New Isocoumarin and Pyrone Derivatives from the Chinese Mangrove Plant Rhizophora mangle-Associated Fungus Phomopsis sp. DHS-11

被引:9
作者
Guo, Zhikai [1 ,2 ]
Chen, Biting [1 ,2 ,3 ]
Chen, Dandan [3 ]
Deng, Xiaoling [3 ]
Yuan, Jingzhe [1 ,2 ]
Zhang, Shiqing [1 ,2 ]
Xiong, Zijun [1 ,2 ]
Xu, Jing [3 ]
机构
[1] Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Hainan Key Lab Trop Microbe Resources, Haikou 571101, Peoples R China
[2] Hainan Inst Trop Agr Resources, Key Lab Biol & Genet Resources Trop Crops Hainan P, Haikou 571101, Peoples R China
[3] Hainan Univ, Sch Chem Engn & Technol, Haikou 570208, Peoples R China
来源
MOLECULES | 2023年 / 28卷 / 09期
基金
中国国家自然科学基金;
关键词
mangrove; endophytic fungus; Phomopsis sp; polyketides; cytotoxic activity; ENDOPHYTIC FUNGUS; METABOLITES;
D O I
10.3390/molecules28093756
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Mangrove-associated fungi are important sources for the discovery of new bioactive natural products. Three new isocoumarins (1-3) and one new pyrone derivative (4) were isolated from the ethyl acetate extract of the fermentation broth of the mangrove endophytic fungus Phomopsis sp. DHS-11. Nuclear magnetic resonance (NMR) spectroscopy (one-dimensional and two-dimensional) and mass spectrometry were used to determine the structures of these new compounds. The absolute configurations for the new isocoumarins 1-3 were determined by comparing their experimental and calculated electronic circular dichroism (ECD) spectra, while the configuration for the new pyrone-derivative 4 was tentatively solved by comparison of its C-13 NMR data with reported data. In the biological activity test, compounds 1 and 3 showed cytotoxic activity against HeLa cells with IC50 values of 11.49 +/- 1.64 mu M and 8.70 +/- 0.94 mu M, respectively. The initial structure and activity relationship (SAR) analysis revealed that the length of the side chain at C-3 for isocoumarin-type compounds 1-3 could affect the cytotoxicity against HeLa cells. Compound 4 exhibited cytotoxic activities against human hepatoma cells HepG2 with an IC50 value of 34.10 +/- 2.92 mu M. All compounds have no immunosuppressive activity.
引用
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页数:10
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