线虫孵化信息素Glycinoeclepin A的生物活性及合成研究进展

doi:10.6023/cjoc202006065

摘要/Abstract

大豆胞囊线虫病作为影响大豆产量的主要病害之一, 非常难以防治, 给全世界大豆主产地带来了严重的经济损失. Glycinoeclepin A是一个从四季豆根系的干粉中提取纯化得到的化学信息素, 能够特异性地促进大豆胞囊线虫孵化, 其生物活性可达10^–12 g/mL (25 ℃, 水溶液), 具有成为新型杀线虫绿色生物农药的巨大潜质. 概述了大豆胞囊线虫的繁殖与传统防治方法、glycinoeclepin A的分离与生物活性以及自其发现以来全世界有机合成化学家对该天然产物的全合成和构效关系研究进展.

关键词: 大豆胞囊线虫, 化学感受作用, glycinoeclepin A, 全合成, 构效关系

Soybean cyst nematode disease, one of the main diseases impacting the production of soybean, is very difficult to control and brings serious economic losses all over the world. Glycinoeclepin A is a chemical pheromone extracted and purified from the dry powder of string bean roots. It can specifically stimulate the hatching of soybean cyst nematodes, with biological activity of 10^–12 g/mL (25 ℃, aqueous solution). Potentially, glycinoeclepin A can serve as a new type of green biological pesticide for controlling soybean cyst nematode disease. A comprehensive overview on soybean cyst nematode disease, current methods in fighting it, the bioactivity studies on glycinoeclepin A, as well as the progress in the total synthesis and structure-activity relationship of this natural product since its discovery is provided.

Key words: soybean cyst nematode, chemoreception, glycinoeclepin A, total synthesis, structure-activity relationship

引用此文

马丁, 敖军礼, 胡乃峰, 梁广鑫. 线虫孵化信息素Glycinoeclepin A的生物活性及合成研究进展[J]. 有机化学, 2021, 41(2): 553-566.

Ding Ma, Junli Ao, Naifeng Hu, Guangxin Liang. Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 553-566.

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图/表 24

图1. 天然产物glycinoeclepin A及其衍生物的结构

Figure 1. Chemical structures of glycinoeclepin A and their derivatives

图式1. Murai课题组关于glycinoeclepin A的逆合成分析

Scheme 1. Retrosynthetic analysis of glycinoeclepin A by Murai?s group

图式2. Murai课题组对光学活性烷基化片段4的制备

Scheme 2. Preparation of optically active piece for alkylation 4 by Murai?s group

图式3. Murai课题组对高级中间体18的立体选择性合成

Scheme 3. Murai group’s stereoselective synthesis of advanced intermediate 18

图式4. Murai课题组关于glycinoeclepin A的全合成

Scheme 4. Murai group’s total synthesis of glycinoeclepin A

图式5. Corey课题组关于glycinoeclepin A的逆合成分析

Scheme 5. Retrosynthetic analysis of glycinoeclepin A by Corey?s group

图式6. Corey课题组对光学活性片段28的制备

Scheme 6. Preparation of optically active piece 28 by Corey?s group

图式7. Corey课题组对光学活性片段35的制备

Scheme 7. Preparation of optically active fragment 35 by Corey?s group

图式8. Corey课题组对[6,5]环系39的高效立体选择性构筑

Scheme 8. Stereoselective preparation of [6,5] ring system 39 by Corey?s group

图式9. Corey 课题组关于glycinoeclepin A 的全合成

Scheme 9. Corey group's total synthesis of glycinoeclepin A

图式10. Corey 课题组关于glycinoeclepin A的仿生合成研究

Scheme 10. Corey group's biomimetic synthetic studies on glycinoeclepin A

图式11. Mori课题组关于glycinoeclepin A 的逆合成分析

Scheme 11. Retrosynthetic analysis of glycinoeclepin A by Mori?s group

图式12. Mori课题组对桥醚片段63的制备

Scheme 12. Preparation of bridged ether piece 53 by Mori?s group

图式13. Mori课题组对中间体71的合成

Scheme 13. Synthesis of intermediate 71 by Mori?s group

图式14. Mori课题组关于glycinoeclepin A的全合成

Scheme 14. Mori group's total synthesis of glycinoeclepin A

图式15. Tanino课题组关于glycinoeclepin A的逆合成分析

Scheme 15. Retro-synthetic analysis of glycinoeclepin A by Tanino?s group

图式16. Tanino课题组对氧桥化合物86的合成

Scheme 16. Synthesis of oxygen bridge compound 86 by Tanino?s group

图式17. Tanino课题组对[6,5]环片段97的合成

Scheme 17. Synthesis of [6,5] ring system 97 by Tanino?s group

图式18. Tanino课题组对glycinoeclepin A的全合成

Scheme 18. Tanino group’s total synthesis of glycinoeclepin A

图2. Murai课题组关于glycinoeclepin A及其类似物的构效关系的研究

Figure 2. Research on structure-activity relationship of glycinoeclepin A and its analogs by Murai’s group

图3. Kraus课题组关于glycinoeclepin A类似物构效关系的研究

Figure 3. Research on structure-activity relationship of analogs of glycinoeclepin A by Kraus’s group

图式19. Corey课题组关于glycinoeclepin A类似物的合成研究

Scheme 19. Synthesis of a glycinoeclepin A analog by Corey’s group

图式20. Sakakibara课题组关于glycinoeclepin A类似物的合成研究

Scheme 20. Research of synthesis about analogs of glycinoeclepin A by Sakakibara’s group

图式21. Sakakibara课题组关于glycinoeclepin A类似物的合成研究

Scheme 21. Synthesis of a glycinoeclepin A analog by Sakakibara’s group

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