title: Melanin biosynthesis inhibitory activity of a compound isolated from young green barley (Hordeum vulgare L.) in B16 melanoma cells.
abstract: In the course to find compounds that inhibit melanin biosynthesis (i.e., whitening agents), we evaluated the effects of the methanol-soluble fraction (i.e., the water-soluble portion of methanol extracts-CHP20P-MeOH eluted fraction) from young green barley leaves on melanin production in B16 melanoma cells. Activity-guided fractionation led to an isolate called tricin (compound 1) as an inhibitory compound of melanin production in B16 melanoma cells. Furthermore, tricin analogs such as tricetin, tricetin trimethyl ether, luteolin, and apigenin were used for analyzing the structure-activity relationships (SAR) of 5,7-dihydroxyflavones studies. Tricin demonstrated stronger inhibitory activity compared to three other compounds. The results suggest that a hydroxyl group at the C-4' position and methoxy groups at the C-3',5' positions of the tricin skeleton may have important roles in this inhibitory activity in B16 melanoma cells. Our results suggest that tricin inhibits melanin biosynthesis with higher efficacy than arbutin, and it could be used as a whitening agent.
authors.affiliation: Faculty of Agriculture, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka, 812-8581, Japan.
authors.forename: Tian Xiao
authors.initials: TX
authors.lastname: Meng
authors.forename: Nobuto
authors.initials: N
authors.lastname: Irino
authors.forename: Ryuichiro
authors.initials: R
authors.lastname: Kondo
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D004353:Drug Evaluation, Preclinical; D005419:Flavonoids / Q000494:pharmacology; D001467:Hordeum / Q000737:chemistry*; D047311:Luteolin / Q000494:pharmacology; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental; D051379:Mice; D010936:Plant Extracts / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D062327:Skin Lightening Preparations / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D005419:Flavonoids; D008543:Melanins; D010936:Plant Extracts; D062327:Skin Lightening Preparations; C017769:tricin; D047311:Luteolin
references.citation: Cancer Chemother Pharmacol. 2006 Jan;57(1):1-6
references.pmid: 16001171
references.citation: J Nat Med. 2013 Jul;67(3):460-7
references.pmid: 22855403
references.citation: Cancer Prev Res (Phila). 2009 Dec;2(12):1031-8
references.pmid: 19934339
references.citation: J Agric Food Chem. 2007 Dec 12;55(25):10086-92
references.pmid: 18001030
references.citation: J Agric Food Chem. 2012 Jun 27;60(25):6260-7
references.pmid: 22681491
references.citation: J Agric Food Chem. 2011 Sep 14;59(17):9581-7
references.pmid: 21851134
references.citation: Molecules. 2014 Oct 10;19(10):16240-65
references.pmid: 25310150
references.citation: Biol Pharm Bull. 2006 Sep;29(9):1966-9
references.pmid: 16946519
references.citation: Planta Med. 2005 Dec;71(12):1128-33
references.pmid: 16395649
references.citation: Spectrochim Acta A Mol Biomol Spectrosc. 2013 Apr 15;107:235-40
references.pmid: 23434549
references.citation: Arch Pharm Res. 2002 Jun;25(3):300-5
references.pmid: 12135101
references.citation: Yao Xue Xue Bao. 2008 Mar;43(3):281-3
references.pmid: 18630264
references.citation: Cancer Epidemiol Biomarkers Prev. 2000 Nov;9(11):1163-70
references.pmid: 11097223
references.citation: J Cell Biochem. 2008 Oct 1;105(2):514-23
references.pmid: 18636546
references.citation: Biochem Pharmacol. 2007 May 1;73(9):1288-96
references.pmid: 17250812