5286-10-2

Lythrine is an alkaloid originally isolated from H. salicifolia that inhibits prostaglandin synthetase (IC₅₀ = 469 μM).

This alkaloid is also present in Heimia salicifolia Link & Otto and is obtained as long, glistening needles from either CH2Clr light petroleum or CH2Cl2-MeOH. It is dextrorotatory with [α]²⁵_D + 40.6° (c 0.3, CHC13) and the ultraviolet spectrum shows two absorption maxima at 260 and 284 mJ.1. The following salts and derivatives have been prepared to characterize the base: the hydrochloride as prisms, m.p. 325-331 °c (dec.); the acetyl derivative, m.p. In-3°C; [o:lf,S + 33.1 ° (c 0.75, CHC13) and the methyl ether, m.p. 239-24loC; the latter yielding a crystalline hydrochloride and hydrobromide containing MeOH of crystalliza_x0002_tion.

ChEBI: (+)-Lythrine is a member of quinolizidines.

Blomster, Schwarting, Bobbitt., LZoydia, 27, 15 (1964) Douglas et aZ., ibid, 27, 25 (1964) Crystal structure: Zacharias et aZ., Experientia, 21, 247 (1965) Stereochemistry: Ferris, Boyce, Briner., J. Amer. Chern. Soc., 93,2942 (1971) Ferris etaZ., ibid, 93,2963 (1971)