Isocoumarindole A, a Chlorinated Isocounnarin and Indole Alkaloid Hybrid Metabolite from an Endolichenic Fungus Aspergillus sp.

被引:61
作者
Chen, Minghua [1 ,2 ,3 ]
Wang, Renzhong [1 ,2 ,4 ]
Zhao, Wuli [1 ,2 ]
Yu, Liyan [1 ,2 ]
Zhang, Conghui [1 ,2 ]
Chang, Shanshan [1 ,2 ]
Li, Yan [1 ,2 ]
Zhang, Tao [1 ,2 ]
Xing, Jianguo [3 ]
Gan, Maoluo [1 ,2 ]
Feng, Feng [4 ]
Si, Shuyi [1 ,2 ]
机构
[1] Chinese Acad Med Sci, Inst Med Biotechnol, NHC Key Lab Microbial Drug Bioengn, Beijing 100050, Peoples R China
[2] Peking Union Med Coll, Beijing 100050, Peoples R China
[3] Inst Mat Med Xinjiang Uygur Autonomous Reg, Key Lab Uighur Med, Urumqi 830004, Peoples R China
[4] China Pharmaceut Univ, Sch Tradit Chinese Pharm, Dept Nat Med Chem, Nanjing 210009, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
DERIVATIVES; DIVERSITY; LICHEN; ACIDS;
D O I
10.1021/acs.orglett.9b00385
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isocoumarindole A (1), a novel polyketide synthetase-nonribosomal peptide synthetase (PKS-NRPS) hybrid metabolite, was isolated from the endolichenic fungus Aspergillus sp. CPCC 400810. The structure of isocoumar-indole A (1) was featured by an unprecedented skeleton containing chlorinated isocoumarin and indole diketopiperazine alkaloid moieties linked by a carbon carbon bond, which was determined by a combination of spectroscopic analyses, Marfey's method, and calculations of NMR chemical shifts, ECD spectra, and optical rotation values. Isocoumarindole A showed significant cytotoxicity and mild antifungal activities.
引用
收藏
页码:1530 / 1533
页数:4
相关论文
共 43 条
[1]   Non-geminal Aliphatic Dihalogenation Pattern in Dichlorinated Diaporthins from Hamigera fusca NRRL 35721 [J].
Almeida, Celso ;
Perez-Victoria, Ignacio ;
Gonzalez-Menendez, Victor ;
de Pedro, Nuria ;
Martin, Jesus ;
Crespo, Gloria ;
Mackenzie, Thomas ;
Cautain, Bastien ;
Reyes, Fernando ;
Vicente, Francisca ;
Genilloud, Olga .
JOURNAL OF NATURAL PRODUCTS, 2018, 81 (06) :1488-1492
[2]  
Arnold A. Elizabeth, 2007, Fungal Biology Reviews, V21, P51, DOI 10.1016/j.fbr.2007.05.003
[3]  
Bode HB, 2002, CHEMBIOCHEM, V3, P619, DOI 10.1002/1439-7633(20020703)3:7<619::AID-CBIC619>3.0.CO
[4]  
2-9
[5]   Molecular Diversity Sculpted by Fungal PKS-NRPS Hybrids [J].
Boettger, Daniela ;
Hertweck, Christian .
CHEMBIOCHEM, 2013, 14 (01) :28-42
[6]   Regioselective Dichlorination of a Non-Activated Aliphatic Carbon Atom and Phenolic Bismethylation by a Multifunctional Fungal Flavoenzyme [J].
Chankhamjon, Pranatchareeya ;
Tsunematsu, Yuta ;
Ishida-Ito, Mie ;
Sasa, Yuzuka ;
Meyer, Florian ;
Boettger-Schmidt, Daniela ;
Urbansky, Barbara ;
Menzel, Klaus-Dieter ;
Scherlach, Kirstin ;
Watanabe, Kenji ;
Hertweck, Christian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) :11955-11959
[7]   Hybrid Isoprenoids from a Reeds Rhizosphere Soil Derived Actinomycete Streptomyces sp CHQ-64 [J].
Che, Qian ;
Zhu, Tianjiao ;
Qi, Xin ;
Mandi, Attila ;
Kurtan, Tibor ;
Mo, Xiaomei ;
Li, Jing ;
Gu, Qianqun ;
Li, Dehai .
ORGANIC LETTERS, 2012, 14 (13) :3438-3441
[8]   Ahmpatinin iBu, a new HIV-1 protease inhibitor, from Streptomyces sp CPCC 202950 [J].
Chen, Ming-Hua ;
Chang, Shan-Shan ;
Dong, Biao ;
Yu, Li-Yan ;
Wu, Ye-Xiang ;
Wang, Ren-Zhong ;
Jiang, Wei ;
Gao, Zeng-Ping ;
Si, Shu-Yi .
RSC ADVANCES, 2018, 8 (10) :5138-5144
[9]   A new trichostatin analog from Streptomyces sp CPCC 203909 [J].
Chen, Ming-Hua ;
Wu, Ye-Xiang ;
Xu, Yan-Ni ;
Liu, Peng ;
Yu, Li-Yan ;
Hong, Bin ;
Jiang, Wei ;
Si, Shu-Yi .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2015, 17 (06) :676-682
[10]   Identification of trichostatin derivatives from Streptomyces sp. CPCC 203909 [J].
Chen, Minghua ;
Wu, Yexiang ;
He, Yi ;
Xu, Yanni ;
Li, Yongzhen ;
Li, Dongsheng ;
Feng, Tingting ;
Yu, Liyan ;
Hong, Bin ;
Jiang, Wei ;
Si, Shuyi .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (03) :562-565