title: Biotransformation of cycloartane-type triterpenes by the fungus Glomerella fusarioides.
abstract: Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3beta,24-diol (4), and cycloartane-3beta,24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3beta,24-diol (8). Compound 3 was converted into two new metabolites, 4alpha,4beta,14alpha-trimethyl-9beta,19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.
authors.affiliation: College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan. akihisa@chem.cst.nihon-u.ac.jp
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Akihisa
authors.forename: Kenji
authors.initials: K
authors.lastname: Watanabe
authors.forename: Risa
authors.initials: R
authors.lastname: Yoneima
authors.forename: Takashi
authors.initials: T
authors.lastname: Suzuki
authors.forename: Yumiko
authors.initials: Y
authors.lastname: Kimura
mesh_terms: D001711:Biotransformation; D007564:Japan; D015394:Molecular Structure; D020081:Phyllachorales / Q000378:metabolism*; D014315:Triterpenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D014315:Triterpenes; C085352:cycloartane