Kang, Hye-Sook
(Faculty of Food Science and Biotechnology)
,
Kim, Hyung-Rak
(Faculty of Food Science and Biotechnology)
,
Byun, Dae-Seok
(Faculty of Food Science and Biotechnology)
,
Son, Byeng-Wha
(Department of Chemistry, Pukyong National University)
,
Nam, Taek-Jeong
(Faculty of Food Science and Biotechnology)
,
Choi , Jae-Sue
(Faculty of Food Science and Biotechnology)
Extracts from seventeen seaweeds were determined for tyrosinase inhibitory activity using mushroom tyrosinase with L-tyrosine as a substrate. Only one of them, Ecklonia stolonifera OKAMURA (Laminariaceae) belonging to brown algae, showed high tyrosinase inhibitory activity. Bioassay-guided fractiona...
Extracts from seventeen seaweeds were determined for tyrosinase inhibitory activity using mushroom tyrosinase with L-tyrosine as a substrate. Only one of them, Ecklonia stolonifera OKAMURA (Laminariaceae) belonging to brown algae, showed high tyrosinase inhibitory activity. Bioassay-guided fractionation of the active ethyl acetate (EtOAc) soluble fraction from the methanolic extract of E. stolonifera, led us to the isolation of phloroglucinol derivatives [phloroglucinol (1), eckstolonol (2), eckol (3), phlorofucofuroeckol A (4), and dieckol (5)]. Compounds 1~5 were found to inhibit the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with $IC_{50}$ values of 92.8, 126, 33.2, 177, and 2.16 ${\mu}g$ /mL, respectively. It was compared with those of kojic acid and arbutin, well-known tyrosinase inhibitors, with $IC_{50}$ values of 6.32 and 112 ${\mu}g$ / mL, respectively. The inhibitory kinetics analyzed from Lineweaver-Burk plots, showed compounds 1 and 2 to be competitive inhibitors with $K_i$ of $2.3{\times}10^{-4}\;and\;3.1{times}10^{-4}$ M, and compounds 3~5 to be noncompetitive inhibitors with $K_i$ of $1.9{\times}10^{-5},\;1.4{\times}10^{-3}\;and\;1.5{\times}10^{-5}$ M, respectively. This work showed that phloroglucinol derivatives, natural compounds found in brown algae, could be involved in the control of pigmentation in plants and other organisms through inhibition of tyrosinase activity using L-tyrosine as a substrate.
Extracts from seventeen seaweeds were determined for tyrosinase inhibitory activity using mushroom tyrosinase with L-tyrosine as a substrate. Only one of them, Ecklonia stolonifera OKAMURA (Laminariaceae) belonging to brown algae, showed high tyrosinase inhibitory activity. Bioassay-guided fractionation of the active ethyl acetate (EtOAc) soluble fraction from the methanolic extract of E. stolonifera, led us to the isolation of phloroglucinol derivatives [phloroglucinol (1), eckstolonol (2), eckol (3), phlorofucofuroeckol A (4), and dieckol (5)]. Compounds 1~5 were found to inhibit the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with $IC_{50}$ values of 92.8, 126, 33.2, 177, and 2.16 ${\mu}g$ /mL, respectively. It was compared with those of kojic acid and arbutin, well-known tyrosinase inhibitors, with $IC_{50}$ values of 6.32 and 112 ${\mu}g$ / mL, respectively. The inhibitory kinetics analyzed from Lineweaver-Burk plots, showed compounds 1 and 2 to be competitive inhibitors with $K_i$ of $2.3{\times}10^{-4}\;and\;3.1{times}10^{-4}$ M, and compounds 3~5 to be noncompetitive inhibitors with $K_i$ of $1.9{\times}10^{-5},\;1.4{\times}10^{-3}\;and\;1.5{\times}10^{-5}$ M, respectively. This work showed that phloroglucinol derivatives, natural compounds found in brown algae, could be involved in the control of pigmentation in plants and other organisms through inhibition of tyrosinase activity using L-tyrosine as a substrate.
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제안 방법
Lineweaver-Burk plots for the inhibition of the mushroom tyrosinase by eckol (A), phlorofucofuroeckol A (B) and dieckol (C). The reaction was done in the presence of eckol [final concentration of 0 (●), 2.5 (♦), 5 (■) and 10 μM(▼)], phlorofucofuroeckol A [0(●), 208 (▽), and 313 μM (▼)] or dieckol [0(●), 5(▼), and 10μM(□)]. Vmax = 0.
Lineweaver-Burk plots for the inhibition of the mushroom tyrosinase by phloroglucinol (A) and eckstolonol (B). The reaction was done in the presence of phloroglucinol [final concentration of 0 (●), 125 (▼), 250 (■) and 500 μM(◆)]or eckstolonol [0(●), 50(♦), 100(■) and 200μM(▼)]. Vmax=0.
To discover the sources with tyrosinase inhibitory activity in marine algae, 17 seaweed extracts i.e. 2 of Chlorophyta, 5 of Phaeophyta, and 10 of Rhodophyta, were screened for their inhibitory effect on mushroom tyrosinase activity using L-tyrosine as a substrate (Table I). Only one of them, Ecklonia stolonifera Okamura (Laminariaceae), which belongs to brown algae, showed an inhibitory activity with an value of 345 ㎍/mL.
대상 데이터
25 mm), and 50% H2SO4 was used as spray reagent. L-lyrosine was purchased from Janssen Chimica (Ge시 Belgium). Arbutin, kojic acid and mushroom tyrosinase (EC 1.
성능/효과
32 and 112 ㎍/mL, respectively. All the compounds inhibited the monophenolase activity of the mushroom tyrosinase, and phloroglucinol(1) and eckol (3) showed stronger inhibitory activity than arbutin, and dieckol (5) displayed three times higher activity than kojic acid, a well-known tyrosinase inhibitor.
Safety is a primary consideration for tyrosinase inhibitors, especially for those used in food and cosmetic products, as these may be regularly utilized in unregulated quantities. This work showed that phlorotannins, natural compounds found in an edible brown alga, could be involved in the control of pigmentation in plants and other organisms through inhibition of tyrosinase activity using L-tyrosine as a substrate.
후속연구
stolonifera contain resorcinol moieties, their tyrosinase inhibitory mode, however, exhibited two different types as described above. It will need the further study for the structureactivity relationships of tyrosinase inhibitors.
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