Patterns of Polyacetylene Production I. The Diatretynes

Abstract

polyacetylenes, is produced by several different organisms (unpublished data, 2, 4, 5, 9, 10). The possibility that this biochemical manifestation may be correlated with the position of the organism in a taxonomic system based on morphological characteristics is examined in this report. The relevance of polyacetylene production to taxonomy of higher plants has been pointed out by S6rensen et al. (14). Working with the Compositae, they ascertained that many members of this family produced polyacetylenes. Matricaria ester was the acetylenic compound most frequently found, while in some species its dehydro derivative also occurred. S6rensen et al. observed that six of the species which they investigated did not contain these compounds and that most of the six contained no acetylenic compounds at all. They suggested that these chemical findings offered further justification for the transfer of these species from the genus Matricaria to the genus Tripleurospermum, a transfer already proposed on morphological grounds. As regards fungi, Bu'Lock (6) observed, in 1956, that the polyacetylenes isolated up to that time were obtained exclusively from two families, the Agaricaceae and the Polyporaceae. According to more recent findings (unpublished) polyacetylenes occur also in other families of the Agaricales (sensu lato). Our data suggest that for the production of particular polyacetylenes, some pattern may exist which is related to the taxonomy of the producing organisms. The present report deals with the pattern of production of the diatretynes. The polyacetylenes, diatretyne amide (I), diatretyne nitrile (II), and diatretyne 3 (III) were isolated from the basidiomycete Clitocybe