Planta Med 2003; 69(6): 559-561
DOI: 10.1055/s-2003-40643
Letter
© Georg Thieme Verlag Stuttgart · New York

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

Jong Keun Son1 , Ji Soo Park1 , Jeong Ah Kim1 , Youngsoo Kim2 , See Ryun Chung1 , Seung Ho Lee1
  • 1College of Pharmacy, Yeungnam University, Kyongsan, Korea
  • 2College of Pharmacy and Research Center for Bioresource and Health, Chungbuk National University, Cheongju, Korea
Further Information

Publication History

Received: October 11, 2002

Accepted: February 9, 2003

Publication Date:
16 July 2003 (online)

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

Professor Seung Ho Lee, Ph. D.

College of Pharmacy

Yeungnam University

Kyongsan 712-749

Korea

Email: seungho@yu.ac.kr

    >