Total Synthesis of Resvebassianol A, a Metabolite of Resveratrol by Beauveria bassiana
- Authors
- Darlami, Om; Shin, Dongyun
- Issue Date
- Oct-2021
- Publisher
- MDPI
- Keywords
- Beauveria bassiana; Glycoslyation; Metabolites; Resvebassianol A; Resveratrol
- Citation
- Antioxidants, v.10, no.10
- Journal Title
- Antioxidants
- Volume
- 10
- Number
- 10
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/82647
- DOI
- 10.3390/antiox10101509
- ISSN
- 2076-3921
- Abstract
- Resveratrol is a well-known dietary polyphenol because it has a variety of beneficial biological activities. The fungus Beauveria bassiana is one of the most frequently used microorganisms for the biotransformation of polyphenols. Recently, resvebassianol A (2), a glycosylated metabolite of resveratrol by B. bassiana, was isolated and structurally elucidated. It was demonstrated to exhibit antioxidant, regenerative, and anti-inflammatory activities with no cytotoxicity. Here, we report the first total synthesis of resvebassianol A, 4′-O-β-(4′′′-O-methylglucopyranosyl)resveratrol (2), and its regiomer, 3-O-β-(4′′′-O-methylglucopyranosyl)resveratrol (3). Key reactions include (i) the construction of a stilbene core via a novel Heck reaction of aryl halides and styrenes, and (ii) glycosylation with unnatural methylglucopyranosyl bromide. The glycosylation step was carefully optimized by varying the bases and solvents. Resveratrol metabolites 2 and 3 were obtained at 7.5% and 6.3% of the overall yield, respectively. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
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