Quantification of terpene trilactones in Ginkgo biloba with a 1H NMR method
Tóm tắt
Ginkgo biloba L. has been used as a herbal medicine in the traditional treatment of insufficient blood flow, memory deficits, and cerebral insufficiency. The terpene trilactone components, the bioactive agents of Ginkgo biloba L., have also been reported to exhibit useful functionality such as anti-inflammatory and neuroprotective effects. Therefore, in the present research, we attempted to analyze quantitatively the terpene trilactone components in Ginkgo biloba leaf extract, with quantitative 1H NMR (qNMR) and obtained almost identical results to data reported using HPLC. Application of the qNMR method for the analysis of the terpene trilactone contents in commercial Ginkgo extract products, such as soft gel capsules and tablets, produced the same levels noted in package labels. Thus, qNMR is an alternative method for quantification of the terpene trilactone components in commercial Ginkgo extract products.
Tài liệu tham khảo
Leistner E, Drewke C (2010) Ginkgo biloba and ginkgotoxin. J Nat Prod 73:86–92
Pharmacopoeia Commission of the People’s Republic of China (2015) Pharmacopoeia of the People’s Republic of China. China Medical Science and Technology Press, Beijing, p 316
Mullaicharam A (2013) A review on evidence based practice of Ginkgo biloba in brain health. Int J Chem Pharm Anal 1:24–30
Burns NR, Bryan J, Nettelbeck T (2006) Ginkgo biloba: no robust effect on cognitive abilities or mood in healthy young or older adults. Hum Psychopharmacol 21:27–37
Hashiguchi M, Ohta Y, Shimizu M, Maruyama J, Mochizuki M (2015) Meta-analysis of the efficacy and safety of Ginkgo biloba extract for the treatment of dementia. J Pharm Health Care Sci. https://doi.org/10.1186/s40780-015-0014-7
Nishida S, Satoh H (2004) Comparative vasodilating actions among terpenoids and flavonoids contained in Ginkgo biloba extract. Clin Chim Acta 339:129–133
Li Y, Wu Y, Yao X, Hao F, Yu C, Bao Y, Wu Y, Song Z, Sun Y, Zheng L, Wang G, Huang Y, Sun Y, Li Y (2017) Ginkgolide A ameliorates LPS-induced inflammatory responses in vitro and in vivo. Int J Mol Sci 18:794. https://doi.org/10.3390/ijms18040794
Wu F, Shi W, Zhou G, Yao H, Xu C, Xiao W, Wu J, Wu X (2016) Ginkgolide B functions as a determinant constituent of Ginkgolides in alleviating lipopolysaccharide-induced lung injury. Biomed Pharmacother 81:71–78
Liou CJ, Lai XY, Chen YL, Wang CL, Wei CH, Huang WC (2015) Ginkgolide C suppresses adipogenesis in 3T3-L1 adipocytes via the AMPK signaling pathway. Evid Based Complement Altern Med. https://doi.org/10.1155/2015/298635
Chandrasekaran K, Mehrabian Z, Spinnewyn B, Drieu K, Fiskum G (2001) Neuroprotective effects of bilobalide, a component of the Ginkgo biloba extract (EGb 761), in gerbil global brain ischemia. Brain Res 922:282–292
van Beek TA (2005) Ginkgolides and bilobalide: their physical, chromatographic and spectroscopic properties. Bioorg Med Chem 13:5001–5012
van Beek TA, Lelyveld GP (1992) Concentration of ginkgolides and bilobalide in Ginkgo biloba leaves in relation to the time of year. Planta Med 58:413–416
van Beek TA, Montoro P (2009) Chemical analysis and quality control of Ginkgo biloba leaves, extracts, and phytopharmaceuticals. J Chromatogr A 1216:2002–2032
Croom E, Pace R, Paletti A, Sardone N, Gray D (2007) Single-laboratory validation for the determination of terpene lactones in Ginkgo biloba dietary supplement crude materials and finished products by high-performance liquid chromatography with evaporative light-scattering detection. J AOAC Int 90:647–658
López-Gutiérrez N, Romero-González R, Martínez Vidal JL, Garrido Frenich A (2016) Quality control evaluation of nutraceutical products from Ginkgo biloba using liquid chromatography coupled to high resolution mass spectrometry. J Pharm Biomed Anal 121:151–160
Krzek J, Czekaj JS, Rzeszutko W, Ekiert RJ (2007) Validation of capillary gas chromatographic method for determination of bilobalide and ginkgolides A, B, C in Ginkgo biloba dry and liquid extracts. Acta Pol Pharm 64:303–310
Carrier DJ, Chauret N, Mancini M, Coulombe P, Neufeld R, Weber M, Archambault J (1991) Detection of ginkgolide A in Ginkgo biloba cell cultures. Plant Cell Rep 10:256–259
Wei F, Furihata K, Miyakawa T, Tanokura M (2014) A pilot study of NMR-based sensory prediction of roasted coffee bean extracts. Food Chem 152:363–369
Kodani Y, Miyakawa T, Komatsu T, Tanokura M (2017) NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep 7:1297
Wei F, Furihata K, Zhang M, Miyakawa T, Tanokura M (2016) Use of NMR-based metabolomics to chemically characterize the roasting process of chicory root. J Agric Food Chem 64:6459–6465
Agnolet S, Jaroszewski JW, Verpoorte R, Staerk D (2010) H NMR-based metabolomics combined with HPLC-PDA-MS-SPE-NMR for investigation of standardized Ginkgo biloba preparations. Metabolomics 6:292–302
Liang T, Wei F, Lu Y, Kodani Y, Nakada M, Miyakawa T, Tanokura M (2015) Comprehensive NMR analysis of compositional changes of black garlic during thermal processing. J Agric Food Chem 63:683–691
Hu F, Furihata K, Kato Y, Tanokura M (2007) Nondestructive quantification of organic compounds in whole milk without pretreatment by two-dimensional NMR spectroscopy. J Agric Food Chem 55:4307–4311
Choi YH, Choi HK, Hazekamp A, Bermejo P, Schilder Y, Erkelens C, Verpoorte R (2003) Quantitative analysis of bilobalide and ginkgolides from Ginkgo biloba leaves and Ginkgo products using (1)H-NMR. Chem Pharm Bull (Tokyo) 51:158–161
Li CY, Lin CH, Wu CC, Lee KH, Wu TS (2004) Efficient 1H nuclear magnetic resonance method for improved quality control analyses of Ginkgo constituents. J Agric Food Chem 52:3721–3725
Napolitano JG, Gödecke T, Rodríguez-Brasco MF, Jaki BU, Chen SN, Lankin DC, Pauli GF (2012) The tandem of full spin analysis and qHNMR for the quality control of botanicals exemplified with Ginkgo biloba. J Nat Prod 75:238–248
Japan Health Food & Nutrition Food Association (2009) Quality specification and standard for health food: Ginkgo biloba extract (unpublished)
Pauli GF, Chen SN, Simmler C, Lankin DC, Gödecke T, Jaki BU, Friesen JB, McAlpine JB, Napolitano JG (2014) Importance of purity evaluation and the potential of quantitative 1H NMR as a purity assay. J Med Chem 57:9220–9231
Nishizaki Y, Tada A, Ishizuki K, Ito Y, Onoda A, Sugimoto N, Akiyama H (2015) Development of a novel method for quantifying quassin and neoquassin in Jamaica quassia extracts using the molar absorption coefficient ratio. Shokuhin Eiseigaku Zasshi 56:185–193
Tanaka R, Inagaki R, Sugimoto N, Akiyama H, Nagatsu A (2017) Application of a quantitative 1H-NMR (1H-qNMR) method for the determination of geniposidic acid and acteoside in Plantaginis semen. J Nat Med 71:315–320
Wei F, Furihata K, Koda M, Hu F, Miyakawa T, Tanokura M (2012) Roasting process of coffee beans as studied by nuclear magnetic resonance: time course of changes in composition. J Agric Food Chem 60:1005–1012