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正十六烷酸己酯和十四种相关脂肪酸酯:来自节胸蜈蚣 Anaulaciulus sp. 的新分泌化合物

n-Hexyl laurate and fourteen related fatty acid esters: new secretory compounds from the julid millipede, Anaulaciulus sp.

机构信息

Faculty of Bioenvironmental Science, Kyoto Gakuen University, Sogabe, Kameoka, Japan.

出版信息

J Chem Ecol. 2012 Jan;38(1):23-8. doi: 10.1007/s10886-012-0063-4. Epub 2012 Jan 18.

DOI:10.1007/s10886-012-0063-4
PMID:22252536
Abstract

A total of fifteen saturated fatty acid esters were newly identified from the secretions of an unidentified Anaulaciulus sp. (Julida: Julidae). The fatty acid components of the esters were composed of normal chain acids (from C(10) to C(14)) and of branched chain acids (from iso-C(12) to iso-C(15) and anteiso-C(15)). The alcohol moieties were all composed of normal chain alcohols varying from n-butanol to n-octanol. The most abundant component found in the total esters was n-hexyl laurate (64.7%). Novel compounds identified from the millipede secretion extracts include six branched iso- and anteiso-fatty esters, an odd-numbered C(11)-fatty acid ester, a C(13)-fatty acid ester, and a C(7)-alcohol ester, all of which were previously undescribed natural products. In addition, a characteristic mixture of benzoquinones, such as 2-methyl-1,4-benzoquinone, 2-methoxy-3-methyl-1,4-benzoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-methoxy-6-methyl-1,4-benzoquinone, and 2,3-dimethoxy-5-methyl-1,4-benzoquinone were identified from the secretions, together with trace amounts of 1,4-benzoquinone.

摘要

总共从一种未鉴定的 Anaulaciulus sp.(Julida:Julidae)分泌物中鉴定出了十五种饱和脂肪酸酯。酯的脂肪酸成分由直链酸(C(10) 到 C(14))和支链酸(异-C(12) 到异-C(15) 和 anteiso-C(15))组成。醇部分均由从正丁醇到正辛醇的直链醇组成。在总酯中发现的最丰富的成分是正己基月桂酸酯(64.7%)。从千足虫分泌物提取物中鉴定出的新型化合物包括六种支链异和 anteiso 脂肪酸酯、一种奇数 C(11)-脂肪酸酯、一种 C(13)-脂肪酸酯和一种 C(7)-醇酯,所有这些都是以前未描述的天然产物。此外,从分泌物中还鉴定出了特征性的苯醌混合物,如 2-甲基-1,4-苯醌、2-甲氧基-3-甲基-1,4-苯醌、2,3-二甲氧基-1,4-苯醌、2-甲氧基-6-甲基-1,4-苯醌和 2,3-二甲氧基-5-甲基-1,4-苯醌,以及痕量的 1,4-苯醌。

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