Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지
DOI QR코드

DOI QR Code

Quantitative Analysis and Enantiomeric Separation of Ephedra Alkaloids in Ma Huang Related Products by HPLC-DAD and UPLC-MS/MS

  • Kyoung-Moon, Han (Center for Advanced Analysis, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Osong Health Technology Administration Complex) ;
  • Jinwoo, Hwang (Center for Advanced Analysis, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Osong Health Technology Administration Complex) ;
  • Sun Hee, Lee (Center for Advanced Analysis, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Osong Health Technology Administration Complex) ;
  • Boreum, Park (Center for Advanced Analysis, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Osong Health Technology Administration Complex) ;
  • Hyungil, Kim (Center for Advanced Analysis, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Osong Health Technology Administration Complex) ;
  • Sun Young, Baek (Center for Advanced Analysis, National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety, Osong Health Technology Administration Complex)
  • Received : 2022.08.10
  • Accepted : 2022.11.08
  • Published : 2022.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

Ephedra is a genus of the Ephedraceae family and is found in temperate regions, such as Central Asia and Europe. Among the various ephedra species, Ma Huang (Ephedra herb) is derived from the aerial parts of Ephedra sinica S tapf, Ephedra equisetina Bunge, and Ephedra intermedia Schrenk & C.A. Mey. Ma Huang contains various ephedra alkaloids, including (-)-ephedrine, (+)-pseudoephedrine, (-)-norephedrine, (+)-norpseudoephedrine, (-)-methylephedrine, and (+)-methylpseudoephedrine, which are found naturally as single enantiomers, although they can be prepared as racemates. Although the use of Ma Huang in foods is prohibited in Korea, products containing Ma Huang can be imported, and so it is necessary to develop a suitable analytical technique for the detection of Ma Huang in foods. Herein, we report the development of analytical methods for the detection of ephedra alkaloids in products containing Ma Huang. Following sample purification by solid phase extraction, quantitative analysis was performed using ultra-performance liquid chromatography-triple quadrupole mass spectrometry (UPLC-MS/MS). Additionally, the enantiomers were successfully separated using HPLC-DAD. We successfully analyzed various food samples, where the ephedra alkaloids were qualitatively and quantitatively determined, and the enantiomers were separated. It is expected that these methods may contribute toward preventing the distribution of illegal products containing Ma Huang.

Keywords

Acknowledgement

This study was conducted with the financial support of the Ministry of Food and Drug Safety, Republic of Korea [Grant numbers 18181MFDS422 and 21201MFDS307].

References

  1. EFSA Panel on food additives and nutrient sources added to food (ANS); EFSA J. 2013, 11, 3467.
  2. Song, M. Y.; Kim, J. O.; Leem, H. H.; Kim, H. J. J. Korean Med. Obes. Res. 2020, 20, 97-108. https://doi.org/10.15429/jkomor.2020.20.2.97
  3. Sander, L. C.; Sharpless, K. E.; Satterfield, M. B.; Ihara, T.; Phinney, K. W.; Yen, J. H.; Wise, S. A.; Gay, M. L.; Lam, J. W.; McCooeye, M.; Gardner, G.; Fraser, C.; Sturgeon, R.; Roman, M. Anal. Chem. 2005, 77, 3101-3112. https://doi.org/10.1021/ac0484530
  4. Zhang, B. M.; Wang, Z. B.; Xin, P.; Wang, Q. H.; Bu, H.; Kuang, H. X. Chin. J. Nat. Med. 2018, 16, 811-828.
  5. Nguyen, N. V. T.; Nguyen, K. N. H.; Nguyen, K. T.; Kim, K. H.; Aboul-Enein, H. Y. In Current Topics in Chirality - From Chemistry to Biology: Chiral Alkaloid Analysis; Akitsu, T. Ed; intechopen; 2021, DOI: 10.5772/intechopen.96009.
  6. Gray, N.; Musenga, A.; Cowan, D. A.; Plumb, R.; Smith, N. W. J. Chromatogr. A. 2011, 1218, 2098-2105. https://doi.org/10.1016/j.chroma.2010.10.104
  7. Gonzalez-Juarez, D. E.; Escobedo-Moratilla, A.; Flores, J.; Hidalgo-Figueroa, S.; Martinez-Taguena, N.; Morales-Jimenez, J.; Muniz-Ramirez, A.; Pastor-Palacios, G.; Perez-Miranda, S.; Ramirez-Hernandez, A.; Trujillo, J.; Bautista, E. Molecules 2020, 25, 3283. https://doi.org/10.3390/molecules25143283
  8. Gay, M. L.; White, K. D.; Obermeyer, W. R.; Betz, J. M.; Musser, S. M. J. AOAC Int. 2001, 84, 761-769. https://doi.org/10.1093/jaoac/84.3.761
  9. Roman, M. C.; Gray, D.; Luo, G.; McClanahan, R.; Perez, R.; Roper, C.; Roscoe, V.; Shevchuk, C.; Suen, E.; Sullivan, D.; Walther, H. J. J. AOAC Int. 2004, 87, 1-14. https://doi.org/10.1093/jaoac/87.1.1
  10. Deventer, K.; Pozo, O. J.; Van Eenoo, P.; Delbeke, F. T. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 2009, 877, 369-374. https://doi.org/10.1016/j.jchromb.2008.12.032
  11. Zheng, Z.; Yan, T.; Chen, W.; Ye, L.; Tang, L.; Liu, Z. Xenobiotica. 2012, 42, 775-783. https://doi.org/10.3109/00498254.2012.658884
  12. Beyer, J.; Peters, F. T.; Kraemer, T.; Maurer, H. H. J. Mass Spectrom, 2007, 42, 150-160. https://doi.org/10.1002/jms.1132
  13. Kim, H. J.; Lee, J. H.; Park, H. J.; Cho, S. H.; Cho, S. Y.; Kim, W. S. Food Addit. Contam. Part A. Chem. Anal. Control Expo. Risk Assess. 2014, 31, 777-783. https://doi.org/10.1080/19440049.2014.888497
  14. Zhang, J.; Zhang, Y.; Wang, Y. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 2016, 1039, 1-7. https://doi.org/10.1016/j.jchromb.2016.11.008
  15. Wang, W.; Cuo, C.; Chen, L.; Qiu, Z.; Yin, X. Xu, J. Environ. Pollut. 2021, 273, 116424. https://doi.org/10.1016/j.envpol.2021.116424
  16. Cui, J. F.; Zhou, T. H.; Zhang, J. S.; Lou, Z. C. Phytochem. Anal. 1991, 2, 116-119.
  17. Li, H. X.; Ding, M. Y.; Lv, K.; Yu, J. Y. J. Chromatogr. Sci. 2001, 39, 370-374.
  18. Kim, H. K.; Choi, Y. H.; Chang, W. T.; Verpoorte, R. Chem. Pharm. Bull. 2003, 51, 1382-1385. https://doi.org/10.1248/cpb.51.1382
  19. Zhang, Q.; Xue, X. Z.; Miao, S. M.; Cui, J. L.; Qin, X. M. Symbiosis. 2020, 81, 115-125. https://doi.org/10.1007/s13199-020-00685-w
  20. ICH Harmonized Tripartite Guideline. Validation of analytical procedures: text and methodology. Q2(R1); International Council for Harmonisation: Switzerland, 2005.
  21. FDA guidance documents: Bioanalytical method validation, Guidance for industry. USA, 2008.
  22. Put InfinityLab Poroshell 120 Chiral innovation to work for your challenging separations; Agilent Technologies Inc.: USA, 2017.
  23. Parsaeimehr, A.; Sargsyan, E. In Natural Products: Ephedra alkaloids-Alkaloids derived by amination reaction: phenylalanine derived; Ramawat, K. G.; Merillon, J. M. Eds; Springer-Verlag Berlin Heidelberg; Switzerland, 2013, pp 909-922.
  24. Kasprzyk-Hordern, B. ; Kondakal, V. V. R. ; Baker, D. R. J. Chromatogr. A. 2010, 1217, 4575-4586.  https://doi.org/10.1016/j.chroma.2010.04.073