Butanolides as a common feature of Iryanthera lancifolia and Virola surinamensis

A comparative phytochemical study between pericarps of Iryanthera lancifolia and Virola surinamensis showed that the first one contains a new pair of epimeric 2-alkenyl-gamma-lactones, besides an aryltetralinic lignan and one tocotrienol, while the second species contains the lignans, galgravin and veraguensin, seven juruenolides: juruenolides C, D, F, G and epi-juruenolides D, F, G, together with three pairs of epimeric aliphatic 2-alkenyl-gamma-lactones. Juruenolide F, epi-juruenolides D, F, G and the 2-alkenyl-gamma-lactones are new natural compounds. (C) 1998 Elsevier B.V. Ltd. All rights reserved.

Gama-Lactones from Iryanthera species

The structure of juruenolide, a constituent of Iryanthera juruensis and I. ulei is revised to (2S, 3R, 4S)-3-hydroxy-4-methyl-2-(19′-piperonyl-1′-n-nonadecyl)-butanolide. The compound is epimeric at C-3 of the γ-lactone unit with grandinolide [(2S, 3S, 4S)-3-hydroxy-4-methyl-2- (19′-phenyl-1′-n-nonadecyl)-butanolide] from I. grandis. An extract of I. juruensis contained additionally juruenolide-B [(4S)-4-methyl-2-(19′-piperonyl-1′-n-nonadec-7′-enyl)-but-2-enolide]. Analogous products with heptadecyl and pentadecyl side chains co-occur with the respective nonadecyl derivatives. © 1983.