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.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
