Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, México, D.F., Mexico.
Molecules. 2011 Nov 15;16(11):9520-33. doi: 10.3390/molecules16119520.
The bulbs and aerial parts of Zephyranthes concolor (Lindl.) Benth. & Hook. f. (Amaryllidaceae), an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution (1)H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution (1)H- and (13)C-NMR spectra were recorded. Unambiguous assignations were achieved with HMBC, and HSQC experiments, and its structure was corroborated by X-ray diffraction. Minimum energy conformation for structures of chlidanthine, and its positional isomer galanthamine, were calculated by molecular modelling. Galanthamine is a well known acetylcholinesterase inhibitor; therefore, the isolated alkaloids were tested for this activity. Chlidanthine and galanthamine N-oxide inhibited electric eel acetylcholinesterase (2.4 and 2.6 × 10(-5) M, respectively), indicating they are about five times less potent than galanthamine, while galwesine was inactive at 10(-3) M. Inhibitory activity of HIV-1 replication, and cytotoxicity of the isolated alkaloids were evaluated in human MT-4 cells; however, the alkaloids showed poor activity as compared with standard anti-HIV drugs, but most of them were not cytotoxic.
墨西哥特有物种葱莲（Zephyranthes concolor (Lindl.) Benth. & Hook. f.，石蒜科）的鳞茎和地上部分含有生物碱垂堇碱、加兰他敏、加兰他敏 N-氧化物、石蒜碱、加利福尼亚新乌头碱和表加兰他敏。由于目前仅可获得垂堇碱醋酸盐的部分和低分辨率（1）H-NMR 数据，且垂堇碱没有相应数据，因此对其进行了 1D 和 2D 高分辨率（1）H 和（13）C-NMR 谱的记录。通过 HMBC 和 HSQC 实验实现了明确的归属，并通过 X 射线衍射证实了其结构。通过分子建模计算了垂堇碱及其位置异构体加兰他敏的最低能量构象。加兰他敏是一种众所周知的乙酰胆碱酯酶抑制剂；因此，对分离出的生物碱进行了该活性测试。垂堇碱和加兰他敏 N-氧化物抑制电鳗乙酰胆碱酯酶（分别为 2.4 和 2.6×10(-5) M），表明其效力比加兰他敏低约五倍，而加利福尼亚新乌头碱在 10(-3) M 时没有活性。在人 MT-4 细胞中评估了分离出的生物碱对 HIV-1 复制的抑制活性和细胞毒性；然而，与标准抗 HIV 药物相比，这些生物碱的活性较差，但大多数生物碱没有细胞毒性。
