title: Two new oxidation products obtained from the biotransformation of asiatic acid by the fungus Fusarium avenaceum AS 3.4594.
abstract: Asiatic acid (AA) is a natural triterpenoid possessing anti-inflammatory, anticancer, neuroprotective, and hepatoprotective activities. Structural modification of AA may provide valuable information for further structure-activity relationship analysis. Biotransformation is an efficient, specific, and environment friendly technology for structural modification of complicated natural products. In this study, the capabilities of twenty-five strains of filamentous fungi to transform AA were screened. Two new and one known oxidation products metabolized by Fusarium avenaceum AS 3.4594 were isolated. Their chemical structures were characterized as 2-oxo-3β,15α,23-trihydroxyurs-12-en-28-oic acid (1), 3-oxo-2,15α,23-trihydroxyurs-1,12-dien-28-oic acid (2), and 2-oxo-3β,23-dihydroxyurs-12-en-28-oic-acid (3) by extensive analysis of spectroscopic data.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
authors.forename: Fei-Xia
authors.initials: FX
authors.lastname: Huang
authors.forename: Xiong-Hao
authors.initials: XH
authors.lastname: Lin
authors.forename: Wen-Ni
authors.initials: WN
authors.lastname: He
authors.forename: Wei
authors.initials: W
authors.lastname: Song
authors.forename: Min
authors.initials: M
authors.lastname: Ye
authors.forename: Wen-Zhi
authors.initials: WZ
authors.lastname: Yang
authors.forename: De-An
authors.initials: DA
authors.lastname: Guo
mesh_terms: D001711:Biotransformation; D005670:Fusarium / Q000737:chemistry / Q000378:metabolism*; D022781:Hepatocytes / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D053978:Pentacyclic Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D013237:Stereoisomerism; D014315:Triterpenes
chemical_list: C578741:2-oxo-3beta,1alpha,23-trihydroxyurs-12-en-28-oic acid; C578742:3-oxo-2,15alpha,23-trihydroxyurs-1,12-dien-28-oic acid; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; C017032:asiatic acid