Cytotoxic Bromine- and Iodine-Containing Cytochalasins Produced by the Mangrove Endophytic Fungus Phomopsis sp. QYM-13 Using the OSMAC Approach

被引:42
作者
Chen, Yan [1 ,2 ]
Yang, Wencong [1 ]
Zou, Ge [1 ]
Wang, Guisheng [2 ]
Kang, Wenyi [2 ]
Yuan, Jie [3 ]
She, Zhigang [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem, Guangzhou 510275, Guangdong, Peoples R China
[2] Henan Univ, Natl R&D Ctr Edible Fungus Proc Technol, Kaifeng 475004, Peoples R China
[3] Sun Yat Sen Univ, Key Lab Trop Dis Control, Minist Educ, Guangzhou 510080, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2022年 / 85卷 / 05期
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
MARINE;
D O I
10.1021/acs.jnatprod.1c01115
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Twelve new cytochalasins, phomopchalasins D-O (1-3, 5-12, and 14), including one brominated (2) and two iodinated cytochalasins (3 and 6), together with six known analogues (4, 13, and 15-18) were isolated from the mangrovederived fungus Phomopsis sp. QYM-13 treated with 3% NaBr or 3% KI in potato liquid medium. Their structures and absolute configurations were established by extensive spectroscopic analysis (1D and 2D NMR, HRESIMS), electronic circular dichroism calculations, and a single-crystal X-ray diffraction experiment. Compounds 3 and 6 represent the first iodinated cytochalasins. Compounds 2, 15, 17, and 18 exhibited significant cytotoxicity against human cancer cell line MDA-MB-435 with IC50 values ranging from 0.2 to 8.2 mu M
引用
收藏
页码:1229 / 1238
页数:10
相关论文
共 27 条
[1]   STRUCTURE OF A NEW [II]CYTOCHALASIN, CYTOCHALASIN-H OR KODO-CYTOCHALASIN-1 [J].
BENO, MA ;
COX, RH ;
WELLS, JM ;
COLE, RJ ;
KIRKSEY, JW ;
CHRISTOPH, GG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (12) :4123-4130
[2]   Armochaeglobines A and B, Two New Indole-Based Alkaloids from the Arthropod-Derived Fungus Chaetomium globosum [J].
Chen, Chunmei ;
Zhu, Hucheng ;
Li, Xiao-Nian ;
Yang, Jing ;
Wang, Jianping ;
Li, Gentao ;
Li, Yan ;
Tong, Qingyi ;
Yao, Guangmin ;
Luo, Zengwei ;
Xue, Yongbo ;
Zhang, Yonghui .
ORGANIC LETTERS, 2015, 17 (03) :644-647
[3]   NaBr-Induced Production of Brominated Azaphilones and Related Tricyclic Polyketides by the Marine-Derived Fungus Penicillium janthinellum HK1-6 [J].
Chen, Min ;
Zheng, Yao-Yao ;
Chen, Zhi-Qi ;
Shen, Nan-Xing ;
Shen, Li ;
Zhang, Feng-Min ;
Zhou, Xiao-Jian ;
Wang, Chang-Yun .
JOURNAL OF NATURAL PRODUCTS, 2019, 82 (02) :368-374
[4]   Cytotoxic and Antibacterial Preussomerins from the Mangrove Endophytic Fungus Lasiodiplodia theobromae ZJ-HQ1 [J].
Chen, Senhua ;
Chen, Dongni ;
Cai, Runlin ;
Cui, Hui ;
Long, Yuhua ;
Lu, Yongjun ;
Li, Chunyuan ;
She, Zhigang .
JOURNAL OF NATURAL PRODUCTS, 2016, 79 (09) :2397-2402
[5]   Ascomylactams A-C, Cytotoxic 12-or 13-Membered-Ring Macrocyclic Alkaloids Isolated from the Mangrove Endophytic Fungus Didymella sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C [J].
Chen, Yan ;
Liu, Zhaoming ;
Huang, Yun ;
Liu, Lan ;
He, Jianguo ;
Wang, Lan ;
Yuan, Jie ;
She, Zhigang .
JOURNAL OF NATURAL PRODUCTS, 2019, 82 (07) :1752-1758
[6]   A new iodinated metabolite and a new alkyl sulfate from the Senegalese sponge Ptilocaulis spiculifer [J].
Diop, M ;
Samb, A ;
Costantino, V ;
Fattorusso, E ;
Mangoni, A .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (03) :271-272
[7]   CYTOCHALASIN-U AND CYTOCHALASIN-V, 2 NEW CYTOCHALASINS, FROM PHOMA-EXIGUA VAR HETEROMORPHA [J].
EVIDENTE, A ;
LANZETTA, R ;
CAPASSO, R ;
VURRO, M ;
BOTTALICO, A .
TETRAHEDRON, 1992, 48 (30) :6317-6324
[8]   Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a [J].
Frank, Marian ;
Hartmann, Rudolf ;
Plenker, Malte ;
Mandi, Attila ;
Kurtan, Tibor ;
Ozkaya, Ferhat Can ;
Mueller, Werner E. G. ;
Kassack, Matthias U. ;
Hamacher, Alexandra ;
Lin, Wenhan ;
Liu, Zhen ;
Proksch, Peter .
JOURNAL OF NATURAL PRODUCTS, 2019, 82 (08) :2159-2166
[9]  
Frisch M. J., 2013, GAUSSIAN09 REVISION
[10]   Immunosuppressive properties of cytochalasin B-induced membrane vesicles of mesenchymal stem cells: comparing with extracellular vesicles derived from mesenchymal stem cells [J].
Gomzikova, M. O. ;
Aimaletdinov, A. M. ;
Bondar, O. V. ;
Starostina, I. G. ;
Gorshkova, N. V. ;
Neustroeva, O. A. ;
Kletukhina, S. K. ;
Kurbangaleeva, S. V. ;
Vorobev, V. V. ;
Garanina, E. E. ;
Persson, J. L. ;
Jeyapalan, J. ;
Mongan, N. P. ;
Khaiboullina, S. F. ;
Rizvanov, A. A. .
SCIENTIFIC REPORTS, 2020, 10 (01)