JOURNAL OF SEPARATION SCIENCE
·
2017
·Vol. 40
·期 24
·4857-4864
·
IF 2.557
Zhongping Huang,Yueting Xu,Yilei Huang,Charles Liu,Kezhi Jiang,Lili Wang
A novel method based on direct analysis in real time integrated with mass spectrometry was established and applied into rapid determination of ginkgolic acids in Ginkgo biloba kernels and leaves. Instrument parameter settings were optimized to obtain the sensitive and accurate determination of ginkgolic acids. At the sample introduction speed of 0.2 mm/s, high intensity of [M–H] – ions for ginkgolic acids were observed in the negative ion mode by utilization of high-purity helium gas at 450°C. Two microliters of methanol extract of G. biloba kernels or leaves dropped on the surface of Quick-Strip module was analyzed after solvent evaporated to dryness. A series of standard solutions of ginkgolic acid 13:0 in the range of 2–50 mg/L were analyzed with a correlation coefficient r = 0.9981 and relative standard deviation ( n = 5) from 12.5 to 13.7%. The limit of detection was 0.5 mg/L. The results of direct analysis in real time-mass spectrometry were in agreement with those observed by thermochemolysis gas chromatography. The proposed method demonstrated significant potential in the application of the high-throughput screening and rapid analysis for ginkgolic acids in dietary supplements.
研究领域:
分析化学
·
植物化学
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2013
·
IF 2.906
Yuanqing Fu,Shan Hong,Duo Li,Songbai Liu
A novel efficient synthesis of ginkgolic acid (13:0) from abundant 2,6-dihydroxybenzoic acid was successfully developed through a state-of-the-art palladium-catalyzed cross-coupling reaction and catalytic hydrogenation with an overall yield of 34% in five steps. The identity of the synthesized ginkgolic acid (13:0) was confirmed by nuclear magnetic resonance, mass spectrometry, infrared, and high-performance liquid chromatography. The reaction sequence of this method can be readily extended to the synthesis of other ginkgolic acids. The synthesized ginkgolic acid (13:0) exhibited promising anti-tyrosinase activity (IC50 = 2.8 mg/mL) that was not correlated to antioxidant activity as probed by 1,1-diphenyl-2-picrylhydrazyl, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), ferric reducing ability of plasma, and oxygen radical absorbance capacity assays. The synthetic strategy developed in this work will significantly facilitate biological studies of ginkgolic acids that have great potential applications in food and pharmaceuticals.
研究领域:
有机化学
·
药物化学
·
食品科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY A
·
2014
·
IF 4.258
Wenhua Ji,Xiuli Ma,Hongkai Xie,Lingxiao Chen,Xiao Wang,Hengqiang Zhao,Luqi Huang
Dummy molecularly imprinted polymers (DMIPs) for simultaneously selective removal and enrichment of ginkgolic acids (GAs) during the processing of Ginkgo biloba leaves have been prepared. Two dummy template molecule with similar structural skeleton to GAs, 6-methoxysalicylic acid (MOSA, DT-1) and 6-hexadecyloxysalicylic acid (HOSA, DT-2), have been designed and synthesized. The performance of the DMIPs and NIPs were evaluated including selective recognition capacity, adsorption isotherm, and adsorption kinetics. The selective recognition capacity of the three GAs with four analogues on the sorbents illustrated that the DMIPs sorbents have high specificity for GAs. An efficient method based on DMIP-HOSA coupled with solid-phase extraction (SPE) was developed for simultaneously selective removal and enrichment of ginkgolic acids (GAs) during the processing of Ginkgo biloba leaves. The method showed excellent recoveries (82.5–88.7%) and precision (RSD 0.5–2.6%, n = 5) for licorice extracts, Gastrodia elata extracts and pepper extracts spiked at three concentration levels each (50, 100, 200 μg mL −1 ). The results indicated that GAs and standardized Ginkgo biloba leaves extracts could be obtained simultaneously through the DMIP-SPE.
研究领域:
植物化学
·
药物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
·
2023
·
IF 6
Qihui Dong,Huimin Wang,Rong Wu,Jun Cao,Fuliang Cao,Erzheng Su
For the quantification of ginkgolic acids (GAs) within ginkgo products, a very effective liquid–liquid microextraction pretreatment method based on hydrophobic deep eutectic solvent (HDES) was created. The HPLC detection conditions for GAs were optimized before establishing the pretreatment method. Then, the DES composition, DES volume, sample amount, extraction temperature and time were investigated to obtain the optimal pretreatment conditions. This developed method had satisfactory analytical performance, the linearity was r 2 = 0.9997, and its low limit of detection (LOD) was 0.81 mg/kg. The recovery value ranged from 95.10 % to 98.75 %. When compared with the Ch.P.2010 and EP10.0 recommended methods, this developed method gave a higher efficiency and showed obvious advantages. Furthermore, the developed method was effectively used to identify GAs in a variety of Ginkgo biloba medications, Ginkgo biloba leaves from various cultivars and collection times. These results highlighted the superiorities of the HDES-based liquid–liquid microextraction pretreatment technique for the measurement of GAs, providing insights for future development of efficient methods in active ingredients analysis.
研究领域:
分析化学
·
药学
✓ 已验证
产品关联
DOI
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2018
·
IF 3.141
Huijiao Yan,Long Chen,Aiying Bai,Hengqiang Zhao,Meng Kong,Li Cui
Ginkgolic acids (GAs), bioactive compounds found in Ginkgo biloba L., have received much attention in pharmacological research. Separation of individual GAs from their mixtures is, however, difficult. Herein, an efficient method for the preparative separation of five major GAs from the sarcotesta of Ginkgo biloba L. was developed using β-cyclodextrin (β-CD) clathration coupled with pH-zone-refining countercurrent chromatography (PZRCCC) and recycling CCC. Clathration by β-CD was employed to enhance the hydrophilicity of the GAs. Separation of β-CD-GA clathrates was achieved by PZRCCC using a two-phase solvent system composed of n-heptane–ethyl acetate–methanol–water (2:1:1.5:1, v/v). The upper phase was acidified with 40 mM HCl (stationary phase), and the lower phase was made alkaline with 5 mM triethylamine. Three GAs were obtained with purities over 98% together with two mixtures. The mixtures were separated in recycling CCC mode using n-heptane–ethyl acetate–methanol–acetic acid (5:4:1:1, v/v) as the solvent system. Five GAs, including C13:0, C15:0, C15:1, C17:1, and C17:2, were successfully separated with purities over 98%, and their structures were confirmed by comparison with a mixture of GA standard samples coupled with ESI-MS data.
研究领域:
植物化学
·
药学
·
分离科学
✓ 已验证
产品关联
DOI
高影响因子
ACS Infectious Diseases
·
2023
·
IF 5.3
Zewen Wen,Cong Wang,Bing Bai,Xinyi Cao,Kewei Fan,Chunyou Hu,Peiyu Li,Qiwen Deng,Zhijian Yu
Streptococcus agalactiae is the major cause of invasive neonatal infections and is a recognized pathogen associated with various diseases in nonpregnant adults. The emergence and spread of antibiotic-resistant S. agalactiae necessitate the development of a novel antibacterial agent. Here, the potential antibacterial activities and mechanisms of ginkgolic acid C15:1 (GA (15:1)) from Ginkgo biloba against clinical S. agalactiae are characterized. The MIC50 and MIC90 values for GA (15:1) against 72 clinical S. agalactiae isolates were 6.25 and 12.5 μM, respectively. GA (15:1) showed a strong bactericidal effect against both planktonic bacteria and bacteria embedded in biofilms as well as significant effectiveness in suppressing the growth of S. agalactiae biofilms. Moreover, GA (15:1) possesses intracellular antibacterial activity and could significantly decrease the bacterial burden in the intraperitoneal infection model of S. agalactiae. Mechanistic studies showed that GA (15:1) triggers membrane damage of S. agalactiae through a unique dual-targeting mechanism of action (MoA). First, GA (15:1) targets phospholipids in the bacterial cytoplasmic membrane. Second, by using mass-spectrometry-based drug affinity responsive target stability (DARTS) and molecular docking, lipoprotein signaling peptidase II (lspA) was identified as a target protein of GA (15:1), whose role is crucial for maintaining bacterial membrane depolarization and permeabilization. Our findings suggest a potential therapeutic strategy for developing GA (15:1) to combat S. agalactiae infections.
研究领域:
微生物学
·
药理学
·
传染病学
·
分子生物学
✓ 已验证
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2025
·
IF 9.8
Qihui Dong,Rong Wu,Jun Cao,Fuliang Cao,Pengfei Yu,Erzheng Su
Ginkgolic acids (GAs) are potent natural antimicrobials, but their poor solubility hinders application. Recent studies have shown that nanoemulsions based on hydrophobic deep eutectic solvents (HDESs) can enhance the bioavailability of hydrophobic active ingredients. In our previous work, two HDESs were designed to efficiently enrich and extract GAs. We further developed HDES-in-water nanoemulsions (HDESNEs) as a delivery system for enhanced antimicrobial performance. Formulation was optimized using orthogonal design and response surface methodology. The resulting HDESNEs showed uniform droplet size (<20 nm), low polydispersity index (<0.1), and high encapsulation efficiency (>99 %). Antimicrobial assays demonstrated that HDESNEs significantly outperformed conventional GAs emulsions against two common foodborne bacteria ( Escherichia coli and Staphylococcus aureus ) and four plant pathogenic fungi ( Aspergillus niger , Penicillium citrinum , Penicillium expansum , and Fusarium graminearum ). These results showed that HDES-based nanoemulsions effectively improved GAs delivery and antimicrobial performance against multiple foodborne bacteria and plant pathogenic fungi. This study provides a green and efficient formulation approach that shows promising potential for antimicrobial applications in food preservation and agricultural protection.
研究领域:
天然产物化学
·
药剂学
·
食品科学
·
植物病理学
·
纳米医学
·
农业生物技术
✓ 已验证
产品关联
DOI
PubMed
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2021
·
IF 5.645
Qihui Dong,Jun Cao,Rong Wu,Tingting Shi,Wen Zhang,Fuliang Cao,Guibin Wang,Erzheng Su
Extract of Ginkgo biloba leaves (EGb) is a widely used phytotherapy drug, while ginkgolic acids (GAs) are considered as potentially hazardous constituents in EGb. In this work, a liquid-liquid microextraction method for removing ginkgolic acids from Ginkgo biloba leaves crude extract using hydrophobic deep eutectic solvent (DES) was reported. After screening and designing, a ternary hydrophobic DES composed of l -menthol, 1-hexanol and lauric acid at a molar ratio of 1:0.8:0.2, named as MHL, gave the highest removal rate of GAs. The removal conditions were optimized based on the removal rate of GAs, and the optimal conditions were 27.5 % (v/v) of ethanol solution used as the aqueous phase for dissolving the Ginkgo biloba leaves crude extract, 180 μL of the hydrophobic DES, removal temperature of 40 °C, and removal time of 24 min, respectively. Under these conditions, the removal rate of GAs in the model EGb solution reached 74.35 ± 1.56 %. Only one step removal could reduce the GAs content in the real Ginkgo biloba leaves crude extract to 4.02 μg/g (below 5.00 mg/kg). Scaling up the removal operation volume by 100 times, the removal rate of GAs did not decrease, but even improved. The retention rates of total flavonoids and ginkgolides always kept at high levels. This work provides the basic for further considering hydrophobic DESs as green media for efficiently removing the GAs in the standardized EGb production.
研究领域:
药学
·
分析化学
·
植物化学
✓ 已验证
产品关联
DOI
高影响因子
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
·
2024
·Vol. 416
·期 27
·6091-6102
·
IF 3.8
Zhong Huimin,Jiang Cong,Zou Jiahui,Zhu Guancheng,Cheng Mengyue,Huang Yanyan
Toxic ginkgolic acids (GAs) are a challenge for Ginkgo biloba- related food. Although a detection method for GAs is available, bulky instruments limit the field testing of GAs. Herein, by assembling gold nanoclusters with copper tannic acid (CuTA), CuAuTA nanocomposites were designed as peroxidase mimics for the colorimetric determination of GAs. Compared with single CuTA, the obtained CuAuTA nanocomposites possessed enhanced peroxidase-like properties. Based on the inhibitory effect of GAs for the catalytic activity of CuAuTA nanozymes, CuAuTA could be utilized for the colorimetric sensing of GAs with a low limit of quantitation of 0.17 μg mL −1 . Using a smartphone and the ImageJ software in conjunction, a nanozyme-based intelligent detection platform was developed with a detection limit of 0.86 μg mL −1 . This sensing system exhibited good selectivity against other potential interferents. Experimental data demonstrated that GAs might bind to the surface of CuAuTA, blocking the catalytically active sites and resulting in decreased catalytic activity. Our CuAuTA nanozyme-based system could also be applied to detect real ginkgo nut and ginkgo powder samples with recoveries of 93.12–111.6% and relative standard deviations less than 0.3%. Our work may offer a feasible strategy for the determination of GAs and expand the application of nanozymes in food safety detection. Graphical abstract
研究领域:
食品安全
·
纳米技术
·
酶模拟物
·
分析化学
·
生物传感器
✓ 已验证
DOI
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2023
·Vol. 103
·期 10
·4993-5003
·
IF 4.1
Fengnan Li,Isaac D Boateng,Xiao-Ming Yang,Yuanyuan Li,Weimin Liu
BACKGROUND Ginkgo biloba leaves contain beneficial flavonoids, bilobalide (BB), and ginkgolides. However, the toxic ginkgolic acid (GA) limit its application. In this study, various traditional processing methods were used to prepare G. biloba leaf tea (GBLT), including white tea, black tea, dark tea, green tea, and freeze-dried as control, followed by investigations of their effects on quality, antioxidant capacity, bioactive components, and cytotoxicity of the tea products. RESULTS Results showed that different processing methods significantly impact the tea products' quality indexes and the principal component analysis (PCA) and hierarchical cluster analysis (HCA) corroborated it. White tea had the highest total sugar (TS) and GA content and the most potent cytotoxicity on HepG2 cells. However, TS and GA content and the cytotoxicity of GBLT markedly decreased during fermentation and fixation. Moreover, white tea possessed higher total phenolic content (TPC), total flavonoid content (TFC), and more vigorous antioxidant activities than green tea, black tea, and dark tea. Terpene trilactones value was stable, but different catechins contents fluctuated according to the manufacturing process of different GBLTs. Among the four GBLTs, dark tea combining fixation and fermentation had the lowest GA content and cytotoxicity, less bioactive components reduction, appropriate quality, and stronger flavor. CONCLUSION These findings demonstrate that fixation and fermentation help reduce GAs during the manufacturing of GBLT. However, their ability to retain bioactive substances needs further optimization in future studies. © 2023 Society of Chemical Industry.
研究领域:
食品科学
·
药理学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF FOOD SCIENCE
·
2024
·
IF 3.2
Desy Anggraini Soetanto,Fengnan Li,Isaac Duah Boateng,Xiao-Ming Yang
Ginkgo biloba leaves (GBLs) contain high phytoconstituents, but ginkgolic acids (GAs, the main toxic compound in GBLs) have limited its applications. Processing Ginkgo biloba dark tea (GBDT) using fixation technology could decrease the toxic compounds; retain flavonoids, ginkgolides, and bilobalide; and improve the product quality. For the first time, various thermal fixations (hot air fixation [HAF], iron pot fixation [IPF], and boiled water fixation [BWF]) followed by rolling, fermentation, and drying were applied to produce GBDT. A comprehensive analysis of the toxicants (GAs), main bioactive compounds (ginkgolides and bilobalide, flavonoids, antioxidants, and phenolic profiles), and product qualities (moisture content, reducing sugar [RS], free amino acids [FAAs], enzyme activity, color properties, antioxidant capacity, etc.) were evaluated. The results revealed that thermal fixations BWF and HAF significantly reduced the GA contents (41.1%–34.6%). Most terpene lactones showed significant differences in control, IPF, and HAF. The HAF had lower total flavonoid content (TFC) than BWF and IPF. The control group (unfixated) had the highest toxic components (GA), terpene trilactones, and TFC compared with various fixations. Adding different fixations to rolling, fermentation, and drying had various impacts on GBDT, and principal component analysis supported the results. Among four thermal fixations, HAF yielded the best results in RS, FAA, total phenolic content, and antioxidant activities, while IPF had the highest TFC. BWF had the lowest content for GA. In conclusion, HAF (6) was chosen as the best technique for producing GBDT since it preserved GBDT's bioactive components while lowering its toxic components.
研究领域:
食品科学
·
药理学
·
植物科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2023
·
IF 5.9
Fengnan Li,Isaac Duah Boateng,Simeng Chen,Xiao-Ming Yang,Desy Anggraini Soetanto,Weimin Liu
Although high temperature processing is a traditional physical processing method used to degrade ginkgolic acid (GA) in Ginkgo biloba L., it leads to loss of abundant bioactive compounds in G. biloba leaves (GBL) such as ginkgo flavonoids , ginkgolides, etc. Pulsed light (PL) is a prospective non-thermal technique that might be a possible solution to the above problem. In this research, the impact of PL and heating pretreatment on GA, ginkgolides and bilobalide, flavonoid profile, polyphenol oxidase (PPO) and peroxidase (POD), antioxidant capacity , and total phenolics content (TPC) of GBL was evaluated. Besides, an ultrahigh-performance liquid chromatography-quadrupole/orbitrap High-resolution mass spectrometry (UPLC-Q-Orbitrap HRMS) was employed to gain insight into the degradation pathway of GA C13:0. The findings showed that fluences of 0.52 J/cm 2 for 300 s reduced GA by 19.94%, while heating at 180 °C for 300 s only reduced the GA by 7.04%. Moreover, the ginkgo flavonoids and terpene trilactones (bilobalide and ginkgolides A to C) in GBL were effectively retained after PL irradiation but significantly reduced by heating at 180 °C. Ginkgo leaves irradiated by PL for 200 s had the highest antioxidant capacity and TPC, while heating produced opposite results. Pulsed light and heating treatments significantly inactivated PPO and POD, but PL preserved color of leaves (lower total color change). UPLC-Q-Orbitrap HRMS results showed that PL irradiation degraded GA C13:0 by removing the hydroxyl or carboxyl group of the benzene ring. These findings demonstrate that PL treatment can improve quality of GBL, opening a broader way for its applications in food industry.
研究领域:
食品科学
·
药理学
·
植物科学
·
分析化学
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）