Diterpenoids with Rearranged 9(10→11)-abeo-10,12-Cyclojatrophane Skeleton and the First (15S)-Jatrophane from Euphorbia helioscopia: Structural Elucidation, Biomimetic Conversion, and Their Immunosuppressive Effects

被引：17
作者：
Xiang, Zhi-Nan [1 ]
Tong, Qi-Lin [1 ]
Su, Jun-Cheng [2 ]
Hu, Zhuo-Fan [1 ]
Zhao, Ning [3 ]
Xia, Ru-Feng [1 ]
Wu, Jia-Le [1 ]
Chen, Chen [1 ]
Chen, Jia-Chun [1 ]
Wan, Luo-Sheng [1 ]
机构：
[1] Huazhong Univ Sci & Technol, Pharm Dept, Hubei Key Lab Nat Med Chem & Resource Evaluat, Tongji Med Sch, Wuhan 430030, Peoples R China
[2] Shanghai Jiao Tong Univ, Renji Hosp, Sch Med, State Key Lab Oncogenes & Related Genes, Shanghai 200127, Peoples R China
[3] Huazhong Univ Sci & Technol, Union Hosp, Tongji Med Coll, Res Ctr Ion Channelopathy, Wuhan 430022, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 02期
基金：
中国国家自然科学基金;
关键词：
DI-PI-METHANE; ION CHANNELS; JATROPHANE; SENSITIZERS; TARGETS;
D O I：
10.1021/acs.orglett.1c04145
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two novel diterpenoids, one with a rearranged trans,trans-fused tricyclo[10.3.0.0(4,6)]pentadecane framework (1) and the other with an unprecedented 15S configuration (2), were isolated from Euphorbia helioscopia. Their structures were elucidated by extensive analysis of HR-ESI-MS, NMR, quantum-chemical calculation, and X-ray crystallographic data. Biosynthetically, 1 has a unique "cyclopropane-shift-like" biogenesis involving an oxa-di-pi-methane (ODPM) rearrangement, which inspired us to accomplish the biomimetic conversion of 3 to 1. Moreover, compound 1 displayed a potent immunosuppressive effect by inhibiting Kv1.3 voltage-gated channels.
引用
收藏
页码：697 / 701
页数：5
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