Abstract
Feeding of [1- 13C]- and [1,2- 13C 2]acetates to cultures of Aspergillus terreus gave labeled quadrone ( 1) and terrecyclic acid ( 2) which were analyzed by high-field 13C NMR. The patterns of enhancements and couplings were used not only in the analysis of the biosynthetic origins of the two metabolites, but also in the assignment of the 13C spectra themselves. The latter assignments were confirmed and further extended by extensive analysis by a combination of 1H COSY, 1H 13C heteroCOSY, and difference NOE spectra of quadrone. The biosynthetic pathway was further probed by incorporation of [3,4- 13C 2]mevalonate, revealing that formation of 1 and 2 involves cleavage of the 3,4-bond of one of the three mevalonte precursors. The results are consistent with the formation of quadrone and terrecyclic acid by cyclization of farnesyl pyrophosphate ( 8).
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