Additional Vinyl Ketones and Their Pyranyl Ketones in Gonyleptid Harvestmen (Arachnida: Opiliones) Suggest These Metabolites Are Widespread in This Family

Autor(es)

Wouters, Felipe C. ^[1] ; Rocha, Daniele F. O. ^[1] ; Goncalves, Caroline C. S. ^[1] ; Machado, Glauco ^[2] ; Marsaioli, Anita J. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, Campinas, SP - Brazil

^[2] Univ Sao Paulo, Inst Biociencias, Dept Ecol, Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Natural Products; v. 76, n. 9, p. 1559-1564, SEP 2013.
• Citações Web of Science: 7

Resumo

Four species of gonyleptid harvestmen, Acanthogonyleptes pulcher, Gonyleptes saprophilus (Gonyleptinae), Sodreana barbiellini, and Sodreana leprevosti (Sodreaninae), were examined by GC-MS and H-1 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, C-13 NMR, and H-1 NMR chemical shifts of the pyranyl moiety. (AU)

• Processo FAPESP: 02/00381-0 - Investimento parental e evolução do comportamento sub-social em opiliões da família Gonyleptidae (Arachnida: Opiliones)
• Beneficiário: Glauco Machado
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 08/06604-7 - Filogenia dos opiliões da família Gonyleptidae (Arachnida: Opiliones) baseada em caracteres morfológicos, moleculares e comportamentais
• Beneficiário: Ricardo Pinto da Rocha
• Modalidade de apoio: Auxílio à Pesquisa - Regular