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Publication Type
Journal Article
UWI Author(s)
Author, Analytic
Lamm, Andrew.S; Chen, A.R.M; Reynolds,W.F.; Reese, Paul B
Author Affiliation, Ana.
n/a
Article Title
Fungal Hydroxylation of (-)- Santonin and its analogues
Medium Designator
n/a
Connective Phrase
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Journal Title
J. Mol. Catal. B: Enzym
Translated Title
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Reprint Status
Refereed
Date of Publication
2009
Volume ID
59
Issue ID
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Page(s)
292 - 296
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
Santonin (1) was incubated with separate growing cultures of Aspergillus niger ATCC 9142, Mucor plumbeus ATCC 4740, Whetzelinia sclerotiorum ATCC 18687, Cunninghamella echinulata var. elegans ATCC 8688a and Phanerochaete chrysosporium ATCC 24725. Three novel metabolites were isolated: 11,13-dihydroxysantonin (3), 6,7-dehydosantonin (5) and 3,6-dihydroxy-9-keto-9,10-seco-selina-1,3,5(10)-trien-12-oic acid-12,6-lactone (7). 11-Hydroxysantonin (2), 14-hydroxysantonin (4) and 3,6,9-trihydroxy-9,10-seco-selina-1,3,5(10)-trien-12-oic acid-12,6-lactone (6) were also isolated. Hydroxylation at C-9 followed by a retro-aldol reaction was postulated to have produced 6 and 7. Through the synthesis and fermentation of the santonin analogues: tetrahydrosantonin (8) and -desmotroposantonin (12), several new compounds were obtained; the most significant being 9-keto-desmotroposantonin (14), which was indicative of C-9 monohydroxylation....
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