Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 57, Issue 10, Pages 4124-4129Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf900006f
Keywords
Ecklonia cava; phlorotannins; 7-phloroeckol; tyrosinase; B16F10 melanoma cell
Funding
- Ministry of Land, Transport, and Maritime, Republic of Korea
- Korea Institute of Marine Science & Technology Promotion (KIMST) [B10400107A280000100] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- National Research Foundation of Korea [핵09B2519] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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In this study, to assess the feasibility of phlorotannins isolated from Ecklonia cava as an inhibitor of melanin formation, we evaluated its inhibitory effects on mushroom tyrosinase and 3-isobutyl-1-methylxanthine (IBMX)-induced melanin formation inhibitory effects in B16F10 melanoma cell. The ethanolic (EtOH) extract and ethyl acetate (EtOAc) soluble fraction obtained from E cava evidenced a marked inhibitory effect on mushroom tyrosinase at a concentration of 50 mu g/mL. Repeated column chromatography of the active EtOAc fraction resulted in the isolation of three phlorotannins. Their structures were elucidated on the basis of spectroscopic techniques [1D and 2D nuclear magnetic resonance (NMR)] and characterized as phloroglucinol (1), dioxinodehydroeckol (2), and 7-phloroeckol (3), respectively. Among the compounds, 7-phloroeckol (3) evidenced more potent tyrosinase inhibitory effect with an IC50 value of 0.85 mu M than arbutin (IC50 = 243.16 mu M) and kojic acid (IC50 = 40.28 mu M), which were used as positive controls. Lineweaver-Burk plots suggest that 7-phloroeckol plays as a noncompetitive inhibitor against tyrosinase. Furthermore, these compounds were evaluated for their inhibitory effects on IBMX-induced melanin formation in B16F10 melanoma cells. Treatment with 7-phloroeckol (6.25-100 mu M) resulted in a significant inhibition of melanin production in the melanoma cells. In this study, we suggest that 7-phloroeckol might prove useful as a novel inhibitor of melanin formation in cosmetic applications.
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