Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Organ / tissue: Life stage: culture broth
Associated disease: infection due to Enterobacter [ICD11: XN9W5 ]
 
The structure was elucidated in this paper
NCBI PubMed ID: 18057703
Publication DOI: 10.1038/ja.2007.93
Journal NLM ID: 0151115
Publisher: London: Nature Publishing Group
Correspondence: nakagawanasu.bio.teikyo-u.ac.jp
Institutions: Department of Biosciences, Teikyo University, Utsunomiya, Japan, Research & Development Center, Nagase & Co., Ltd., Nishi-ku, Japan, Pharmacovigilance Department, Astellas Pharma Inc., Itabashi-ku, Japan, Fermentation Research Laboratories, Drug Discovery Research, Astellas Pharma Inc., Tsukuba, Japan

A novel melanogenesis inhibitor, byelyankacin (1), was isolated from the fermentation broth of a bacterial strain. The producing organism, designated B20, was identified as a member of the genus Enterobacter based on taxonomic characteristics. 1 was obtained as a white powder from the culture medium by solvent extraction and serial chromatographic purification. The structure of 1 was determined as (E)-4-(2-isocyanovinyl)phenyl α-L-rhamnopyranoside on the basis of spectroscopic data. 1 potently inhibited mushroom tyrosinase and melanogenesis of B16-2D2 melanoma cells with IC50 value of 2.1 nM and 30 nM, respectively

byelyankacin, melanogenesis inhibitor, mushroom tyrosinase, B16-2D2 melanoma cell, Enterobacter sp.

Structure type: monomer ; 292.1187 [M+H]+
C₁₅H₁₇NO₅
Location inside paper: Fig. 1, Fig. 3
Trivial name: byelyankacin
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
 
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, HPLC, UV, extraction, optical rotation measurement, CC, cell growth, enzymatic assay, cytotoxicity assay, evaporation
Biological activity: byelyankacin potently inhibits mushroom tyrosinase and melanogenesis of B16-2D2 melanoma cells with IC50 value of 2.1 nM and 30 nM, respectively
Comments, role: atom enumeration in NMR spectra is according to the Fig. 1 in the paper
 
Related record ID(s): 47263, 47267, 47269
NCBI Taxonomy refs (TaxIDs): 1349645
Show glycosyltransferases
 
NMR conditions: in CD3OD        [as TSV]

1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 4 aLRhap 5.45 3.98 3.82 3.45 3.57 1.20     Subst 6.99 6.52 7.40 7.06 7.06 7.40

13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 4      aLRhap 99.7 71.9 72.2 73.7 70.8 18.0          Subst 137.6 110.6 164.7 128.3 129.5 117.8 159.0 117.8 129.5

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