6-alkyl-3,4-dihydro-2H -pyrans: Chemical secretion compounds in neotropical harvestmen

Daniele F.O. Rocha, Kerry Hamilton, Caroline C.S. Gonçalves, Glauco MacHado, Anita J. Marsaioli

Research output: Contribution to journalArticle

17 Citations (Scopus)

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-3-methyl-1,4-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.

Original languageEnglish (US)
Pages (from-to)658-663
Number of pages6
JournalJournal of Natural Products
Volume74
Issue number4
DOIs
StatePublished - Apr 25 2011
Externally publishedYes

Fingerprint

Chemical compounds
Biological Products
Picea
Cycloaddition Reaction
Nuclear magnetic resonance
2-ethyl-3-methyl-1,4-benzoquinone
1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone
3,4-dihydro-(2H)-pyran
2,3-dimethyl-2,5-cyclohexadiene-1,4 dione
Forests

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

6-alkyl-3,4-dihydro-2H -pyrans : Chemical secretion compounds in neotropical harvestmen. / Rocha, Daniele F.O.; Hamilton, Kerry; Gonçalves, Caroline C.S.; MacHado, Glauco; Marsaioli, Anita J.

In: Journal of Natural Products, Vol. 74, No. 4, 25.04.2011, p. 658-663.

Research output: Contribution to journalArticle

Rocha, Daniele F.O. ; Hamilton, Kerry ; Gonçalves, Caroline C.S. ; MacHado, Glauco ; Marsaioli, Anita J. / 6-alkyl-3,4-dihydro-2H -pyrans : Chemical secretion compounds in neotropical harvestmen. In: Journal of Natural Products. 2011 ; Vol. 74, No. 4. pp. 658-663.
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