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Melanogenesis‐Inhibitory Activity and Cancer Chemopreventive Effect of Glucosylcucurbic Acid from Shea ( Vitellaria paradoxa ) Kernels
Author(s) -
Zhang Jie,
Kurita Masahiro,
Ebina Kodai,
Ukiya Motohiko,
Tokuda Harukuni,
Yasukawa Ken,
Masters Eliot T.,
Shimizu Naoto,
Akihisa Momoko,
Feng Feng,
Akihisa Toshihiro
Publication year - 2015
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.201400424
Subject(s) - chemistry , microphthalmia associated transcription factor , dmba , microbiology and biotechnology , tumor promotion , biochemistry , in vivo , nordihydroguaiaretic acid , carcinogenesis , tyrosinase , biology , gene , enzyme , arachidonic acid
Two jasmonate derivatives, glucosylcucurbic acid ( 1 ) and methyl glucosylcucurbate ( 2 ), were isolated from the MeOH extract of defatted shea ( Vitellaria paradoxa ; Sapotaceae) kernels. These and their deglucosylated derivatives, cucurbic acid ( 3 ) and methyl cucurbate ( 4 ), were evaluated for their melanogenesis‐inhibitory and cancer chemopreventive potencies. Compounds 1, 3 , and 4 exhibited potent melanogenesis‐inhibitory activities in α ‐melanocyte‐stimulating hormone ( α ‐MSH)‐stimulated B16 melanoma cells. Western ‐blot analysis revealed that compounds 1 and 3 reduced the protein levels of MITF (=microphthalmia‐associated transcription factor), tyrosinase, TRP‐1 (=tyrosine‐related protein 1), and TRP‐2 mostly in a concentration‐dependent manner. In addition, compound 1 exhibited inhibitory effects against Epstein Barr virus early antigen (EBV‐EA) activation induced with 12‐ O ‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells, against TPA‐induced inflammation in mice, and against skin tumor promotion in an in vivo two‐stage mouse skin carcinogenesis test based on 7,12‐dimethylbenz[ a ]anthracene (DMBA) as initiator, and with TPA as promoter.