer of the glycosyl group from nucleoside diphosphate-activated sugars (e.g., UDP-sugars) to (A) Grapes (cv Cabernet Sauvignon) at a vineyard in the TOMI NO OKA Winery, Yamanashi Prefecture, Japan.…”

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confidence: 99%

Functional Differentiation of the Glycosyltransferases That Contribute to the Chemical Diversity of Bioactive Flavonol Glycosides in Grapevines (Vitis vinifera)

et al. 2010

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We identified two glycosyltransferases that contribute to the structural diversification of flavonol glycosides in grapevine (Vitis vinifera): glycosyltransferase 5 (Vv GT5) and Vv GT6. Biochemical analyses showed that Vv GT5 is a UDP-glucuronic acid:flavonol-3-O-glucuronosyltransferase (GAT), and Vv GT6 is a bifunctional UDP-glucose/UDP-galactose:flavonol-3-Oglucosyltransferase/galactosyltransferase. The Vv GT5 and Vv GT6 genes have very high sequence similarity (91%) and are located in tandem on chromosome 11, suggesting that one of these genes arose from the other by gene duplication. Both of these enzymes were expressed in accordance with flavonol synthase gene expression and flavonoid distribution patterns in this plant, corroborating their significance in flavonol glycoside biosynthesis. The determinant of the specificity of Vv GT5 for UDP-glucuronic acid was found to be Arg-140, which corresponded to none of the determinants previously identified for other plant GATs in primary structures, providing another example of convergent evolution of plant GAT. We also analyzed the determinants of the sugar donor specificity of Vv GT6. Gln-373 and Pro-19 were found to play important roles in the bifunctional specificity of the enzyme. The results presented here suggest that the sugar donor specificities of these Vv GTs could be determined by a limited number of amino acid substitutions in the primary structures of protein duplicates, illustrating the plasticity of plant glycosyltransferases in acquiring new sugar donor specificities. INTRODUCTIONGrapevine (Vitis vinifera) ( Figure 1A) has been one of the most important fruit crops from the beginning of human civilization (McGovern et al., 1997). Dietary intake of grapevine-based products results in diverse biological effects that are beneficial to human health, in part due to polyphenols, such as flavonoids (e.g., flavonols, proanthocyanidins, and anthocyanins) (Renaud and de Lorgeril, 1992;Corder et al., 2001Corder et al., , 2006Baur et al., 2006). Flavonols, such as kaempferol, quercetin, and isorhamnetin, are an important class of bioactive flavonoids, which are most abundant as their 3-O-glycosides (i.e., glucoside, glucuronoside, galactoside, and rutinoside) in the berries, seeds, and leaves of grapevine (Hmamouchi et al., 1996;Castillo-Munoz et al., 2009).In this plant, biosynthesis of flavonol glycosides primarily serves to protect the plant from excess UV light (Price et al., 1995;Matus et al., 2009). Flavonol aglycons are biosynthesized from dihydroflavonols by the action of flavonol synthase (Vv FLS), a 2-oxoglutarate-dependent dioxygenase, which is temporally regulated by an R2R3-Myb transcription factor, Vv MYBF1 (Fujita et al., 2006;Czemmel et al., 2009). Subsequently, glycosylation of flavonols enhances their water solubility, such that high concentrations of flavonols can accumulate in plant cells.From a food chemistry perspective, flavonol glycosides define the color of wine grapes and products by acting as copigments (Yoshitama et al., 1992;Boulto...

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“…Oxygenation at the 3-position, however, and probably other oxygenation steps too, occurs at an earlier stage in flavonoid biosynthesis, prior to the formation of the flavone nucleus. The dihydroflavone naringenin (dihydroapigenin) is thought to be the substrate for these oxygenations (Heller & Forkmann 1994) and, thus, can be considered the precursor to all flavonoids found in Hebe. The flavonoids occur predominantly in their glycosidic form, and the 36 different glycosidic forms found in Hebe and Leonohebe, as well as the glycosidic forms found for each of the different 15 aglycone types, are listed in Table 2.…”

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confidence: 99%

Composition and taxonomic distribution of leaf flavonoids inHebeandLeonohebe(Plantaginaceae) in New Zealand — 1. “Buxifoliatae”, “Flagriformes”, andLeonohebe

Markham¹,

Mitchell²,

Bayly

et al. 2005

New Zealand Journal of Botany

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A taxonomic revision of Hebe and Leonohebe in New Zealand has involved studies of both plant morphology and flavonoid chemistry. This paper is the first in a series that summarises the composition and taxonomic distribution of leaf flavonoids in the two genera. It describes the flavonoid glycosides encountered in a survey of c. 700 samples (from throughout the two genera), and outlines the distribution of flavonoids in species of "Buxifoliatae" and "Flagriformes" (informal infrageneric groups of Hebe) and in Leonohebe. The structures of 83 of the most commonly occurring flavonoids are identified (or tentatively identified); also recorded are 32 unidentified or partly identified flavonoids that are generally less common. Twenty-eight of the flavonoid glycosides have not previously been reported in other plant genera. Most species, in each of "Buxifoliatae", "Flagriformes", and Leonohebe, can be distinguished by their flavonoid profiles, generally through possession of unique combinations of compounds.

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Biosynthesis of flavonoids

Cited by 136 publications

References 211 publications

Foliar phenolic compounds of ten wild species of Verbenacea as antioxidants and specific chemomarkers

Foliar phenolic compounds of ten wild species of Verbenacea as antioxidants and specific chemomarkers

Functional Differentiation of the Glycosyltransferases That Contribute to the Chemical Diversity of Bioactive Flavonol Glycosides in Grapevines (Vitis vinifera)

Composition and taxonomic distribution of leaf flavonoids inHebeandLeonohebe(Plantaginaceae) in New Zealand — 1. “Buxifoliatae”, “Flagriformes”, andLeonohebe

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