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

Abstract

Two novel lathyrane-type diterpenoids, the Euphorbia factors L(2a) (1) and L(2b) (2), and their stereoisomer Euphorbia factor L(2) (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 IC(50) value of 0.87 μM

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