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Current Pharmaceutical Analysis

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ISSN (Print): 1573-4129
ISSN (Online): 1875-676X

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Research Article

Application of Quantitative Proton Nuclear Magnetic Resonance Spectroscopy for Determination of the Content of Geniposide in Gardeniae fructus

Author(s): Jian-Wei Dong*, Ya-Li Li, Xue-Jiao Li*, Xiao-Xin Xu and Feng-Xian Li

Volume 20, Issue 9, 2024

Published on: 08 November, 2024

Page: [1066 - 1071] Pages: 6

DOI: 10.2174/0115734129352488241105104605

Price: $65

Abstract

Background: Gardeniae fructus (Zhi-Zi) is the dry ripe fruit of the plant Gardenia jasminoides Ellis (Rubiaceae), which can be used as both food and medicine. Geniposide, a key constituent of Gardeniae fructus, serves as an indicator component for evaluating the quality of Gardeniae fructus. Traditionally, the quantification of geniposide in Gardeniae fructus is achieved through High-performance Liquid Chromatography (HPLC)-based methods.

Objectives: The present study aimed to introduce a rapid approach to quantifying geniposide content in Gardeniae fructus along with validating its effectiveness.

Methods: The experiments involved finding a suitable deuterium solvent, Internal Standard (IS), specific peak, and Nuclear Magnetic Resonance (NMR) parameters for quantitation, and validating specificity, accuracy, precision, and stability.

Results: The results have indicated that methanol-d4 as a solvent has facilitated excellent signal separation in the proton Nuclear Magnetic Resonance (1H NMR) spectroscopy, with trimethyl 1,3,5- benzenetricarboxylate emerging as the ideal IS. The specific signal at δ 7.45, corresponding to H-3 in geniposide, has been identified as the optimal peak for integration. The application of distinctive signals from the 1H NMR spectroscopy has allowed for the precise quantification of geniposide in Gardeniae fructus.

Conclusion: This study has suggested using 1H NMR to quantify geniposide in Gardeniae fructus to be a viable alternative to HPLC-based methods, providing a suitable approach for quality control of Gardeniae fructus.

Keywords: Gardeniae fructus, proton nuclear magnetic resonance, geniposide, quantitative determination, validation, quality control.

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[1]
Chinese Pharmacopoeia Committee; Pharmacopoeia of the People's Republic of China; China Medical Science and Technology Press: Beijing, 2020, pp. 52-54.
[2]
Cao, Y.G.; Ren, Y.J.; Liu, Y.L.; Wang, M.N.; He, C.; Chen, X.; Fan, X.L.; Zhang, Y.L.; Hao, Z.Y.; Li, H.W.; Zheng, X.K.; Feng, W.S. Iridoid glycosides and lignans from the fruits of Gardenia jasminoides Eills. Phytochemistry, 2021, 190, 112893.
[http://dx.doi.org/10.1016/j.phytochem.2021.112893] [PMID: 34332297]
[3]
Chen, Q.C.; Zhang, W.Y.; Youn, U.; Kim, H.; Lee, I.; Jung, H.J.; Na, M.; Min, B.S.; Bae, K. Iridoid glycosides from Gardeniae Fructus for treatment of ankle sprain. Phytochemistry, 2009, 70(6), 779-784.
[http://dx.doi.org/10.1016/j.phytochem.2009.03.008] [PMID: 19368947]
[4]
Zhou, X.Q.; Bi, Z.M.; Li, P.; Tang, D.; Cai, H.X. A new iridoid glycoside from Gardenia jasminoides. Chin. Chem. Lett., 2007, 18(10), 1221-1223.
[http://dx.doi.org/10.1016/j.cclet.2007.08.019]
[5]
Yu, S.F.; Huang, X.J.; Fu, S.N.; Wu, C.; Ye, W.C.; Zhou, G.X. New Monoterpenoids from Fruits of Gardenia jasminoides var. radicans. Helv. Chim. Acta, 2015, 98(9), 1267-1272.
[http://dx.doi.org/10.1002/hlca.201500063]
[6]
Yang, L.; Peng, K.; Zhao, S.; Chen, L.; Qiu, F. Monoterpenoids from the fruit of Gardenia jasminoides Ellis (Rubiaceae). Biochem. Syst. Ecol., 2013, 50, 435-437.
[http://dx.doi.org/10.1016/j.bse.2013.06.012]
[7]
Wei-Min, Z.; Jun-Ping, X.; Guo-Wei, Q.; Ren-Sheng, X. Two monoterpenes from fruits of Gardenia jasminoides. Phytochemistry, 1994, 37(4), 1079-1081.
[http://dx.doi.org/10.1016/S0031-9422(00)89532-1]
[8]
Yu, Y.; Gao, H.; Dai, Y.; Xiao, G.K.; Zhu, H.J.; Yao, X.S. Guaiane-type sesquiterpenoid glucosides from Gardenia jasminoides Ellis. Magn. Reson. Chem., 2011, 49(5), 258-261.
[http://dx.doi.org/10.1002/mrc.2730] [PMID: 21491483]
[9]
Lu, D.; Zhang, W.; Jiang, Y.; Zhang, Y.; Pan, D.; Zhang, D.; Yao, X.; Yu, Y. Two new triterpenoids from Gardenia jasminoides fruits. Nat. Prod. Res., 2019, 33(19), 2789-2794.
[http://dx.doi.org/10.1080/14786419.2018.1502764] [PMID: 30518256]
[10]
Wang, J.; Lu, J.; Lv, C.; Xu, T.; Jia, L. Three new triterpenoid saponins from root of Gardenia jasminoides Ellis. Fitoterapia, 2012, 83(8), 1396-1401.
[http://dx.doi.org/10.1016/j.fitote.2012.07.004] [PMID: 22796399]
[11]
Wang, L.; Chen, S.; Liu, S.; Biu, A.M.; Han, Y.; Jin, X.; Liang, C.; Liu, Y.; Li, J.; Fang, S.; Chang, Y. A comprehensive review of ethnopharmacology, chemical constituents, pharmacological effects, pharmacokinetics, toxicology, and quality control of gardeniae fructus. J. Ethnopharmacol., 2024, 320, 117397.
[http://dx.doi.org/10.1016/j.jep.2023.117397] [PMID: 37956915]
[12]
Tian, J.; Qin, S.; Han, J.; Meng, J.; Liang, A. A review of the ethnopharmacology, phytochemistry, pharmacology and toxicology of Fructus Gardeniae (Zhi-zi). J. Ethnopharmacol., 2022, 289, 114984.
[http://dx.doi.org/10.1016/j.jep.2022.114984] [PMID: 35066066]
[13]
Liu, H.; Chen, Y.F.; Li, F.; Zhang, H.Y. Fructus Gardenia ( Gardenia jasminoides J. Ellis) phytochemistry, pharmacology of cardiovascular, and safety with the perspective of new drugs development. J. Asian Nat. Prod. Res., 2013, 15(1), 94-110.
[http://dx.doi.org/10.1080/10286020.2012.723203] [PMID: 23211013]
[14]
Kim, H.J.; Kim, E.J.; Seo, S.H.; Shin, C.G.; Jin, C.; Lee, Y.S. Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus. J. Nat. Prod., 2006, 69(4), 600-603.
[http://dx.doi.org/10.1021/np050447r] [PMID: 16643034]
[15]
Chen, L.; Li, M.; Yang, Z.; Tao, W.; Wang, P.; Tian, X.; Li, X.; Wang, W. Gardenia jasminoides Ellis: Ethnopharmacology, phytochemistry, and pharmacological and industrial applications of an important traditional Chinese medicine. J. Ethnopharmacol., 2020, 257, 112829.
[http://dx.doi.org/10.1016/j.jep.2020.112829] [PMID: 32311486]
[16]
Park, K.J.; Ha, H-C.; Kim, H-S.; Chiba, K.; Yeo, I-H.; Lee, S-Y. The neuroprotective and neurotrophic effects of Korean gardenia (Gardenia jasminoides Ellis) in PC12h cells. Food Sci. Biotechnol., 2006, 15, 735-738.
[17]
Hou, Z.; Sun, L.; Jiang, Z.; Zeng, T.; Wu, P.; Huang, J.; Liu, H.; Xiao, P. Neuropharmacological insights into Gardenia jasminoides Ellis: harnessing therapeutic potential for central nervous system disorders. Phytomedicine, 2024, 125, 155374.
[http://dx.doi.org/10.1016/j.phymed.2024.155374] [PMID: 38301302]
[18]
Hong, Y.J.; Yang, K.S. Anti-inflammatory activities of crocetin derivatives from processed Gardenia jasminoides. Arch. Pharm. Res., 2013, 36(8), 933-940.
[http://dx.doi.org/10.1007/s12272-013-0128-0] [PMID: 23636885]
[19]
Chen, S-c.; Zhao, X.; Yi, R-k.; Qian, J.; Shi, Y-h.; Wang, R. Anticancer effects of Gardenia jasminoides in HepG2 human hepatoma cells. BRI, 2017, 28, 716-726.
[20]
Chang, W.L.; Wang, H.Y.; Shi, L.S.; Lai, J.H.; Lin, H.C. Immunosuppressive iridoids from the fruits of Gardenia jasminoides. J. Nat. Prod., 2005, 68(11), 1683-1685.
[http://dx.doi.org/10.1021/np0580816] [PMID: 16309325]
[21]
Debnath, T.; Park, P.J.; Deb Nath, N.C.; Samad, N.B.; Park, H.W.; Lim, B.O. Antioxidant activity of Gardenia jasminoides Ellis fruit extracts. Food Chem., 2011, 128(3), 697-703.
[http://dx.doi.org/10.1016/j.foodchem.2011.03.090]
[22]
Lv, S.; Ding, Y.; Zhao, H.; Liu, S.; Zhang, J.; Wang, J. Therapeutic potential and effective components of the Chinese Herb Gardeniae Fructus in the treatment of Senile disease. Aging Dis., 2018, 9(6), 1153-1164.
[http://dx.doi.org/10.14336/AD.2018.0112] [PMID: 30574425]
[23]
Jin, C.; Zongo, A.W.S.; Du, H.; Lu, Y.; Yu, N.; Nie, X.; Ma, A.; Ye, Q.; Xiao, H.; Meng, X. Gardenia ( Gardenia jasminoides Ellis) fruit: A critical review of its functional nutrients, processing methods, health-promoting effects, comprehensive application and future tendencies. Crit. Rev. Food Sci. Nutr., 2023, 1-28.
[http://dx.doi.org/10.1080/10408398.2023.2270530] [PMID: 37882781]
[24]
Pyun, B.J.; Lee, J.Y.; Kim, Y.J.; Ji, K.Y.; Jung, D.H.; Park, K.S.; Jo, K.; Choi, S.; Jung, M.A.; Kim, Y.H.; Kim, T. Gardenia jasminoides Attenuates Allergic Rhinitis-induced inflammation by inhibiting Periostin production. Pharmaceuticals (Basel), 2021, 14(10), 986.
[http://dx.doi.org/10.3390/ph14100986] [PMID: 34681210]
[25]
Xu, J.; Zhou, R.; Luo, L.; Dai, Y.; Feng, Y.; Dou, Z.; Calokerinos, A.C. Quality evaluation of decoction pieces of Gardeniae Fructus based on qualitative analysis of the HPLC fingerprint and Triple-Q-TOF-MS/MS combined with quantitative analysis of 12 representative components. J. Anal. Methods Chem., 2022, 2022, 1-13.
[http://dx.doi.org/10.1155/2022/2219932] [PMID: 35256913]
[26]
Gao, Y.; Sun, Y.; Wang, Y.; Zhang, J.; Xu, B.; Zhang, H.; Song, D. A practical and rapid method for the simultaneous isolation, purification and quantification of geniposide from the fruit of Gardenia jasminoides Ellis by MSPD extraction and UFLC analysis. Anal. Methods, 2013, 5(16), 4112-4118.
[http://dx.doi.org/10.1039/c3ay40638e]
[27]
Bergonzi, M.C.; Righeschi, C.; Isacchi, B.; Bilia, A.R. Identification and quantification of constituents of Gardenia jasminoides Ellis (Zhizi) by HPLC-DAD–ESI–MS. Food Chem., 2012, 134(2), 1199-1204.
[http://dx.doi.org/10.1016/j.foodchem.2012.02.157] [PMID: 23107748]
[28]
Geng, T.; Wang, G.; Ma, X.; Zhang, Z.; Liu, T.; Ge, Y.; Jin, J.; Sun, X.; Zhang, Y.; Yang, D.; Ma, M. Discovery of tryptamine derivatives from Bacillus sp. PKU-TA00001. J. Chin. Pharm. Sci., 2019, 28(8), 527-536.
[http://dx.doi.org/10.5246/jcps.2019.08.050]
[29]
Xiaolu, Y.; Xue, X.; Lin, Y.; Huang, Q.; Mo, M.; Wang, S.; Meng, J. Chemical constituents from the Moutan Cortex charcoal and their potential coagulation activities. J. Chin. Pharm. Sci., 2018, 27(9), 608-616.
[http://dx.doi.org/10.5246/jcps.2018.09.062]
[30]
Dona, A.C.; Kyriakides, M.; Scott, F.; Shephard, E.A.; Varshavi, D.; Veselkov, K.; Everett, J.R. A guide to the identification of metabolites in NMR-based metabonomics/metabolomics experiments Comput Struct Biotechnol J, 2016, 14, 135-153.
[http://dx.doi.org/10.1016/j.csbj.2016.02.005]
[31]
Zhou, J.; Yin, Y. Strategies for large-scale targeted metabolomics quantification by liquid chromatography-mass spectrometry. Analyst (Lond.), 2016, 141(23), 6362-6373.
[http://dx.doi.org/10.1039/C6AN01753C] [PMID: 27722450]
[32]
Tanaka, R.; Inagaki, R.; Sugimoto, N.; Akiyama, H.; Nagatsu, A. Application of a quantitative 1H-NMR (1H-qNMR) method for the determination of geniposidic acid and acteoside in Plantaginis semen. J. Nat. Med., 2017, 71(1), 315-320.
[http://dx.doi.org/10.1007/s11418-016-1040-y] [PMID: 27631429]
[33]
Dong, J.W.; Li, X.J.; Cai, L.; Shi, J.Y.; Li, Y.F.; Yang, C.; Li, Z.J. Simultaneous determination of alkaloids dicentrine and sinomenine in Stephania epigeae by 1H NMR spectroscopy. J. Pharm. Biomed. Anal., 2018, 160, 330-335.
[http://dx.doi.org/10.1016/j.jpba.2018.08.007] [PMID: 30114611]
[34]
Li, X.J.; Dong, J.W.; Liu, Z.F.; Shi, J.Y.; Zhang, F.M.; Fa, Y.M.; Li, Y.L.; Wang, X.X. Application of a quantitative proton nuclear magnetic resonance method for the determination of protopine in Radix Dactylicapnotis. Curr. Pharm. Anal., 2023, 19(7), 527-532.
[http://dx.doi.org/10.2174/1573412919666230823144117]
[35]
Beyer, T.; Schollmayer, C.; Holzgrabe, U. The role of solvents in the signal separation for quantitative 1H NMR spectroscopy. J. Pharm. Biomed. Anal., 2010, 52(1), 51-58.
[http://dx.doi.org/10.1016/j.jpba.2009.12.007] [PMID: 20060676]
[36]
Bharti, S.K.; Roy, R. Quantitative 1H NMR spectroscopy. Trends Analyt. Chem., 2012, 35, 5-26.
[http://dx.doi.org/10.1016/j.trac.2012.02.007]

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