title: Additional vinyl ketones and their pyranyl ketones in gonyleptid harvestmen (Arachnida: Opiliones) suggest these metabolites are widespread in this family.
abstract: Four species of gonyleptid harvestmen, Acanthogonyleptes pulcher, Gonyleptes saprophilus (Gonyleptinae), Sodreana barbiellini, and Sodreana leprevosti (Sodreaninae), were examined by GC-MS and ¹³H 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.
authors: Chemistry Institute, State University of Campinas , Campinas, SP, Brazil.
authors: Felipe C
authors: FC
authors: Wouters
authors: Daniele F O
authors: DF
authors: Rocha
authors: Caroline C S
authors: CC
authors: Gonçalves
authors: Glauco
authors: G
authors: Machado
authors: Anita J
authors: AJ
authors: Marsaioli
mesh_terms: D000818:Animals; D001097:Arachnida / Q000737:chemistry* / Q000145:classification / Q000235:genetics; D008401:Gas Chromatography-Mass Spectrometry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011714:Pyrans / Q000737:chemistry*; D012543:Scent Glands / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D007659:Ketones; D011714:Pyrans; D014753:Vinyl Compounds