Melanogenesis‐Inhibitory Activity and Cancer Chemopreventive Effect of Glucosylcucurbic Acid from Shea ( Vitellaria paradoxa ) Kernels | Zendy

Zhang Jie | Zendy; Kurita Masahiro | Zendy; Ebina Kodai | Zendy; Ukiya Motohiko | Zendy; Tokuda Harukuni | Zendy; Yasukawa Ken | Zendy; Masters Eliot T. | Zendy; Shimizu Naoto | Zendy; Akihisa Momoko | Zendy; Feng Feng | Zendy; Akihisa Toshihiro | Zendy

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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.

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