Journal
ORGANIC LETTERS
Volume 24, Issue 2, Pages 697-701Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04145
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Funding
- National Natural Science Foundation of China [31870330, 82003605, 81773869, 81503359]
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Two novel diterpenoids were isolated from Euphorbia helioscopia, with unique structures and biosynthetic pathways. Compound 1 exhibited potent immunosuppressive effect and inspired further study through biomimetic conversion research.
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.
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