title: Inhibitors of melanogenesis in B16 melanoma 4A5 cells from flower buds of Lawsonia inermis (Henna).
abstract: The methanolic extract of Lawsonia inermis L. (henna) showed significant inhibitory activity toward melanogenesis in B16 melanoma 4A5 cells. Among the constituents isolated from the methanolic extract, luteolin, quercetin, and (±)-eriodictyol showed stronger inhibitory activity than the reference compound, arbutin. Several structure-activity relationships of the flavonoids were suggested, and OGlc<H=OH at the 3-position, OGlc<OH at the 4'-position, and the double bond between the 2- and 3-positions were important. The active constituents suppressed tyrosinase, tyrosinase related protein (TRP)-1, and TRP-2 mRNA expression. The suppression was considered as one of the mechanisms of action. Furthermore, the methanolic extract and several constituents, including luteoloside and spiraeoside, showed anti-plasmin activity, which is considered to play a key role in UV-stimulated melanogenesis in human skin.
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan; N. T. H Co., Ltd, 1-8-11 4F Sky-ebisu Bldg., Ebisu, Shibuya-ku, Tokyo 150-0013, Japan. Electronic address: nakashima@nthhenna.co.jp.
authors.forename: Souichi
authors.initials: S
authors.lastname: Nakashima
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan; N. T. H Co., Ltd, 1-8-11 4F Sky-ebisu Bldg., Ebisu, Shibuya-ku, Tokyo 150-0013, Japan.
authors.forename: Yoshimi
authors.initials: Y
authors.lastname: Oda
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Seikou
authors.initials: S
authors.lastname: Nakamura
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Jiang
authors.initials: J
authors.lastname: Liu
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Koko
authors.initials: K
authors.lastname: Onishi
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Miki
authors.initials: M
authors.lastname: Kawabata
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Hisako
authors.initials: H
authors.lastname: Miki
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Yugo
authors.initials: Y
authors.lastname: Himuro
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
mesh_terms: D000818:Animals; D000933:Antifibrinolytic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D035264:Flowers / Q000737:chemistry; D006801:Humans; D019746:Intramolecular Oxidoreductases / Q000037:antagonists & inhibitors / Q000235:genetics; D031564:Lawsonia Plant / Q000737:chemistry*; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000188:drug therapy* / Q000235:genetics / Q000378:metabolism*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000235:genetics; D010088:Oxidoreductases / Q000037:antagonists & inhibitors / Q000235:genetics; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry; D012333:RNA, Messenger / Q000235:genetics / Q000378:metabolism; D012334:RNA, Neoplasm / Q000235:genetics / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D000933:Antifibrinolytic Agents; D005419:Flavonoids; D008543:Melanins; D010936:Plant Extracts; D012333:RNA, Messenger; D012334:RNA, Neoplasm; D010088:Oxidoreductases; C064056:tyrosinase-related protein-1; D014442:Monophenol Monooxygenase; D019746:Intramolecular Oxidoreductases; C042501:dopachrome isomerase
keywords: Anti-melanogenic activity; Ayurvedic plant; Henna; Lawsonia inermis; Plasmin