Inhibitory Effects of Naringenin and Its Novel Derivatives on Hyaluronidase

  • Published : 2009.02.28

Abstract

Naringenin is a bioactive flavanone containing antioxidative, anti-inflammatory, and anticarcinogenic properties. The inhibitory effects on hyaluronidase of naringenin and its novel derivatives were evaluated. Among these flavonoids at $200{\mu}M$ concentration, 7-O-butyl naringenin had the highest inhibitory effect on hyaluronidase with 44.84%. In addition, For naringenin at concentrations of 0, 150, and $190{\mu}M$, the apparent Michaelis constants ($_{app}K_m$) were calculated to be $0.60{\pm}0.02$, $0.43{\pm}0.02$, and $0.41{\pm}0.01\;mg/mL$ of substrate, respectively; for 7-O-butyl naringenin at 0, 20, and $30{\mu}M$ concentrations, those were $0.44{\pm}0.03$ and $0.27{\pm}0.03\;mg/mL$, respectively. The $V_{max}$ values at 150 and $190{\mu}M$ naringenin were $0.59{\pm}0.02$ and $0.56{\pm}0.01\;mg/mL/min$, respectively; and those at 20 and $30{\mu}M$ 7-O-butyl naringenin were $0.50{\pm}0.02$ and $0.33{\pm}0.02\;mg/mL/min$, respectively. However, the slopes of each inhibitory reaction were not significantly different. Therefore, naringenin and 7-O-butyl naringenin were shown to be uncompetitive inhibitors. These results demonstrate the potential use of 7-O-butyl naringenin as an anti-inflammatory substance.

Keywords

References

  1. GlaBer G, Graefe EU, Struck F, Veit M, Gebhardt R. Comparison of anti oxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites. Phytomedicine 9: 33-40 (2002) https://doi.org/10.1078/0944-7113-00080
  2. Lee JY, Moon SO, Kwon YJ, Rhee SJ, Park HR, Choi SW. Identification and quantification of anthocyanins and flavonoids in mulberry cultivars. Food Sci. Biotechnol. 2: 176-184 (2002)
  3. Maksimoviae Z, Malendieiae D, Kovaeeviae N. Polyphenol contents and antioxidant activity of Maydis stigma extracts. Bioresource Technol. 96: 873-877 (2005) https://doi.org/10.1016/j.biortech.2004.09.006
  4. Makris DP, Boskou G, Andrikopoulos NK. Recovery of antioxidant phenolics from white vinification solid by-products employing water/ethanol mixtures. Bioresource Technol. 98: 2963-2967 (2007) https://doi.org/10.1016/j.biortech.2006.10.003
  5. Khatib AF, Kim MY, Chung SK. Anti-inflammatory activities of Cinamomum burmanni BI. Food Sci. Biotechnol. 14: 223-227 (2005)
  6. Rodney G, Swanso AL, Wheeler LM, Smith GN, Worrel CS. The effects of series of flavonoids on hyaluronidase and some other related enzymes. J. Biol. Chem. 183: 739-741 (1950)
  7. Sekar T, Francis F. A preliminary investigation of some Maruthamali forest plants for phytochemical compounds. Bioresource Technol. 70: 303-304 (1999) https://doi.org/10.1016/S0960-8524(99)00021-8
  8. Wilcox LJ, Borradaile NM, Huff MW. Antiatherogenic properties of naringenin, a citrus flavonoid. Cardiovasc. Drug Rev. 17: 160-178 (1999) https://doi.org/10.1111/j.1527-3466.1999.tb00011.x
  9. Kim HK, Bang CS, Choi YM, Lee JS. Antioxidant and antiproliferative activities of methanol extracts from leafY vegetables consumed in Korea. Food Sci. Biotechnol. 16: 802-806 (2007)
  10. Duthie ES, Chain EA. A mucolytic enzyme in tests extract. Nature 144: 977 (1939)
  11. Kakegawa H, Matsumoto H, Satoh T. Inhibitory effects of some natural products on the activation of hyaluronidase and their anti-anergic action. Chem. Pharm. Bull. 40: 1439-1442 (1999)
  12. Cameron E, Pauling L, Leibovitz B. Ascorbic acid and cancer: A review. Cancer Res. 39: 663-681 (1979)
  13. Meyer K. The biological significance of hyaluronic acid hyaluronidase. Physiol. Rev. 27: 335-359 (1947) https://doi.org/10.1152/physrev.1947.27.3.335
  14. Lee KK, Choi JD. The effects of Areca catechu L. extract on antiinflammation and anti-melanogenesis. Int. J. Cosmetic Sci. 21: 275-284 (1999) https://doi.org/10.1046/j.1467-2494.1999.196590.x
  15. Shibata T, Fujimoto K, Nagayama K, Yamaguchi K, Yamaguchi K, Nakamura T. Inhibitory activity of brown algal phlorotannins against hyaluronidase. Int. J. Food Sci. Tech. 37: 703-709 (2002) https://doi.org/10.1046/j.1365-2621.2002.00603.x
  16. Jeong SJ, Kim NY, Ahn NH, Kim YC. Screening of hyaluronidase inhibitory activity using a microplate assay. Korean J. Pharmacogn. 29: 131-137 (1997)
  17. Kim KT, Yeo EJ, Han YS, Nah SY, Paik HD. Antimicrobial, antiinflammatory, and anti-oxidative effects of water-and ethanol-extracted Brazilian propolis. Food Sci. Biotechnol. 14: 474-478 (2005)
  18. Kuppusamy UR, Das NP. Inhibitory effects of flavonoids on several venom hyaluronidase. Experientia 47: 1196-1200 (1991) https://doi.org/10.1007/BF01918384
  19. Forrester N, Balaz EA. Inhibition of phagocytosis by high molecular hyaluronate. Immunology 40: 435-446 (1990)
  20. Bleacher JC, Adolph YR, Dillon PW, Krummel TM. Fetal tissue repair and wound healing. Dermatol. Clin. 11: 677-683 (1993)
  21. Kuppusamy UR, Khoo HE, Das NP. Structure-activity studies of flavonoids as inhibitors of hyaluronidase. Biochem. Pharmacol. 40:397-401 (1990) https://doi.org/10.1016/0006-2952(90)90709-T