117405-48-8Relevant articles and documents
New aurone glucosides and new phenylpropanoid glucosides from Bidens pilosa
Sashida,Ogawa,Kitada,Karikome,Mimaki,Shimomura
, p. 709 - 711 (1991)
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Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates
Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi
supporting information, p. 838 - 847 (2021/02/09)
Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.
Glycosidase-Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids
Bassanini, Ivan,Kape?ová, Jana,Petrásková, Lucie,Pelantová, Helena,Marko?ová, Kristína,Rebro?, Martin,Valentová, Kate?ina,Kotik, Michael,Káňová, Kristyna,Bojarová, Pavla,Cva?ka, Josef,Turková, Lucie,Ferrandi, Erica E.,Bayout, Ikram,Riva, Sergio,K?en, Vladimír
, p. 2627 - 2637 (2019/05/15)
Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time-consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure-activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS. (Figure presented.).
Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)
Regos, Ionela,Urbanella, Andrea,Treutter, Dieter
body text, p. 5843 - 5852 (2010/06/17)
Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phen
