Isolation and Identification of Two Psoralen Derivatives as Antioxidative Compounds from the Aerial Parts of Angelica keiskei

신선초에 함유된 항산화활성물질 Psoralen 유도체들의 단리 및 동정

  • Kim, So-Joong (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Cho, Jeong-Yong (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Wee, Ji-Hyang (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Jang, Mi-Young (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Rim, Yo-Sup (Division of Environmental and Agricultural Science, Sunchon National University) ;
  • Kim, Cheol (SHALOM Industries Co., Ltd.) ;
  • Shin, Soo-Cheol (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Moon, Jae-Hak (Division of Food Science, Sunchon National University) ;
  • Park, Keun-Hyung (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University)
  • 김소중 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 조정용 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 위지향 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 장미영 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 임요섭 (순천대학교 환경농업과학부) ;
  • 김철 (샬롬산업(주)) ;
  • 신수철 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 문제학 (순천대학교 식품과학부) ;
  • 박근형 (전남대학교 식품공학과 및 기능성식품연구센터)
  • Published : 2005.08.31

Abstract

Hot water extracts of Angelica keiskei aerial parts were solvent-fractionated with ethyl acetate (EtOAc) and buffers (5% $NaHCO_3$, pH 8.0; 1.0 N HCl, pH 3.0) to obtain EtOAc-soluble acidic and neutral fractions. EtOAc-soluble neutral fraction was purified by Sephadex LH-20 column chromatography and reverse phase HPLC. Assay for purification of antioxidative compounds was performed by spraying DPPH solution on thin layer chromatography. Two isolated substances were identified as pseudoisopsoralen and 8-methoxypsoralen(xanthotoxin) by FAB-MS and NMR analyses.

신선초의 기능성 해명과 유용 기능성성분 탐색연구의 일환으로 신선초 지상부로부터 항산화활성물질을 분리하여 구조 해석하였다. 신선초 지상부의 열수추출물을 용매분획하여 ethyl acetate 가용 중성획분을 얻었다. 이를 Sephadex LH-20 column chromatography와 HPLC로 정제하여 항산화활성물질 2종을 단리하고, 그들 각각의 화합물을 대상으로 FAB-MS와 NMR 분석을 실시한 결과, pseudoisopsoralen과 8-methoxypsoralen(xanthotoxin)으로 동정하였다.

Keywords

References

  1. Halliwell B. Free radicals, antioxidants and human disease: Curiosity, cause, or consequency. Lancet 344: 721-724 (1994) https://doi.org/10.1016/S0140-6736(94)92211-X
  2. Karlsson, J. Antioxidants and Exercise. Human Kinetics Press, Champaign, IL, USA. pp. 97-106 (1997)
  3. Bidlack WR, Omaye ST, Meskin MS, Topham DKW. Phytochemicals as Bioactive Agents. CRC press, Boca Raton, FL, USA. pp. 241-270 (2000)
  4. Shi J, Mazza G, Maguer ML. Functional foods: Biochemical and Processing Aspects. Vol. 2. CRC press, Boca Raton, FL, USA. pp. 367-393 (2002)
  5. Mazza G, Functional foods: Biochemical and Processing Aspects. Technomic Publishing Co., Inc., Lancaster, PA, USA. pp. 403-437 (2002)
  6. Seo GW, Cho JY, Kuk JH, Moon JH, Park KH. Identification of antioxidative substances in Allium fistulosum L. by GC-MS. Korean J. Food Sci. Technol. 35: 988-993 (2003)
  7. Yoshihiko I, Kimiye B, Hiroshi T, Masahiko T, Kouji N, Mitsugi K. Chemical components of Angelica keiskei. VI. Antibacterial activity of two chalcones, xanthoangelol and 4-hydroxyderricin, isolated from the root of Angelica keiskei Koidzumi. Chem. Pharm. Bull. 39: 1604-1605 (1991) https://doi.org/10.1248/cpb.39.1604
  8. Masaharu M, Yoshiyuki K, Kouji N, Kimiye B, Hiromichi O. Artery relaxation by chalcones isolated from the roots of Angelica keiskei. Planta Medica 67: 230-235 (2001) https://doi.org/10.1055/s-2001-12011
  9. Kouji N, Kimie B. Histamine release-inhibiting activity of Angelica keiskei. Nat. Med. 55: 32-34 (2001)
  10. Okuyama T, Takata M, Takayasu J, Hasegawa T, Tokuda H, Nishino A, Nishino H, Iwashima A. Anti-tumor-promotion by principles obtained from Angelica keiskei. Planta Medica 57: 242-246 (1991) https://doi.org/10.1055/s-2006-960082
  11. Kimye B, Tadashi K, Yuko Y, Masahiko T, Mitsugi K. Chemical components of Angelica keiskei Koidzumi. (V). Components of the fruits, and comparison of coumarins and chalcones in the fruits, roots and the leaves. Shoyakugaku Zasshi 44: 235-239 (1990)
  12. Emiko S, Aisumi H, Rumiko T, Yasuo A, Tetsuo M, Koichi K. Effects of angiotensin 1-converting enzyme inhibitor from Ashitaba (Angelica keiskei) on blood pressure of spontaneously hypertensive rats. J. Nutr. Sci. Vitaminol 45: 375-383 (1999) https://doi.org/10.3177/jnsv.45.375
  13. Park JR, Park JC, Choi SH. Screening and characterization of anticholesterogenic substances from food plant extracts. J. Korean Soc. Food Sci. Nutr. 26: 236-241 (1997)
  14. Park JC, Park JG, Kim HJ, Hur JM, Lee JH, Sung NJ, Chung SK, Choi JW. Effects of extract from Angelica keiskei and its component, cynaroside, on the hepatic bromobenzene-metabolizing enzyme system in rats. Phytother. Res. 16: 24-27 (2002) https://doi.org/10.1002/ptr.783
  15. Park JC, Cho YS, Park SK, Park JR, Chun SS, Ok KD, Choi JW. Isolation of flavone 7-O-glycosides from the aerial parts of Angelica keiskei and antihyperlipidemic effects. Saengyak Hakhoechi 26: 337-343 (1995)
  16. Shim JS, Kim SD, Kim TS, Kim KN. Biological activities of flavonoid glycosides isolated from Angelica keiskei. Korean J. Food Sci. Technol. 37: 78-83 (2005)
  17. Kim SJ, Cho JY, Wee JH, Jang MY, Kim C, Rim YS, Shin SC, Ma SJ, Moon JH, Park KH. Isolation and characterization of antioxidative compounds from the aerial parts of Angelica keiskei. Food Sci. Biotechnol. 14: 58-63 (2005)
  18. Lu YR, Foo LY. Identification and quantification of major polyphenols in apple pomace. Food Chem. 59: 187-194 (1997) https://doi.org/10.1016/S0308-8146(96)00287-7
  19. Moon JH, Terao J. Antioxidant activity of caffeic acid and dihydrocaffeic acid in lard and human low-density lipoprotein. J. Agric. Food Chem. 46: 5062-5065 (1998) https://doi.org/10.1021/jf9805799
  20. Takao T, Kitatani F, Sakata K. A Simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotech. Biochem. 5: 1780-1783 (1994)
  21. Torssell KBG. Natural Products Chemistry: A Mechanistic and Biosynthetic Approach to Secondary Metabolism. John Wiley & Sons Ltd., NY, USA. pp. 88-91 (1983)
  22. Harayama T, Nishita Y. Efficient and convenient synthesis of angular furanocoumarins from hydroxycoumarins. Chem. Pharmacol. Bull. 44: 1986-1988 (1996) https://doi.org/10.1248/cpb.44.1986
  23. Elgamal MHA, Elewa NH, Elkhrisy EAM, Ouddeck H. $^{13}C$ NMR chemical shifts and carbon-proton coupling constants of some furocoumarins and furochromones. Phytochemistry 18: 139-143 (1979) https://doi.org/10.1016/S0031-9422(00)90932-4
  24. Guiotto A, Manzini A, Chilin Pastorini G, Rodighiero P. $^{13}C-NMR$ spectra and carbon-proton coupling constants of variously annulated furocoumarins. J. Heterocyclic Chem. 22: 649-656 (1985) https://doi.org/10.1002/jhet.5570220306
  25. Sardari S, Mori Y, Horita K, Micetich RG, Nishibe S, Daneshtalab M. Synthesis and antifungal activity of coumarins and angular furanocoumarins. Bioorg. Med. Chem. 7: 1933-1940 (1999) https://doi.org/10.1016/S0968-0896(99)00138-8
  26. Bose AK, Fujiwara H. $^{13}C$ NMR spectra of some furocoumarins. Tetrahedron 35: 13-16 (1979) https://doi.org/10.1016/0040-4020(79)85002-4
  27. Murry RDH, Jorge ZD. A simple method for differentiating between angular and liner 5-methoxyfuranocoumarins. Phytochemistry 23: 697-699 (1984) https://doi.org/10.1016/S0031-9422(00)80416-1
  28. Baba K, Nakata K, Taniguchi M, Kido T, Kazawa M. Chalcones from Angelica keiskei. Phytochemistry 29: 3907-3910 (1990) https://doi.org/10.1016/0031-9422(90)85357-L