Quantitative GC-FID and UHPLC-DAD Evaluation of Bioactive Compounds Extracted from Ginkgo biloba

Page: [893 - 904] Pages: 12

  • * (Excluding Mailing and Handling)

Abstract

Background: The official compendium of the quantification of ginkgo flavonoids from Ginkgo biloba extract has been proposed using HPLC. The drawbacks of this technique appear to be due to the restricted efficiency in terms of the recovery results and suitability of the system for the quantification of these compounds. This study investigated the potential advantages and limitations of the development of efficient extraction methods for the recovery of flavonol glycosides (quercetin, kaempferol and isorhamnetin) and terpene trilactones (bilobalide, ginkgolide A, ginkgolide B and ginkgolide C) using extraction, quantification and detection techniques, namely, GC-FID and UHPLC-DAD, which are alternatives to those techniques available in the literature.

Methods: Two different extraction methodologies have been developed for the determination of flavonoids (quercetin, kaempferol and isorhamnetin) and terpene trilactones (bilobalide, ginkgolide A, ginkgolide B and ginkgolide C) using ultra-high-pressure liquid chromatography coupled to a diode array detector and gas chromatography coupled to a flame ionization detector.

Results: In this study, the Ginkgo biloba extract mass, hydrolysis preparation method (with or without reflux), and volume of the extraction solution seemed to affect the ginkgo flavonoid recovery. The UHPLC-based method exhibited higher extraction efficiency for ginkgo flavonoid quantification compared to the pharmacopoeial method. The developed method exhibited higher extraction efficiency for terpene quantification compared to the previous method that used extractive solution without pH adjustment, with less time of extraction and less amount of the sample and organic solvent aliquots.

Conclusion: The UHPLC and GC analysis methods established in this study are both effective and efficient. These methods may improve the quality control procedures for ginkgo extract and commercial products available in today´s natural health product market. The results indicate that redeveloped extraction methods can be a viable alternative to traditional extraction methods.

Keywords: Extraction, flavonoids, Ginkgo biloba, terpene trilactones, UHPLC, bioactive compounds.

Graphical Abstract

[1]
Guidelines for the appropriate use of herbal medicines. (WHOWPRO). 1998.Available from:. http://apps.who.int/medicinedocs/en/d/Jh2945e/ (Accessed May 19, 2019)
[2]
Liu, X.G.; Yang, H.; Cheng, X.L.; Liu, L.; Qin, Y.; Wang, Q.; Qi, L-W.; Li, P. Direct analysis of 18 flavonol glycosides, aglycones and terpene trilactones in Ginkgo biloba tablets by matrix solid phase dispersion coupled with ultra-high performance liquid chromatography tandem triple quadrupole mass spectrometry. J. Pharm. Biomed. Anal., 2014, 97, 123-128.
[http://dx.doi.org/10.1016/j.jpba.2014.04.027] [PMID: 24876067]
[3]
Walkoviak, A.; Ledziński, Ł.; Zapadka, M.; Kupcewicz, B. Detection of adulterants in dietary supplements with Gingko biloba extract by attenuated total reflectance Fourier transform infrared spectroscopy and multivariate methods PLS-DA and PCA. Spectrochim. Acta - Part A. Mol. and Biomol. Spec., 2019, 208, 222-228.
[http://dx.doi.org/10.1016/j.saa.2018.10.008]
[4]
Li, B.; Neumann, E.K.; Ge, J.; Gao, W.; Yang, H.; Li, P.; Sweedler, J.V. Interrogation of spatial metabolome of Ginkgo biloba with high-resolution matrix-assisted laser desorption/ionization and laser desorption/ionization mass spectrometry imaging. Plant Cell Environ., 2018, 41(11), 2693-2703.
[http://dx.doi.org/10.1111/pce.13395] [PMID: 29966033]
[5]
Hosseini, S.; Imenshahidi, M.; Hosseinzadeh, H.; Karimi, G. Effects of plant extracts and bioactive compounds on attenuation of bleomycin-induced pulmonary fibrosis. Biomed. Pharmacother., 2018, 107, 1454-1465.
[http://dx.doi.org/10.1016/j.biopha.2018.08.111] [PMID: 30257362]
[6]
Cao, J.; Chen, L.; Li, M.; Cao, F.; Zhao, L.; Su, E. Efficient extraction of proanthocyanidin from Ginkgo biloba leaves employing rationally designed deep eutectic solvent-water mixture and evaluation of the antioxidant activity. J. Pharm. Biomed. Anal., 2018, 158, 317-326.
[http://dx.doi.org/10.1016/j.jpba.2018.06.007] [PMID: 29913356]
[7]
Shan, S-J.; Zhang, P.P.; Luo, J.; Kong, L-Y. Two new phenolic glycosides isolated from Ginkgo seeds. Chin. J. Nat. Med., 2018, 16(7), 505-508.
[http://dx.doi.org/10.1016/S1875-5364(18)30086-4] [PMID: 30080649]
[8]
Gunawardena, D.; Govindaraghavan, S.; Münch, G. Anti-inflammatory properties of cinnamon polyphenols and their monomeric precursors. Polyphenol. Human Health Dis., 2014, 1, 409-425.
[http://dx.doi.org/10.1016/B978-0-12-398456-2.00030-X]
[9]
Ma, Y.C.; Mani, A.; Cai, Y.; Thomson, J.; Ma, J.; Peudru, F.; Chen, S.; Luo, M.; Zhang, J.; Chapman, R.G.; Shi, Z-T. An effective identification and quantification method for Ginkgo biloba flavonol glycosides with targeted evaluation of adulterated products. Phytomedicine, 2016, 23(4), 377-387.
[http://dx.doi.org/10.1016/j.phymed.2016.02.003] [PMID: 27002408]
[10]
Yang, J.; Wang, A-Q.; Li, X-J.; Fan, X.; Yin, S-S.; Lan, K. A chemical profiling strategy for semi-quantitative analysis of flavonoids in Ginkgo extracts. J. Pharm. Biomed. Anal., 2016, 123, 147-154.
[http://dx.doi.org/10.1016/j.jpba.2016.02.017] [PMID: 26907698]
[11]
Jemmali, Z.; Chartier, A.; Dufresne, C.; Elfakir, C. Optimization of the derivatization protocol of pentacyclic triterpenes prior to their gas chromatography-mass spectrometry analysis in plant extracts. Talanta, 2016, 147, 35-43.
[http://dx.doi.org/10.1016/j.talanta.2015.09.026] [PMID: 26592573]
[12]
Powdered Ginkgo Extract, U.S.P. United States Pharmacopeia, 2014.https://www.uspnf.com/official-text/proposal-statuscomment ary/usp-37-nf-32
[13]
Stephan, S.; Jakob, C.; Hippler, J.; Schmitz, O.J. A novel four-dimensional analytical approach for analysis of complex samples. Anal. Bioanal. Chem., 2016, 408(14), 3751-3759.
[http://dx.doi.org/10.1007/s00216-016-9460-9] [PMID: 27038056]
[14]
Li, K.L.; Sheu, J.S. Determination of flavonoids and alkaloids in the scute-coptis herb couple by capillary electrophoresis. Anal. Chim. Acta, 1995, 313, 113-120.
[http://dx.doi.org/10.1016/0003-2670(95)00190-B]
[15]
Xu, X.; Yu, L.; Chen, G. Determination of flavonoids in Portulaca oleracea L. by capillary electrophoresis with electrochemical detection. J. Pharm. Biomed. Anal., 2006, 41(2), 493-499.
[http://dx.doi.org/10.1016/j.jpba.2006.01.013] [PMID: 16516429]
[16]
Careri, M.; Elviri, L.; Mangia, A.; Musci, M. Spectrophotometric and coulometric detection in the high-performance liquid chromatography of flavonoids and optimization of sample treatment for the determination of quercetin in orange juice. J. Chromatogr. A, 2000, 881(1-2), 449-460.
[http://dx.doi.org/10.1016/S0021-9673(00)00256-9] [PMID: 10905727]
[17]
Wang, L.T.; Fan, X.H.; Jian, Y.; Dong, M.Z.; Yang, Q.; Meng, D.; Fu, Y.J. A sensitive and selective multiple reaction monitoring mass spectrometry method for simultaneous quantification of flavonol glycoside, terpene lactones, and biflavonoids in Ginkgo biloba leaves. J. Pharm. Biomed. Anal., 2019, 170, 335-340.
[http://dx.doi.org/10.1016/j.jpba.2019.03.058] [PMID: 30986686]
[18]
Krzymiński, K.K.; Roshal, A.D.; Rudnicki-Velasquez, P.B.; Żamojć, K. On the use of acridinium indicators for the chemiluminescent determination of the total antioxidant capacity of dietary supplements. Luminescence, 2019, 34(5), 512-519.
[http://dx.doi.org/10.1002/bio.3629] [PMID: 30972942]
[19]
Zhou, W.; Yang, Z.; Huang, S.; Fang, Z.; Chen, B.; Ma, M. Rapid quantitative analysis of ginkgo flavonoids using paper spray mass spectrometry. J. Pharm. Biomed. Anal., 2019, 171, 158-163.
[http://dx.doi.org/10.1016/j.jpba.2019.04.018] [PMID: 30999226]
[20]
Wu, H.; Guo, J.; Chen, S.; Liu, X.; Zhou, Y.; Zhang, X.; Xu, X. Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography-mass spectrometry. J. Pharm. Biomed. Anal., 2013, 72, 267-291.
[http://dx.doi.org/10.1016/j.jpba.2012.09.004] [PMID: 23031576]
[21]
Le, V.N.H.; Lee, W.; Kima, Y.H.; Chaea, G.H.; Chinc, Y-W.; Kima, K.T.; Kanga, J.S. High-performance liquid chromatography method development for the quality control of Ginkgonis Semen. Arab. J. Chem., 2017, 10, 792-800.
[http://dx.doi.org/10.1016/j.arabjc.2016.10.007]
[22]
van Beek, T.A.; Montoro, P. Chemical analysis and quality control of Ginkgo biloba leaves, extracts, and phytopharmaceuticals. J. Chromatogr. A, 2009, 1216(11), 2002-2032.
[http://dx.doi.org/10.1016/j.chroma.2009.01.013] [PMID: 19195661]
[23]
Rostagno, M.A.; Villares, A.; Guillamón, E.; García-Lafuente, A.; Martínez, J.A. Sample preparation for the analysis of isoflavones from soybeans and soy foods. J. Chromatogr. A, 2009, 1216(1), 2-29.
[http://dx.doi.org/10.1016/j.chroma.2008.11.035] [PMID: 19041977]