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通过烯烃复分解反应合成新型芳基油菜素甾醇及其初步生物学研究

Synthesis of novel aryl brassinosteroids through alkene cross-metathesis and preliminary biological study.

作者信息

Korinkova Petra, Bazgier Vaclav, Oklestkova Jana, Rarova Lucie, Strnad Miroslav, Kvasnica Miroslav

机构信息

Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University & Institute of Experimental Botany ASCR, Šlechtitelů 27, 783 71 Olomouc, Czech Republic.

Regional Centre of Advanced Technologies and Material, Department of Physical Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech Republic.

出版信息

Steroids. 2017 Nov;127:46-55. doi: 10.1016/j.steroids.2017.08.010. Epub 2017 Aug 31.

DOI:10.1016/j.steroids.2017.08.010
PMID:28837783
Abstract

A series of phenyl analogues of brassinosteroids was prepared via alkene cross-metathesis using commercially available styrenes and 24-nor-5α-chola-2,22-dien-6-one. All derivatives were successfully docked into the active site of BRI1 using AutoDock Vina. Plant growth promoting activity was measured using the pea inhibition biotest and Arabidopsis root sensitivity assay and then was compared with naturally occuring brassinosteroids. Differences in the production of plant hormone ethylene were also observed in etiolated pea seedlings after treatment with the new and also five known brassinosteroid phenyl analogues. Antiproliferative activity was also studied using normal human fibroblast and human cancer cell lines.

摘要

通过使用市售苯乙烯和24-降-5α-胆甾-2,22-二烯-6-酮进行烯烃交叉复分解反应，制备了一系列油菜素甾醇的苯基类似物。使用AutoDock Vina将所有衍生物成功对接至BRI1的活性位点。使用豌豆抑制生物测试和拟南芥根敏感性测定法测量植物生长促进活性，然后与天然存在的油菜素甾醇进行比较。在用新型以及五种已知的油菜素甾醇苯基类似物处理后，在黄化豌豆幼苗中也观察到植物激素乙烯产生的差异。还使用正常人成纤维细胞和人类癌细胞系研究了抗增殖活性。

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