Conversion of puerarin into its 7-O-glycoside derivatives by Microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties.
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.
Jiang
Jie-rong
JR
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.
Yuan
Sheng
S
Ding
Juan-fang
JF
Zhu
Shou-chuang
SC
Xu
Hai-dong
HD
Chen
Ting
T
Cong
Xiao-dong
XD
Xu
Wen-ping
WP
Ye
Hui
H
Dai
Yi-jun
YJ
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
D006027:Glycosides; D007529:Isoflavones; D014665:Vasodilator Agents; C033607:puerarin