Skeleton Rearranged and Oxygenated ent-Rosane Diterpenoids with Antiadipogenic Activity from Euphorbia milii

Qin-Qin Song; Yue Guo; Peng Sun; Yao-Yue Fan; Kai-Long Ji

doi:10.1002/cjoc.202400749

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3211 -3218. DOI: 10.1002/cjoc.202400749

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Skeleton Rearranged and Oxygenated ent-Rosane Diterpenoids with Antiadipogenic Activity from Euphorbia milii

Qin-Qin Song ¹
, Yue Guo ¹^,²^,³
, Peng Sun ⁴
, Yao-Yue Fan ¹^,²^,³^,^†
, Kai-Long Ji ⁴^,^†

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Abstract

Comprehensive Summary:Five unreported and oxygenated ent-rosane diterpenoids ( ent-RDs), Euphomillanols A—E ( 1— 5), were isolated from Euphorbia milii. Among them, compounds 1 and 2 are unprecedented 7/7/6-fused tricyclic 5, 10-seco- ent-RDs and possess a unique 11-oxabicyclo[4.4.1]undeca-1(10), 5-diene moiety, while 3 is characterized by a 1-methyl-6-oxabicyclo[3.2.1]oct-2-ene motif of ring A. Their structures with absolute configurations were unambiguously determined by the extensive spectroscopic methods, X-ray crystallography, and ECD calculation. Putative biosynthetic pathways for compounds 1— 3 are proposed. All compounds exhibited antiadipogenic effects in 3T3-L1 adipocytes, and the most potent compound 4 showed an EC ₅₀ value of 3.92 µmol/L with low cytotoxicity (IC ₅₀ > 89.54 µmol/L).

Keywords

ent-Rosane diterpenoids / Euphorbia milii / Structure elucidation / Configuration determination / Biosynthetic pathway hypothesis / Oxidation / Biological activity / Antiadipogenic activity

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Qin-Qin Song, Yue Guo, Peng Sun, Yao-Yue Fan, Kai-Long Ji. Skeleton Rearranged and Oxygenated ent-Rosane Diterpenoids with Antiadipogenic Activity from Euphorbia milii. Chinese Journal of Chemistry, 2024, 42(24): 3211-3218 DOI:10.1002/cjoc.202400749