A stilbene glycoside (resvebassianol A) (1) with a unique sugar unit, 4-O-methyl-D-glucopyranose, was identified through biotransformation of resveratrol (RSV) by the entomopathogenic fungus Beauveria bassiana to obtain a superior RSV metabolite with enhanced safety. Its structure, including its absolute configurations, was determined using spectroscopic data, HRESIMS, and chemical reactions. Microarray analysis showed that the expression levels of filaggrin, HAS2-AS1, and CERS3 were higher, while those of IL23A, IL1A, and CXCL8 were lower in the resvebassianol A-treated group than in the RSV-treated group, as confirmed by qRT-PCR. Compound 1 exhibited the same regenerative and anti-inflammatory effects as RSV with no cytotoxicity in skin keratinocytes and TNF-α/IFN-γ-stimulated HIEC-6 cells, suggesting that compound 1 is a safe and stable methylglycosylated RSV. Our findings suggest that our biotransformation method can be an efficient biosynthetic platform for producing a broad range of natural glycosides with enhanced safety.
resveratrol, biotransformation, Beauveria bassiana, cell rejuvenation, microarray analysis
NCBI PubMed ID: 34067529Publication DOI: 10.3390/biomedicines9050555Journal NLM ID: 101691304Publisher: Basel, Switzerland: MDPI AG
Correspondence: Choi I
; Kim KH ; Kim SY
Institutions: School of Pharmacy, Sungkyunkwan University, Suwon, South Korea, College of Pharmacy, Gachon University, Incheon, South Korea, Division of Food Functionality Research, Korea Food Research Institute, Wanju, South Korea, Division of Food Biotechnology, University of Science and Technology, Daejeon, South Korea, Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon, South Korea
Methods: 13C NMR, 1H NMR, IR, ELISA, acid hydrolysis, UV, extraction, optical rotation measurement, LC-MS, RP-HPLC, cell growth, HR-ESI-MS, cell viability assay, evaporation, sonication, centrifugation, MTT, cell proliferation assay, cell migration assay
Found