菊欧氏杆菌(Erwinia chrysanthemi)产生新抗生素Echcin Ⅰ的化学结构分析

Chemical Structure Determination of Echcin I, a New Antibiotic Produced by Erwinia Chrysanthemi

Echcin Ⅰ是一种新的广谱抗生素,EI/MS谱显示Echcin Ⅰ的分子离子峰为654,FAB/MS和SCI/MS谱均有一强的655峰(M+H)^+,根据高分辨质谱和元素分析结果显示Echcin Ⅰ的分子式为C_(10)H_(87)ON_5,精确分子量为653,6856。Echcin Ⅰ的紫外吸收为189nm;主要的红外吸收峰是3367,3282,1605(-NH_2)∶2920,2849(-CH_2-),722(-C-(CH_2)_n-C-)。~1H-NMR的主要谱线有(δ_(TMS)^(CD_3OD))∶0.84t,1.25s,1.36d,1.46m,1.55m,2.63s,2.70m和3.56d。尽管使用了高分辨的核磁共振仪进行测量,Echcin Ⅰ的^(13)C-NMR谱仅出现15条谱线,即(ppm)∶14.7(-CH_3),23.9,26.9,27.0,27.1,27.2,30.8,31.1,33.4,37.6,39.0,39.7,40.9(-CH_2-),52.5(-CH-)和71.2(-CH-),结合使用无畸变极化转移增强法分析,得出Echcin Ⅰ的化学结构为3-羟基-11,19,27,35-四氨基-正四十烷胺。

Echcin Ⅰ is a new antibiotic which has broad spectrum killing against Gram-negtive bacteri a,Gram-positive bacteria, fungi and cancer cells. The chloride of Echcin Ⅰ is water soluble. In water containing NaCl, the radial crystal of chlorinated Echcin Ⅰ has been obtained. Echcin Ⅰ gave negative reaction with Molish's, ninhydrin and Sakaguchi's reagents, and positive reaction with Mayer' s, Drogendorff's, Wagner's and Bertrad's reagents. The El-MS analysis of Echcin Ⅰ showed a molecular ion (M^+) at m/z 654, FAB-MS and SCI-MS at m/z 655 (M+H)^+. The molecular formula is C_(40)H_7ON_5 based on the element composition from high resolution mass spectrum analysis and to the re sults of element analysis. The UV analysis of chlorinated Echcin Ⅰ showed only end absorption in 189nm. The mayer bands (cm^(-1)) of IR spectrum and probably assignments are3367,3282,1605 (— NH_2); 2920,2849(—CHz—), 722 (—C—(CH_2)n—C—). The ~1H-NMR spectrum of Echcin Ⅰ in CDaOD showed _(TMS)^(CD_2OD): 0. 84t, 1. 25S, 1. 36d, 1. 46m, 1. 55m, 2,63s, 2. 70m, 3.56d. Although used high resolution NMR (AM 500), the ^(13)C-NMR spectrum and DEPT show only 15 bands (ppm): 14.7 (—CH_3); 23.9,26.9,27.0,27. 1,27. 2,30.8,31.1,33./1,37.6,39.0,39.7,40.9(—CH_2—): 52.5 (—CH—); 71.2(—CH—). Mayer fragment ions of El MS appeared at 654,638,592,565, 464,438,337,311,227,210,184,127,100,56,et al. On the basis of physical and chemical studies, Echcin 1 has been elucidated as 3-hydroxy- 11,19,27,35-tetraamino-tetracontyl amine.