Isolation of Antibacterial Prenylated Flavonoids from Cudrania tricuspidata

꾸지뽕나무로부터 항균성 Prenylated Flavonoids의 분리

  • Lee, Byong-Won (Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Kang, Nam-Suk (Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Park, Ki-Hun (Department of Agricultural Chemistry, Gyeongsang National University)
  • Published : 2004.06.30

Abstract

Two prenylated flavonoids were isolated from a chloroform extract of the root bark of Cudrania tricuspidata. Both compounds (1, 2) showed antibacterial activity against Gram positive bacteria, Staphylococcus aureus, Bacillus subtilis and Bacillus cereus. Their structures were determined as euchrestaflavanone B (1) and euchrestaflavanone C (2) on the basis of $^1H\;NMR,\;^{13}C\;NMR$ and long-range coupling NMR techniques.

꾸지뽕나무(Cudrania tricuspidata Bureau)의 클로로포름 추출물로부터 2종의 prenylated flavonoid 항균 물질을 분리하였다. 분리할 화합물에 대하여 항균활성을 실험 한 결과 화합물 1과 2는 $10\;{\mu}g/disk$의 농도에서 Gram 양성균인 Staphylococcus aureus, Bacillus subtilis 그리고 Bacillus cereus에 대하여 활성을 보였다. 이들의 구조를 $^lH\;NMR,\;^{13}C\;NMR$ 및 2D NMR을 포함한 분광학적인 방법을 통하여 분석한 결과, 화합물 1과 2는 euchrestaflavanone B와 euchrestaflavanone C로 각각 동정 되었다.

Keywords

References

  1. Jang, I. M. (2003) In Treatise on Asian Herbal Medicines, Natural Products Science Seoul National University Press, Seoul
  2. Nomura, T., Hano, Y. and Fujimoto, T. (1983) Three new isopreny1ated xanthones, cudraxanthone A, B and C, from the root bark of Cudrania Tricuspidata (carr.) bur. Heterocycles 20, 213-218 https://doi.org/10.3987/R-1983-02-0213
  3. Fujimoto, T., Hano, Y. and Nomura, T. (1984) Components of root bark of Cudrania tricuspidata 1. Structures of four new isopreny1ated xanthones, cudraxanthones A, B, C and D. Planta Med. 50, 218-221 https://doi.org/10.1055/s-2007-969682
  4. Hano, Y., Matsumoto, Y., Sun, J. Y. and Nomura, T. (1990) Structures of four new isopreny1ated xanthones, cudraxanthones H, I, J, and K. Planta Med. 56, 478-481 https://doi.org/10.1055/s-2006-961016
  5. Hano, Y., Matsumoto, Y., Sun, J. Y. and Nomura, T. (1990) Structures of three new isopreny1ated xanthones, Cudraxanthones E, F, and G. Planta Med. 56, 399-402 https://doi.org/10.1055/s-2006-960993
  6. Hano, Y., Matsumoto, Y., Shinora, K., Sun, J. Y. and Nomura, T. (1991) Structures of four new isoprenylated xanthones, cudraxanthones L, M, N, and O from Cudrania tricuspidata. Planta Med. 57, 172-175 https://doi.org/10.1055/s-2006-960059
  7. Fujimoto, T., Hano, Y., Nomura, T. and Uzawa, J. (1984) Components of root bark of Cudrania tricuspidata 2. Structures of two new isopreny1ated flavones, cudraflavones A and B. Planta Med. 50, 161-163 https://doi.org/10.1055/s-2007-969660
  8. Fujimoto, T. and Nomurfl, T. (1984) Structures of cudraflavanone A and euchrestaflavanone C. Heterocycles 22, 997-1003 https://doi.org/10.3987/R-1984-05-0997
  9. Young, H. S., Park, H. J. and Choi, J. S. (1989) Chemical study on the stem of Cudrania tricuspidata. Arch. Pharm. Res. 12, 39-41 https://doi.org/10.1007/BF02855744
  10. Lee, I. K., Kim, C. J., Song, K. S., Kim, H. M., Koshino, H., Uramoto, M. and Yoo, I, D. (1996) Cytotoxic benzyl dihydroflavonols from Cudrania tricuspidata. Phytochemistry 41, 213-216 https://doi.org/10.1016/0031-9422(95)00609-5
  11. Fujimoto, T. and Nomura, T. (1985) Components of root bark of Cudrania tricuspidata; 3. Isolation and structure studies on the flavonoids. Planta Med. 51, 190-193 https://doi.org/10.1055/s-2007-969453
  12. Cha, J. Y., Kim, H. J., Chung, C. H. and Cho, Y. S. (1999) Antioxidative activities and contents of polyphenolic compound of Cudrania tricuspidata. J. Korean Soc. Food Sci. Nutr. 28, 1310-1315
  13. Cha, J. Y., Kim, H. J. and Cho, Y. S, (2000) Effect of water soluble extract from leaves of Moms alba and Cudrania tricuspidata on the lipid peroxidation in tissues of rats. J. Korean Soc. Food Sci. Nutr. 29, 531-536
  14. Kim, H. J., Cha, J. Y., Choi, M. R. and Cho, Y. S. (2000) Antioxidative activities by water-soluble extracts of Moms alba and Cudrania tricuspidata. J. Korean Soc. Agric. Chem. 43, 148-152
  15. Kang, D. G., Hur, T. Y., Lee, G. M., Oh, H. C., Kwon, T. O., Sohn, E. J. and Lee, H. S. (2002) Effects of Cudrania tricuspidata water extract on blood pressure and renal functions in NO-dependent hypertension. Life Sci. 70, 2599-2609 https://doi.org/10.1016/S0024-3205(02)01547-3
  16. Lee, I. K., Kim, C. J., Song, K. S., Kim, H. M., Koshino, H., Uramoto, M. and Yoo, I. D. (1996) Cytotoxic benzyl dihydroflavono1s from Cudrania tricuspidata. Phytochemistry 41, 213-216 https://doi.org/10.1016/0031-9422(95)00609-5
  17. Piddok, L. J. V. (1990) Techniques used for the determination of· antibacterial resistance and sensitivity in bacteria. J. Appl. Bacteriol. 68, 307-318 https://doi.org/10.1111/j.1365-2672.1990.tb02880.x
  18. The Chinese Academy of Sciences (1981) In Manual Identification of Flavonoids. Publishing House of Science. Baijing
  19. Shirataki, Y., Manaka, A., Yokoe, I. and Komatsu, M. (1982) Two prenylflavanones from euchresta japonica. Phytochemistry 21, 2959-2963 https://doi.org/10.1016/0031-9422(80)85077-1