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莪术主要抗真菌成分对甲氧基肉桂酸乙酯的分离

Isolation of Ethyl p-methoxycinnamate, the major antifungal principle of Curcumba zedoaria.

作者信息

Gupta S K, Banerjee A B, Achari B

出版信息

Lloydia. 1976 Jul-Aug;39(4):218-22.

PMID:785141
Abstract

An antifungal principle of the dried rhizomes of Curcuma zedoaria was extracted with hot ethanol. By successive chromatography on neutral alumina and silica gel, three antibiotic compounds A, B, and C, all active against Trichophyton rubrum, Aspergillus niger and Saccharomyces cerevisiae, were obtained in chemically pure form. By uv, ir, pmr and ms analysis, the structure of the most abundant one of these compounds (C, 69.8%; H, 6,8%; and 0.23.4%) was assigned as ethyl p-methoxycinnamate (EPMC). The proposed structure was confirmed by synthesis and comparison of the chemical and biological properties of the natural and synthetic products. EPMC inhibits the growth of Trichophyton rubrum, Aspergillus niger, Saccharomyces cerevisiae and Epidermophyton floccosum at a concentration less than 10 mug/ml; A. fumigatus, Penicillium purpurogenum, Trignoposis variabilis, Microsporum gypseum, Sclerotium rolifsii, Geotricular candiade, Fusarium oxysporum and Helminthosporium oryzale at a concentration less than 25 mug/ml; and Candida krusei and T. mentagrophytes At a concentration less than 50 mug/ml. The spores of T. rubrum Lose viability or ability to germinate when wxposed to its ethanolic solution (30 mug/ml) for 2 hours.

摘要

莪术干燥根茎的抗真菌成分用热乙醇提取。通过在中性氧化铝和硅胶上连续色谱分离,得到了三种对红色毛癣菌、黑曲霉和酿酒酵母均有活性的抗生素化合物A、B和C,并获得了化学纯品。通过紫外、红外、核磁共振和质谱分析,确定了这些化合物中含量最高的一种(C,69.8%;H,6.8%;O,23.4%)的结构为对甲氧基肉桂酸乙酯(EPMC)。通过合成以及对天然产物和合成产物的化学和生物学性质进行比较,证实了所提出的结构。EPMC在浓度小于10微克/毫升时可抑制红色毛癣菌、黑曲霉、酿酒酵母和絮状表皮癣菌的生长;在浓度小于25微克/毫升时可抑制烟曲霉、产紫青霉、变异三角酵母、石膏样小孢子菌、立枯丝核菌、白地霉、尖孢镰刀菌和稻瘟病菌的生长;在浓度小于50微克/毫升时可抑制克鲁斯念珠菌和须癣毛癣菌的生长。红色毛癣菌的孢子在暴露于其乙醇溶液(30微克/毫升)2小时后会失去活力或发芽能力。

相似文献

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Isolation of Ethyl p-methoxycinnamate, the major antifungal principle of Curcumba zedoaria.莪术主要抗真菌成分对甲氧基肉桂酸乙酯的分离
Lloydia. 1976 Jul-Aug;39(4):218-22.
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