7, 8, 4'-Trihydroxyisoflavone from Fermented Soybean Food and Its Biological Activity

전통 콩발효 식품 유래 7, 8, 4'-Trihydroxyisoflavone의 피부 생리활성 연구

  • 박준성 ((주)아모레퍼시픽 기술연구원 피부과학연구소) ;
  • 김동현 ((주)아모레퍼시픽 기술연구원 피부과학연구소) ;
  • 심진섭 ((주)아모레퍼시픽 기술연구원 피부과학연구소) ;
  • 김지성 ((주)아모레퍼시픽 기술연구원 피부과학연구소) ;
  • 최권영 (서울대학교 화학생물공학부) ;
  • 김병기 (서울대학교 화학생물공학부) ;
  • 김덕희 ((주)아모레퍼시픽 기술연구원 피부과학연구소) ;
  • 김한곤 ((주)아모레퍼시픽 기술연구원 피부과학연구소)
  • Received : 2010.09.10
  • Accepted : 2010.09.25
  • Published : 2010.09.30

Abstract

A rare isoflavone, 7, 8, 4'-trihydroxyisoflavone, was isolated from a 10-year-old fermented soybean food. 7, 8, 4'-trihydroxyisoflavone was isolated for the first time from a Korean fermented soybean food. Evaluation tests of biological activity showed significantly inhibition activity for free radical scavenging on both non-enzymatic (DPPH system) and enzymatic method (xanthine oxidase system). DPPH radical scavenging effect of 7, 8, 4'-trihydroxyisoflavone was similar with vitamin C in a dose-dependent manner. In xanthine oxidase (XO) system 7, 8, 4'-trihydroxyisoflavone showed superoxide radical inhibition activity of 50 % at a concentration of $6.6{\pm}0.4\;{\mu}M$. Also, the compound significantly suppressed cellular MMP-1 formation. These results suggest that 7, 8, 4'-trihydroxyisoflavone could be developed as a potential preventive or therapeutic agent against skin aging.

10년 이상 자연 발효된 콩 발효 식품에서 희귀 이소플라본 성분인 7, 8, 4'-trihydroxyisoflavone을 분리하였고, 분리된 성분의 항산화 효과를 비효소적인 방법으로는 DPPH 법을, 효소적인 방법으로는 xanthine oxidase법을 이용하여 확인하였다. 그 결과 7, 8, 4'-trihydroxyisoflavone는 농도 의존적으로 비타민 C와 유사한 DPPH 라디칼 소거 효능을 가지고 있음을 보여주었고 $6.6{\pm}0.4\;{\mu}M$ 농도에서 xanthine oxidase에서 생성된 superoxide 라디칼을 50 % 수준까지 낮춤을 보여주었다. 또한, 이 희귀 이소플라본 성분은 UVB로 유도된 MMP-1의 생성을 초기 수준으로 억제하는 것으로 나타나 피부 노화 억제에 유용한 성분임을 확인할 수 있었다.

Keywords

References

  1. E. D. Son, G. H. Choi, H. K. Kim, B. S. Lee, I. S. Chang, and J. S. Hwang, Alpha-ketoglutarate stimulates procollagen production in cultured human dermal fibroblasts, and decreases UVB-Induced wrinkle formation following topical application on the dorsal skin of hairless mice, Biol. Pharm. Bull., 30(8), 1395 (2007). https://doi.org/10.1248/bpb.30.1395
  2. Y. Lu and L. Y. Foo, Antioxidant and radical scavenging activities of polyphenols from apple pomance, Food Chemistry., 68, 81 (2000). https://doi.org/10.1016/S0308-8146(99)00167-3
  3. S. H. Yang and Y. J. Chung, Optimization of the taste components composition in traditional Korean soybean paste, J. Korean Soc. Food Nutr., 21, 449 (1992).
  4. S. S. Hong, Anticancer effect of Korean traditional soy-bean paste, Food Technol., 7, 56 (1994).
  5. Z. I. Shin, C. W. Ahn, H. S. Nam, H. J. Lee, H. J. Lee, and T. H. Moon, Fractionation of angiotensin converting enzyme(ACE) inhibitory peptides from soybean paste, Korean J. Food Sci. Technol., 27, 230 (1995).
  6. K. Y. Park, S. H. Moon, H. S. Cheigh, and H. S. Baik, Antimutagenic effects of Doenjang, J. Food Sci. Nutr., 25, 151 (1996).
  7. S. Barnes, H. Kim, TG Peterson, and J. Xu, Isoflavones and cancer-the estrogen paradox, Korea Soybean Digest., 15, 81 (1998).
  8. M. Messina and V. Messina, Increasing use of soyfoods and their potential role in cancer prevention, J Am Diet Asso., 91, 836 (1991).
  9. K. O. Jung, S. Y. Park, and K. Y. Park, Longer aging time increases the anticancer and antimetastatic properties of doenjang, Nutrition, 22, 539 (2006). https://doi.org/10.1016/j.nut.2005.11.007
  10. E. Hideo, O. Hiromichi, M. Yasujiro, K. Shunro, and M. Toshihiko, Potent antioxidative isoflavones isolated from soybeans fermented with aspergillus saitoi, Biosci. Biotechnol. Biochem., 62, 740 (1998). https://doi.org/10.1271/bbb.62.740
  11. P. Cos, L. Ying, M. Calomme, J. P. Hu, K. Cimanga, B. V. Poel, L. Pieters, A. J. Vlietinck, and D. V. Berghe, Structureactivity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J. Nat. Prod., 61, 71 (1998). https://doi.org/10.1021/np970237h
  12. P. Valentao, E. Fernandes, F. Carbalho, P. B. Andrade, R. M. Seabra, and M. L. Bastos, Antioxidant activity of Centaurium erythraea infusion evidenced by its superoxide radical scavenging and xanthine oxidase inhibitory activity. J. Agric. Food Chem., 49, 3476 (2001). https://doi.org/10.1021/jf001145s
  13. K. E. Heim, A. R. Tagliaferro, and D. J. Bobilya, Flavonoid antioxidants: Chemistry, metabolism and structure-activity relationships. J. Nutr. Biochem., 13, 572 (2002). https://doi.org/10.1016/S0955-2863(02)00208-5