Exserolides A-F, new isocoumarin derivatives from the plant endophytic fungus Exserohilum sp.

被引:35
作者
Li, Ruxin [1 ,2 ]
Chen, Shenxi [2 ]
Niu, Shubin [2 ]
Guo, Liangdong [3 ]
Yin, Jun [1 ]
Che, Yongsheng [2 ]
机构
[1] Shenyang Pharmaceut Univ, Sch Tradit Chinese Mat Med, Dev & Utilizat Key Lab Northeast Plant Mat, Shenyang 110016, Peoples R China
[2] Beijing Inst Pharmacol & Toxicol, State Key Lab Antitox Drugs & Toxicol, Beijing 100850, Peoples R China
[3] Chinese Acad Sci, Inst Microbiol, Beijing 100190, Peoples R China
基金
北京市自然科学基金;
关键词
Endophytic fungus; Exserohilum sp; Isocoumarins; Antifungal activity; Antibacterial activity; ABSOLUTE-CONFIGURATION; NATURAL-PRODUCTS; METABOLITES; ROSTRATUM; LACTONES; NMR;
D O I
10.1016/j.fitote.2014.04.013
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Six new isocoumarin derivatives, exserolides A-F (1-6), were isolated from solid cultures of the plant endophytic fungus Exserohilum sp., together with four known metabolites (7-10). The structures of 1-6 were elucidated primarily by NMR experiments. The absolute configuration of the C-3 methine carbon in 1-5 was deduced via the circular dichroism data, whereas that of the 1,3-diol moiety in 6 was assigned from the H-1 NMR data of its (R)- and (S)-MTPA diesters. Compounds 3 and 9 showed antifungal activity against the plant pathogen Fusarium oxysporum, whereas 6 displayed significant inhibitory effects against a small panel of bacteria. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:88 / 94
页数:7
相关论文
共 27 条
[1]   METABOLITES OF HELMINTHOSPORIUM-MONOCERAS - STRUCTURES OF MONOCERIN AND RELATED BENZOPYRANS [J].
ALDRIDGE, DC ;
TURNER, WB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (18) :2598-&
[2]   Fungal endophytes from higher plants: a prolific source of phytochemicals and other bioactive natural products [J].
Aly, Amal H. ;
Debbab, Abdessamad ;
Kjer, Julia ;
Proksch, Peter .
FUNGAL DIVERSITY, 2010, 41 (01) :1-16
[3]  
[Anonymous], 2002, CLSI document M27-A2, V2nd
[4]  
ARAKAWA H, 1969, LIEBIGS ANN CHEM, V728, P152
[5]  
Bermejo A, 1999, PHYTOCHEM ANALYSIS, V10, P127, DOI 10.1002/(SICI)1099-1565(199905/06)10:3<127::AID-PCA451>3.3.CO
[6]  
2-X
[7]   INSECTICIDAL SECONDARY METABOLIC PRODUCTS FROM THE ENTOMOGENOUS FUNGUS FUSARIUM-LARVARUM [J].
CLAYDON, N ;
GROVE, JF ;
POPLE, M .
JOURNAL OF INVERTEBRATE PATHOLOGY, 1979, 33 (03) :364-367
[8]   Photinides A-F, Cytotoxic Benzofuranone-Derived γ-Lactones from the Plant Endophytic Fungus Pestalotiopsis photiniae [J].
Ding, Gang ;
Zheng, Zhihui ;
Liu, Shuchun ;
Zhang, Hua ;
Guo, Liangdong ;
Che, Yongsheng .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (05) :942-945
[9]   Lasionectrin, a Naphthopyrone from a Lasionectria sp. [J].
El Aouad, Noureddine ;
Perez-Moreno, Guiomar ;
Sanchez, Paula ;
Cantizani, Juan ;
Javier Ortiz-Lopez, Francisco ;
Martin, Jesus ;
Gonzalez-Menendez, Victor ;
Ruiz-Perez, Luis M. ;
Gonzalez-Pacanowska, Dolores ;
Vicente, Francisca ;
Bills, Gerald ;
Reyes, Fernando .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (06) :1228-1230
[10]   Asymmetric Synthesis of 4,8-Dihydroxyisochroman-1-one Polyketide Metabolites Using Chiral Hypervalent Iodine(III) [J].
Fujita, Morifumi ;
Mori, Kazuhiro ;
Shimogaki, Mio ;
Sugimura, Takashi .
ORGANIC LETTERS, 2012, 14 (05) :1294-1297