Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 34067529Publication DOI: 10.3390/biomedicines9050555Journal NLM ID: 101691304Publisher: Basel, Switzerland: MDPI AG
Correspondence: Choi I <choiw
kfri.re.kr>; Kim KH <khkim83
skku.edu>; Kim SY <sunnykim
gachon.ac.kr>
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
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
Structure type: monomer ; 403.1395 [M-H]-
C
21H
24O
8Location inside paper: Table 1
Trivial name: resvebassianol A
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
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
Comments, role: NMR temperature was not specified
NCBI Taxonomy refs (TaxIDs): 176275
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14
4',4 Me 61.1
4' bDGlcp 102.2 75.1 78.1 80.7 77.3 62.2
Subst 141.0 106.0 159.8 103.1 159.8 106.0 133.2 128.7 118.0 158.8 118.0 128.7 128.7 129.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14
4',4 Me 3.59
4' bDGlcp 4.90 3.478 3.57 3.21 3.43 3.71-3.86
Subst - 6.46 - 6.18 - 6.46 - 7.45 7.07 - 7.07 7.45 6.88 6.99
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14
4',4 Me 61.1/3.59
4' bDGlcp 102.2/4.90 75.1/3.478 78.1/3.57 80.7/3.21 77.3/3.43 62.2/3.71-3.86
Subst 106.0/6.46 103.1/6.18 106.0/6.46 128.7/7.45 118.0/7.07 118.0/7.07 128.7/7.45 128.7/6.88 129.1/6.99
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 |
|---|
| 4',4 | Me | 3.59 | |
| 4' | bDGlcp | 4.90 | 3.478 | 3.57 | 3.21 | 3.43 | 3.71
3.86 | |
| | Subst |
| 6.46 |
| 6.18 |
| 6.46 |
| 7.45 | 7.07 |
| 7.07 | 7.45 | 6.88 | 6.99 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 |
|---|
| 4',4 | Me | 61.1 | |
| 4' | bDGlcp | 102.2 | 75.1 | 78.1 | 80.7 | 77.3 | 62.2 | |
| | Subst | 141.0 | 106.0 | 159.8 | 103.1 | 159.8 | 106.0 | 133.2 | 128.7 | 118.0 | 158.8 | 118.0 | 128.7 | 128.7 | 129.1 |
|
There is only one chemically distinct structure:
Found 
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