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KMID : 1134820180470070765
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Journal of the Korean Society of Food Science and Nutrition
2018 Volume.47 No. 7 p.765 ~ p.769
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Tyrosinase Inhibitory Effects of Degraded Products from Rosmarinic Acid by Gamma-Irradiation
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Jeong Gyeong-Han
Jeong Yun-Hee
Kim Tae-Hoon
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Abstract
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Melanin is one of the most important factors affecting skin color, and inhibition of tyrosinase activity can effectively regulated melanin biosynthesis in the human skin. As part of our continuing investigation into creating bioactive compounds from major natural secondary metabolites, we herein report the radiolytic degradation of rosmarinic acid under γ-irradiation conditions into newly modified compounds 1∼4 exhibiting significantly enhanced inhibitory effects against tyrosinase compared to the parent rosmarinic acid. The structures of newly formed compounds, rosmarinosin A (1), rosmarinosin B (2), rosmarinosin C (3), and (S)-oresbiusin (4), were elucidated on the basis of interpretation of nuclear magnetic resonance (NMR) and mass spectroscopic data. The unusual phenylpropanoid derivative (2) containing γ-lactone moiety exhibited significantly enhanced inhibitory effects against tyrosinase with an IC50 value of 190.4±1.4 μM, when compared to the parent rosmarinic acid. Thus, γ-irradiation of rosmarinic acid can be used to produce degraded products 1∼4 of rosmarinic acid with enhanced tyrosinase inhibitory effects.
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KEYWORD
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gamma-irradiation, rosmarinic acid, degradation, tyrosinase inhibition, phenylpropanoid
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