Qualitative Analysis of Phenolic Substances in Artemisia capillaris by LC-MS

LC-MS에 의한 사철쑥에 존재하는 페놀성 화합물의 정성분석

  • Nugroho, Agung (Department of Applied Plant Sciences, Graduate School, Sangji University) ;
  • Lim, Sang-Cheol (Department of Applied Plant Sciences, Graduate School, Sangji University) ;
  • Park, Hee-Juhn (Department of Pharmaceutical Engineering, Sangji University)
  • Received : 2012.11.27
  • Accepted : 2012.12.14
  • Published : 2012.12.31

Abstract

The herb of Artemisia capillaris in Chinese medicine is used to treat hepatic diseases. In this research, qualitative analysis was performed using a UPLC/Q-TOF-ESI-MS/MS method for rapid identification of phenolic substances from A. capillaris: three caffeoylquinic acids (chlorogenic acid, 3,5-di-O-caffeoylquinic acid, and 4,5-di-O-caffeoylquinic acid), three flavonoids (hyperoside, isorhamnetin 3-O-robinobioside and quercetin) and three prenylated coumarins (6,8-diprenylumbelliferone, cedrelopsin and osthol) were identified. The three prenylated coumarins have not been reported from A. capillaris.

Keywords

References

  1. Kim, S. K., Woo, M. H., Lee, J. H., Choi, J. S. and Min, B. S. (2010) Quantitative determination of bioactive compounds in some Artemisia capillaris by high-performance liquid chromatography. Nat. Prod. Sci. 16: 233-238.
  2. Hong, J. H., Hwang, E. Y., Kim, H. J., Jeong, Y. J. and Lee, I. S. (2009) Artemisia capillaris inhibits lipid accumulation in 3T3-L1 adipocytes and obesity in C57BL/6J mice fed a high fat diet. J. Med. Food 12: 736-745. https://doi.org/10.1089/jmf.2008.1240
  3. Kim, E. K., Han, M. J., Song, M. Y., Lee, J. H., Lv, N., Choi, K. B.., Ryu, D. G., Kim, K. S., Park, J. W. and Park, B. H. (2007) Inhibitory effect of Artemisia capillaris extract on cytokine-induced nitric oxide formation and cytotoxicity of RINm5F cells. Int. J. Mol. Med. 19: 535-540.
  4. Choi, J. H., Kim, D. W., Yun, N., Choi, J. S., Islam, M. N., Kim, Y. S. and Lee, S. M. (2011) Protective effects of hyperoside against carbon tetrachloride-induced liver damage in mice. J. Nat. Prod. 74: 1055-1060 (2011). https://doi.org/10.1021/np200001x
  5. Kwon, Y.S. 2006. Pharmacognosy, Dongmyungsa, Seoul, pp. 469-471.
  6. Park, M. S., Nam, B. M. and Chung, G. Y. (2011) Taxonomic identities of Artemisia capillaris Thunb. and A. scoparia Waldst.. Korean J. Pl. Taxon. 41: 1-9. https://doi.org/10.11110/kjpt.2011.41.1.001
  7. Park, M. S. and Chung, G. Y. (2012) A palynological study of the genus Artemisia (Asteraceae) in Korea. Kor. J. Pl. Taxon. 42: 24-39. https://doi.org/10.11110/kjpt.2012.42.1.024
  8. Ren, M. T., Li, H. J., Sheng, L. S., Liu, P. and Li, P. (2009) Rapid analysis of constituents of Radix Cyathulae using hydrophilic interaction reverse phase LC-MS. J. Sep. Sci. 32: 3988-3995. https://doi.org/10.1002/jssc.200900390
  9. Su, S., Guo, J., Duan, J. A., Wang, T., Qian, D., Shang, E. and Tang, Y. (2010) Ultra-performance liquid chromatography- tandem mass spectrometry analysis of the bioactive components and their metabolites of Shaofu Zhuyu decoction active extract in rat plasma. J. Chromatogr. B 878: 355-362. https://doi.org/10.1016/j.jchromb.2009.11.048
  10. Wu, T. S., Tsang, Z. J., Wu, P. L., Lin, F. W., Li, C.Y., Teng, C. M. and Lee, K. H. (2001) New constituents and antiplatelet aggregation and anti-HIV principles of Artemisia capillaries. Bioorg. Med. Chem. 9: 77-83. https://doi.org/10.1016/S0968-0896(00)00225-X
  11. Wang, X., Sun, H., Lv, H., Wu, Z., Wang, P., Liu, L. and Cao, H. (2008) Analysis of the constituents in the rat plasma after oral administration of Yin Chen Hao Tang by UPLC/Q-TOFMS/ MS. J. Pharm. Biomed. Anal. 46: 477-490. https://doi.org/10.1016/j.jpba.2007.11.014
  12. Lai, J. P., Lim, Y. H., Shen H. M. and Ong, C. N. (2007) Identification and characterization of major flavonoids and caffeoylquinic acids in three Compositae plants by LC/DADAPCI/ MS. J. Chromatogr. B 848: 215-225. https://doi.org/10.1016/j.jchromb.2006.10.028
  13. Clifford, M. N., Knight, S. and Kuhnert, N. (2005) Discriminating between the six isomers of dicaffeoylquinic acid by LC-MSn. J. Agric. Food Chem. 53: 3821-3832. https://doi.org/10.1021/jf050046h
  14. Liu, P., Yang, B. and Kallio, H. (2010) Characterization of phenolic compounds in Chinese hawthorn (Crataegus pinnatifida Bge. var. major) fruit by high performance liquid chromatography-electrospray ionization mass spectrometry. Food Chem. 121: 1188-1197. https://doi.org/10.1016/j.foodchem.2010.02.002
  15. Hitotsuyanagi, Y., Kojima, H., Ikuta, H., Takeya, K. and Itokawa, H. (1996) Identification and structure-activity relationship studies of osthol, a cytotoxic principle from Cnidium monnieri. Bioorg. Med. Chem. Lett. 6: 1791-1794. https://doi.org/10.1016/0960-894X(96)00315-0
  16. Yuan, Z., Xu, H., Wang, K., Zhao, Z. and Hu, M. (2009) Determination of osthol and its metabolites in a phase I reaction system and the Caco-2 cell model by HPLC-UV and LC-MS/MS. J. Pharm. Biomed. Anal. 49: 1226-1232. https://doi.org/10.1016/j.jpba.2008.12.001
  17. Sajjadi, S. E., Zeinvand, H. and Shokoonhinia, Y. (2009) Isolation and identification of osthol from the fruits and essential oil composition of the leaves of Prangos asperula Boiss. Res. Pharm. Sci. 4: 19-23.
  18. Um, B.H., Lobstein, A., Weiniger, B., Spiegel, C., Yice, F. and Rakotoarison, O., Andriantsihaina, R. and Anton, R. (2003) New coumarins from Cedrelopsis greviei. Fitoterapia 74: 638-642. https://doi.org/10.1016/S0367-326X(03)00181-3
  19. Patre, R. E., Parameswaran, P. S., Tilve, S. G. (2011) Synthesis of the naturally occurring prenylated coumarins balsamiferone and cedrelopsin by domino reactions. ARKIVOC ix: 68-76.
  20. Rao, G. V., Rao, K. S., Annamalai, T. and Mukhopadhyay, T. (2009) New coumarin diol from plant, Chloroxylon swietenia DC. Indian J. Chem. 48B: 1042-1044.
  21. Kwon, O. S., Choi, J. S., Islam, M. N., Kim, Y. S. and Kim, H.P. (2011) Inhibition of 5-lipoxygenase and skin inflammation by the aerial parts of Artemisia capillaris and its constituents. Arch. Pharm. Res. 34: 1561-1569. https://doi.org/10.1007/s12272-011-0919-0