title: Melanogenesis-inhibitory activity and cancer chemopreventive effect of glucosylcucurbic acid from shea (Vitellaria paradoxa) kernels.
abstract: 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.
authors: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
authors: Jie
authors: J
authors: Zhang
authors: Masahiro
authors: M
authors: Kurita
authors: Kodai
authors: K
authors: Ebina
authors: Motohiko
authors: M
authors: Ukiya
authors: Harukuni
authors: H
authors: Tokuda
authors: Ken
authors: K
authors: Yasukawa
authors: Eliot T
authors: ET
authors: Masters
authors: Naoto
authors: N
authors: Shimizu
authors: Momoko
authors: M
authors: Akihisa
authors: Feng
authors: F
authors: Feng
authors: Toshihiro
authors: T
authors: Akihisa
mesh_terms: D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry* / Q000494:pharmacology*; D000956:Antigens, Viral / Q000378:metabolism; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor / Q000187:drug effects; D005960:Glucosides / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008543:Melanins / Q000378:metabolism*; D008546:Melanoma, Experimental / Q000188:drug therapy / Q000473:pathology; D008815:Mice, Inbred Strains; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000378:metabolism; D010088:Oxidoreductases / Q000378:metabolism; D054883:Oxylipins / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry; D029632:Sapotaceae / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D012878:Skin Neoplasms / Q000188:drug therapy / Q000473:pathology; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology; D023041:Xenograft Model Antitumor Assays / Q000379:methods; D000521:alpha-MSH / Q000378:metabolism / Q000494:pharmacology
chemical_list: D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; D000972:Antineoplastic Agents, Phytogenic; C033305:Epstein-Barr virus early antigen; D005960:Glucosides; D008543:Melanins; D054883:Oxylipins; D010936:Plant Extracts; C000607296:glucosylcucurbic acid; D000521:alpha-MSH; D010088:Oxidoreductases; C064056:tyrosinase-related protein-1; D014442:Monophenol Monooxygenase; D013755:Tetradecanoylphorbol Acetate
keywords: Anti-inflammatory activity; EpsteinBarr virus early antigen (EBV-EA); Glucosylcucurbic acid; Melanogenesis inhibition; Mouse skin carcinogenesis; Shea kernel; Vitellaria paradoxa