Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: Structures of karapinchamines A and B

A methanolic extract and its ethyl acetate-soluble fraction from Sri Lankan curry-leaf, the leaves of Murraya koenigii, inhibited melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Two new carbazole alkaloids, karapinchamines A and B, were isolated from the ethyl acetate-soluble...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 2013-03, Vol.21 (5), p.1043-1049
Hauptverfasser:	Nakamura, Seikou, Nakashima, Souichi, Oda, Yoshimi, Yokota, Nami, Fujimoto, Katsuyoshi, Matsumoto, Takahiro, Ohta, Tomoe, Ogawa, Keiko, Maeda, Sayuri, Nishida, Shino, Matsuda, Hisashi, Yoshikawa, Masayuki
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetates - chemistry Acetic acid Alkaloids Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Animals Carbazole Carbazole alkaloid Carbazoles - chemistry Carbazoles - isolation & purification Carbazoles - pharmacology Cell Differentiation - drug effects Cell Line, Tumor Chemical Fractionation chemistry Curry-leaf Gene Expression Regulation - drug effects Karapinchamine Leaves Magnetic Resonance Spectroscopy Melanins - metabolism melanogenesis Melanogenesis inhibitor Melanoma Mice Molecular Conformation Murraya Murraya - chemistry Murraya koenigii Plant Extracts - chemistry Plant Extracts - pharmacology Plant Leaves - chemistry
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Zusammenfassung:	A methanolic extract and its ethyl acetate-soluble fraction from Sri Lankan curry-leaf, the leaves of Murraya koenigii, inhibited melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Two new carbazole alkaloids, karapinchamines A and B, were isolated from the ethyl acetate-soluble fraction together with 12 known carbazole alkaloids. The structures of karapinchamines A and B were determined by physicochemical analyses. The principal alkaloid constituents were found to display potent melanogenesis inhibitory activity. The structural requirements of the carbazole alkaloids for melanogenesis inhibitory activity were discussed.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2013.01.012