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

Toshio Morikawa, Niichiro Kitagawa, Genzoh Tanabe, Kiyofumi Ninomiya, Shuhei Okugawa, Chiaki Motai, Iyori Kamei, Masayuki Yoshikawa, I-Jung Lee, Osamu Muraoka
2016 Molecules  
A quantitative analytical method for five aporphine alkaloids, nuciferine (1), nornuciferine (2), N-methylasimilobine (3), asimilobine (4), and pronuciferine (5), and five benzylisoquinoline alkaloids, armepavine (6), norarmepavine (7), N-methylcoclaurine (8), coclaurine (9), and norjuziphine (10), identified as the constituents responsible for the melanogenesis inhibitory activity of the extracts of lotus flowers (the flower buds of Nelumbo nucifera), has been developed using liquid
more » ... g liquid chromatography-mass spectrometry. The optimum conditions for separation and detection of these 10 alkaloids were achieved on a πNAP column, a reversed-phase column with naphthylethyl group-bonded silica packing material, with CH 3 CN-0.2% aqueous acetic acid as the mobile phase and using mass spectrometry equipped with a positive-mode electrospray ionization source. According to the protocol established, distributions of these 10 alkaloids in the petal, receptacle, and stamen parts, which were separated from the whole flower, were examined. As expected, excellent correlations were observed between the total alkaloid content and melanogenesis inhibitory activity. Among the active alkaloids, nornuciferine (2) was found to give a carbamate salt (2 11 ) via formation of an unstable carbamic acid (2 1 ) by absorption of carbon dioxide from the air.
doi:10.3390/molecules21070930 pmid:27447599 fatcat:ohngc6sumjgvvfehnmnhekyvb4