Chemistry Institute, State University of Campinas, POB 6154 13083-970 Campinas, SP, Brazil.
J Nat Prod. 2011 Apr 25;74(4):658-63. doi: 10.1021/np100719f. Epub 2011 Feb 25.
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.
五种产自巴西大西洋森林的长脚盲蛛（盲蛛目：管颚科）的防御分泌物通过 GC-MS 和 NMR 方法进行了分析和化学特性鉴定。这三种物种（Cobania picea、Roweria virescens 和 Serracutisoma proximum）分泌的混合物中含有 2,3-二甲基-1,4-苯醌和 2-乙基-3-甲基-1,4-苯醌。另外两种物种（Iporangaia pustulosa 和 Neosadocus maximus）产生的分泌物主要成分包括 1-庚烯-3-酮、5-甲基-1-己烯-3-酮和 1-(6-丁基-3,4-二氢-2H-吡喃-2-基)戊酮（1），以及 2,3-二甲基-1,4-苯醌和 2-乙基-3-甲基-1,4-苯醌作为次要成分。二氢吡喃 1-(6-丁基-3,4-二氢-2H-吡喃-2-基)戊酮（1）是一种新的天然产物，由两个 1-庚烯-3-酮亚基以杂 Diels-Alder 反应的形式正式连接而成。该天然产物被证明为外消旋体，其生物发生起源也进行了讨论。
