Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity

作者: Toshio Morikawa , Niichiro Kitagawa , Genzoh Tanabe , Kiyofumi Ninomiya , Shuhei Okugawa

DOI: 10.3390/MOLECULES21070930

关键词: AlkaloidBenzylisoquinolinePetalAcetic acidChemistryChromatographyCoclaurineNuciferineCarbamic acidStereochemistryElectrospray ionization

摘要: A quantitative analytical method for five aporphine alkaloids, nuciferine (1), nornuciferine (2), N-methylasimilobine (3), asimilobine (4), and pronuciferine (5), benzylisoquinoline armepavine (6), norarmepavine (7), N-methylcoclaurine (8), coclaurine (9), norjuziphine (10), identified as the constituents responsible melanogenesis inhibitory activity of extracts lotus flowers (the flower buds Nelumbo nucifera), has been developed using liquid chromatography-mass spectrometry. The optimum conditions separation detection these 10 alkaloids were achieved on a πNAP column, reversed-phase column with naphthylethyl group-bonded silica packing material, CH3CN–0.2% aqueous acetic acid mobile phase mass spectrometry equipped positive-mode electrospray ionization source. According to protocol established, distributions in petal, receptacle, stamen parts, which separated from whole flower, examined. As expected, excellent correlations observed between total alkaloid content activity. Among active (2) was found give carbamate salt (2′′) via formation an unstable carbamic (2′) by absorption carbon dioxide air.

参考文章(30)
Jih-Jung Chen, Ya-Ling Chang, Che-Ming Teng, Wei-Yu Lin, Yu-Chang Chen, Ih-Sheng Chen, A new tetrahydroprotoberberine N-oxide alkaloid and anti-platelet aggregation constituents of Corydalis tashiroi Planta Medica. ,vol. 67, pp. 423- 427 ,(2001) , 10.1055/S-2001-15820
Zhongduo Yang, Zhuwen Song, Weiwei Xue, Jie Sheng, Zongmei Shu, Yin Shi, Jibei Liang, Xiaojun Yao, Synthesis and structure–activity relationship of nuciferine derivatives as potential acetylcholinesterase inhibitors Medicinal Chemistry Research. ,vol. 23, pp. 3178- 3186 ,(2014) , 10.1007/S00044-013-0905-9
Luke J. Murphy, Katherine N. Robertson, Richard A. Kemp, Heikki M. Tuononen, Jason A. C. Clyburne, Structurally simple complexes of CO2 Chemical Communications. ,vol. 51, pp. 3942- 3956 ,(2015) , 10.1039/C4CC08510H
D.C.H. Fischer, M.I. Gonçalves, F. Oliveira, M.A. Alvarenga, Constituents from Siparuna apiosyce Fitoterapia. ,vol. 70, pp. 322- 323 ,(1999) , 10.1016/S0367-326X(99)00021-0
Ruilin Hu, Xiaojing Dai, Yanbin Lu, Yuanjiang Pan, Preparative separation of isoquinoline alkaloids from Stephania yunnanensis by pH-zone-refining counter-current chromatography Journal of Chromatography B. ,vol. 878, pp. 1881- 1884 ,(2010) , 10.1016/J.JCHROMB.2010.05.005
Helene De Wet, Fanie R. Van Heerden, Ben-Erik Van Wyk, Alkaloidal variation in cissampelos capensis (Menispermaceae) Molecules. ,vol. 16, pp. 3001- 3009 ,(2011) , 10.3390/MOLECULES16043001
Toshio Morikawa, Yusuke Nakanishi, Kiyofumi Ninomiya, Hisashi Matsuda, Souichi Nakashima, Hisako Miki, Yu Miyashita, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka, Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox Journal of Natural Medicines. ,vol. 68, pp. 539- 549 ,(2014) , 10.1007/S11418-014-0832-1
Zheng Zhenjia, Wang Minglin, Wang Daijie, Duan Wenjuan, Wang Xiao, Zheng Chengchao, Preparative separation of alkaloids from Nelumbo nucifera leaves by conventional and pH-zone-refining counter-current chromatography Journal of Chromatography B. ,vol. 878, pp. 1647- 1651 ,(2010) , 10.1016/J.JCHROMB.2010.04.020