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美登素类化合物对欧洲玉米螟(Ostrinia nubilalis (Hübner))的作用的构效关系。

Structure-activity relationships among maytansinoids in their effect on the European corn borer,Ostrinia nubilalis (Hübner).

机构信息

U.S. Department of Agriculture, Northern Regional Research Center Agricultural Research Service, 61604, Peoria, Illinois.

出版信息

J Chem Ecol. 1985 Apr;11(4):501-6. doi: 10.1007/BF00989561.

DOI:10.1007/BF00989561
PMID:24310072
Abstract

Five maytansinoids fromMaytenus (Celastraceae) andPutterlickia (Rhamnaceae) species were tested for biological activity against the European corn borerOstrinia nubilalis. Maytanbutine, maytansine, and maytanvaline, all of which contain an amino acid residue at C-3, were active and comparable in their effect on larvae to trewiasine, a known active, amino acid-containing maytansinoid fromTrewia nudiflora. Maytanacine, which has an acetate group at C-3, was not as active as maytansine, maytanvaline, maytanbutine, or trewiasine, but significantly retarded the development of the larvae. Normaysine, which has no oxygen substituent at C-3, had no significant effect on mortality and only moderate effect on development of the larvae. The presence of the amino acid moiety at C-3 appears to be an important factor for the biological activity of maytansinoids.

摘要

五种来自卫矛科(Celastraceae)美登木属(Maytenus)和鼠李科(Rhamnaceae)朴提里克属(Putterlickia)的美登木素类化合物被测试了对欧洲玉米螟(Ostrinia nubilalis)的生物活性。美登布汀、美登司汀和美登缬氨酸均在 C-3 位含有一个氨基酸残基,对幼虫的作用与 trewiasine 相当,后者是已知的来自 Trewia nudiflora 的具有生物活性的含氨基酸美登木素类化合物。C-3 位的醋酸酯基使美登宁酸的活性不如美登司汀、美登缬氨酸、美登布汀或 trewiasine,但对幼虫的发育有明显的抑制作用。Normaysine 则在 C-3 位没有含氧取代基,对死亡率没有显著影响,对幼虫的发育只有中等影响。C-3 位氨基酸部分的存在似乎是美登木素类化合物生物活性的一个重要因素。

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本文引用的文献

1
Biological activities ofTrewia nudiflora extracts against certain economically important insect pests.轮叶扁担木提取物对某些重要经济昆虫的生物活性。
J Chem Ecol. 1982 Feb;8(2):409-18. doi: 10.1007/BF00987789.
2
Letter: Novel maytansinoids. Naturally occurring and synthetic antileukemic esters of maytansinol.信函:新型美登素类化合物。美登醇的天然及合成抗白血病酯类。
J Am Chem Soc. 1975 Sep 3;97(18):5294-5. doi: 10.1021/ja00851a054.
3
The maytansinoids. Isolation, structural elucidation, and chemical interrelation of novel ansa macrolides.
J Org Chem. 1977 Jul 8;42(14):2349-57. doi: 10.1021/jo00434a001.
4
Structural requirements for antileukemic activity among the naturally occurring and semisynthetic maytansinoids.天然和半合成美登素类化合物中抗白血病活性的结构要求。
J Med Chem. 1978 Jan;21(1):31-7. doi: 10.1021/jm00199a006.
5
A bioassay for plant-derived pest control agents using the European corn borer.
J Econ Entomol. 1979 Aug;72(4):541-5. doi: 10.1093/jee/72.4.541.