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

详细信息    查看全文

• 作者：Daniele F. O. Rocha ; Kerry Hamilton ; Caroline C. S. Gonc抬alves ; Glauco Machado ; Anita J. Marsaioli
• 刊名：Journal of Natural Products
• 出版年：2011
• 出版时间：April 25, 2011
• 年：2011
• 卷：74
• 期：4
• 页码：658-663
• 全文大小：792K
• 年卷期：v.74,no.4(April 25, 2011)
• ISSN：1520-6025

文摘

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鈭扐lder reaction. The natural product was proven to be racemic, and its biogenetic origin is discussed.