6-Alkyl-3,4-dihydro-2H-pyrans: Chemical Secretion Compounds in Neotropical Harvestmen

Author(s)

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

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

^[2] Univ Sao Paulo, Inst Biociencias, Dept Ecol, BR-05508090 Sao Paulo - Brazil

• Document type: Journal article
• Source: Journal of Natural Products; v. 74, n. 4, p. 658-663, APR 2011.
• Web of Science Citations: 16

Abstract

The defensive, secretions, of five neotropical) species of harvestmen, (Opiliones: Gonyleptidae) from the Brazilian Atlantic Forest were analyzed and chemically characterized by GC-MS and NMR Methods. Three of the species, Cobania picea, Roweria virescens, and Serracutisoma proximum, secrete a mixture of 2,3-dimethyl-1,4-benzoquinone and 2-ethyl-3methyl-1,4,4-benzoquinone. The secretions produced,by the Other two species Iporangaia pustulosa and Neosadocus maximus, contain 1-hepten-3-one, 5-methyl-1-hexen-3-one, and 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone. (1)as major components, as well as,2,3-dimethyl-1.,4-benzoquinone and 2-ethyl-3 methyl-1,4-benzoquinone as minor,constituents. The. dihydropyran 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone (1) is a new natural product, composed of two 1-hepten-3-one, subunits formally linked in a hetero-Diels-Alder reaction. The natural product was proven to be racemic, and its biogenetic origin is discussed. (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