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Decalactone derivatives from corynespora cassiicola, an endophytic fungus of the mangrove plant laguncularia racemosa

文献类型： 外文期刊

作者： Ebrahim, Weaam 2 ; Aly, Amal H. 2 ; Mandi, Attila 1 ; Totzke, Frank 4 ; Kubbutat, Michael H. G. 4 ; Wray, Victor 5 ; L 1 ;

作者机构： 1.Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary

2.Univ Dusseldorf, Inst Pharmazeut Biol & Biotechnol, D-40225 Dusseldorf, Germany

3.Mansoura Univ, Fac Pharm, Dept Pharmacognosy, Mansoura 35516, Egypt

4.ProQinase GmbH, D-79106 Freiburg, Germany

5.Helmholtz Ctr Infect Res, D-38124 Braunschweig, Germany

6.Peking Univ, Natl Res Labs Nat & Biomimet Drugs, Hlth Sci Ctr, Beijing 100083, Peoples R China

7.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Haikou 571101, Hainan, Peoples R China

关键词： Conformation analysis;Drug discovery;Fungi;Lactones;Medicinal chemistry;Natural products;Structure elucidation

期刊名称：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：3.021； 五年影响因子：2.79 ）

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收录情况： SCI

摘要： Chemical investigation of the ethyl acetate extract of Corynespora cassiicola, isolated from leaf tissues of the Chinese mangrove medicinal plant Laguncularia racemosa, yielded four new secondary metabolites, including three decalactones, xestodecalactones D-F (1-3) as well as corynesidone C (4), in addition to four known compounds. The structures of the new compounds were determined on the basis of one- and two-dimensional NMR spectroscopy as well as by high-resolution mass spectrometry. Absolute configurations of the optically active compounds 1-3 were determined by TDDFT ECD calculations of their solution conformers, proving that they belong to the (11S) series of xestodecalactones, opposite to the (11R) configuration of the known xestodecalactones A-C. All compounds were tested against a panel of human protein kinases. Among the isolated compounds, two inhibited several kinases such as IGF1-R and VEGF-R2 with IC _(50) values mostly in the low micromolar range. Three new xestodecalactones D-F (1-3) and a new corynesidone C were isolated from Corynespora cassiicola. The structures were determined by 1D and 2D NMR spectroscopy as well as by high-resolution mass spectrometry. The absolute configurations of 1-3 were determined by TDDFT ECD calculations. All compounds were tested against a panel of human protein kinases.

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[1]Polyketides from the plant endophytic fungus Cladosporium sp IFB3lp-2. Wuringege,Wei, Wei,Jiao, Rui-Hua,Yan, Tong,Zang, Le-Yun,Jiang, Rong,Tan, Ren-Xiang,Ge, Hui-Ming,Guo, Zhi-Kai. 2013

[2]Genome-wide comparative analysis of putative Pth11-related G protein-coupled receptors in fungi belonging to Pezizomycotina. Xu, Xihui,Li, Lu,Chen, Chen,Li, Guopeng,Su, Zhenzhu. 2017

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