1 research outputs found
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, <i>Acanthogonyleptes
pulcher</i>,<i> Gonyleptes saprophilus</i> (Gonyleptinae), <i>Sodreana barbiellini</i>, and <i>Sodreana leprevosti</i> (Sodreaninae), were examined by GC-MS and <sup>1</sup>H 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, <i>rac</i>-4-methyl-1-hexen-3-one, and (<i>S</i>)-4-methyl-1-hexen-3-one
were synthesized. Natural 4-methyl-1-hexen-3-one is present as a single
stereoisomer and has the <i>R</i>-configuration. Vinyl ketone
dimers (HDA dimers) were also observed in the scent gland exudate
and characterized by HRMS, <sup>13</sup>C NMR, and <sup>1</sup>H NMR
chemical shifts of the pyranyl moiety