tuberostemonine

개요This novel alkaloid has been isolated from Sternona sessilifolia and S. tuberosa and was first given the formula C19H29O4N, subsequently altered to that given above. It crystallizes in colourless needles from MeOH with 1 mole of solvent, m.p. 65-88°C (dec.) and has [α]D - 25.4° (Me2CO). It is a non-phenolic, tertiary base and yields a hydrobromide, m.p. 120°C (dec.) and a perchlorate, m.p. 242°C (dec.). The methiodide monohydrate has m.p. 236-8°C (dec.) and the methochloride, dihydrate, m.p. 172°C. A methosulphate has also been prepared, m.p. 253°C (dec.). The base is not hydrolyzed by acids but in the presence of excess PtO2 it gives the dihydro derivative, m.p. 133°C, furnishing a hydrochloride, m.p. 281 ° C. Oxidation with KMnO4 gives a C17 compound, whereas oxidation with silver oxide forms a neutral substance, C22H29O4N, m.p. 178°C which still contains the lactone groups and gives a positive Ehrlich pyrrole reaction.

용도Tuberostemonine is elucidated as one of the major components of Radix Stemonae and has been shown to display therapeutic effects against cigarette smoke-induced acute lung inflammation.