Melanogenesis‐Inhibitory Activity and Cancer Chemopreventive Effect of Glucosylcucurbic Acid from Shea (Vitellaria paradoxa) Kernels. Issue 4 (April 2015)

• Record Type: Journal Article
• Authors: Zhang, Jie; Kurita, Masahiro; Ebina, Kodai; Ukiya, Motohiko; Tokuda, Harukuni; Yasukawa, Ken; Masters, Eliot T.; Shimizu, Naoto; Akihisa, Momoko; Feng, Feng; Akihisa, Toshihiro
• Is Part Of: Chemistry & biodiversity. Volume 12:Issue 4(2015:Apr.)
• Page Start: 547
• Page End: 558
• Publication Date: 2015-04
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201400424
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Two jasmonate derivatives, glucosylcucurbic acid (<bold>1</bold>) and methyl glucosylcucurbate (<bold>2</bold>), were isolated from the MeOH extract of defatted shea (<italic>Vitellaria paradoxa</italic>; Sapotaceae) kernels. These and their deglucosylated derivatives, cucurbic acid (<bold>3</bold>) and methyl cucurbate (<bold>4</bold>), were evaluated for their melanogenesis‐inhibitory and cancer chemopreventive potencies. Compounds <bold>1, 3</bold>, and <bold>4</bold> exhibited potent melanogenesis‐inhibitory activities in <italic>α</italic>‐melanocyte‐stimulating hormone (<italic>α</italic>‐MSH)‐stimulated B16 melanoma cells. <italic>Western</italic>‐blot analysis revealed that compounds <bold>1</bold> and <bold>3</bold> 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 <bold>1</bold> exhibited inhibitory effects against <italic>Epstein</italic><italic>Barr</italic> virus early antigen (EBV‐EA) activation induced with 12‐<italic>O</italic>‐tetradecanoylphorbol‐13‐acetate (TPA) in <italic>Raji</italic> cells, against TPA‐induced inflammation in mice, and against skin tumor promotion in an <italic>in vivo</italic> two‐stage mouse skin carcinogenesis test based on 7, 12‐dimethylbenz[<italic>a</italic>]anthracene (DMBA) as initiator, and with TPA as promoter.</p> </abstract>