Fungal hydroxylation of (−)-santonin and its analogues |
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| Authors: | Andrew S Lamm Avril RM Chen William F Reynolds Paul B Reese |
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| Institution: | aDepartment of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica;bDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6 |
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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: 11β,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). 11β-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 α-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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| Keywords: | Cunninghamella blakesleeana Cunninghamella echinulata var elegans Mucor plumbeus Whetzelinia sclerotiorum Sclerotinia sclerotiorum Phanerochaete chrysosporium Aspergillus niger Biotransformation Santonin Sesquiterpene Hydroxylation |
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