2013
DOI: 10.1128/aem.00409-13
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Enzymatic Synthesis of Novel Phloretin Glucosides

Abstract: A UDP-glycosyltransferase from Bacillus licheniformis was exploited for the glycosylation of phloretin. The in vitro glycosylation reaction confirmed the production of five phloretin glucosides, including three novel glucosides. Consequently, we demonstrated the application of the same glycosyltransferase for the efficient whole-cell biocatalysis of phloretin in engineered Escherichia coli. P hloretin is a dihydrochalcone, an intermediate of the biosynthetic pathway of flavonoids in plants, which is abundantly… Show more

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Cited by 80 publications
(80 citation statements)
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“…However, an unexpected result was that the concentration of resveratrol 3-O-␤-D-glucoside was higher after a 1-h incubation period and lower concentrations were detected after 2 h and 3 h of incubation (data not shown). This decrease in the amount of product initially formed could be due to the instability of the product, or the product may be readily converted to resveratrol and UDP-D-glucose in a reverse-glycosylation reaction mediated by YjiC as previously reported for phloretin glycosylation (56). In addition, the product However, resveratrol 3,5,4=-O-␤-D-triglucoside was not detected, and this may be due to a lack of excess UDP-D-glucose in the reaction mixture.…”
Section: Enzymatic Synthesis Of Resveratrol Glucosidesmentioning
confidence: 70%
See 1 more Smart Citation
“…However, an unexpected result was that the concentration of resveratrol 3-O-␤-D-glucoside was higher after a 1-h incubation period and lower concentrations were detected after 2 h and 3 h of incubation (data not shown). This decrease in the amount of product initially formed could be due to the instability of the product, or the product may be readily converted to resveratrol and UDP-D-glucose in a reverse-glycosylation reaction mediated by YjiC as previously reported for phloretin glycosylation (56). In addition, the product However, resveratrol 3,5,4=-O-␤-D-triglucoside was not detected, and this may be due to a lack of excess UDP-D-glucose in the reaction mixture.…”
Section: Enzymatic Synthesis Of Resveratrol Glucosidesmentioning
confidence: 70%
“…AAU40842.1) from Bacillus licheniformis DSM 13, with a flexible donor and acceptor substrate profile was selected in order to synthesize glycodiversified resveratrol derivatives. YjiC has been shown to accept geldanamycin analogues (52), epothilone A (53), various flavonoids (54,55), chalcone (56), and isoflavonoids (57) as substrates for glucosylation. In this study, resveratrol was used as an acceptor substrate and various rare nucleotide diphosphate sugars were used as sugar donor substrates to produce glycodiversified resveratrol derivatives that have not been previously described.…”
mentioning
confidence: 99%
“…Phloretin (Calliste et al, 2001;Chao and Henry, 2010;Rezk et al, 2002;Sukhorukov et al, 2001) and its most abundant and best characterized glycoside, phloretin 2'-␤-d-glucopyranoside or phlori(d)zin (Boccia et al, 1999;Ehrenkranz et al, 2005;Veeriah et al, 2006), are known to exert a wide variety of biological effects. Other characterized phloretin glycosides that have either been isolated from natural sources or have been chemically or enzymatically synthesized are the ribose analog of phloridzin (Gupte and Buolamwini, 2009), a 2'-␤-xylogalactoside (Lu and Foo, 1997), the 4'-␤-d-glucoside (Farkas et al, 1965;Gosch et al, 2010;Jorio, 1959;Pandey et al, 2013), a 4'-glucorhamnoside (Jorio, 1959), a number of 4'-␤-linked disaccharides (Kamiya et al, 1975), the 4,4'-, 4,2'-and 4,2',4'-␤-d-glucosides (Pandey et al, 2013) and the 3',5'-␤-d-glucoside (Ito et al, 2014;Sato et al, 2006). We now report the first synthesis of phloretin glycosides in which the sugar is attached in the ␣ configuration.…”
mentioning
confidence: 99%
“…Effects of Phloretin include decrease of oxidative stress [11], inhibition of inflammation [12], increase endothelial nitric oxide production and vasodilation [13,14], downregulation of endothelial adhesion molecules [15], and inhibition of platelet activation [15]. Some of the effects are due to estrogenic activity of the substance [13,14,16].…”
Section: Introductionmentioning
confidence: 99%