Biosynthesis of a water solubility-enhanced succinyl glucoside derivative of luteolin and its neuroprotective effect.

Abstract

SummaryThe natural flavonoids luteolin and luteoloside have anti‐bacterial, anti‐inflammatory, anti‐oxidant, anti‐tumour, hypolipidemic, cholesterol lowering and neuroprotective effects, but their poor water solubility limits their application in industrial production and the pharmaceutical industry. In this study, luteolin‐7‐O‐β‐(6″‐O‐succinyl)‐d‐glucoside, a new compound that was prepared by succinyl glycosylation of luteolin by the organic solvent tolerant bacterium Bacillus amyloliquefaciens FJ18 in an 8.0% DMSO (v/v) system, was obtained and identified. Its greater water solubility (2293 times that of luteolin and 12 232 times that of luteoloside) provides the solution to the application problems of luteolin and luteoloside. The conversion rate of luteolin (1.0 g l−1) was almost 100% at 24 h, while the yield of luteolin‐7‐O‐β‐(6″‐O‐succinyl)‐d‐glucoside reached 76.2%. In experiments involving the oxygen glucose deprivation/reoxygenation injury model of mouse hippocampal neuron cells, the cell viability was significantly improved with luteolin‐7‐O‐β‐(6″‐O‐succinyl)‐d‐glucoside dosing, and the expressions of the anti‐oxidant enzyme HO‐1 in the nucleus increased, providing a neuroprotective effect for ischemic cerebral cells. The availability of biosynthetic luteolin‐7‐O‐β‐(6″‐O‐succinyl)‐d‐glucoside, which is expected to replace luteolin and luteoloside, would effectively expand the clinical application value of luteolin derivatives.