Trichoderones A and B: Two Pentacyclic Cytochalasans from the Plant Endophytic Fungus Trichoderma gamsii

被引:43
作者
Ding, Gang [2 ,3 ,4 ,5 ]
Wang, Hailou [2 ,3 ]
Li, Li [5 ]
Chen, Amanda Juan [2 ,3 ]
Chen, Lin [2 ,3 ]
Chen, Hong [6 ]
Zhang, Hongwu [2 ,3 ]
Liu, Xinzhong [1 ]
Zou, Zhongmei [2 ,3 ]
机构
[1] Chinese Acad Sci, Key Lab Systemat Mycol & Lichenol, Inst Microbiol, Beijing 100080, Peoples R China
[2] Chinese Acad Med Sci, Key Lab Bioact Subst & Resources Utilizat Chinese, Minist Educ, Inst Med Plant Dev, Beijing 100193, Peoples R China
[3] Peking Union Med Coll, Beijing 100193, Peoples R China
[4] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Substance & Funct Nat Med, Beijing 100050, Peoples R China
[5] Peking Union Med Coll, Beijing 100050, Peoples R China
[6] Med Coll Chinese Peoples Armed Police Force, Tianjin 300162, Peoples R China
基金
中国国家自然科学基金;
关键词
Structure elucidation; Natural products; Cytotoxicity; Configuration determination; CONSTRUCTION;
D O I
10.1002/ejoc.201200053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new cytochalasans, trichoderones A (1) and B (2), and three known analogues, aspochalasins D (3), J (4), and I (5), were isolated from the endophytic fungus Trichoderma gamsii. Their structures were determined by analysis of their spectroscopic data. The absolute configurations of 1 and 2 were established by quantum chemical electronic circular dichroism calculations. Compounds 3 and 4 displayed cytotoxic activity against the HeLa cell line. Trichoderone A (1) possesses an unprecedented 7/6/6/5/5 pentacyclic system, whereas trichoderone B (2) contains the rare 6/5/6/6/5 pentacyclic skeleton with a 12-oxatricyclo [6.3.1.02,7] moiety.
引用
收藏
页码:2516 / 2519
页数:4
相关论文
共 16 条
[1]  
[Anonymous], TETRAHEDRON LETT
[2]   Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].
Berova, Nina ;
Di Bari, Lorenzo ;
Pescitelli, Gennaro .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931
[3]   Identification of an unexpected 2-oxonia[3,3]sigmatropic rearrangement/aldol pathway in the formation of oxacyclic rings. Total synthesis of (+)-aspergillin PZ [J].
Canham, Stephen M. ;
Overman, Larry E. ;
Tanis, Paul S. .
TETRAHEDRON, 2011, 67 (51) :9837-9843
[4]   Chaetoglobosin U, a cytochalasan alkaloid from endophyfle Chaetomium globosum IFB-E019 [J].
Ding, G ;
Song, YC ;
Chen, JR ;
Xu, C ;
Ge, HM ;
Wang, XT ;
Tan, RX .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (02) :302-304
[5]   Antifungal metabolites from the plant endophytic fungus Pestalotiopsis foedan [J].
Ding, Gang ;
Liu, Shuchun ;
Guo, Liangdong ;
Zhou, Yuguang ;
Che, Yongsheng .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (04) :615-618
[6]   Pestaloquinols A and B, Isoprenylated Epoxyquinols from Pestalotiopsis sp. [J].
Ding, Gang ;
Zhang, Fan ;
Chen, Hong ;
Guo, Liangdong ;
Zou, Zhongmei ;
Che, Yongsheng .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (02) :286-291
[7]   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
[8]  
Frisch M. J., 2016, Gaussian 03 Revision B.03
[9]   Chaetoglobins A and B, two unusual alkaloids from endophytic Chaetomium globosum culture [J].
Ge, Hui Ming ;
Zhang, Wei Yun ;
Ding, Gang ;
Saparpakorn, Patchareenart ;
Song, Yong Chun ;
Hannongbua, Supa ;
Tan, Ren Xiang .
CHEMICAL COMMUNICATIONS, 2008, (45) :5978-5980
[10]   Spicochalasin A and New Aspochalasins from the Marine-Derived Fungus Spicaria elegans [J].
Lin, Zhenjian ;
Zhu, Tianjiao ;
Wei, Hongjuan ;
Zhang, Guojian ;
Wang, Hui ;
Gu, Qianqun .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (18) :3045-3051