Advanced search
Start date
Betweenand
Related content
(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

Full text
Author(s):
Wouters, Felipe C. [1] ; Rocha, Daniele F. O. [1] ; Goncalves, Caroline C. S. [1] ; Machado, Glauco [2] ; Marsaioli, Anita J. [1]
Total Authors: 5
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, Campinas, SP - Brazil
[2] Univ Sao Paulo, Inst Biociencias, Dept Ecol, Sao Paulo - Brazil
Total Affiliations: 2
Document type: Journal article
Source: Journal of Natural Products; v. 76, n. 9, p. 1559-1564, SEP 2013.
Web of Science Citations: 7
Abstract

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)

FAPESP's process: 08/06604-7 - Cladistics of the harvestmen of the family Gonyleptidae (Arachnida: Opiliones) based on morphological, behavioral and molecular characters
Grantee:Ricardo Pinto da Rocha
Support Opportunities: Regular Research Grants