Simultaneous Analysis of Bioactive Metabolites from Lonicera japonica Flower Buds by HPLC-DAD-MS/MS

HPLC-DAD-MS/MS를 이용한 금은화 생리활성 물질의 동시분석

  • Ryu, Sung-Kwang (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Jeon, Ju-Eun (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Kang, Gyoung-Won (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Kang, Sam-Sik (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Shin, Jong-Heon (Natural Products Research Institute, College of Pharmacy, Seoul National University)
  • 유성광 (서울대학교 약학대학 천연물과학연구소) ;
  • 전주은 (서울대학교 약학대학 천연물과학연구소) ;
  • 강경원 (서울대학교 약학대학 천연물과학연구소) ;
  • 강삼식 (서울대학교 약학대학 천연물과학연구소) ;
  • 신종헌 (서울대학교 약학대학 천연물과학연구소)
  • Published : 2008.12.31

Abstract

A high-performance liquid chromatography (HPLC) with diode array detector (DAD) and electrospray ionization mass spectrometry (ESI-MS) was established for the simultaneous determination of chlorogenic acid (1), sweroside (2), luteolin-7-O-glucoside (3), (E)-aldosecologanin (4) and 3,5-dicaffeoylquinic acid (5) from Lonicera joponica flower buds. The optimal chromatographic conditions were obtained on an ODS column (5 ${\mu}m$, 4.6${\times}$150 mm) with the column temperature $25^{\circ}C$. The mobile phase was composed of (A) water with 0.1% formic acid and (B) acetonitrile with 0.1% formic acid using a gradient elution, the flow rate was 0.3 ml/min. Detection wavelength was set at 250 nm. All calibration curves showed good linear regression ($r^2$>0.994) within test ranges. The developed method provided satisfactory precision and accuracy with overall intra-day and inter-day variations of 0.05${\sim}$1.95% and 0.15${\sim}$2.26%, respectively, and the overall recoveries of 97.71${\sim}$103.65% for the five compounds analyzed. The verified method was successfully applied to quantitative determination of the three types (phenolic compounds, iridoids and flavonoids) of bioactive compounds in 21 commercial L. japonica flower buds samples from different markets in Korea and China. The analytical results demonstrated that the contents of the five analytes vary significantly with sources.

Keywords

References

  1. 정보섭, 김일혁, 김재가 : 원색 천연물대사전 상권, 남산당, p. 12 (1984)
  2. 진재인 : 도설한방의학대사전(중국약학대전) I, 강담사, p. 160 (1982)
  3. Pharmacopoeia of the people's republic of China, Chemical Industry Press, Peking, p. 152 (2005)
  4. Chang, C.-W., Lin, M.-T., Lee, S.-S., Liu, K. C. S. C., Hsu, F.-L. and Lin, J.-Y. : Differential inhibition of reverse transcriptase and cellular DNA polymerase-a activities by lignans isolated from Chinese herbs, Phyllanthus myrtifolius Moon, and tannins from Lonicera japonica Thunb and Castanopsis hystrix. Antiviral Res. 27, 367 (1995) https://doi.org/10.1016/0166-3542(95)00020-M
  5. Xiang, T., Xiong, Q. B., Ketut, A. I., Tezuka, Y., Nagaoka, T., Wu, L. J. and Kadota, S. : Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei. Planta Medica 67, 322 (2001) https://doi.org/10.1055/s-2001-14337
  6. Chang, W.-C. and Hsu, F.-L. : Inhibition of platelet activation and endothelial cell injury by polyphenolic compounds isolated from Lonicera japonica Thunb. Prost. Leuk. Essen. Fatty Acids 45, 307 (1992) https://doi.org/10.1016/0952-3278(92)90088-Z
  7. Leung, H. W.-C., Kuo, C.-L., Yang, W.-H., Lin, C.-H. and Lee, H.-Z. : Antioxidant enzymes activity involvement in luteolininduced human lung squamous carcinoma CH27 cell apoptosis. Eur. J. Pharmacol. 534, 12 (2006) https://doi.org/10.1016/j.ejphar.2006.01.021
  8. Lee, S. J., Choi, J. H., Chang, H. W., Kang, S. S. and Kim, H. P. : Suppression of mouse lymphocyte proliferation in vitro by naturally-occurring biflavonoids. Life Sci. 57, 551 (1995) https://doi.org/10.1016/0024-3205(95)00305-P
  9. Peng, Y., Liu, F. and Ye, J. : Determination of phenolic acids and flavones in lonicera japonica thumb. by capillary electrophoresis with electrochemical detection. Electroanal. 17, 356 (2005) https://doi.org/10.1002/elan.200403102
  10. 정규찬, 권동렬, 백석환, 김성환, 장현욱 : 금은화 (Lonicerae Flos)의 ethyl acetate 분획이 돌연변이원성에 미치는 영향(Effects of Lonicerae Flos' ethyl acetate fraction on mutagenicity). 약학회지 32, 328 (1988)
  11. Peng, L.-Y., Mei, S.-X., Jiang, B., Zhou, H. and Sun, H.-D. : Constituents from Lonicera japonica. Fitoterapia 71, 713 (2000) https://doi.org/10.1016/S0367-326X(00)00212-4
  12. Song, Y., Li, S.-L., Wu, M.-H., Li, H.-J. and Li, P. : Qualitative and quantitative analysis of iridoid glycosides in the flower buds of Lonicera species by capillary high performance liquid chromatography coupled with mass spectrometric detector. Anal. Chim. Acta 564, 211 (2006) https://doi.org/10.1016/j.aca.2006.01.068
  13. Machida, K., Sasaki, H., Iijima, T. and Kikuchi, M. : Studies on the constituents of Lonicera species. XVII. New iridoid glycosides of the stems and leaves of Lonicera japonica THUNB. Chem. Pharm. Bull. 50, 1041 (2002) https://doi.org/10.1248/cpb.50.1041
  14. Xing, J. and Li, P. : Research on chemical constituents of Lonicera : A review and prospects. J. Chin. Med. Mater. 22, 366 (1999)
  15. Rahimuddin, S. A., Khoja, S. M., Zuhair, M. M., Howell, N. K. and Brown, J. E. : Inhibition of lipid peroxidation in UVAtreated skin fibroblasts by luteolin and its glucosides. Eur. J. Lipid Sci. Technol. 109, 647 (2007) https://doi.org/10.1002/ejlt.200700012
  16. Qian, Z.-M., Li, H.-J., Li, P., Ren, M.-T. and Tang, D. : Simultaneous qualitation and quantification of thirteen bioactive compounds in Flos Lonicerae by high-performance liquid chromatography with diode array detector and mass spectrometry. Chem. Pharm. Bull. 55, 1073 (2007) https://doi.org/10.1248/cpb.55.1073