Synthesis of Vulculic Acid from Nimbya alternantherae

Abstract

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:

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[J]. Chem. J. Chinese Universities, 2010, 31(10): 2010.

References

[1]ZHENG Xiao-Lian(郑晓莲), DONG Jin-Gao(董金皋), QI Qiu-Suo(齐秋锁), LI Dong-Mei(李冬梅). Acta Phytopathologica Sinica(植物病理学报)[J], 1998, 28(3): 269—271 [2]Evidente A., Capasso R., Cutignano A., Taglialatela Scafati O., Vurro M., Zonno M., Motta A.. Phytochemistry[J], 1998, 48(7): 1131—1137 [3]Evidente A., Andolfi A., Vurro M., Zonno M., Motta A.. Phytochemistry[J], 2000, 53(2): 231—237 [4]Evidente A., Cimmino A., Andolfi A., Vurro M., Zonno M., Motta A.. Journal of Agricultural and Food Chemistry[J], 2008, 56(3): 884—888 [5]XIANG Mei-Mei(向梅梅), LIU Ren(刘任), ZENG Yong-San(曾永三). Mycosystema(菌物系统)[J], 1998, 17(3): 283—288 [6]XIANG Mei-Mei(向梅梅), ZENG Yong-San(曾永三), LIU Ren(刘任), CHEN Sheng-Qing(陈圣清), CAI Jun-Hong(蔡军宏), YOU Ming-Long(游明龙). Acta Phytopathologica Sinica(植物病理学报)[J], 2002, 32(3): 286—287 [7]XIANG Mei-Mei(向梅梅), ZENG Yong-San(曾永三), LIU Ren(刘任), QIN Xiao-Lin(覃肖林). Chinese Journal of Biological Control(中国生物防治)[J], 2002, 18(2): 87—89 [8]ZHOU Yi-Pin(周遗品), XIANG Mei-Mei(向梅梅), JIANG Zi-De(姜子德), LI Hua-Ping(李华平), SUN Wei(孙伟), LIN Hai-Lin(林海琳), FAN Huai-Zhong(范怀忠). Chem. J. Chinese Universities(高等学校化学学报)[J], 2006, 27(8): 1485—1487 [9]ZENG Yong-San(曾永三), XIANG Mei-Mei(向梅梅), XIE Yan-Ping(谢燕平). Journal of Zhongkai University of Agriculture and Technology(仲恺农业技术学院学报)[J], 2005, 18(4): 1—5 [10]Kimura Y., Nishibe M., Nakajima H., Hamasaki T.. Agric. Biol. Chem.[J], 1991, 55(4): 1137—1138 [11]Patra A., Mukhopadhyay P. K.. J. India. Chem. Soc.[J], 1983, 60(3): 265—268 [12]Sober D. J., Chang J., Fairchild E. H., Fowble J. W., Mukhopadhyay A., Feller D. R., Miller D. D.. J. Med. Chem.[J], 1981, 24(8): 970—974 [13]Cason J., Lynch D. M.. J. Org. Chem.[J], 1966, 13(6): 1883—1887 [14]Pyuskulev B., Rindone B., Scolastico C.. Tetrahedron[J], 1973, 29(18): 2849—2850 [15]Kamal A., Qureshi A. A., Ahmad A., Rickards R. W.. Tetrahedron[J], 1965, 21(6): 1411—1415 [16]McMills M. C., Wright D. L., Weekly R. M.. Syn. Comm.[J], 2002, 32(15): 2417—2425 [17]Tang G., Ding K., Nikolovska-Coleska Z., et al.. J. Med. Chem.[J], 2007, 50(14): 3163—3166 [18]Jing X., Gu W., Bie P., Ren X., Pan X.. Syn. Comm.[J], 2001, 31(6): 861—867 [19]Bishop M., Bott S. G., Barron A. R.. J. Chem. Soc., Dalton Trans.[J], 2000, (18): 3100—3105 [20]Tyman J. H. P., Payne P. B.. J. Appl. Polym. Sci. [J], 2007, 105(2): 420—423