title: Structure-activity relationship of prenyl-substituted polyphenols from Artocarpus heterophyllus as inhibitors of melanin biosynthesis in cultured melanoma cells.
abstract: A series of prenylated, flavone-based polyphenols, compounds 1-8, were isolated from the wood of Artocarpus heterophyllus. These compounds, which have previously been shown not to inhibit tyrosinase activity, were found to be active inhibitors of the in vivo melanin biosynthesis in B16 melanoma cells, with little or no cytotoxicity. To clarify the structural requirement for inhibition, some structure-activity relationships were studied, in comparison with related compounds lacking prenyl side chains. Our experiments indicate that both prenyl and OH groups, as well as the type of substitution pattern, are crucial for the inhibition of melanin production in B16 melanoma cells.
authors: Department of Forest Product, Faculty of Forestry, Mulawarman University, Samarinda, East Kalimantan, 75123, Indonesia.
authors: Enos Tangke
authors: ET
authors: Arung
authors: Kuniyoshi
authors: K
authors: Shimizu
authors: Ryuichiro
authors: R
authors: Kondo
mesh_terms: D000818:Animals; D031622:Artocarpus / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000378:metabolism*; D009387:Neoprene / Q000737:chemistry; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D059808:Polyphenols; D012878:Skin Neoplasms / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D005419:Flavonoids; D008543:Melanins; D010636:Phenols; D059808:Polyphenols; C016077:prenyl; D009387:Neoprene