Prenylated flavonoids, promising nutraceuticals with impressive biological activities

Yang, Xiaoman; Jiang, Yueming; Yang, Jiali; He, Jirui; Jian, Sun; Chen, Feng; Zhang, Mingwei; Yang, Bao

doi:10.1016/j.tifs.2015.03.007

Cited by 141 publications

(110 citation statements)

References 78 publications

(74 reference statements)

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“…Hence, prenylated flavonoids are highly diverse, and they include approximately 1,000 compounds that are increasingly examined for their antioxidant, antitumor, antibacterial, antiviral and estrogenic activities (Yazaki et al 2009). Although some of the properties are common to flavonoids with no prenyl groups, it is generally accepted that prenyl moieties increase lipophilicity and membrane permeability, and tend to potentiate the bioactivities of flavonoids (Botta et al 2005, Yazaki et al 2009, Yang et al 2015). Prenylation of flavonoids is catalyzed by prenyltransferases (PTs), which transfer prenyl moieties from allylic prenyl diphosphate to flavonoid skeletons.…”

Section: Introductionmentioning

confidence: 99%

Molecular Characterization of Soybean Pterocarpan 2-Dimethylallyltransferase in Glyceollin Biosynthesis: Local Gene and Whole-Genome Duplications of Prenyltransferase Genes Led to the Structural Diversity of Soybean Prenylated Isoflavonoids

2016

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Soybean (Glycine max) accumulates several prenylated isoflavonoid phytoalexins, collectively referred to as glyceollins. Glyceollins (I, II, III, IV and V) possess modified pterocarpan skeletons with C5 moieties from dimethylallyl diphosphate, and they are commonly produced from (6aS, 11aS)-3,9,6a-trihydroxypterocarpan [(−)-glycinol]. The metabolic fate of (−)-glycinol is determined by the enzymatic introduction of a dimethylallyl group into C-4 or C-2, which is reportedly catalyzed by regiospecific prenyltransferases (PTs). 4-Dimethylallyl (−)-glycinol and 2-dimethylallyl (−)-glycinol are precursors of glyceollin I and other glyceollins, respectively. Although multiple genes encoding (−)-glycinol biosynthetic enzymes have been identified, those involved in the later steps of glyceollin formation mostly remain unidentified, except for (−)-glycinol 4-dimethylallyltransferase (G4DT), which is involved in glyceollin I biosynthesis. In this study, we identified four genes that encode isoflavonoid PTs, including (−)-glycinol 2-dimethylallyltransferase (G2DT), using homology-based in silico screening and biochemical characterization in yeast expression systems. Transcript analyses illustrated that changes in G2DT gene expression were correlated with the induction of glyceollins II, III, IV and V in elicitor-treated soybean cells and leaves, suggesting its involvement in glyceollin biosynthesis. Moreover, the genomic signatures of these PT genes revealed that G4DT and G2DT are paralogs derived from whole-genome duplications of the soybean genome, whereas other PT genes [isoflavone dimethylallyltransferase 1 (IDT1) and IDT2] were derived via local gene duplication on soybean chromosome 11.

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Section: Introductionmentioning

confidence: 99%

Molecular Characterization of Soybean Pterocarpan 2-Dimethylallyltransferase in Glyceollin Biosynthesis: Local Gene and Whole-Genome Duplications of Prenyltransferase Genes Led to the Structural Diversity of Soybean Prenylated Isoflavonoids

2016

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“…Moreover, the dimethylallyl moiety also is the most common prenylation pattern present in prenylated flavonoids, which are mostly found in the following families: Cannabaceae, Guttiferae, Leguminosae, Moraceae, Rutaceae, and Umbelliferae. The longer form of the dimethylallyl moiety, geranyl and lavandulyl moiety, also has been reported in prenylated flavonoids (Botta et al, 2005;Yang et al, 2015b). During the biosynthesis of these prenylated stilbenoids and prenylated flavonoids, prenyltransferases are responsible for dimethylallylation and geranylation, attaching DMAPP and GPP, respectively, to different positions of the stilbenoid and flavonoid skeletons.…”

Section: Biosynthesis Of Prenylated Stilbenoids In Peanut Hairy Rootmentioning

confidence: 75%

A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

et al. 2016

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Prenylated stilbenoids synthesized in some legumes exhibit plant pathogen defense properties and pharmacological activities with potential benefits to human health. Despite their importance, the biosynthetic pathways of these compounds remain to be elucidated. Peanut (Arachis hypogaea) hairy root cultures produce a diverse array of prenylated stilbenoids upon treatment with elicitors. Using metabolic inhibitors of the plastidic and cytosolic isoprenoid biosynthetic pathways, we demonstrated that the prenyl moiety on the prenylated stilbenoids derives from a plastidic pathway. We further characterized, to our knowledge for the first time, a membrane-bound stilbenoid-specific prenyltransferase activity from the microsomal fraction of peanut hairy roots. This microsomal fraction-derived resveratrol 4-dimethylallyl transferase utilizes 3,3-dimethylallyl pyrophosphate as a prenyl donor and prenylates resveratrol to form arachidin-2. It also prenylates pinosylvin to chiricanine A and piceatannol to arachidin-5, a prenylated stilbenoid identified, to our knowledge, for the first time in this study. This prenyltransferase exhibits strict substrate specificity for stilbenoids and does not prenylate flavanone, flavone, or isoflavone backbones, even though it shares several common features with flavonoid-specific prenyltransferases.

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“…Saturejin, a new O-prenylated flavonoid, belongs to a unique class of naturally occurring compounds that have proved to be an important source of chemically diverse novel metabolites [45]. Also, prenylation usually provides flavonoids with improved bioactivities [46,47].…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…According to a recent comprehensive review on prenylated flavonoids [45], they have been detected to have diversely structural characteristics and among numerous prenylation groups, 3,3-dimethylallyl group is the most common pattern presented. However, further oxidation, cyclization, dehydration and reduction can lead to more modifications of terpenoid chains.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

A new bioactive monoterpene–flavonoid from Satureja khuzistanica

et al. 2015

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Prenylated flavonoids, promising nutraceuticals with impressive biological activities

Cited by 141 publications

References 78 publications

Molecular Characterization of Soybean Pterocarpan 2-Dimethylallyltransferase in Glyceollin Biosynthesis: Local Gene and Whole-Genome Duplications of Prenyltransferase Genes Led to the Structural Diversity of Soybean Prenylated Isoflavonoids

Molecular Characterization of Soybean Pterocarpan 2-Dimethylallyltransferase in Glyceollin Biosynthesis: Local Gene and Whole-Genome Duplications of Prenyltransferase Genes Led to the Structural Diversity of Soybean Prenylated Isoflavonoids

A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

A new bioactive monoterpene–flavonoid from Satureja khuzistanica

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