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Kaempferol and Kaempferol Rhamnosides with Depigmenting and Anti-Inflammatory Properties
R & D Center, AmorePacific Corporation, Yongin, Korea
College of Biomedical Science, Kangwon National University, Chuncheon, Korea
Skin Biotechnology Center, Kyung Hee University, Suwon, Korea
R & D Center, Morechem Corporation, Seoul, Korea
Department of Genetic Engineering, Sungkyunkwan University, Suwon, Korea
* Authors to whom correspondence should be addressed.
Received: 24 March 2011; in revised form: 14 April 2011 / Accepted: 15 April 2011 / Published: 18 April 2011
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.
Keywords: kaempferol; rhamnoside; depigmentation; anti-inflammation
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Rho, H.S.; Ghimeray, A.K.; Yoo, D.S.; Ahn, S.M.; Kwon, S.S.; Lee, K.H.; Cho, D.H.; Cho, J.Y. Kaempferol and Kaempferol Rhamnosides with Depigmenting and Anti-Inflammatory Properties. Molecules 2011, 16, 3338-3344.
Rho HS, Ghimeray AK, Yoo DS, Ahn SM, Kwon SS, Lee KH, Cho DH, Cho JY. Kaempferol and Kaempferol Rhamnosides with Depigmenting and Anti-Inflammatory Properties. Molecules. 2011; 16(4):3338-3344.
Rho, Ho Sik; Ghimeray, Amal Kumar; Yoo, Dae Sung; Ahn, Soo Mi; Kwon, Sun Sang; Lee, Keun Ha; Cho, Dong Ha; Cho, Jae Youl. 2011. "Kaempferol and Kaempferol Rhamnosides with Depigmenting and Anti-Inflammatory Properties." Molecules 16, no. 4: 3338-3344.