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Publication Type
Journal Article
UWI Author(s)
Author, Analytic
Collins, D.O. ; Ruddock, P.L.D. ; Chiverton de Grasse, J. ; Reynolds, W.F. ; Reese, Paul B
Author Affiliation, Ana.
Department of Chemistry
Article 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
Medium Designator
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Connective Phrase
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Journal Title
Phytochemistry
Translated Title
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Reprint Status
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Date of Publication
2002
Volume ID
59
Issue ID
5
Page(s)
479-488
Language
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Connective Phrase
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Location/URL
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ISSN
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Notes
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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 2a,13-dihydroxy derivative along with four other metabolites. Methyl ursolate (21) was transformed to a new compound, methyl 3,7,21-trihydroxyursa-9(11),12-dien-28-oate (22). Two other triterpenoids, 3,28-dihydroxyurs-12-ene (uvaol) (23) and 3,28-bis(dimethylcarbamoxy)urs-12-ene (24) were not transformed by the micro-organism, however....
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