(E)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (α-Acariolal) and (E)-2-(2-Hydroxyethyl)-6-methyl-2,5-heptadienal (β-Acariolal), Two New Types of Isomeric Monoterpenes…
(E)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (α-Acariolal) and (E)-2-(2-Hydroxyethyl)-6-methyl-2,5-heptadienal (β-Acariolal), Two New Types of Isomeric Monoterpenes…
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(E)-2-(2-羟基亚乙基)-6-甲基-5-庚烯醛(α-螨醛)和(E)-2-(2-羟乙基)-6-甲基-2,5-庚二烯醛(β-螨醛) ），两种新型同分异构单萜……
DOI：
10.1271/bbb.67.308
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发表时间：
2003
期刊：
影响因子：
--
通讯作者：
Y. Kuwahara
中科院分区：
文献类型：
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作者：
Nobuhiro Shimizu;Hirokazu Tarui;N. Mori;R. Nishida;Y. Kuwahara
螨虫Caloglyphus polyphyllae 的角腺分泌物含有两种新的单萜，(E)-2-(2-羟亚乙基)-6-甲基-5-庚烯醛(1) 和(E)-2-(2-羟乙基)-6-甲基-2,5-庚二烯醛(2)，我们将其分别命名为α-和β-螨醛。分别为 α- 和 β- 螨虫醛（3 和 4）。 1 结构的阐明主要根据部分纯化后的 1H-NMR 和 GC/MS 光谱数据，以及从硅胶柱中回收的 1 的极性比分泌物中存在的 α- 和 β-螨虫醛（3 和 4）极性更强的事实。化合物 2 是在与 1 的混合物相同的馏分中获得的。根据 GC/MS 分析，2 与 1 具有相同的分子量和相同的极性，因此化合物 2 被认为是 1 的结构类似物。化合物 1 和 2 的结构通过从 α-溴-γ-丁内酯开始分别经过九步和十步的合成得到证实。
The opisthonotal gland secretion of the acarid mite, Caloglyphus polyphyllae, contained two new monoterpenes, (E)-2-(2-hydroxyethylidene)-6-methyl-5-heptenal (1) and (E)-2-(2-hydroxyethyl)-6-methyl-2,5-heptadienal (2), to which we have given the trivial names α- and β-acariolal in relation to α- and β-acaridial (3 and 4), respectively. Elucidation of the structure of 1 was established mainly from 1H-NMR and GC/MS spectral data after partial purification, together with the fact that 1 was recovered in the more-polar fraction from a silica gel column than α- and β-acaridial (3 and 4) present in the secretion. Compound 2 was obtained in the same fraction as a mixture with 1. Based on the facts that 2 had the same molecular weight by GC/MS and the same polarity as that of 1, compound 2 was assumed to be a structural analog of 1. The structures of compounds 1 and 2 were confirmed by their synthesis in nine and ten respective steps starting from α-bromo-γ-butyrolactone.