Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A

doi:10.6023/cjoc202006065

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 553-566.DOI: 10.6023/cjoc202006065 Previous Articles Next Articles

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线虫孵化信息素Glycinoeclepin A的生物活性及合成研究进展

马丁^a^,^b, 敖军礼^a^,^b, 胡乃峰^a, 梁广鑫^b^,^*()

a 南开大学元素有机化学国家重点实验室天津 300071
b 上海科技大学物质科学与技术学院上海 201210

收稿日期:2020-06-29 修回日期:2020-08-04 发布日期:2020-09-09
通讯作者: 梁广鑫
作者简介:
* Corresponding author. E-mail: lianggx@shanghaitech.edu.cn
基金资助:
国家重点研发计划(2017YFD0201404)

Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A

Ding Ma^a^,^b, Junli Ao^a^,^b, Naifeng Hu^a, Guangxin Liang^b^,^*()

a State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071
b School of Physical Science and Technology, Shanghai Tech University, Shanghai 201210

Received:2020-06-29 Revised:2020-08-04 Published:2020-09-09
Contact: Guangxin Liang
Supported by:
the National Key Research and Development Program of China(2017YFD0201404)

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

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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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Fig. & Tab. 24

Figure 1. Chemical structures of glycinoeclepin A and their derivatives

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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线虫孵化信息素Glycinoeclepin A的生物活性及合成研究进展

Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A

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