Lathyrane and Jatrophane Diterpenoids from Euphorbia helioscopia Evaluated for Cytotoxicity against a Paclitaxel-Resistant A549 Human Lung Cancer Cell Line

A phytochemical investigation on the aerial parts of Euphorbia helioscopia resulted in the isolation of 27 macrocyclic diterpenoids, including three previously unreported lathyrane derivatives, euphohelioscopoids A-C (1-3). Their structures were elucidated by spectroscopic data interpretation. Three jatrophanes, euphoscopin C (4), euphorbiapene D (6), and euphoheliosnoid A (5), showed cytotoxicity against a paclitaxel-resistant A549 human lung cancer cell line with IC so values of 6.9, 7.2, and 9.5 mu M, respectively, but were inactive against the parent A549 human lung cancer cell line (IC50 > 10 mu M). It was found that jatrophanes with a benzoyloxy or a nicotinoyloxy substituent at C-7 showed more potent cytotoxic activity than their analogues containing acetyloxy and hydroxy groups at this position.

Automated summary

A phytochemical investigation of Euphorbia helioscopia yielded 27 macrocyclic diterpenoids, including three previously unreported lathyrane derivatives. Three of these compounds exhibited cytotoxicity against a paclitaxel-resistant lung cancer cell line, but showed no activity against the parent cancer cell line. It was observed that compounds with benzoyloxy or nicotinoyloxy substituents at a specific position displayed enhanced cytotoxic activity.