title: Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi.
abstract: Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2α,3α,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (2), 2α,3β,19α-trihydroxy-ursolic acid-28-O-β-d-glucopyranoside (3), oleanolic acid 28-O-β-d-glucopyranosyl ester (4), oleanolic acid-3-O-β-d-glucopyranoside (5), 3-O-(β-d-glucopyranosyl)-oleanolic acid-28-O-β-d-glucopyranoside (6), 2α,3β,19a-trihydroxy-oleanolic acid-28-O-β-d-glucopyranoside (7), 21β-hydroxyl oleanolic acid-28-O-β-d-glucopyranoside (8), 21β-hydroxyl oleanolic acid (9), and 7α,21β-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.
authors.affiliation: Tianjin Key Laboratory for Biomarkers of Occupational and Environmental Hazard, Tianjin, China. liudailinlch@hotmail.com
authors.forename: Dai-Lin
authors.initials: DL
authors.lastname: Liu
authors.forename: Ying
authors.initials: Y
authors.lastname: Liu
authors.forename: Feng
authors.initials: F
authors.lastname: Qiu
authors.forename: Ying
authors.initials: Y
authors.lastname: Gao
authors.forename: Jing-Ze
authors.initials: JZ
authors.lastname: Zhang
mesh_terms: D000528:Alternaria / Q000378:metabolism*; D001711:Biotransformation; D002681:China; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism*; D010407:Penicillium / Q000378:metabolism*
chemical_list: D009828:Oleanolic Acid