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Comparison of chemical constituents among licorice, roasted licorice, and roasted licorice with honey

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Abstract

Licorice (root and rhizome of Glycyrrhiza uralensis Fisch.) is sometimes used as crude drug after processing. In this report, we prepared roasted licorice with or without honey using 3 lots of crude drug samples derived from wild G. uralensis, and analyzed the constituents in unprocessed, roasted, and honey-roasted licorice samples by high performance liquid chromatography–electrospray ionization-ion trap-time of flight mass spectrometry (HPLC–ESI-IT-TOF-MSn) with principal component analysis. We found that the areas of 41 peaks were noticeably changed by processing. Among them, the areas of 12 peaks, viz. isoliquiritin, isoliquiritigenin, glucoisoliquiritin, 6″-O-acetylisoliquiritin, 6″-O-acetylisoliquiritin apioside, glycyrrhetinic acid 3-O-glucuronide, 5 kinds of sugar-derivatives and one compound whose molecular weight was 386 Da were increased by roasting in all 3 lots, and those peak areas were increased by higher heating temperatures. Among the increased peaks, 3 kinds of sugar-derivatives had larger areas, and 6″-O-acetylisoliquiritin had lower areas than those in honey-roasted licorice. Those sugar-derivatives were the only characteristics differing between honey-roasted licorice and roasted licorice. Meanwhile, the areas of 9 peaks, four of them identified as 6″-O-acetylliquiritin, 6″-O-acetylliquiritin apioside, formononetin and gancaonin l, were decreased by roasting in all 3 lots, but there were no differences between roasted licorice with or without honey. Those compounds whose amounts were changed by processing could be used as markers for the quality control of roasted and honey-roasted licorice.

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References

  1. Chinese Pharmacopoeia Commission (2015) The 2015 edition of pharmacopoeia of the People’s Republic of China, vol 1. Chemical Industry Press, Beijing

    Google Scholar 

  2. The Ministry of Health, Labour and Welfare (2016) The Japanese pharmacopoeia, Practical guide, 17th edn. Hirokawa Shoten Ltd., Gunma

  3. Ota M, Mikage M, Cai SQ (2015) Herbological study on the medicinal effects of roasted licorice and honey-roasted licorice. Yakushigaku Zasshi 50:38–45

    PubMed  Google Scholar 

  4. Kuwajima H, Taneda Y, Chen WZ, Kawanishi T, Hori K, Taniyama T, Kobayashi M, Ren J, Kitagawa I (1999) Variation of chemical constituents in processed licorice roots: quantitative determination of saponin and flavonoid constituents in bark removed and roasted licorice roots. Yakugaku Zasshi 119:945–955

    Article  CAS  PubMed  Google Scholar 

  5. Sung MW, Li PC (2004) Chemical analysis of raw, dry-roasted, and honey-roasted licorice by capillary electrophoresis. Electrophoresis 25:3434–3440

    Article  CAS  PubMed  Google Scholar 

  6. Zhou C, Yang YY, Zhang ZQ, Liu R, Li WM (2011) HPLC with switching wavelength simultaneous determination of seven constituents in licorice and its processed products. Chin J Pharm Anal 31:2067–2072

    CAS  Google Scholar 

  7. Zhou Q, Sun LL (2013) Changes of chemical constituents in Radix Glycyrrhizae before and after honey processing. Chin Pharm J 48:768–772

    CAS  Google Scholar 

  8. Shi MJ, Gao JC, Wang WF, Qin ML, Yang L (2012) Comparison of HPLC before and after processing of Licorice. China Pharm 21:12–13

    CAS  Google Scholar 

  9. Su BZ, Zhou Q, Sun LL (2011) Fingerprint of ethyl acetate extract of Glycyrrhizae Radix et Rhizoma Praeparta. Chin Tradit Pat Med 33:203–207

    CAS  Google Scholar 

  10. Zhou Q, Lu J, Li GH, Shi DH, Dai YP, Sun LL (2010) HPLC fingerprint spectrum of honey-fried Radix Glycyrrhizae. China J Chin Materia Medica 35:1547–1550

    CAS  Google Scholar 

  11. Zhou YZ, Han L, Liu XH, Fu XS, Xu H, Li JS, Cai BC, Tutiguli A (2012) Study on HPCE fingerprint of Glycyrrhizae Radix et Rhizoma. Chin JMAP 29:405–409

    CAS  Google Scholar 

  12. Editorial committee of Beijingshi zhongyao yinpian paozhi guifa (2008) Beijingshi zhongyao yinpian paozhi guifa. Beijing Food and Drug Administration, Beijing

    Google Scholar 

  13. Tsuchida T, Komatsu K, Feng YX, Chen H, Namba T (2000) Pharmacognostical studies on the Chinese crude drug “Gancao”. J Tradit Med 17:261–271

    Google Scholar 

  14. Editorial committee of Zhongyao yinpian paozhi gongyi yu zhiliang biaozhun ji GMP shiyong shouce, (2006) Zhongyao yinpian paozhi gongyi yu zhiliang biaozhun ji GMP shiyong shouce. China Press of Traditional Chinese Medicines, Beijing

    Google Scholar 

  15. Qiao X, Ji S, Yu SW, Lin XH, Jin HW, Duan YK, Zhang LR, Guo DA, Ye M (2014) Identification of key licorice constituents which interact with cytochrome P450: evaluation by LC/MS/MS cocktail assay and metabolic profiling. AAPS J 16:101–112

    Article  CAS  PubMed  Google Scholar 

  16. Wang S, Chen L, Leng J, Chen P, Fan X, Cheng Y (2014) Fragment ion diagnostic strategies for the comprehensive identification of chemical profile of Gui-Zhi-Tang by integrating high-resolution MS, multiple-stage MS and UV information. J Pharm Biomed Anal 98:22–35

    Article  CAS  PubMed  Google Scholar 

  17. Kitagawa I, Chen WZ, Hori K, Kobayashi M, Ren J (1998) Chemical studies of Chinese licorice-roots. II. Five new flavonoid constituents from the roots of Glycyrrhiza aspera PALL. collected in Xinjiang. Chem Pharm Bull 46:1511–1517

    Article  CAS  Google Scholar 

  18. Farag MA, Porzel A, Wessjohann LA (2012) Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC–MS, LC–MS and 1D NMR techniques. Phytochemistry 76:60–72

    Article  CAS  PubMed  Google Scholar 

  19. Tan G, Zhu Z, Zhang H, Zhao L, Liu Y, Dong X, Lou Z, Zhang G, Chai Y (2010) Analysis of phenolic and triterpenoid compounds in licorice and rat plasma by high-performance liquid chromatography diode-array detection, time-of-flight mass spectrometry and quadrupole ion trap mass spectrometry. Rapid Commun Mass Spectrom 24:209–218

    Article  CAS  PubMed  Google Scholar 

  20. Xu T, Yang M, Li Y, Chen X, Wang Q, Deng W, Pang X, Yu K, Jiang B, Guan S, Guo DA (2013) An integrated exact mass spectrometric strategy for comprehensive and rapid characterization of phenolic compounds in licorice. Rapid Commun Mass Spectrom 27:2297–2309

    Article  CAS  PubMed  Google Scholar 

  21. Tanaka K, Ina A, Hayashi K, Komatsu K (2010) Comparison of chemical constituents in Glycyrrhiza uralensis from various sources using a multivariate statistical approach. J Tradit Med 27:210–216

    Google Scholar 

  22. Shen FJ, Hu JF, Yu YC, Xu ZD (1995) Studies on chemical constituents of Glycyrrhiza uralensis Fisch. Chem J Chin Univ 16:572–574

    CAS  Google Scholar 

  23. Lee JE, Lee JY, Kim J, Lee K, Choi SU, Ryu SY (2015) Two minor chalcone acetylglycosides from the roots extract of Glycyrrhiza uralensis. Arch Pharm Res 38:1299–1303

    Article  CAS  PubMed  Google Scholar 

  24. Zheng X, Shi P, Cheng Y, Qu H (2008) Rapid analysis of a Chinese herbal prescription by liquid chromatography-time-of-flight tandem mass spectrometry. J Chromatogr A 1206:140–146

    Article  CAS  PubMed  Google Scholar 

  25. Zhang L, Jiang Z, Yang J, Li Y, Wang Y, Chai X (2015) Chemical material basis study of Xuefu Zhuyu decoction by ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. J Food Drug Anal 23:811–820

    Article  CAS  PubMed  Google Scholar 

  26. Li YJ, Chen J, Li Y, Li Q, Zheng YF, Fu Y, Li P (2011) Screening and characterization of natural antioxidants in four Glycyrrhiza species by liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Chromatogr A 1218:8181–8191

    Article  CAS  PubMed  Google Scholar 

  27. Jing J, Ren W, Chen X, Wang Y, Yu Q, Wang G, Davey AK, Wang J, Jing N (2008) Glucuronide-sulfate diconjugate as a novel metabolite of glycyrrhetic acid in rat bile. Drug Metab Pharmacokinet 23:175–180

    Article  CAS  PubMed  Google Scholar 

  28. Chaturvedula VSP, Yu O, Mao G (2014) Isolation and NMR spectral assignments of 18-glycyrrhetinic acid-3-O-D-glucuronide and 18-glycyrrhetinic acid. IOSR J Pharm 4:44–48

    CAS  Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, 38 Xue Yuan Road, Beijing, 100191, China

    Misato Ota, Feng Xu, Yao-Li Li, Ming-Ying Shang & Shao-Qing Cai

  2. Department of Pharmacognosy, Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-Dori, Mizuho-ku, Nagoya, Aichi, 467-8603, Japan

    Misato Ota & Toshiaki Makino

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  1. Misato Ota
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  2. Feng Xu
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  3. Yao-Li Li
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  4. Ming-Ying Shang
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  5. Toshiaki Makino
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  6. Shao-Qing Cai
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Correspondence to Shao-Qing Cai.

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Ota, M., Xu, F., Li, YL. et al. Comparison of chemical constituents among licorice, roasted licorice, and roasted licorice with honey. J Nat Med 72, 80–95 (2018). https://doi.org/10.1007/s11418-017-1115-4

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  • DOI: https://doi.org/10.1007/s11418-017-1115-4

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