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Melanogenesis‐Inhibitory Saccharide Fatty Acid Esters and Other Constituents of the Fruits of Morinda citrifolia (Noni)
Author(s) -
Akihisa Toshihiro,
Tochizawa Shun,
Takahashi Nami,
Yamamoto Ayako,
Zhang Jie,
Kikuchi Takashi,
Fukatsu Makoto,
Tokuda Harukuni,
Suzuki Nobutaka
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201100349
Subject(s) - morinda , chemistry , glycoside , fatty acid , glycosidic bond , cytotoxicity , biochemistry , stereochemistry , traditional medicine , in vitro , medicine , enzyme
Abstract 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 EpsteinBarr virus early antigen (EBV‐EA) activation induced with 12‐ O ‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells.