Korean Journal of Pharmacognosy (생약학회지)

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Analysis of Liquiritigenin, an Aglycone of Liquiritin in Licorice by High Performance Liquid Chromatography

감초 중 리퀴리티게닌 분석법 개발 및 함량분석

  • Lee, Jong-Hwa (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Ze, Keum-Ryon (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Kim, Do-Hoon (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Park, Ju-Young (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Shim, Young-Hoon (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Kim, Jong-Hwan (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Lim, Sook (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Shin, Jin-Seon (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Kim, In-Seon (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Kim, Ji-Yeon (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Seong, Sang-Hyun (College of Pharmacy, Seoul National University) ;
  • Jang, Seung-Yeup (Biopharmaceuticals and Herbal Medicine Evaluation Department, Korea Food & Drug Administration) ;
  • Kim, Dong-Seup (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation) ;
  • Seong, Rack-Seon (Herbal Medicine Research Division, National Institute of Food and Drug Safety Evaluation)
  • 이종화 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 제금련 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 김도훈 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 박주영 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 심영훈 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 김종환 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 임숙 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 신진선 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 김인선 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 김지연 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 성상현 (서울대학교 약학대학) ;
  • 장승엽 (식품의약품안전청 바이오생약심사부) ;
  • 김동섭 (식품의약품안전평가원 의료제품연구부 생약연구과) ;
  • 성락선 (식품의약품안전평가원 의료제품연구부 생약연구과)
  • Published : 2009.12.31
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Abstract

Licorice(Glycyrrhizae Radix et Rhizoma) is recorded as the root of Glycyrrhiza uralensis Fischer or Glycyrrhiza glabra Linne or Glycyrrhiza inflata Bat.(Leguminosae) in Korean Pharmacopoeia $9^{th}$ edition (KP9) and Chinese Pharmacopoeia 2005(CP2005), Glycyrrhiza uralensis Fischer or Glycyrrhiza glabra Linne in Japanese Pharmacopoeia 2005(JP2005). It is established the content standard of Glycyrrhizin 2.5 % and liquiritin 1% in KP9 and CP2005. But, according to the reports, all Licorice species were not sufficient for content standard of liquiritin 1.0% for licorice in KP9 and CP2005. It shows different content of liquiritin among G. uralensis, G. glabra and G. inflata. Also, it was reported liquiritin, liquiritin apioside are transformed into liquiritigenin by human internal flora. Therefore, we have studied for the pre-treatment condition and analytical method of liquiritigenin; It was good efficinet in 2M HCl reflux(1 hr) for hydrolysis and in methylene chloride for solvent fractionation. And 1% acetic acid in DW(A) and acetonitrile(B) with gradient condition as a mobile phase was most effective in HPLC analytical condition. According to these experimental methods, we have anlayzed content of liquiritigenin about 77 Licorice sample. In this research, it was also examined the content of liquiritin and liquiritigenin for Glycyrrhizae Radix related growing area. According to the results, we suggested the content standard of glycyrrhizin more than 2.5%, liquiritigenin more than 0.7%(after hydrolysis) of licorice.

Keywords

References

  1. 대한약전 제9개정 (2007), 903. 식품의약품안전청, 서울.
  2. 한방약리학 (2006), 115. 신일상사, 서울
  3. 한약재 생리활성성분의 효능 확인 연구 결과보고서 (2006), 34-41. 식품의약품안전청
  4. Gujral, M. L., Sareen, K. N., Tangri, K. K., Roy, A. K., Gupta, G. P. and Amma, M. K. (1959) Antiarthritic acitivity of Glycyrrhiza glabra Linn.. Indian J. Psychol., 3: 39-47
  5. Herold, A., Cremer, L., Calugaru, A., Tamas, V., Inonescu, F., Manea, S. and Szegli, G. (2003) Hydroalcoholic plant extracts with anti-inflammatory activity. Roum. Arch. Microbial. Immunol. 62: 117-129
  6. Akamatsu, H., Komura, J., Asada, Y. and Niwa, Y. (1991) Mechanism of anti-inflammatory action of glycyrrhizin : Effects on Neutrophil functions including reactive oxygen species generation. Planta Med. 7: 119-121
  7. Rao, B. N. N., Anderson, M. B., Musser, J. H., Gilbert, J. H., Schaefer, M. E., Foxal, C. and Brandley, B. K. (1994) Sialyl Lewis X mimics derived from a pharmacophere search are selection inhibitors with anti-inflammatory activity. J. Biol. Chem. 269: 19663-19666
  8. 한약재 생리활성성분 분리 및 효능 유전자 확인 연구 (감초, 지실) 결과보고서 (2006), 90-94, 식품의약품안전청,
  9. Wang, Y.-C. and Yang, Y.-S. (2007) Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC. J. Chromatography B, 850: 392-399 https://doi.org/10.1016/j.jchromb.2006.12.032
  10. Kenji, K., Mao, S., Rie, N., Takashi, M. and Yukihiro, S. (2007) Constituent Properties of Licorices Derived from Glycyrrhiza uralensis, G. glabra, or G. inflata Identified by Genetic Information. Biol. Pharm. Bull. 30: 1271-1277 https://doi.org/10.1016/j.jchromb.2006.12.032
  11. Takayuki, A., Kazuhisa I., Takashi, M., Shuichi, T. and Masaki, A. (2003) Permeability of the flavonoids liquiritigenin and its glycosides in licorice roots and davidigenin, a hydrogenated metabolite of liquiritigenin, using human intestinal cell line Caco-2. J. Ethnopharmcol. 89: 285-289 https://doi.org/10.1016/j.jep.2003.09.009
  12. Kim, Y. W., Ki, S. H., Lee, J. R., Lee, S. J. Kim, C. W. Kim, S. C. and Kim, S. G. (2006) Liquiritigenin, an aglycone of liquiritin in Glycyrrhizae radix, prevents acute liver injuries in rats induced by acetaminophen with or without buthionine sulfoximine. Chem. Biol. Interact. 161: 125-138 https://doi.org/10.1016/j.cbi.2006.03.008
  13. 이주상, 김정아, 조세훈, 손애량, 장태수, 소명숙, 정시련, 이승호. 감초의 Tyrosinase 활성 억제 성분. 생약학회지 34: 33-39 (2003)
  14. Junzo, K., Rie, N., Hiroyuki, I. and Masayoshi, K. (2003) Antitussive principles of Glycyrrhizae radix, a main component of the Kampo preparations Bakumondo-to (Mai-mendong-tang). Eur. J. Pharmacol. 469: 159-163 https://doi.org/10.1016/S0014-2999(03)01728-X
  15. Rui-ting, L., Li-bo, Z. and Qiu-jun, L. (2009) Liquiritigenin inhibits $A\beta_{25-35}$-induced neurotoxicity and secretion of $A\beta_{1-40}$ in rat hippocampal neurons. Acta. Pharmacol. Sin. 30: 899-906 https://doi.org/10.1038/aps.2009.74
  16. Kim, Y. W., Zhao, R. J., Park, S. J., Lee, J. R., Cho, I. J., Yang, C. H., Kim, S. G. and Kim, S. C. (2008) Anti-inflammatory effects of liquiritigenin as a consequence of the inhibition of NF-$\kappa$B-dependent iNOS and proinflammatory cytokines production. Br. J. Pharmacol.. 154: 165-173 https://doi.org/10.1038/bjp.2008.79.
  17. Jennifer, E. M., Nitzan, L., Richard, E. S., Scott, B., Tetjana, Z., Sylvia, C., William, A. R., Mary, T., Issac, C., Leonard, F. B., Dale, C. L. (2008) Liquiritigenin is a plant-derived highly selective estrogen $\beta$‚ receptor agonist. Mol. Cell. Endocrinol.. 283: 49-57 https://doi.org/10.1016/j.mce.2007.11.020.
  18. Lee, J. Y., Lee, J. H., Park, J. H., Kim, S. Y., Choi, J. Y., Lee, S. H., Kim, Y. S., Kang, S. S., Jang E. C. and Han, Y. M. (2009) Liquiritigenin, a licorice flavonoid, helps mice resist disseminated candidiasis due to Candida albicans by Th1 immune response, whereas liquiritin, its glycoside form, does not. Int. Immunopharmacol.. 9: 632-638 https://doi.org/10.1016/j.intimp.2009.02.007
  19. Kim, S. C., Byun, S. H., Yang, C. H., Kim, C. Y., Kim, J. W. and Kim, S. G. (2004) Cytoprotective effets of Glycyrrhizae radix extract and its active component liquiritigenin against cadmium-induced toxicity (effects on bad translocation and cytochrome c-mediated PARP cleavage). Toxicology. 197: 239-251 https://doi.org/10.1016/j.tox.2004.01.010