title: Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1(10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740.
abstract: The sesquiterpenes cadina-4,10(15)-dien-3-one (1) and aromadendr-1(10)-en-9-one (squamulosone) (14) along with the triterpenoid methyl ursolate (21) were incubated with the fungus Mucor plumbeus ATCC 4740. Substrates 1, 14 and ursolic acid (20) were isolated from the plant Hyptis verticillata in large quantities. M. plumbeus hydroxylated 1 at C-12 and C-14. When the iron content of the medium was reduced, however, hydroxylation at these positions was also accompanied by epoxidation of the exocyclic double bond. In total nine new oxygenated cadinanes have been obtained. Sesquiterpene 14 was converted to the novel 2alpha,13-dihydroxy derivative along with four other metabolites. Methyl ursolate (21) was transformed to a new compound, methyl 3beta,7beta,21beta-trihydroxyursa-9(11),12-dien-28-oate (22). Two other triterpenoids, 3beta,28-dihydroxyurs-12-ene (uvaol) (23) and 3beta,28-bis(dimethylcarbamoxy)urs-12-ene (24) were not transformed by the micro-organism, however.
authors.affiliation: Department of Chemistry, University of the West Indies, Mona, Kingston 7, West Indies, Jamaica.
authors.forename: Dwight O
authors.initials: DO
authors.lastname: Collins
authors.forename: Peter L D
authors.initials: PL
authors.lastname: Ruddock
authors.forename: Jessica
authors.initials: J
authors.lastname: Chiverton de Grasse
authors.forename: William F
authors.initials: WF
authors.lastname: Reynolds
authors.forename: Paul B
authors.initials: PB
authors.lastname: Reese
mesh_terms: D019686:Lamiaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009089:Mucor / Q000378:metabolism*; D009281:Naphthalenes / Q000493:pharmacokinetics*; D012717:Sesquiterpenes / Q000493:pharmacokinetics*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D014315:Triterpenes / Q000493:pharmacokinetics*
chemical_list: D009281:Naphthalenes; D012717:Sesquiterpenes; D014315:Triterpenes; C454321:methyl ursolate; C436754:squamulosone; C096642:cadina-4,10(15)-dien-3-one