title: Conversion of puerarin into its 7-O-glycoside derivatives by Microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties.
abstract: Microbacterium oxydans strain NJ 6 isolated from soil samples converted puerarin into two novel compounds, puerarin-7-O-glucoside and puerarin-7-O-isomaltoside, via an unreported O-glycosylation of the phenolic hydroxyl group at the 7-position of puerarin. Sucrose, maltotriose, and maltose could be used as glucosyl donors for glycosylation of puerarin, but uridine-diphosphate glucose, glucose, fructose, lactose, cyclodextrin, and starch could not. Regardless of the position of B-ring in the (iso)flavonoids core structure, the glycosylation of the phenolic hydroxyl group at the 7-position of (iso)flavonoids was governed by the presence or absence of a glucosyl residue at 8-C. The apparent solubility of puerarin-7-O-glucoside and puerarin-7-O-isomaltoside was approximately 18 and 100 times that of natural puerarin, respectively. Like parent puerarin, puerarin-7-O-glucoside maintained its physiological ability to relax the contractions of isolated rat thoracic aortic rings in vitro induced by phenylephrine. However, puerarin-7-O-glucoside was able to maintain higher plasma concentrations and have a longer mean residence time in the blood than the parent puerarin.
authors.affiliation: Nanjing Research Center for Microbial Engineering and Technology, Jiangsu Key Laboratory for Biodiversity and Biotechnology, College of Life Science, Nanjing Normal University, 1 Wenyuan Rd, Nanjing, 210046, People's Republic of China.
authors.forename: Jie-rong
authors.initials: JR
authors.lastname: Jiang
authors.forename: Sheng
authors.initials: S
authors.lastname: Yuan
authors.forename: Juan-fang
authors.initials: JF
authors.lastname: Ding
authors.forename: Shou-chuang
authors.initials: SC
authors.lastname: Zhu
authors.forename: Hai-dong
authors.initials: HD
authors.lastname: Xu
authors.forename: Ting
authors.initials: T
authors.lastname: Chen
authors.forename: Xiao-dong
authors.initials: XD
authors.lastname: Cong
authors.forename: Wen-ping
authors.initials: WP
authors.lastname: Xu
authors.forename: Hui
authors.initials: H
authors.lastname: Ye
authors.forename: Yi-jun
authors.initials: YJ
authors.lastname: Dai
mesh_terms: D000192:Actinomycetales / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D000818:Animals; D001013:Aorta, Thoracic / Q000187:drug effects; D001711:Biotransformation; D005260:Female; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism / Q000493:pharmacokinetics*; D066298:In Vitro Techniques; D007529:Isoflavones / Q000737:chemistry* / Q000378:metabolism* / Q000493:pharmacokinetics; D007700:Kinetics; D008297:Male; D051381:Rats; D017207:Rats, Sprague-Dawley; D012988:Soil Microbiology; D012995:Solubility; D014664:Vasodilation; D014665:Vasodilator Agents / Q000737:chemistry / Q000378:metabolism / Q000493:pharmacokinetics
chemical_list: D006027:Glycosides; D007529:Isoflavones; D014665:Vasodilator Agents; C033607:puerarin