莲子草假隔链格孢毒素Vulculic Acid的合成

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (10): 2010.

莲子草假隔链格孢毒素Vulculic Acid的合成

陈迁2, 叶柳2, 孙媚华1, 施祖荣1, 向梅梅1, 周遗品1, 宋光泉1

1. 仲恺农业工程学院, 广州 510225;
2. 中国科学院广州生物医药与健康研究院, 广州 510663

收稿日期:2009-11-09 出版日期:2010-10-10 发布日期:2010-10-10
通讯作者: 向梅梅, 女, 博士，教授, 从事植物病原真菌及其代谢产物研究. E-mail: mm_xiang@163.com
基金资助:
国家自然科学基金(批准号: 30671382)资助.

Synthesis of Vulculic Acid from Nimbya alternantherae

CHEN Qian2, YE Liu2, SUN Mei-Hua1, SHI Zu-Rong1, XIANG Mei-Mei1*, ZHOU Yi-Pin1, SONG Guang-Quan1

1. Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China;
2. Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510663, China

Received:2009-11-09 Online:2010-10-10 Published:2010-10-10
Contact: XIANG Mei-Mei. E-mail: mm_xiang@163.com
Supported by:
国家自然科学基金(批准号: 30671382)资助.

摘要/Abstract

摘要： Vulculic acid是从莲子草假隔链格孢(Nimbya alternantherae)的代谢产物中分离得到的一种真菌毒素, 它对空心莲子草(Alternanthera philoxeroides)等多种杂草有致病活性, 是一种潜在的除草活性物质. 本文报道了Vulculic acid的化学合成. 从可商业购买的3,4,5-三甲氧基苯乙酸出发, 经甲酯化、傅克乙酰化、脱三甲基化、选择性上单甲基化以及水解等5步反应合成了目标产物, 总产率为21%. 生物活性测试结果表明, 合成的Vulculic acid对空心莲子草有致病活性, 所致症状与天然Vulculic acid一致.

关键词: 莲子草假隔链格孢, 真菌毒素, Vulculic acid, 化学合成

Abstract: Vulculic acid is a kind of phytotoxin separated from the metabolite of Nimbya alternantherae, which is a leaf spot fungus isolated from alligatorweed. This phytotoxin can result in plant withered and is a potential herbicide to alligatorweed. The synthesis of Vulculic acid using the commercially available 3,4,5-trimethoxyphenylacetic acid as the starting material was described. The whole route involved five steps in 21% overall yield with methyl esterification, followed by Friedel-Crafts acylation, demethylation, selective methylation and hydrolysis reaction. This synthesis takes advantage of a selective methylation reaction using borax as the chelating agent. Synthesized vulculic acid was dissolved in distilled water to detect its effect on alligatorweed leaf through the method of leaf-puncture-soak. The results show that synthetic Vulculic acid could cause leaf spot, same as the symptom by the native Vulculic acid, at the level of 50 μg/mL after treating for 24 h. These results suggest that synthesized Vulculic acid should be good prospect for the application in the control of alligatorweed.

Key words: Nimbya alternantherae, Phytotoxin, Vulculic acid, Chemical synthesis

TrendMD:

陈迁, 叶柳, 孙媚华, 施祖荣, 向梅梅, 周遗品, 宋光泉. 莲子草假隔链格孢毒素Vulculic Acid的合成. 高等学校化学学报, 2010, 31(10): 2010.

CHEN Qian, YE Liu, SUN Mei-Hua, SHI Zu-Rong, XIANG Mei-Mei*, ZHOU Yi-Pin, SONG Guang-Quan . Synthesis of Vulculic Acid from Nimbya alternantherae. Chem. J. Chinese Universities, 2010, 31(10): 2010.

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