RRC ID 37023
Author Zhang J, Kurita M, Ebina K, Ukiya M, Tokuda H, Yasukawa K, Masters ET, Shimizu N, Akihisa M, Feng F, Akihisa T.
Title Melanogenesis-inhibitory activity and cancer chemopreventive effect of glucosylcucurbic acid from shea (Vitellaria paradoxa) kernels.
Journal Chem Biodivers
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.
Volume 12(4)
Pages 547-58
Published 2015-4-1
DOI 10.1002/cbdv.201400424
PMID 25879500
MeSH Animals Anticarcinogenic Agents / chemistry* Anticarcinogenic Agents / pharmacology* Antigens, Viral / metabolism Antineoplastic Agents, Phytogenic / chemistry Antineoplastic Agents, Phytogenic / pharmacology Cell Line, Tumor / drug effects Glucosides / chemistry Glucosides / pharmacology* Humans Melanins / metabolism* Melanoma, Experimental / drug therapy Melanoma, Experimental / pathology Mice, Inbred Strains Molecular Structure Monophenol Monooxygenase / metabolism Oxidoreductases / metabolism Oxylipins / chemistry Oxylipins / pharmacology* Plant Extracts / chemistry Sapotaceae / chemistry* Seeds / chemistry Skin Neoplasms / drug therapy Skin Neoplasms / pathology Tetradecanoylphorbol Acetate / pharmacology Xenograft Model Antitumor Assays / methods alpha-MSH / metabolism alpha-MSH / pharmacology
IF 2.039
Times Cited 7
Human and Animal Cells HL60(RCB0041) A549(RCB0098) SK-BR-3(RCB2132)