Identification of Antioxidative Components from Ethanol Extracts of Dalbergia odorifera T.CHEN

강진향(Dalbergia odorifera T.CHEN) 에탄올 추출물로부터 항산화 활성물질의 구조동정

  • Choi, Ung (Department of Hotel Culinary Arts and Nutrition, Sohae College) ;
  • Kim, In-Won (Faculty of Biotechnology (Food Science and Technology Major), Chonbuk National University) ;
  • Baek, Nam-In (Department of Life Science, Oriental Medicals and Processing, Kyunghee University) ;
  • Shin, Dong-Hwa (Faculty of Biotechnology (Food Science and Technology Major), Chonbuk National University)
  • 최웅 (서해대학교 호텔조리영양과) ;
  • 김인원 (전북대학교 응용생물공학부 (농업과학기술연구소)) ;
  • 백남인 (경희대학교 생명과학부 한방재료가공학) ;
  • 신동화 (전북대학교 응용생물공학부 (농업과학기술연구소))
  • Published : 2002.10.01

Abstract

The chloroform layer from 75% ethanol extract of Dalbergia odorifera T.CHEN showed strong antioxidative activity on lard and palm oil as tested by Rancimat method. Antioxidative active compound isolated and identified by silica gel column chromatography, thin layer chromatography, mass spectrophotometer, $^1H-NMR$ and $^{13}C-NMR$ was identified as mucronulatol (3(R&S)-3,7-Dihydroxy-2',4-dimethoxyisoflavan). Results of Rancimat method revealed the induction period of Mucronulatol increased longer than those of synthetic antioxidant, BHA and BHT, at the same concentration. Mucronulatol combined with ${\delta}-tocopherol(200ppm)$, and with ascorbic acid (200 ppm) and citric acid (200 ppm) on lard and palm oil, respectively, showed strong synergistic effects.

강진향(Dalbergia odorifera T.CHEN)은 콩과에 속하는 한약재로 한방에서는 진통(鎭痛), 지혈(止血)의 목적으로 사용되어 왔다. Rancimat method로 항산화 활성이 인정된 강진향 75% 에탄올 추출물의 클로로포름 층을 가지고 항산화 활성 물질을 확인하기 위하여 silica gel chromatography 와 thin layer chromatography로 물질을 분리하고, mass spectrometer, $^1H-NMR$$^{13}C-NMR$을 통해 순수물질을 동정하였다. 순수 분리된 물질은 flavonoid 화합물 중 isoflavan 골격을 가지는 mucronulatol(3(R&S)-3',7-dihydroxy-2',4-dimethoxyisoflavan) 로 동정되었다. 이 물질에 대한 ascorbic acid, citric acid 및 ${\delta}-tocopherol$과의 synergist 효과를 비교하기 위해 돈지, 함유, 대두유, 옥배유를 기질로 하여 Rancimat 방법으로 시험한 결과, 돈지에 대해서는 mucronulatol(600 ppm)만 처리시 AI가 7.71, ${\delta}-tocopherol(200ppm)$과의 병용시 AI가 10.97로 약 1.5배의 상승효과가 있었으며, 식물성 유지인 팜유에 대해서는 mucronulatol(600 ppm)만 처리시 AI가 1.42, ascorbic acid(200 ppm), citric acid(200 ppm) 첨가시 AI가 각각 2.04, 2.04로 약 1.5배의 상승효과를 보였으며, 대두유와 옥배유에 대해서는 뚜렷한 상승효과를 보이지 않았다.

Keywords

References

  1. Okezie, I.A. Free radicals, oxidative stress and antioxidants in human health and disease. J. Am. Oil Chem. Soc. 75: 199-212 (1998) https://doi.org/10.1007/s11746-998-0032-9
  2. Suzuki, Y., Kondo, Y., Himeno, S., Nemoto, K., Akimoto, M. and Imura, N. Role of antioxidant system in human androgen-independent prostate cancer cells. The Prostate. 43: 144-149 (2000) https://doi.org/10.1002/(SICI)1097-0045(20000501)43:2<144::AID-PROS9>3.0.CO;2-H
  3. Owen, R.W., Giacosa, A., Hull, W.E., Haubner, R., Spiegaelhalder, B. and Bartsch, H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Eur. J. Cancer. 36: 1235-1247 (2000) https://doi.org/10.1016/S0959-8049(00)00103-9
  4. Verhagen, H., Schilderman, P.A. and Kleinjans, J.C. Butylated hydroxyanisole in perspective. Chemico-Biological Interactions. 80: 109-134 (1991) https://doi.org/10.1016/0009-2797(91)90019-4
  5. Suh, H.J., Lee, J.M., Cho, J.S., Kim, Y.S. and Chung, S.H. Radical scavenging compounds in onion skin. Food Res. Int. 32: 659-664 (1999) https://doi.org/10.1016/S0963-9969(99)00141-6
  6. Kim, Y.S. and Shin, D.H. Effect of Rhus verniciflua Stokes on the oxidative stability of fried potato chips during storage. Food Sci. Biotechnol. 10: 418-422 (2001)
  7. Kalt, W., McDonald, J.E and Donner, H. Anthocyanins, phenolics, and antioxidant capacity of processed lowbush blueberry products. Food Chem. Toxicol. 65: 390-393 (2000)
  8. Yun, B.S., Lee, I.K., Kim, J.P. and Yoo, I.D. Two p-terphenyls from mushroom Paxillus panuoides with free radical scavenging activity. J. Microbiol. Biotechnol. 10: 233-237 (2000)
  9. Kim, I.W., Shin, D.H. and Choi, U. Isolation of antioxidative components from the bark of Rhus verniciflua Stokes screened from some chinese medicinal plants. Korean J. Food Sci. Technol. 31: 855-863 (1999)
  10. Kim, I.W., Shin, D.H. and Baek, N.I. Identification of antioxidative components from ethanol extracts of Rhus verniciflua Stokes. Korean J. Food Sci. Technol. 31: 1654-1660 (1999)
  11. Lim, K.T. Hu, C. and Kitts, D.D. Antioxidant activity of Rhus verniciflua Stokes ethanol extract. Food Chem. Toxicol. 39: 229-237 (2001) https://doi.org/10.1016/S0278-6915(00)00135-6
  12. Cuvellier, M.E., Berset, C. and Richard, H. Use of new test for determining comparative antioxidative activity of BHA, BHT, $\alpha$ and $\beta$-tocopherols and extracts from rosemary and sage. Sciences des Aliments. 10: 797-810 (1991)
  13. Djarmati, Z., Jankov, R.M., Schwirtlich, E., Djulinac, B. and Djordjevic, A. High antioxidant activity of extracts obtained from sage by supercritical $CO_2$ extraction. J. Am. Oil Chem. Soc. 68: 731-734 (1991) https://doi.org/10.1007/BF02662161
  14. Pokorny, J., Nquyen, H.T.T. and Korczak, J. Antioxidant activities of rosemary and sage extracts in sunflower oil. Nahrung 3: 176-182 (1997)
  15. Hong, S.G., Kang, B.J., Kang, S.M. and Cho, D.W. Antioxidative effects of traditional korean herbal medicines on AAPH induced oxidative damage. Food Sci. Biotechnol. 10: 183-187 (2001)
  16. Cheah, P.B. and Gan, S.P. Antioxidative/antimicrobial effects of galangal and $\alpha$ -tocopherol in minced beef. J. Food Prot. 63: 404-407 (2000) https://doi.org/10.4315/0362-028X-63.3.404
  17. Lee, H.J. and Koh, K.H. Antioxidant and free radical scavenging activities of Korean wind. Food Sci. Biotechnol. 10: 566-571 (2001)
  18. Gaulejac, N.S.C. Glories, Y. and Vivas, N. Free radical scavenging of effect anthocyanins in red wines. Food Res. Int. 32: 327-333 (1999) https://doi.org/10.1016/S0963-9969(99)00093-9
  19. Shin, M.K. Coloured Limsangbonchohak. Namsandang, Seoul, Korea (1986)
  20. Park, J.D., Lee, Y.H., Baek, N.I., Kim, S.I. and Ahn, B.Z. Isolation of antitumor agent from the heartwood of Dalbergia odorifera. Korean J. Phamacogn. 26: 323-326 (1995)
  21. Seoul National University Natural Products Research Institute. Traditional Oriental Medicines Database. Seoul systems CO., LTD. (1996)
  22. Harbone J.B. and Baxter, H. Phytochemical Dictionary. Burgess Science Press, Basingstoke, England (1995)
  23. Choi, U. Development of new natural antioxidant from Dalbergia odorifera T.CHEN and Caesalpinia sappan L. and food application. Ph. D. thesis, Chonbuk National Univ., Chonju, Chonbuk, Korea (1998)
  24. Frankel, E.N., Huang, S.W. and Aeschbach, R. Antioxidant activity of green teas in different lipid system. J. Am. Oil Chem. Soc. 74: 1309-1315 (1997) https://doi.org/10.1007/s11746-997-0062-8
  25. Frankel, E.N. Antioxidants in lipid foods and their impact on food quality. Food Chem. 57: 51-55 (1996) https://doi.org/10.1016/0308-8146(96)00067-2
  26. Button, G.W. and Ingold, K.I. Autooxidation of biological molecules. 1. The antioxidant activity of vitamin E and relating chainbreaking phenolic antioxidants in vitro. J. Am. Chem. Soc. 106: 6472 (1981) https://doi.org/10.1021/ja00313a014