Prenylated Flavonoids from the Roots of Sophora flavescens with Tyrosinase Inhibitory Activity

Abstract

Prenylated flavonoids containing the resorcinol moiety were isolated as tyrosinase inhibitors from the roots of Sophora flavescens by activity-guided fractionation. Among the 12 compounds isolated, kuraridin, kurarinone and norkurarinol showed stronger inhibitory potencies (IC₅₀ = 1.1, 1.3 and 2.1 μM, respectively) than that of kojic acid (IC₅₀ = 11.3 μM), a well known tyrosinase inhibitor. Substitution of a lavandulyl or hydroxylavandulyl group at the C-8 position and a methoxy or hydroxy group at the C-5 position are essential for the inhibitory effect.

References

• 1 Hearing V J, Tsukamoto K. Enzymatic control of pigmentation in mammals.  Federation of American Society for Experimental Biology. 1991;  5 2902-9
• 2 Iozumi K, Hoganson G E, Pennella R, Everett M A, Fuller B B. Role of tyrosinase as the determinant of pigmentation in cultured human melanocytes.  Journal of Investigative Dermatology. 1993;  100 806-11
• 3 Ikeda T, Tsutsumi T. Function and skin depigmental activity of crude drugs.  Fragrance Journal. 1990;  6 59-66
• 4 Shin N H, Lee K S, Min K R, Lee S H, Kim Y. Inhibitory effects of herbal extract on DOPA oxidase activity of tyrosinase.  Natural Product Sciences. 1997;  3 111-21
• 5 Bensky D, Gamble A. Chinese herbal medicine. Seattle; Eastland Press 1992: p. 117
• 6 Wu L J, Miyase T, Ueno A, Kuroyanagi M, Noro T, Fukushima S. Studies on the constituents of Sophora flavescens. III.  Yakugaku Zasshi. 1985;  105 736-41
• 7 Wu L J, Miyase T, Ueno A, Kuroyanagi M, Noro T, Fukushima S. Studies on the constituents of Sophora flavescens. II.  Chemical Pharmaceutical Bulletin. 1985;  33 3231-6
• 8 Ryu S Y, Kim S K, No Z, Ahn J. A novel flavonoid from Sophora flavescens .  Planta Medica. 1996;  62 361-3
• 9 Shirataki Y, Yokoe I, Noguchi M, Tomimori T, Komatsu M. Studies on the constituents of Sophora species. XXII. Constituents of the root of Sophora moorcroftiana .  Chemical Pharmaceutical Bulletin. 1988;  36 2220-5
• 10 Wu L J, Miyase T, Ueno A, Kuroyanagi M, Noro T, Fukushima S, Sasaki S. Studies on the constituents of Sophora flavescens. IV.  Yakugaku Zasshi. 1985;  105 1934-9
• 11 Komatsu M, Hatayama K. Studies on the constituents of Sophora species. V. Constituents of the root of Sophora angustifolia. 2.  Chemical Pharmaceutical Bulletin. 1971;  19 2126-31
• 12 Kyogoku K, Hatayama K, Komatsu M. Constituents of Chinese crude drug ”Kushen” (the root of Sophora flavescens). Isolation of five new flavonoids and formononetin.  Chemical Pharmaceutical Bulletin. 1973;  21 2733-8
• 13 Matsuda H, Nakamura S, Kubo M. Studies of cuticle drugs from natural sources. II. Inhibitory effects of Prunus plants of melanin biosynthesis.  Biological Pharmaceutical Bulletin. 1994;  17 1417-20