Biotransformation of Resveratrol: New Prenylated trans-Resveratrol Synthesized by Aspergillus sp. SCSIOW2

• Published in: Molecules (Basel, Switzerland) Vol. 21; no. 7; p. 883
• Main Authors: Wang, Liyan, Wu, Yanhua, Chen, Yongtao, Zou, Jiaxin, Li, Xiaofan
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 06.07.2016; MDPI
• Subjects: Animals; Antioxidants - chemistry; Antioxidants - metabolism; Antioxidants - pharmacology; Aspergillus; Aspergillus - metabolism; Aspergillus sp. SCSIOW2; Bioavailability; Biocatalysts; Biotransformation; Cardiovascular disease; Chemical synthesis; Circular Dichroism; DPPH scavenging activity; ECD; Erythrocyte Membrane - drug effects; erythrocyte protection activity; Fermentation; Free Radicals - antagonists & inhibitors; Fungi; Life sciences; Magnetic Resonance Spectroscopy; Metabolites; Microorganisms; Molecular Structure; Oceanography; prenylation; Rabbits; Resveratrol; Stilbenes - chemistry; Stilbenes - metabolism; Stilbenes - pharmacology; China; prenylation; Aspergillus sp. SCSIOW2; erythrocyte protection activity; DPPH scavenging activity; resveratrol; ECD
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules21070883

Arahypin-16 (1), a new prenylated resveratrol with a unique dihydrobenzofuran ring, has been isolated as a microbial metabolite of resveratrol (2) from whole-cell fermentation of Aspergillus sp. SCSIOW2. The stereochemistry of 1 was determined by ECD calculations. 1 showed about half of the extracellular radical scavenging effect (IC50 = 161.4 μM) compared with resveratrol (IC50 = 80.5 μM), while on biomembranes it exhibited the same range of protection effects against free radicals generated from AAPH (IC50 = 78.6 μM and 87.9 μM).