Melanogenesis-Inhibitory Saccharide Fatty Acid Esters and Other Constituents of the Fruits of Morinda citrifolia (Noni)

• Published in: Chemistry & biodiversity Vol. 9; no. 6; pp. 1172 - 1187
• Main Authors: Akihisa, Toshihiro, Tochizawa, Shun, Takahashi, Nami, Yamamoto, Ayako, Zhang, Jie, Kikuchi, Takashi, Fukatsu, Makoto, Tokuda, Harukuni, Suzuki, Nobutaka
• Format: Journal Article
• Language: English
• Published: Zürich WILEY-VCH Verlag 01-06-2012; WILEY‐VCH Verlag
• Subjects: alpha-MSH - metabolism; Animals; Antigens, Viral - chemistry; Antigens, Viral - metabolism; Cell Line, Tumor; Cell Survival - drug effects; Esters; Fatty acid esters; Fatty Acids - chemistry; Fruit - chemistry; Glycosides; Glycosides - chemistry; Glycosides - pharmacology; Glycosides - therapeutic use; Hemiterpene glycosides; Humans; Inhibitors; Iridoid glycosides; Magnetic Resonance Spectroscopy; Melanogenesis-inhibitory activity; Melanoma, Experimental - drug therapy; Mice; Molecular Conformation; Morinda - chemistry; Morinda citrifolia; Noniosides P - T; Saccharides
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201100349

Five new saccharide fatty acid esters, named nonioside P (3), nonioside Q (4), nonioside R (8), nonioside S (10), and nonioside T (14), and one new succinic acid ester, butyl 2‐hydroxysuccinate (=4‐butoxy‐3‐hydroxy‐4‐oxobutanoic acid) (31), were isolated, along with 26 known compounds, including eight saccharide fatty acid esters, 1, 2, 5, 6, 7, 9, 12, and 13, three hemiterpene glycosides, 15, 17, and 18, six iridoid glycosides, 21–25, and 27, and nine other compounds, 20, 28, 29, and 32–37, from a MeOH extract of the fruit of Morinda citrifolia (noni). Upon evaluation of these and five other glycosidic compounds, 11, 16, 19, 26, and 30, from M. citrifolia fruit extract for their inhibitory activities against melanogenesis in B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), most of the saccharide fatty acid esters, hemiterpene glycosides, and iridoid glycosides showed inhibitory effects with no or almost no toxicity to the cells. These compounds were further evaluated with respect to their cytotoxic activities against two human cancer cell lines (HL‐60 and AZ521) and their inhibitory effects on EpsteinBarr virus early antigen (EBV‐EA) activation induced with 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells.