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KMID : 0620720200260020171
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Natural Product Sciences
2020 Volume.26 No. 2 p.171 ~ p.175
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NMR Assignments of Rotameric Aporphine Alkaloids from Liriodendron tulipifera
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Park In-Wha
Na Min-Kyun
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Abstract
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Liriodendron tulipifera, belonging to the family Magnoliaceae, is commonly called tulip tree. Four Nacetylated aporphine alkaloids, N-acetylnornuciferine (1), N-acetylanonaine (2), N-acetyl-3-methoxynornuciferine (3), and N-acetyl-3-methoxynornantenine (4) were isolated from the roots of L. tulipifera. Although the purity of each compound (1 - 4) was determined to be 97, 96, 99, and 98%, respectively, the 1H and 13C NMR spectroscopic data of the aporphine alkaloids 1 - 4 displayed all signals in duplicate, indicating the presence of two rotamers due to restricted rotation of N-COCH3 functionality in solution status. The absolute configurations of 1 - 4 w ere established by measuring specific rotation and comparison with the reported data. This is the first report on the 1H and 13C NMR assignments of N-acetyl-3-methoxynornuciferine (3) and N-acetyl-3-methoxynornantenine (4). This study provides advanced NMR spectroscopic data for the structure determination of rotameric aporphine alkaloids.
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KEYWORD
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Liriodendron tulipifera, Magnoliaceae, Rotameric aporphine alkaloid, NMR assignment
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