Quantitative Analysis of Coumarins from Angelica gigas Using $^1H$-NMR

  • Yoo, Jong-Su (Acupuncture and Meridian Science Research Center, Kyung Hee University) ;
  • Ahn, Eun-Mi (Department of Herbal Foodceutical Science, Daegu Haany University) ;
  • Song, Myoung-Chong (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Bang, Myun-Ho (Gyeonggi Bio-Center, Kyung Hee University) ;
  • Kim, Dong-Hyun (School of Chemistry, The University of Manchester) ;
  • Han, Min-Woo (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Kwak, Ho-Young (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Lee, Dae-Young (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Lyu, Ha-Na (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University) ;
  • Baek, Nam-In (Graduate School of Biotechnology and Plant Metabolism Research Center, Kyung Hee University)
  • 발행 : 2008.06.30

초록

$^1H$-Nuclear magnetic resonance (NMR) spectrometry was applied to the quantitative analysis of coumarins in the roots of Angelica gigas without any chromatographic purification. The experiment was performed by the analysis of each singlet germinal methyl, which was well separated in the range of 1.0-2.0 ppm in the $^1H$-NMR spectrum. The quantity of the compounds was calculated by the ratio of the intensity of each compound to the known amount of internal standard (dimethyl terephthalate). These results were compared with the conventional gas chromatography (GC) method. The contents of decursin and decursinol angelate in A. gigas were determined $1.98{\pm}0.07$, $1.13{\pm}0.08%$ in quantitative $^1H$-NMR method and $2.06{\pm}0.24$, $1.17{\pm}0.24%$ in GC method, respectively. The advantages of quantitative $^1H$-NMR analysis are that can be analyzed to identify and quantify, and no reference compounds required for calibration curves. Besides, it allows rapid and simple quantification for coumarins with an analysis time for only 10 min without any preprocessing.

키워드

참고문헌

  1. Giuido FP, Birgit UJ, David CL. Quantitative $^1H$-NMR: Development and potential of a method for natural products analysis. J. Nat. Prod. 68: 133-149 (2005) https://doi.org/10.1021/np0497301
  2. Jang KW, Park SH, Ha SD. Technology trends in functional foods. Food Sci. Ind. 36: 8-16 (2003)
  3. Kim HY, Lee YJ, Hong KH, Kwon YK, Sim KC, Lee JY, Cho HY, Kim IS, Han SB, Lee CW, Shin IS, Cho JS. Isolation of antimicrobial substances from natural products and their preservative effect. Food Sci. Biotechnol. 10: 59-71 (2001)
  4. Kim YC, Kim MY, Takaya Y, Niwa M, Chung SK. Phenolic antioxidants isolated from mulberry leaves. Food Sci. Biotechnol. 16: 854-857 (2007)
  5. Kim HM, Kim JS, Lee SH, Lee SJ, Lee GP, Kang SS, Cho SH, Cheoi DS. Quantitative analysis of lignans in the fruits of Acanthopanax species by HPLC. Food Sci. Biotechnol. 15: 778-780 (2006)
  6. Shin YS, Lee MJ, Bang KH, Kim SY, Lee SS, Hyun DY, An TJ, Cha SW, Seong NS. Metabolite analysis of Panax ginseng C.A. Meyer by HPLC according to root age. Food Sci. Biotechnol. 16: 636-640 (2007)
  7. Lee JH, Lee JY, Kim KN, Kim HS. Quantitative analysis of two major flavonoid aglycones in acid hydrolyzed samples of Angelica keiskei by HPLC. Food Sci. Biotechnol. 12: 415-418 (2003)
  8. Lee YJ, Adlerereutz H, Kwon HJ. Quantitative analysis of isoflavones and lignans in sea vegetables consumed in Korea using isotope dilution gas chromatography-mass spectrometry. Food Sci. Biotechnol. 15: 102-106 (2006)
  9. Song MC, Yoo JS, Baek NI. Quantitative analysis of tcinnamaldehyde of Cinnamomum cassia by $^1H$-NMR spectrometry. J. Korean Soc. Appl. Biol. Chem. 48: 267-272 (2005)
  10. Kim HK, Choi YH, Chang WT, Verpoorte R. Quantitative analysis of ephendrine analogues from Ephedra species using $^1H$-NMR. Chem. Pharm. Bull. 51: 1382-1385 (2005) https://doi.org/10.1248/cpb.51.1382
  11. Malz F, Janke H. Validation of quantitative NMR. J. Pharmaceut. Biomed. 38: 813-823 (2005) https://doi.org/10.1016/j.jpba.2005.01.043
  12. Choi YH, Choi HK, Peltenburg-Looman AMG, Lefeber AWM, Verpoorte R. Quantitative analysis of ginkgolic acids from ginkgo leaves and products using $^1H$-NMR. Phytochem. Analysis 15: 325-330 (2004) https://doi.org/10.1002/pca.786
  13. Choi YH, Kim HK, Wilson EG, Erkelens C, Trijzelaar B, Verpoorte R. Quantitative analysis of retinol and retinol palmitate in vitamin tablets using $^1H$-nuclear magnetic resonance spectroscopy. Anal. Chim. Acta 512: 141-147 (2004) https://doi.org/10.1016/j.aca.2004.02.024
  14. Berregi I, Santos JI, del Campo G, Miranda JI. Quantitative determination of (-)-epicatechin in cider apple juices by $^1H$-NMR. Talanta 61 139-145 (2003) https://doi.org/10.1016/S0039-9140(03)00236-4
  15. Yoo JS, Song MC, Ahn EM, Lee YH, Rho YD, Baek NI. Quantitative analysis of paeoniflorin from Paeonia lactiflora using $^1H$-NMR. Nat. Prod. Sci. 12: 237-240 (2006)
  16. Yook CS. Colored Medicinal Plants of Korea. Academy Book Co., Seoul, Korea. p. 390 (1990)
  17. Kang SA, Jang KH, Lee JE, Ahn DK, Park SK. Differences of hematopoietic effects of Angelica gigas, A. sinensis, and A. acutiloba extract on cyclophosphamide-induced anemic rats. Korean J. Food Sci. Technol. 35: 1204-1208 (2003)
  18. Chi HJ, Kim HS. Studies on the components Umbelliferae plants in Korea pharmacological study of decursin, decursinol, and nodakenin. Korean J. Pharmacogn. 1: 25-32 (1970)
  19. Kang YG, Lee JH, Chae HJ, Kim DH, Lee SH, Park SY. HPLC analysis and extraction methods of decursinol and decursinol angelate in Angelica gigas roots. Korean J. Pharmacogn. 34: 201- 205 (2003)
  20. Ahn KS, Sim WS, Kim IH. Decursin: A cytosoxic agent protein kinase C activator from the root of Angelica gigas. Planta Med. 62: 7-9 (1996) https://doi.org/10.1055/s-2006-957785
  21. Ahn KS, Sim WS, Lee IK, Seu YB, Kim IH. Decursinol angelate: A cytotoxic and protein kinase C activating agent from the root of Angelica gigas. Planta Med. 63: 360-361 (1997) https://doi.org/10.1055/s-2006-957701
  22. Kim HS, Park JS, Park HJ, Chi HJ. A study of the effects of the root components of Angelica gigas Nakai on voluntary activity in mice. Korean J. Pharmacogn. 11: 11-14 (1980)
  23. Shin KH, Han JM, Lee IR. Effect of the constituents of Angelica giganstis radix on hepatic drug metabolizing enzymes. Korean J. Pharmacogn. 27: 323-327 (1996)
  24. Hwang JB, Yang MO. Comparision of chemical components of Angelica gigas Nakai and Angelica acupiloba Kitagawa. Korean J. Food Sci. Technol. 29: 1113-1118 (1997)
  25. Yook CS, Kim TH. Studies on the determination of decursin in Angelica gigantis Radix and some Umbelliferae plants. Bull. K. H. Pharma. Sci. 18: 133-140 (1990)
  26. Lee JP, Chang SY, Park SY. Validations of analysis methods for decursin and decursinol angelate of Angelica gigantis radix by reverse-phase liquid chromatography. Nat. Prod. Sci. 10: 262-267 (2004)
  27. Ryu KS, Hong ND, Kim NJ, Kong YY. Isolation of decursinol angelate and assay of decursinol angelate and decursin. Korean J. Pharmacogn. 21: 64-68 (1990)
  28. Lee SH, Shin DS, Kim JS, Oh KB, Kang SS. Antibacterial coumarins from Angelica gigas roots. Arch. Pharm. Res. 26: 449- 452 (2003) https://doi.org/10.1007/BF02976860
  29. Lee SH, Jung SH, Lee YS, Shin KH. Coumarins from Angelica gigas roots having rat lens aldose reductase activity. J. Appl. Pharmacol. 10: 85-88 (2002)
  30. Kang JH, Chung, ST, Row KH. Estimation of solubility of the useful components in some natural products. Hwahak Konghak 39: 390-396 (2001)