Chemical constituents from the stems of Liriodendron tulipifera

Chemistry of Natural Compounds
2012.0

Abstract

Liriodendron tulipifera is a fast growing hardwood tree species native to the United State, which is used for wood and pulp products [1, 2]. Earlier investigations on the chemical constituents of L. tulipifera dealt with several alkaloids and sesquiterpenes [3–11]. These studies have shown the isolated products from the stems of L. tulipifera. L. tulipifera was chosen for further phytochemical investigation. The MeOH extract of the plant was subjected to solvent partitioning and chromatographic separation to afford 21 pure substances. The chemical constituents in the plants of L. tulipifera were separated with column chromatography.Investigation of the MeOH extract of the plants has led to the isolation of 21 compounds, among which are four alkaloids: liriodenine (1) [12], (–)-anonaine (2) [13], (–)-norglaucine (3), and (–)-glaucine (4) [14]; three lignans: (–)-eudesmin (5) [15], (+)-syringaresinol (6) [16], and (+)-yangambin (7) [17]; four steroids: β-sitosterol (8), stigmasterol (9) [18], β-sitostenone (10), and stigmastenone (11) [19]; and ten benzenoids: methyl 4-hydroxy-2-methylbenzoate (12) [20], methyl β-orcinol carboxylate (13), methyl haematommate (14) [21], coniferyl aldehyde (15) [22], vanillin (16) [23], vanillic acid (17) [24], methyl vanillate (18) [25], p-hydroxybenzoic acid (19) [26], syringic acid (20) [27], and 2,6-dimethoxy-p-quinone (21) [28]. These compounds were obtained and characterized by the comparison of their physical and spectral data (UV, IR, NMR and MS) with values obtained in the literature. In addition to 5, all of these compounds were found for the first time from this species.

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