论大戟科植物的活性成分。西[1]南非大戟(Euphorbia tirucalli L.)的皮肤刺激性和促肿瘤二萜酯。

G Fürstenberger, E Hecker
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引用次数: 32

摘要

分离了产自南非大戟(Euphorbia tirucalli L.)乳胶的刺激性和促肿瘤成分。它们分别是由不饱和脂肪酸和乙酸以及多官能团二萜亲本醇4-脱氧酚、酚酚和ingenol衍生的刺激性烯烷和tigliane型二萜酯。4-脱氧磷的刺激性和促肿瘤的酯是主要的,并充分表征了化学和生物学。它们是位置异构体12,13-酰基酸酯,醋酸酯,例如大戟因子Ti1-Ti4。作为酰基,它们携带同源的高度不饱和脂肪酸,一般结构为CH3-(CH2)m-(CH = CH)n-COOH (m = 2,4;N = 1,2,3,4,5;N = 2n + m + 2)。还存在相应的4-脱氧-4 α -苯酚二酯,这些二酯具有生物活性。对4-脱氧酚12,13-二酯的结构和生物活性的比较表明,对于酰基部分的c原子总数(N)不同,共轭双键(N)的增加可能会增加刺激性,但降低促肿瘤活性。氢(相应的4-脱氧磷-12,13-二酯)取代C-4(磷-12,13-二酯)上的羟基功能不会从本质上改变生物活性。4-脱氧酚-12,13-二酯在C-4上的外映可以消除生物活性。这种特殊的化学性质表明,在芦荟胶乳和所有植物部位中都含有二萜酯刺激物,这可能有助于在试验中消除潜在的癌症风险,特别是在职业性大规模生产和处理这种植物的过程中。分离得到的大戟因子的一些结构活性关系使其成为肿瘤实验研究中分析肿瘤发生机制的良好工具。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
On the active principles of the spurge family (Euphorbiaceae). XI. [1] The skin irritant and tumor promoting diterpene esters of Euphorbia tirucalli L. originating from South Africa.

The irritant and tumor-promoting constituents of latex of Euphorbia tirucalli L. originating from South Africa were isolated. They were identified as irritant ingenane and tigliane type diterpene esters derived from unsaturated aliphatic acids and acetic acid and the polyfunctional diterpene parent alcohols 4-deoxyphorbol, phorbol and ingenol, respectively. The irritant and tumor-promoting esters of 4-deoxyphorbol are predominant and were fully characterized chemically and biologically. They are positionally isomeric 12,13-acylates, acetates e.g. Euphorbiafactors Ti1-Ti4. As acyl groups they carry homologous, highly unsaturated aliphatic acids of the general structure CH3-(CH2)m-(CH = CH)n-COOH (m = 2,4; n = 1,2, 3,4,5; N = 2n + m + 2). Corresponding diesters of 4-deoxy-4 alpha-phorbol are also present which are biologically inactive. Comparison of structures and biological activities of 12,13-diesters of 4-deoxyphorbol indicates that--for a distinct total number of C-atoms (N) in the acyl moiety--an increasing number of conjugated double bonds (n) may increase the irritant but decrease the tumor-promoting activity. Replacement of the hydroxyl function at C-4 (phorbol-12,13-diesters) by hydrogen (corresponding 4-deoxyphorbol-12,13-diesters) does not essentially alter biological activities. Epimerization of 4-deoxyphorbol-12,13-diesters at C-4 abolishes biological activities. The specific chemical properties demonstrated for the diterpene ester irritants contained in the latex of E. tirucalli and hence in all plant parts may be useful in trials to abolish the potential risk of cancer involved especially in occupational mass production and handling of the plant. Some of the structure activity relations of the Euphorbia factors isolated made them excellent tools in experimental cancer research for the analysis of mechanisms of tumorigenesis.

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