Quinazolines of Aspergillus Species

Tryptoquivaline (104) and Nortryptoquivalone. A strain of the fungus, Aspergillus clavatus, isolated from mold-damaged rice, produces these two, highly toxic, tremorigenic metabolites 46). The quinazoline structures of 

Chart 5. Quinazoline alkaloids from Aspergillus spec. 

Buchi et al. (30) have isolated four new mycotoxins related to (104) which are produced by the same species. 

Nortryptoquivaline (105). The H-nmr spectrum of (105) is identical with that of tryptoquivaline, except that signals associated with the geminal dimethyl group in the latter have been replaced by those of a secondary methyl group. The CD curve of (105) indicates the relative stereochemistry shown, and an X-ray crystallographic analysis by Springer (211) has 

Deoxytryptoquivaline gives a negative TTC test for hydroxylamines. It is only weakly basic and is not extracted from organic solvents by IN aqueous HCl. The alkaloid differs from tryptoquivaline in the absence of an oxygen atom. The proposed structure was confirmed by oxidation with m-chloroperbenzoic acid to (104). 

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