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Publication Type
Journal Article
UWI Author(s)
Author, Analytic
McCook, Kayanne P; Chen, A.R.M.; Reynolds, W.F.; Reese, Paul B.
Author Affiliation, Ana.
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Article Title
The potential of Cyathus africanus for transformation of terpene substrates.
Medium Designator
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Connective Phrase
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Journal Title
Phytochemistry
Translated Title
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Reprint Status
Refereed
Date of Publication
2012
Volume ID
82
Issue ID
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Page(s)
61 - 66p.
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 insecticidal sesquiterpenes cadina-4,10(15)-dien-3-one and aromadendr-1(10)-en-9-one were administered to the fungus Cyathus africanus ATCC 35853. Biotransformation of the former produced (4R)-9-hydroxycadin-10(15)-en-3-one, while the latter gave 2-hydroxyaromadendr-1(10)-en-9-one, 2-hydroxyaromadendr-1(10)-en-9-one and 10-hydroxy-1,2-epoxyaromadendran-9-one. The bioconversion of santonin led to the production of two analogues, 11,13-dihydroxysantonin and the hitherto unreported 8,13-dihydroxysantonin, while cedrol yielded 3,8-dihydroxycedrane and 3,8-dihydroxycedrane. Stemod-12-ene, a diterpene, was transformed to 2-oxostemar-13-ene, a hitherto unknown analogue with a rearranged carbon framework. When methyl betulonate, a triterpenoid belonging to the lupane family, was supplied to the fungus 18-ursane and 18-oleanane derivatives, namely 19-hydroxy-3-oxo-18-oleanan-28-oic acid and 19-hydroxy-3-oxo-18-ursan-28-oic acids, were generated. There are no previous reports of fungal transformation of a triterpene in which a skeletal rearrangement occurred. All substrate administration experiments were done in the presence of the terpene cyclase inhibitor chlorocholine chloride (CCC), using the single phase - pulse feed method....
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