The identification of cholesterol and other steroids in Euphorbia pulcherimma

The 4-desmethyl tetracycles of the whole poinsettia plant (Euphorbia pulcherimma) less roots amounted to 0.07% of the wet wt and were shown by ¹H NMR spectroscopy to be steroids and not euphoids. The most abundant component was cholesterol, constituting half the mixture, followed in order of decreasing concentration by 24α-ethylcholesterol (sitosterol), 24α-methylcholesterol (campesterol) and 24β-methylcholesterol (22-dihydrobrassicasterol). The relative amount of cholesterol in this plant is the highest found so far in a tracheophyte. The 4,4-dimethyl compounds (0.1% of wet wt) included lanosterol (5%), 24-dihydrolansterol (5%), β-amyrin (25%), germanicol (50%), an unidentified pentacyclic triterpenoid (8%) and two or more (7%) unidentified components. Both the 4,4-dimethyl- and the 4-desmethylsterols were in the configurational series with a 20α-H-atom. Dihydrolanosterol and lanosterol are the probable intermediates from cycloartenol to cholesterol and 24-alkylcholesterol, respectively. Such a sequence would differ from that operating in most angiosperms, where the alkylation is thought to precede the opening of the 9,19-cyclopropane ring.