色氨酸类似物的合成与杀菌活性——意想不到的腊梅科生物碱衍生物

Synthesis and fungicidal activity of tryptophan analogues - the unexpected calycanthaceous alkaloid derivatives.

作者信息

Zheng Shaojun, Gu Yongdong, Li Longbo, Zhu Rui, Cai Xingwei, Bai Hongjin, Zhang Jiwen

机构信息

a School of Environmental and Chemical Engineering , Jiangsu University of Science and Technology , Zhenjiang , P.R. China.

d Collaborative Innovation Center of Ship Technology in Jiangsu Colleges and Universities/Marine Equipment and Technology Institute for Jiangsu University of Science and Technology , Zhenjiang , P.R. China.

出版信息

Nat Prod Res. 2017 May;31(10):1142-1149. doi: 10.1080/14786419.2016.1230117. Epub 2016 Sep 21.

DOI:10.1080/14786419.2016.1230117

PMID:27653454

Abstract

A series of 21 N-protected tryptophan derivatives were synthesised from tryptophan in good yields. Their structures were characterised by IR, H NMR, C NMR, DEPT (90° and 135°) and MS analysis. The synthesised compounds were evaluated against a wide variety of plant pathogen fungi. Compounds a19 and a21 displayed activity against Fusarium oxysporum (F. oxysporum), and compound a21 showed high activity against F. oxysporum and Eggplant Verticillium, with EC values of 58.27 and 77.39 μg mL, respectively. Considering that the bioassay of the title compounds was evaluated, effects of the chain alkyl substituents may contribute to the significant variations in fungicidal potency. Their structure-antifungal activity relationships were also discussed. These results will pave the way for further design, structural modification and development of calycanthaceous alkaloids as antimicrobial agents.

摘要

以色氨酸为原料，高产率合成了一系列21种N-保护色氨酸衍生物。通过红外光谱（IR）、氢核磁共振（¹H NMR）、碳核磁共振（¹³C NMR）、DEPT（90°和135°）以及质谱（MS）分析对其结构进行了表征。对合成的化合物针对多种植物病原真菌进行了评估。化合物a19和a21对尖孢镰刀菌（Fusarium oxysporum）表现出活性，化合物a21对尖孢镰刀菌和茄子黄萎病菌表现出高活性，其半数有效浓度（EC）值分别为58.27和77.39 μg/mL。考虑到对标题化合物进行了生物测定，链状烷基取代基的影响可能导致杀菌效力的显著差异。还讨论了它们的构效关系。这些结果将为进一步设计、结构修饰和开发作为抗菌剂的蜡梅科生物碱铺平道路。