Additional Vinyl Ketones and Their Pyranyl Ketones in Gonyleptid Harvestmen (Arachnida: Opiliones) Suggest These Metabolites Are Widespread in This Family
Four species of gonyleptid harvestmen, Acanthogonyleptes pulcher, Gonyleptes saprophilus (Gonyleptinae), Sodreana barbiellini, and Sodreana leprevosti (Sodreaninae), were examined by GC-MS and 1H NMR. All of these species release vinyl ketones, and three of them produce the corresponding pyranyl ket...
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Published in | Journal of natural products (Washington, D.C.) Vol. 76; no. 9; pp. 1559 - 1564 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society and American Society of Pharmacognosy
27.09.2013
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Subjects | |
Online Access | Get full text |
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Summary: | Four species of gonyleptid harvestmen, Acanthogonyleptes pulcher, Gonyleptes saprophilus (Gonyleptinae), Sodreana barbiellini, and Sodreana leprevosti (Sodreaninae), were examined by GC-MS and 1H NMR. All of these species release vinyl ketones, and three of them produce the corresponding pyranyl ketones, which are presumed hetero-Diels–Alder (HDA) dimers. The vinyl ketones 5-methyl-1-hexen-3-one, rac-4-methyl-1-hexen-3-one, and (S)-4-methyl-1-hexen-3-one were synthesized. Natural 4-methyl-1-hexen-3-one is present as a single stereoisomer and has the R-configuration. Vinyl ketone dimers (HDA dimers) were also observed in the scent gland exudate and characterized by HRMS, 13C NMR, and 1H NMR chemical shifts of the pyranyl moiety. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0163-3864 1520-6025 |
DOI: | 10.1021/np4001569 |