Isolation and structures of indoloditerpenes, possible biosynthetic intermediates to the tremorgenic mycotoxin, paxilline, from Emericella striata

Journal of the Chemical Society, Perkin Transactions 1
1988.0

Abstract

Together with paspaline (7), two indoloditerpenes designated dehydroxypaxilline (5), C₂₇H₃₁NO₃, and emindole SB (6), C₂₇H₃₁NO₂ were isolated from the mycelium of Emericella striata. The structures of dehydroxypaxilline (5) and emindole SB (6) were determined on the basis of spectroscopic investigation of these compounds. It is very interesting that emindole SB (6), paspaline (7), and dehydroxypaxilline (5) were isolated from the same fungus, E. striata, on consideration of the biogenesis of paxilline (1) which had also been isolated from the same fungus as one of the main components. Recently we reported the isolation of a tremorgenic mycotoxin, paxilline (1), from the mycelial extract of Emericella striata as one of the major metabolites, and from E. desertorum as a minor component. During our search for compounds related to (1), novel indoloditerpenes, i.e., emindoles DA (2), DB (3), and emindole SA (4) from E. desertorum and E. striata, respectively, were isolated. Recently, two compounds related to the biosynthetic intermediates to (1) designated dehydroxypaxilline (5) and emindole SB (6) were isolated along with paspaline (7), which was originally isolated from the mycelium of Claviceps paspali, from the non-polar fraction of the mycelial acetone extract, and the structures of compounds (5) and (6) are reported in this paper.

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