Dichloroisocoumarins with Potential Anti-Inflammatory Activity from the Mangrove Endophytic Fungus Ascomycota sp CYSK-4

被引:49
作者
Chen, Yan [1 ]
Liu, Zhaoming [2 ]
Liu, Hongju [2 ,3 ]
Pan, Yahong [2 ]
Li, Jing [3 ]
Liu, Lan [1 ,4 ]
She, Zhigang [1 ,2 ,4 ]
机构
[1] Sun Yat Sen Univ, Sch Marine Sci, Guangzhou 510006, Guangdong, Peoples R China
[2] Sun Yat Sen Univ, Sch Chem, Guangzhou 510275, Guangdong, Peoples R China
[3] Guangdong Med Univ, Sch Pharm, Dongguan 523808, Peoples R China
[4] Sun Yat Sen Univ, South China Sea Bioresource Exploitat & Utilizat, Guangzhou 510275, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
isocoumarin; endophytic fungus; Pluchea indica; Ascomycota sp; anti-inflammatory; antibacterial; BONTIOIDES A. GRAY; TRICHODERMA SP 09; ISOCOUMARIN; METABOLITES; POLYKETIDES; CELLS; ACID;
D O I
10.3390/md16020054
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Three new isocoumarinsdichlorodiaportintone (1), desmethyldichlorodiaportintone (2) and desmethyldichlorodiaportinol (3)as well as six known analogues (4-9) were isolated from the culture of the mangrove endophytic fungus Ascomycota sp. CYSK-4 from Pluchea indica. Their structures were elucidated by analysis of spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by the modified Mosher's method. Compound 2 showed significant anti-inflammatory activity by inhibiting the production of NO in LPS-induced RAW 264.7 cells with IC50 value of 15.8 M, while compounds 1, 5, and 6 exhibited weak activities with IC50 values of 41.5, 33.6, and 67.2 M, respectively. In addition, compounds 1, 5, and 6 showed antibacterial effects against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae, and Acinetobacter calcoaceticus with the MIC values in the range of 25-50 gmL(-1).
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页数:10
相关论文
共 24 条
[1]   Bioactive metabolites from the endophytic fungus Ampelomyces sp isolated from the medicinal plant Urospermum picroides [J].
Aly, Amal H. ;
Edrada-Ebel, RuAngelie ;
Wray, Victor ;
Mueller, Werner E. G. ;
Kozytska, Svitlana ;
Hentschel, Ute ;
Proksch, Peter ;
Ebel, Rainer .
PHYTOCHEMISTRY, 2008, 69 (08) :1716-1725
[2]   Antibacterial cannabinoids from Cannabis sativa:: A structure-activity study [J].
Appendino, Giovanni ;
Gibbons, Simon ;
Giana, Anna ;
Pagani, Alberto ;
Grassi, Gianpaolo ;
Stavri, Michael ;
Smith, Eileen ;
Rahman, Mukhlesur .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (08) :1427-1430
[3]   Isocoumarins and benzofurans from the mangrove endophytic fungus Talaromyces amestolkiae possess α-glucosidase inhibitory and antibacterial activities [J].
Chen, Senhua ;
Liu, Yayue ;
Liu, Zhaoming ;
Cai, Runlin ;
Lu, Yongjun ;
Huang, Xishan ;
She, Zhigang .
RSC ADVANCES, 2016, 6 (31) :26412-26420
[4]   Cathepsin B Inhibitory Tetraene Lactones from the Fungus Talaromyces wortmannii [J].
Dong, Yuesheng ;
Lin, Jie ;
Lu, Xinhua ;
Zheng, Zhihui ;
Ren, Xiao ;
Zhang, Hun ;
He, Jiangong ;
Yang, Junshan .
HELVETICA CHIMICA ACTA, 2009, 92 (03) :567-574
[5]   New Isocoumarins from a Cold-Adapted Fungal Strain Mucor sp and Their Developmental Toxicity to Zebrafish Embryos [J].
Feng, Chun-Chi ;
Chen, Guo-Dong ;
Zhao, Yan-Qiu ;
Xin, Sheng-Chang ;
Li, Song ;
Tang, Jin-Shan ;
Li, Xiao-Xia ;
Hu, Dan ;
Liu, Xing-Zhong ;
Gao, Hao .
CHEMISTRY & BIODIVERSITY, 2014, 11 (07) :1099-1108
[6]   BARCELONEIC ACID-A, A NEW FARNESYL-PROTEIN TRANSFERASE INHIBITOR FROM A PHOMA SPECIES [J].
JAYASURIYA, H ;
BALL, RG ;
ZINK, DL ;
SMITH, JL ;
GOETZ, MA ;
JENKINS, RG ;
NALLINOMSTEAD, M ;
SILVERMAN, KC ;
BILLS, GF ;
LINGHAM, RB ;
SINGH, SB ;
PELAEZ, F ;
CASCALES, C .
JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (07) :986-991
[7]   A novel isocoumarin derivative induces mitotic phase arrest and apoptosis of human multiple myeloma cells [J].
Kawano, Takeshi ;
Agata, Naoki ;
Kharbanda, Surender ;
Avigan, David ;
Kufe, Donald .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 2007, 59 (03) :329-335
[8]  
LAI S, 1991, HETEROCYCLES, V32, P297
[9]   Dichlorodiaportin, diaportinol, and diaportinic acid:: Three novel isocoumarins from Penicillium nalgiovense [J].
Larsen, TO ;
Breinholt, J .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (08) :1182-1184
[10]   Dichlorodiaportinol A - A new chlorine-containing isocoumarin from an endophytic fungus Trichoderma sp 09 from Myoporum bontioides A. Gray and its cytotoxic activity [J].
Li, Chunyuan ;
Gong, Bing ;
Cox, Daniel G. ;
Li, Caili ;
Wang, Jinhua ;
Ding, Weijia .
PHARMACOGNOSY MAGAZINE, 2014, 10 (37) :S153-S156