Four new mycotoxins of Aspergillus clavatus related to tryptoquivaline

The Journal of Organic Chemistry
1977.0

Abstract

The hydroxylamine nortryptoquivaline (2) and the three secondary amines deoxytryptoquivaline (3), deoxynortryptoquivaline (4), and deoxynortryptoquivalone (8) were found to be toxic metabolites of Aspergillus clavatus. They were accompanied by the two previously described tremor producing agents tryptoquivaline (1) and nortryptoquivalone (7). The only weakly basic secondary amines 3, 4, and 8 were oxidized to the corresponding hydroxylamines 1,2, and 7 with m-chloroperbenzoic acid. The preparation of L-isopodophyllotoxin (5), L-isopicropodophyllin (7), and L-isopodophyllotoxone (12) is described. With these compounds the eight possible diastereomeric C-4 alcohols (toxins) and four possible C-4 ketones of the L series2 are all known. Alcohol 5 instead of its epimer 6 was obtained by sodium borohydride reduction of 12 contrary to predictions based on previously reported reduction of DL-12.

Knowledge Graph

Similar Paper