title: Kaempferol and kaempferol rhamnosides with depigmenting and anti-inflammatory properties.
abstract: The objective of this study was to examine the biological activity of kaempferol and its rhamnosides. We isolated kaempferol (1), a-rhamnoisorobin (2), afzelin (3), and kaempferitrin (4) as pure compounds by far-infrared (FIR) irradiation of kenaf (Hibiscus cannabinus L.) leaves. The depigmenting and anti-inflammatory activity of the compounds was evaluated by analyzing their structure-activity relationships. The order of the inhibitory activity with regard to depigmentation and nitric oxide (NO) production was kaempferol (1) > a-rhamnoisorobin (2) > afzelin (3) > kaempferitrin (4). However, a-rhamnoisorobin (2) was more potent than kaempferol (1) in NF-kB-mediated luciferase assays. From these results, we conclude that the 3-hydroxyl group of kaempferol is an important pharmacophore and that additional rhamnose moieties affect the biological activity negatively.
authors.affiliation: R & D Center, AmorePacific Corporation, Yongin, Korea. thiocarbon@freechal.com
authors.forename: Ho Sik
authors.initials: HS
authors.lastname: Rho
authors.forename: Amal Kumar
authors.initials: AK
authors.lastname: Ghimeray
authors.forename: Dae Sung
authors.initials: DS
authors.lastname: Yoo
authors.forename: Soo Mi
authors.initials: SM
authors.lastname: Ahn
authors.forename: Sun Sang
authors.initials: SS
authors.lastname: Kwon
authors.forename: Keun Ha
authors.initials: KH
authors.lastname: Lee
authors.forename: Dong Ha
authors.initials: DH
authors.lastname: Cho
authors.forename: Jae Youl
authors.initials: JY
authors.lastname: Cho
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D004797:Enzyme-Linked Immunosorbent Assay; D006801:Humans; D044949:Kaempferols / Q000737:chemistry / Q000494:pharmacology*; D008543:Melanins / Q000378:metabolism; D008546:Melanoma, Experimental / Q000201:enzymology / Q000378:metabolism / Q000473:pathology; D016328:NF-kappa B / Q000378:metabolism; D009569:Nitric Oxide / Q000096:biosynthesis; D052247:Nitric Oxide Synthase Type II / Q000235:genetics; D012333:RNA, Messenger / Q000235:genetics; D020133:Reverse Transcriptase Polymerase Chain Reaction; D012880:Skin Pigmentation / Q000187:drug effects*; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000893:Anti-Inflammatory Agents; D044949:Kaempferols; D008543:Melanins; D016328:NF-kappa B; D012333:RNA, Messenger; D009569:Nitric Oxide; C006552:kaempferol; D052247:Nitric Oxide Synthase Type II