Two lathyrane diterpenoid stereoisomers containing an unusual trans-gem-dimethylcyclopropane from the seeds of Euphorbia lathyris

Linwei Li; Jianan Huang; Hui Lyu; Fuqin Guan; Pirui Li; Mei Tian; Shu Xu; Xingzeng Zhao; Fei Liu; Christian Paetz; Xu Feng; Yu Chen

doi:10.1039/d0ra10724g

Two lathyrane diterpenoid stereoisomers containing an unusual trans-gem-dimethylcyclopropane from the seeds of Euphorbia lathyris

RSC Adv. 2021 Jan 14;11(5):3183-3189. doi: 10.1039/d0ra10724g. eCollection 2021 Jan 11.

Authors

Linwei Li¹, Jianan Huang¹, Hui Lyu^{1

2}, Fuqin Guan¹, Pirui Li¹, Mei Tian¹, Shu Xu¹, Xingzeng Zhao¹, Fei Liu¹, Christian Paetz², Xu Feng¹, Yu Chen¹

Affiliations

¹ Jiangsu Key Laboratory for the Research and Utilization of Plant Resources, The Jiangsu Provincial Platform for Conservation and Utilization of Agricultural Germplasm, Institute of Botany, Jiangsu Province and Chinese Academy of Sciences Nanjing China yuchen1007@hotmail.com liufeiseu@163.com.
² Max-Planck Institute for Chemical Ecology Jena Germany.

Abstract

Two novel lathyrane-type diterpenoids, the Euphorbia factors L_2a (1) and L_2b (2), and their stereoisomer Euphorbia factor L₂ (3) were obtained from seeds of Euphorbia lathyris. Both Euphorbia factors L_2a and L_2b possess an unprecedented trans-gem-dimethylcyclopropane as structural feature. Also, the Euphorbia factor L_2a is the first example of a lathyrane diterpenoid with an endocyclic 12(Z)-double bond. The structures of the molecules and their absolute configurations were elucidated by comprehensive spectroscopic analyses, Cu-Kα radiation X-ray diffraction, and comparison with calculated electronic circular dichroism (ECD) data. The Euphorbia factor L_2b exhibited an inhibitory effect against U937 cell line with an IC₅₀ value of 0.87 μM.