Rapid Determination of Ginkgolic Acids in Ginkgo biloba Leaf Using Online Column Switching High-Performance Liquid Chromatography-Diode Array Detection and Confirmation by Liquid Chromatography-tandem Mass Spectrometry

Lee, Hyounyoung; Lim, Heung-Youl; Yang, Juhong; Hong, Jongki

doi:10.5012/bkcs.2013.34.12.3629

Cited by 12 publications

(11 citation statements)

References 24 publications

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“…Numerous techniques exist for ginkgolic acid detection in Ginkgo biloba or its extracts, including on-line mass spectrometry [23], high performance liquid chromatography (HPLC) [24,25], and UPLC-MS/MS [26]. In our study, Raman spectroscopy, chosen for its rapid and non-destructive traits, stands out.…”

Section: Discussionmentioning

confidence: 99%

The Rapid Determination of Three Toxic Ginkgolic Acids in the Decolorized Process of Ginkgo Ketone Ester Based on Raman Spectroscopy and ResNeXt50 Deep Neural Network

Liu,

Jiang,

Wang

et al. 2023

Chemosensors

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The decolorization process plays a pivotal role in refining Ginkgo ketone ester by primarily eliminating ginkgolic acids, a toxic component. Presently, the conventional testing method involves sending samples for analysis, causing delays that impact formulation production. Hence, the development of a rapid process control method becomes imperative. This study introduces a swift detection approach for three ginkgolic acids during Ginkgo ketone ester’s decolorization. Initially, an ultra-high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method assessed ginkgolic acid C13:0, ginkgolic acid C15:1, and ginkgolic acid C17:1 concentrations in 91 decolorized solution samples, establishing reference values. Subsequently, using a portable Raman spectrometer, Raman spectra of the decolorized liquid within the 3200–200 cm−1 wavelength range were collected. Ultimately, employing partial least squares regression (PLSR) and ResNeXt50 deep learning algorithms, two quantitative calibration models correlated the ginkgolic acid content to Raman spectral data. Both models exhibited high predictive accuracy, with the ResNeXt50 model demonstrating superior performance. The prediction set correlation coefficients (Rp2) for ginkgolic acid C13:0, ginkgolic acid C15:1, and ginkgolic acid C17:1 were 0.9962, 0.9971, and 0.9974, respectively, with root mean square error of prediction (RMSEP) values of 0.0144, 0.0130, and 0.0122 μg/mL. In contrast, the PLSR model yielded Rp2 values of 0.9862, 0.9839, and 0.9480, with RMSEP values of 0.0273, 0.0305, and 0.0545 μg/mL for the three ginkgolic acids. The ResNeXt50 model not only showcased higher precision but also enhanced interpretability, as analyzed through gradient-weighted class activation mapping (Grad-CAM). The integration of Raman spectroscopy and the ResNeXt50 quantitative calibration model furnishes a real-time and precise approach to monitor ginkgolic acid content in the decolorized solution during Ginkgo ketone ester preparation. This significant advancement establishes a robust framework for implementing quality control measures in the decolorization process.

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Section: Discussionmentioning

confidence: 99%

The Rapid Determination of Three Toxic Ginkgolic Acids in the Decolorized Process of Ginkgo Ketone Ester Based on Raman Spectroscopy and ResNeXt50 Deep Neural Network

Liu,

Jiang,

Wang

et al. 2023

Chemosensors

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“…It can be seen that when the concentration of the standard GA was the same, the response value measured using the European Pharmacopoeia was much higher than the response value measured using the Chinese Pharmacopoeia. This is because 210 nm was the strong absorption of the phenyl ring of GA, and its intensity was much higher than 310 nm [23]. The absorption of the carboxyl group on the phenyl ring of GA was at 210 nm, and the detection sensitivity was higher.…”

Section: Comparison Of Ga Detection Methods Between European Pharmaco...mentioning

confidence: 97%

“…Figure S1A,C show five sharp, symmetrical absorption peaks for GA, with consistent retention times. Since the benzene ring of ginkgolic acid has strong absorption at 210 nm, its absorption intensity is much higher than that of the carboxyl group on the benzene ring at 310 nm [23]. Therefore, the response value in Figure S1C is ~10× that in Figure S1A (regarding peak height).…”

Section: Selection Of Wavelength For Detecting Ginkgol and Gamentioning

confidence: 93%

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Development, Validation, and Application of High-Performance Liquid Chromatography with Diode-Array Detection Method for Simultaneous Determination of Ginkgolic Acids and Ginkgols in Ginkgo biloba

Boateng,

Li,

Yang

2024

Foods

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Ginkgo biloba leaves (GBLs), which comprise many phytoconstituents, also contain a toxic substance named ginkgolic acid (GA). Our previous research showed that heating could decarboxylate and degrade GA into ginkgols with high levels of bioactivity. Several methods are available to measure GA in GBLs, but no analytical method has been developed to measure ginkgols and GA simultaneously. Hence, for the first time, an HPLC-DAD method was established to simultaneously determine GA and ginkgols using acetonitrile (0.01% trifluoroacetic acid, v/v) as mobile phase A and water (0.01% trifluoroacetic acid, v/v) as mobile phase B. The gradient elution conditions were: 0–30 min, 75–90% phase A; 30–35 min, 90–90% phase A; 35–36 min, 90–75% phase A; 36–46 min, 75–75% phase A. The detection wavelength of GA and ginkgol were 210 and 270 nm, respectively. The flow rate and injection volume were 1.0 mL/min and 50 μL, respectively. The linearity was excellent (R2 > 0.999), and the RSD of the precision, stability, and repeatability of the total ginkgols was 0.20%, 2.21%, and 2.45%, respectively, in six parallel determinations. The recoveries for the low, medium, and high groups were 96.58%, 97.67%, and 101.52%, respectively. The limit of detection of ginkgol C13:0, C15:1, and C17:1 was 0.61 ppm, 0.50 ppm, and 0.06 ppm, respectively. The limit of quantification of ginkgol C13:0, C15:1, and C17:1 was 2.01 ppm, 1.65 ppm, and 0.20 ppm, respectively. Finally, this method accurately measured the GA and ginkgol content in ginkgo leaves and ginkgo tea products (ginkgo black tea, ginkgo dark tea, ginkgo white tea, and ginkgo green tea), whereas principal component analysis (PCA) was performed to help visualize the association between GA and ginkgols and five different processing methods for GBLs. Thus, this research provides an efficient and accurate quantitative method for the subsequent detection of GA and ginkgols in ginkgo tea.

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“…20 The major problem with HPLC techniques is the inadequate resolution of GAs differing by carbon number and unsaturation, such as C13:0 and C15:1 or C15:0 and C17:1, as well as the inability to resolve double bond positional isomers. Lee et al 21 used column switching (heart cutting) to minimize matrix effects and improve resolution. The method was validated, and the LOD and LOQ for the C15:1 and C17:1 GAs were 10 and 40 ppb with a diode array detector.…”

Section: ■ Introductionmentioning

confidence: 99%

High-Resolution Gas Chromatography/Mass Spectrometry Method for Characterization and Quantitative Analysis of Ginkgolic Acids in Ginkgo biloba Plants, Extracts, and Dietary Supplements

Wang¹,

Zhao²,

Avula³

et al. 2014

J. Agric. Food Chem.

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A high-resolution gas chromatography/mass spectrometry (GC/MS) with selected ion monitor method focusing on the characterization and quantitative analysis of ginkgolic acids (GAs) in Ginkgo biloba L. plant materials, extracts, and commercial products was developed and validated. The method involved sample extraction with (1:1) methanol and 10% formic acid, liquid-liquid extraction with n-hexane, and derivatization with trimethylsulfonium hydroxide (TMSH). Separation of two saturated (C13:0 and C15:0) and six unsaturated ginkgolic acid methyl esters with different positional double bonds (C15:1 Δ8 and Δ10, C17:1 Δ8, Δ10, and Δ12, and C17:2) was achieved on a very polar (88% cyanopropyl) aryl-polysiloxane HP-88 capillary GC column. The double bond positions in the GAs were determined by ozonolysis. The developed GC/MS method was validated according to ICH guidelines, and the quantitation results were verified by comparison with a standard high-performance liquid chromatography method. Nineteen G. biloba authenticated and commercial plant samples and 21 dietary supplements purported to contain G. biloba leaf extracts were analyzed. Finally, the presence of the marker compounds, terpene trilactones and flavonol glycosides for Ginkgo biloba in the dietary supplements was determined by UHPLC/MS and used to confirm the presence of G. biloba leaf extracts in all of the botanical dietary supplements.

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Rapid Determination of Ginkgolic Acids in Ginkgo biloba Leaf Using Online Column Switching High-Performance Liquid Chromatography-Diode Array Detection and Confirmation by Liquid Chromatography-tandem Mass Spectrometry

Cited by 12 publications

References 24 publications

The Rapid Determination of Three Toxic Ginkgolic Acids in the Decolorized Process of Ginkgo Ketone Ester Based on Raman Spectroscopy and ResNeXt50 Deep Neural Network

The Rapid Determination of Three Toxic Ginkgolic Acids in the Decolorized Process of Ginkgo Ketone Ester Based on Raman Spectroscopy and ResNeXt50 Deep Neural Network

Development, Validation, and Application of High-Performance Liquid Chromatography with Diode-Array Detection Method for Simultaneous Determination of Ginkgolic Acids and Ginkgols in Ginkgo biloba

High-Resolution Gas Chromatography/Mass Spectrometry Method for Characterization and Quantitative Analysis of Ginkgolic Acids in Ginkgo biloba Plants, Extracts, and Dietary Supplements

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