Abstract
Resveratrol is a typical plant phenolic compound whose derivatives are synthesized through hydroxylation, O-methylation, prenylation, and oligomerization. Resveratrol and its derivatives exhibit anti-neurodegenerative, anti-rheumatoid, and anti-inflammatory effects. Owing to the diverse biological activities of these compounds and their importance in human health, this study attempted to synthesize five resveratrol derivatives (isorhapontigenin, pterostilbene, 4-methoxyresveratrol, piceatannol, and rhapontigenin) using Escherichia coli. Two-culture system was used to improve the final yield of resveratrol derivatives. Resveratrol was synthesized in the first E. coli cell that harbored genes for resveratrol biosynthesis including TAL (tyrosine ammonia lyase), 4CL (4-coumaroyl CoA ligase), STS (stilbene synthase) and genes for tyrosine biosynthesis such as aroG (deoxyphosphoheptonate aldolase) and tyrA (prephenate dehydrogenase). Thereafter, culture filtrate from the first cell was used for the modification reaction carried out using the second E. coli harboring hydroxylase and/or O-methyltransferase. Approximately, 89.8 mg/L of resveratrol was synthesized and using the same, five derivatives were prepared with a conversion rate of 88.2% to 22.9%. Using these synthesized resveratrol derivatives, we evaluated their anti-inflammatory activity. 4-Methoxyresveratrol, pterostilbene and isorhapontigenin showed the anti-inflammatory effects without any toxicity. In addition, pterostilbene exhibited the enhanced anti-inflammatory effects for macrophages compared to resveratrol.
Highlights
Resveratrol is a natural phenolic compound that belongs to the stilbenoid group
Major resveratrol derivatives are synthesized via hydroxylation, glycosylation, O-methylation, and prenylation [3]; resveratrol derivatives from oligomerization have been
Mixture of mono, di, and tri-O-methylated resveratrol was synthesized from glucose in E. coli [14]
Summary
Resveratrol is a natural phenolic compound that belongs to the stilbenoid group. Resveratrol and its glucoside (resveratrol 3-O-glucoside, piceid) are the two major stilbenoids found in nature [1]. Chong et al Appl Biol Chem (2021) 64:33 and supplementation with additional p-coumaric acid and malonyl-CoA [3]. These approaches included pathway engineering to enhance the supplementation of tyrosine and malonyl-CoA or modulation of the entire pathway. Using Saccharomyces cerevisiae, 415.7 mg/L of resveratrol was synthesized from glucose via tyrosine and malonyl-CoA overproduction in fed-batch fermentation [9]. In Escherichia coli, the resveratrol synthesis pathway was introduced, following different strategies, to increase the pool of malonyl-CoA; the resulting strains produced 304.5 mg/L resveratrol from glucose [11] and 238.71 mg/L resveratrol from tyrosine [12]. Mixture of mono-, di-, and tri-O-methylated resveratrol was synthesized from glucose in E. coli [14]. Overexpression of acetate and malonate assimilation pathways along with additional supply of malonate in the culture medium yielded 124 mg/L of piceatannol (3-hydroxyresveratrol) in E. coli [17]
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