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

Two novel diterpenoids, one with a rearranged trans,trans-fused tricyclo­[10.3.0.04,6]­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-chem...

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Bibliographic Details
Published in:Organic letters 2022-01, Vol.24 (2), p.697-701
Main Authors: Xiang, Zhi-Nan, Tong, Qi-Lin, Su, Jun-Cheng, Hu, Zhuo-Fan, Zhao, Ning, Xia, Ru-Feng, Wu, Jia-Le, Chen, Chen, Chen, Jia-Chun, Wan, Luo-Sheng
Format: Article
Language:English
Subjects:
Animals
Biomimetics
Crystallography, X-Ray
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Euphorbia - chemistry
Humans
Immunosuppressive Agents - chemistry
Immunosuppressive Agents - isolation & purification
Immunosuppressive Agents - pharmacology
Molecular Structure
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Summary:Two novel diterpenoids, one with a rearranged trans,trans-fused tricyclo­[10.3.0.04,6]­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-π-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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c04145