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

Authors :: Xiang ZN
Tong QL
Su JC
Hu ZF
Zhao N
Xia RF
Wu JL
Chen C
Chen JC
Wan LS
Source :: Organic letters [Org Lett] 2022 Jan 21; Vol. 24 (2), pp. 697-701. Date of Electronic Publication: 2021 Dec 29.
Publication Year :: 2022
Abstract: Two novel diterpenoids, one with a rearranged trans , trans -fused tricyclo[10.3.0.0 <superscript>4,6</superscript> ]pentadecane framework ( 1 ) and the other with an unprecedented 15 S 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.

Subjects :: Molecular Structure
Crystallography, X-Ray
Humans
Animals
Biomimetics
Euphorbia chemistry
Diterpenes chemistry
Diterpenes pharmacology
Diterpenes isolation & purification
Immunosuppressive Agents chemistry
Immunosuppressive Agents pharmacology
Immunosuppressive Agents isolation & purification

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