An incorporation study of [1-(13)C] and [1,2-(13)C2] labeled sodium acetates into sorbicillinol 1 established a ring closure system between C-1 and C-6 and the positions that were oxidized and/or methylated on a hexaketide chain. Subsequent investigations, using 13C-labeled 1 prepared from [1-(13)C] labeled sodium acetate, clearly demonstrated that both bisorbicillinol 2 and sorbicillin 6 incorporated 13C-labeled 1 into their carbon skeletons. 13C-labeled bisorbicillinols 2 derived from [1-(13)C]- and [2-(13)C]-labeled sodium acetates clearly indicate that these were on the biosynthetic route from 1 to bisorbibutenolide (bislongiquinolide) 3 and bisorbicillinolide 4 via 2 as a branching point in the fungus.
Biosynthetic incorporation of labeled sodium acetate into oxosorbicillinol in Trichoderma sp. USF-2690 suggests that oxosorbicillinol is derived from six acetate units, and subsequent bioconversion of the labeled oxosorbicillinol to bisvertinolone in the fermentation of the strain suggests that bisvertinolone is biosynthesized from oxosorbicillinol and sorbicillinol in a Michael-type reaction.
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