Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1(10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740

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 2α,13-dihydroxy derivative along with four other metabolites. Methyl ursolate ( 21) was transformed to a new compound, methyl 3β,7β,21β-trihydroxyursa-9(11),12-dien-28-oate ( 22). Two other triterpenoids, 3β,28-dihydroxyurs-12-ene (uvaol) ( 23) and 3β,28-bis(dimethylcarbamoxy)urs-12-ene ( 24) were not transformed by the micro-organism, however. When incubated with M. plumbeus the cadinane was converted to 9 compounds. The aromadendrane gave 5 products, one of which was new. The triterpene ester was transformed to a single metabolite.