Biotransformation of quinovic acid glycosides by microbes: direct conversion of the ursane to the oleanane triterpene skeleton by Nocardia sp. NRRL 5646.
[reaction: see text] Quinovic acid glycosides were microbially deglycosylated by a Nocardia sp. to their aglycon quinovic acid and its biogenetic counterpart, cincholic acid (3), via an unprecedented carbon skeleton rearrangement involving a methyl group migration. The structures of the metabolites were established by ESI-LC/MS and 2D-NMR techniques.
Cheng
Zhi-Hong
ZH
Department of Complex Prescription of TCM, China Pharmaceutical University, Nanjing 210038, People 's Republic of China.
Yu
Bo-Yang
BY
Cordell
Geoffrey A
GA
Qiu
Sheng-Xiang
SX
D001711:Biotransformation; D002384:Catalysis; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D009615:Nocardia / Q000201:enzymology / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D021241:Spectrometry, Mass, Electrospray Ionization; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D006027:Glycosides; D014315:Triterpenes; C413246:oleanane; D009828:Oleanolic Acid; C472605:quinovic acid; D006026:Glycoside Hydrolases