Collins, Dwight O.; Ruddock, Peter L.; de Grasse, Jessica C.; Reynolds, William F.; Reese, Paul B.
Author Affiliation, Ana.
Department of Chemistry
Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1 (10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740
Date of Publication
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 adn C-14. When the iron content of the medium was reduced however, hydroxylation at these positions was also accompanied by expoxidation of the exocyclic double bond. In total nine new oxygenated cadinanes have been obtained. Sesquiterpene 14 was converted to the novel 2a, 13-dihydroxy derivative along with four other metabolites. Methyl ursolate (21) was transformed to a new compound, methyl 3b, 7b, 21b-trihydroxyursa-9(11),12-dien-28-oate (22). Two other triterpenoids, 3b, 28-dihydroxyurs-12-ene (uvaol) (23) and 3b, 28-bis(dimethylcarbamoxy)urs-12-ene (24) were not transformed by the micro-organism, however.....