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 inJournal of natural products (Washington, D.C.) Vol. 76; no. 9; pp. 1559 - 1564
Main Authors Wouters, Felipe C, Rocha, Daniele F. O, Gonçalves, Caroline C. S, Machado, Glauco, Marsaioli, Anita J
Format Journal Article
LanguageEnglish
Published United States American Chemical Society and American Society of Pharmacognosy 27.09.2013
Subjects
Animals
Arachnida
Arachnida - chemistry
Arachnida - classification
Arachnida - genetics
Gas Chromatography-Mass Spectrometry
Ketones - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Opiliones
Pyrans - chemistry
Scent Glands - chemistry
Scent Glands - secretion
Stereoisomerism
Vinyl Compounds - chemistry
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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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ISSN:0163-3864
1520-6025
DOI:10.1021/np4001569