Conversion of puerarin into its 7-O-glycoside derivatives by Microbacterium oxydans (CGMCC 1788) to improve its water solubility and pharmacokinetic properties

• Published in: Applied microbiology and biotechnology 2008-12, Vol.81 (4), p.647-657
• Main Authors: Jiang, Jie-rong, Yuan, Sheng, Ding, Juan-fang, Zhu, Shou-chuang, Xu, Hai-dong, Chen, Ting, Cong, Xiao-dong, Xu, Wen-ping, Ye, Hui, Dai, Yi-jun
• Format: Article
• Language: English
• Subjects: Actinomycetales - chemistry; Actinomycetales - isolation & purification; Actinomycetales - metabolism; Angina pectoris; Animals; Antioxidants; Aorta, Thoracic - drug effects; Biotechnological Products and Process Engineering; Biotechnology; Biotransformation; Carbon; Cardiovascular disease; Chromatography; Female; Flavonoids; Glucose; Glycosides - chemistry; Glycosides - metabolism; Glycosides - pharmacokinetics; In Vitro Techniques; Isoflavones - chemistry; Isoflavones - metabolism; Isoflavones - pharmacokinetics; Kinetics; Laboratories; Lactose; Life Sciences; Male; Microbacterium; Microbial Genetics and Genomics; Microbiology; Nitrogen; NMR; Nuclear magnetic resonance; Optimization; Pharmacokinetics; Phenols; Rats; Rats, Sprague-Dawley; Sensors; Soil Microbiology; Solubility; Studies; Sucrose; Vasodilation; Vasodilator Agents - chemistry; Vasodilator Agents - metabolism; Vasodilator Agents - pharmacokinetics
• ISSN: 0175-7598; 1432-0614
• DOI: 10.1007/s00253-008-1683-z

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.