槐庶尺蛾性信息素腺体EAG活性成分绝对构型的鉴定(英文)

›› 2012, Vol. 55 ›› Issue (2): 162-167.doi:

槐庶尺蛾性信息素腺体EAG活性成分绝对构型的鉴定(英文)

孔祥波, 王鸿斌, 张真

收稿日期:2011-07-22 修回日期:2012-02-09 出版日期:2012-02-20 发布日期:2012-02-20
通讯作者: 孔祥波 E-mail:kongxbo@hotmail.com
作者简介:孔祥波，男， 1971年生，山东人，副研究员，主要从事昆虫化学生态研究,E-mail:kongxbo@hotmail.com

Determination of the absolute configuration of an EAG active component in the sex pheromone gland of Semiothisa cinerearia Bremer et Grey (Lepidoptera: Geometridae) (In English)

KONG Xiang-Bo, WANG Hong-Bin, ZHANG Zhen

Received:2011-07-22 Revised:2012-02-09 Online:2012-02-20 Published:2012-02-20
Contact: KONG Xiang-Bo E-mail:kongxbo@hotmail.com
About author:kongxbo@hotmail.com

摘要/Abstract

摘要： 槐庶尺蛾Semiothisa cinerearia Bremer et Grey （鳞翅目：尺蛾科）是我国北方国槐Sophora japonica L.上的重要食叶害虫。本研究的主要目的是阐明槐庶尺蛾性信息素成分化学结构的绝对构型，为在城市地区环境友好地防控槐庶尺蛾的为害提供一种新方法。经与标准品比较气相色谱保留时间和质谱特征离子，从槐庶尺蛾处女雌蛾（2-3日龄）性信息素腺体溶剂提取物中检测到顺6, 顺9-顺-3, 4-环氧-十七碳二烯烃和顺3, 顺6, 顺9-3, 6, 9-十七碳三烯烃2种成分，在腺体中以100∶4.8±1.3 （N=12）的比例存在。槐庶尺蛾性信息素腺体提取物进一步经手性毛细管色谱柱（CycloSil-B， 30 m×0.25 mm×0.25 μm 液膜厚）分离，在优化的程序升温条件下发现腺体成分顺6, 顺9-顺-3, 4-环氧-十七碳二烯烃具有3R, 4S的绝对构型。两种合成的对映异构体混合物顺6, 顺9-3R, 4S-环氧-十七碳二烯烃和顺6, 顺9-3S, 4R-环氧-十七碳二烯烃以1.28∶1的比例加到腺体提取物中，比例变为1.55∶1。根据这一分析，腺体成分顺6, 顺9-顺-3, 4-环氧-十七碳二烯烃进一步确认具有3R, 4S的绝对构型。该研究结论将为生产上研发高效的槐庶尺蛾性信息素诱芯奠定坚实的基础。

关键词: 槐庶尺蛾, 性信息素, 顺6, 顺9-3R, 4S-环氧-十七碳二烯烃, 绝对构型, 气相色谱-质谱, 手性分离

Abstract: The Chinese scholar tree looper, Semiothisa cinerearia Bremer et Grey (Lepidoptera: Geometridae), is the major defoliator of the Chinese scholar tree Sophora japonica L. in China. The elucidation of the absolute chemical structure of the sex pheromone component of S. cinerearia may provide a potential chemical for the pest control against the S. cinerearia infestations in the urban area. In this study, two sex pheromone gland compounds, i.e., (6Z, 9Z)6, 9cis-3, 4-epoxy-heptadecadiene (6Z, 9Z-cis-3, 4-epoxy-17: H) and (3Z, 6Z, 9Z)-3, 6, 9-heptadecatriene (3Z, 6Z, 9Z-17: H), were detected in a 100∶4.8±1.3 ratio (N=12) during analyses of solvent extracts from virgin female S. cinerearia (2-3 d old) by comparison of their gas chromatography (GC) retention time and mass spectra (MS) with those of synthetic standards. Furthermore, the absolute configuration of 6Z, 9Z-cis-3, 4-epoxy-17: H in the sex pheromone gland of S. cinerearia was determined as (6Z, 9Z)-3R, 4S-epoxy-heptadecadiene by using a chiral capillary column (CycloSil-B, 30 m × 0.25 mm × 0.25 μm film) GC under the optimized oven temperature program. The mixture of the two synthetic enantiomers of 6Z, 9Z-3R, 4S-epoxy-17: H and 6Z, 9Z-3S, 4R-epoxy-17: H in a ratio of 1.28∶1 was injected into the female extracts, and thus the ratio was changed to 1.55∶1. Based on this analysis, the absolute configuration of the gland component 6Z, 9Z-cis-3, 4-epoxy-17: H was further confirmed as 3R, 4S. It is anticipated that control of S. cinerearia infestation with enantiomerically pure materials will be much more effective.

Key words: Semiothisa cinerearia, sex pheromone, (6Z, 9Z)-3R, 4S-epoxy-heptadecadiene , absolute configuration, GC-MS, chiral separation

孔祥波, 王鸿斌, 张真. 槐庶尺蛾性信息素腺体EAG活性成分绝对构型的鉴定(英文)[J]. , 2012, 55(2): 162-167.

KONG Xiang-Bo, WANG Hong-Bin, ZHANG Zhen. Determination of the absolute configuration of an EAG active component in the sex pheromone gland of Semiothisa cinerearia Bremer et Grey (Lepidoptera: Geometridae) (In English)[J]. , 2012, 55(2): 162-167.

0
/ / 推荐

导出引用管理器 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

链接本文: http://www.insect.org.cn/CN/

http://www.insect.org.cn/CN/Y2012/V55/I2/162

[1]	徐翔, 孔德生, 冯波, 钱凯, 杜永均. 玉米桃蛀螟雌蛾性信息素的微量组分鉴定及其性信息素诱芯组分的配比优化[J]. , 2018, 61(10): 1184-1191.
[2]	陈庆华, 曾娟, 曾伟, 李庆, 陈晓娟, 邹禹. 稻纵卷叶螟雄蛾内生殖系统形态指标在性诱测报中的应用[J]. , 2017, 60(8): 927-935.
[3]	胡俊杰, 孟翔, 周佳滨杨陆兴, 刘善海, 李润钊. 扶桑绵粉蚧转录组分析[J]. , 2017, 60(1): 9-17.
[4]	万新龙, 李江辉, 劳冲, 杜永均. 斜纹夜蛾触角叶神经元及其对植物气味和性信息素的反应[J]. , 2015, 58(3): 223-236.
[5]	林欣大, 劳冲, 姚云, 杜永均. 性信息素对斜纹夜蛾雄蛾嗅觉相关基因 abp, pbp 和 or 表达的影响[J]. , 2015, 58(3): 237-243.
[6]	Leila MAHMOODI, Oroj VALIZADEGAN, Vahid MAHDAVI. 印度藏茴香植物精油对温室棉蚜的熏蒸毒性及其成分分析（英文）[J]. , 2015, 58(2): 147-153.
[7]	贾小俭, 郝少东, 杜艳丽, 张民照, 覃晓春, 王进忠, 王海香, 冀卫荣. 桃蛀螟性信息素结合蛋白Cpun-PBP1的cDNA克隆、表达谱及其与配体化合物的结合特性分析[J]. , 2015, 58(11): 1167-1176.
[8]	李文海, 黄兴龙, 王敦, 冯纪年. 核桃举肢蛾性信息素结合蛋白2的分子克隆和免疫荧光定位[J]. , 2015, 58(10): 1054-1062.
[9]	何月秋, 池树友, 杜永均. 黄杨绢野螟雌蛾性信息素的鉴定及诱蛾活性[J]. , 2015, 58(10): 1081-1090.
[10]	杨美红, 刘红霞, 刘金龙, 范丽华, 荆小院,张金桐, 宗世祥, 骆有庆. 榆木蠹蛾雄蛾对性信息素不同组分及其不同比例和剂量混合物的风洞行为反应[J]. , 2015, 58(1): 38-44.
[11]	闫硕，李慧婷，朱威龙，朱家林，张青文，刘小侠. 光强度对棉铃虫交配行为的影响[J]. , 2014, 57(9): 1045-1050.
[12]	刘曼，杨茂发，徐思远，姚松林. 竹织叶野螟成虫求偶行为及其雌蛾性信息素分泌腺超微结构[J]. , 2014, 57(8): 879-888.
[13]	范荫荫, 安世恒, 王琼, 刘孝明, 李为争, 郭线茹, 原国辉. 烟夜蛾性肽受体基因的克隆与表达模式分析[J]. , 2014, 57(11): 1281-1288.
[14]	纪萍, 刘靖涛, 谷少华, 朱晓强, 张永军, 郭予元. 绿盲蝽气味结合蛋白AlucOBP7的表达及气味结合特性[J]. , 2013, 56(6): 575-583.
[15]	程冬保. 白蚁信息素研究进展[J]. , 2013, 56(4): 419-426.