Alkaloids of Liriodendron tulipifera

Chemistry of Natural Compounds
1975.0

Abstract

Continuing the separation of the ether-soluble fraction of the combined alkaloids of the leaves of Liriodendron tulipifera L. (family Magnoliaceae) gathered in Tashkent in September 1974 via silica gel column chromatography, we isolated, in addition to previously obtained alkaloids, N-methylcrotsparine, lanuginosine, and a new base with the composition C18H21NO3 (named liridinine, I) with mp. 142-144°C (acetone), [α]D-38° (c 0.095; chloroform), M+ 311. The UV, IR, and NMR spectra of liridinine were characterized; its acetylation with acetic anhydride in pyridine yielded O-acetate (II), methylation with diazomethane gave O-methyl ether (III), and oxidation of III with chromium trioxide in pyridine led to a compound (IV) identical with liridine (O-methylmoschatoline), leading to the assignment of liridinine as 6-hydroxy-5,7-dimethoxyaporphine. From the total alkaloids of the roots of Aconitum orientale Mill. collected in the flowering period in the environs of Lake Gek-Gel, a new amorphous base named aconorine (I) with composition C32H44N2O7 (mol. wt. 568) was isolated; its perchlorate has mp 237°C (with effervescence). The IR spectrum of aconorine showed absorption bands at 1695 cm-1 (ester carbonyl) and 1595 cm-1 (aromatic ring), and its NMR spectrum contained signals of an ethyl group, acetyl group, and two methoxy groups. Alkaline hydrolysis of aconorine in 10% caustic soda in aqueous ethanol gave amino alcohol C23H37NO5 (II) (mp 140-141°C, hexane-acetone) and acid C9H9NO3 (mp 172°C, identified as acetylanthranilic acid). The mass spectrum of II is characteristic of alkaloids with the lycoctonine skeleton; pyrolysis of diacetylaconorine (III) yielded isopyroacetylaconorine (IV), indicating a hydroxy group at C8 and a methoxy group at C15 in aconorine. The NMR spectrum of II showed a hydroxy group at C10, and the mass spectrum of II revealed an α-oriented methoxy group at C1.

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