Alkaloids of Liriodendron tulipifera

Chemistry of Natural Compounds
1977.0

Abstract

Two studies on plant alkaloids are described. 1) Continuing investigations of Liriodendron tulipifera L. (Magnoliaceae), young branches collected during the flowering period on May 10, 1974 from the Botanical Garden of the Academy of Sciences of the Uzbek SSR (Tashkent) were analyzed. Chloroform extraction yielded 0.12% combined alkaloids, which were separated into phenolic and nonphenolic fractions. Silica gel column chromatography of the nonphenolic ether-soluble fraction isolated liriodenine, glaucine, base I, and a new base II. From the phenolic fraction, d-caaverine, asimilobine, and predieentrine were identified using UV, NMR, mass spectra, and salt preparation. Base I (C₁₉H₁₉NO₂, mp 88-90°C) was identical to dehydroremerine, and base II (C₁₉H₁₇NO₃, mp 143-145°C), a new base, was identified as dehydroisolaureline. 2) Continuing the separation of combined alkaloids from the epigeal part of Delphinium dictyocarpum DC. (collected in the flowering phase near the village of Topolevsky, Dzhungarian Ala-tau), a new base (I, C₃₃H₄₆O₉N₂, mp 118-120°C, M⁺ 614) was isolated. IR, NMR, and mass spectral data, along with acetylation experiments, showed the new base to be 10-O-acetyldelectine, a diterpene alkaloid with a lycoctonine skeleton acylated with anthranilic and acetic acids.

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