Quantitative Analysis of Paeoniflorin from Paeonia lactiflora Using $^1H-NMR$

  • Yoo, Jong-Su (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Song, Myoung-Chong (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University) ;
  • Ahn, Eun-Mi (Department of Herbal Foodceutical Science, Daegu Haany University) ;
  • Lee, Youn-Hyung (Department of Horticultural Biotechnology, Kyung Hee University) ;
  • Rho, Yeong-Deok (College of Life Science, Institute of Life Science & Resources, Kyung Hee University) ;
  • Baek, Nam-In (Graduate School of Biotechnology & Plant Metabolism Research Center, Kyung Hee University)
  • 발행 : 2006.12.30

초록

Paeoniflorin, the major component of the root of Paeonia lactiflora, was quantitatively analyzed using $^1H-NMR$ spectrometry. The quantity of paeoniflorin was calculated by the ratio of the intensity of the signals (H-9, H-10, H-2', 6') to the aldehyde peak of the known amount of internal standard, 2,4,6-trihydroxybenzaldehyde. These results were compared with the conventional HPLC method. The contents of paeoniflorin in P. lactiflora, which were respectively calculated by H-9, H-10, H-2', 6' in the $^1H-NMR$ spectra and HPLC, were determined $2.60{\pm}0.07,\;2.44{\pm}0.09,\;2.77{\pm}0.12\;and\;2.46{\pm}0.16%$. 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 paeoniflorin with an analysis time for only 20 min without any preprocessing.

키워드

참고문헌

  1. Aimi, N., Inaba, M., Watanabe, M., and Shibata, S., Peoniflorin, a glucoside of Chinese paeony root. Tetrahedron, 25(9), 1825-1838 (1969) https://doi.org/10.1016/S0040-4020(01)82804-0
  2. Choi, Y.H., Choi, H.K., Peltenburg-Looman, A.M.G., Lefeber, A.W.M., and Verpoorte, R., Quantitative analysis of ginkgolic acids from Ginkgo leaves and products using $^{1}H$-NMR. Phytochemical analysis. 15(5), 325-330 (2004a) https://doi.org/10.1002/pca.786
  3. Choi, Y.H., Kim, H.K., Wilson, E.G., Erkelens, C., Trijzelaar, B., and Verpoorte, R., Quantitative analysis of retinol and retinol palmitate in vitamin tablets using $^{1}H$-nuclear magnetic resonance spectroscopy. Analytica Chimica Acta, 512(1), 141-147 (2004b) https://doi.org/10.1016/j.aca.2004.02.024
  4. Hsu, F.L., Lai, C.W., and Cheng, J.T., Antihyperglycemic effects of paeoniflorin and 8-debenzoylpaeoniflorin, glucosides from the root of Paeonia lactiflora. Planta medica, 63(4), 323-325 (1997) https://doi.org/10.1055/s-2006-957692
  5. Ikeda, N., Fukuda, T., Jyo, H., Shimada, Y., Murakami, N., Saka, M., and Yoshikawa, M., Quantitative analysis of monoterpene glycosides constituents of Paeoniae Radix by means of high performance liquid chromatography. Comparative characterization of the external figures, processing method and the cultivated areas. Yakugaku Zasshi, 116(2), 138-147 (1996) https://doi.org/10.1248/yakushi1947.116.2_138
  6. Kaneda, M., Iitaka, Y., and Shibata, S., Absolute structure of paeoniflorin, albiflorin, oxypaeoniflorin, and benzoylpaeoniflorin isolated from Chinese paeony root. Tetrahedron, 28(16), 4309-4317 (1972) https://doi.org/10.1016/S0040-4020(01)88953-5
  7. Kang, S.S., Kim, J.S., Yun-Choi, H.S., and Han, B.H., Phytochemical studies on Paeoniae Radix. Korean Journal of Pharmacognosy, 24(3), 247-50 (1993)
  8. Kang, S.S., Shin, K.H., and Chi, H.J., Galloylpaeoniflorin, a new acylated monoterpene glucoside from Paeony root. Archives of Pharmacal Research, 14(1), 52-54 (1991) https://doi.org/10.1007/BF02857815
  9. Kim, K.J., You, O.J., Jeong, Y.S., Park, S.D., Shin, J.H., Hwang, H.B., and Choi, B.S., Changes of root yield and paeoniflorin content by cultivated years in Paeonia lactiflora PALLS. Korean Journal of Medicinal Crop Science, 4(1), 168-73 (1996)
  10. Kim, K.S. and Kim, H.C., Analytical method for the determination of standard compounds in oriental medicine materials listed in the Korean Pharmacopoeia (KPVIII). Korean Journal of Crop Science, 49(1), 117-145 (2004)
  11. Kim, N.S., Park, K.R., Park, I.S., and Park, Y.H., Application of novel HPLC method to the analysis of regional and seasonal variation of the active compounds in Paeonia lactiflora. Food Chemistry, 96(3), 496-502 (2006) https://doi.org/10.1016/j.foodchem.2005.04.011
  12. Lee, S.C., Kwon, Y.S., Son, K.H., Kim, H.P., and Heo, M.Y., Antioxidative constituents from Paeonia lactiflora. Archives of Pharmacal Research, 28(7), 775-783 (2005) https://doi.org/10.1007/BF02977342
  13. Liu, D.F., Wei, W., and Song, L.H., Protective effect of paeoniflorin on immunological liver injury induced by bacillus calmette-guerin plus lipopolysaccharide: modulation of tumor necrosis factor-alpha and interleukin-6 mRNA. Clinical and Experimental Pharmacology and Physiology, 33(4), 332-339 (2006) https://doi.org/10.1111/j.1440-1681.2006.04371.x
  14. Malz, F. and Jancke, H., Validation of quantitative NMR. Journal of pharmaceutical and biomedical analysis, 38(5), 813-823 (2005) https://doi.org/10.1016/j.jpba.2005.01.043
  15. Son, D.J. and Park, Y.H., Effect of extract from Paeonia radix on rabbit platelets. The Korean Society of Food Science and Nutrition, 31(3), 511-515 (2002) https://doi.org/10.3746/jkfn.2002.31.3.511
  16. Song, M.C., Yoo, J.S., and Baek, N.I., Quantitative analysis of tcinnamaldehyde of Cinnamomum cassia by $^{1}H$-NMR spectrometry. Journal of Korean Society for Applied Biological Chemistry, 48(3), 267-272, (2005)
  17. Sugishita, E., Amagaya, S., and Ogihara, Y., Studies on the combination of Glycyrrhizae Radix in Shakuyakukanzo-To. Journal of pharmacobio-dynamics, 7(7), 427-435 (1984) https://doi.org/10.1248/bpb1978.7.427
  18. Okamoto, M. and Noguchi, M., Evaluation of 3-cyanopropyltrichlorosilane treated thin layer chromatographic plates. Application to analysis of paeoniflorin in paeony roots. Yakugaku Zasshi, 106(9), 837-839 (1986) https://doi.org/10.1248/yakushi1947.106.9_837
  19. Wu, H.K. and Sheu, S.J., Capillary electrophoretic determination of the constituents of Paeoniae Radix. Journal of Chromatography A, 753(1), 139-146 (1996) https://doi.org/10.1016/S0021-9673(96)00525-0
  20. Yamahara, J., Yamada, T., Kimura, H., Sawada, T., and Fujimura, H., Anti-allergic principles in 'Shoseiryu-To' anti-inflammatory properties of paeoniflorin and its derivatives. Journal of pharmacobio-dynamics, 5(11), 921-929 (1982) https://doi.org/10.1248/bpb1978.5.921
  21. Ye, J., Duan, H., Yang, X., Yan, W., and Zheng, X., Anti-thrombosis effect of paeoniflorin: evaluated in a photochemical reaction thrombosis model in vivo. Planta Medica, 67(8), 766-767 (2001) https://doi.org/10.1055/s-2001-18364
  22. Yu, J., Elix, J.A., and Iskander, M.N., Lactiflorin, a monoterpene glycoside from peony root. Phytochemistry, 29(12), 3859-3863 (1990) https://doi.org/10.1016/0031-9422(90)85347-I