Screening of Terpene Lactones and Flavonoid Glycosides in &lt;i&gt;gingko biloba&lt;/i&gt; Capsule by UPLC- Orbitrap High Resolution MS, with Emphasis on Isomer Differentiation

Zhou, Haiyun; Tang, Weiquan; Zeng, Jin; Tang, Chengfang

doi:10.12691/jfnr-2-7-7

Cited by 10 publications

(6 citation statements)

References 18 publications

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“…Compared to flavonoid glycosides found in gingko biloba [ 43 ], we tentatively characterized the compound as kaempferol-3-O- glucose- rhamnoside. Fragmentation of the compound at m/z 609 produced an ion at m/z 301, attributed to [M-H-146–162]– through loss of 308 units from a rhamnose (146 u) plus a glucose (162 u), indicating the compound is a rutin.…”

Section: Resultsmentioning

confidence: 99%

Eugenia aurata and Eugenia punicifolia HBK inhibit inflammatory response by reducing neutrophil adhesion, degranulation and NET release

Costa

Jesus

Lopes

et al. 2016

BMC Complement Altern Med

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Background Eugenia spp. are used in popular medicine in the treatment of pain, diabetes, intestinal disorders and cough. The aim of the work is to evaluate, ex vivo and in vivo, the anti-inflammatory activity of the hydroethanolic extracts of the leaves of Eugenia aurata (EA) and Eugenia punicifolia HBK (EP) upon neutrophils.MethodsEx vivo, isolated human neutrophils were sensitized by Eugenia extracts (0.1–1000 μg/mL) and stimulated by PMA. In these conditions, different neutrophil activities related to inflammatory process were measured: adhesion, degranulation and NET release. Neutrophil viability and tumor line cells were monitored. In vivo, neutrophil influx was evaluated by peritonitis model performed in mice pretreated with different concentrations of Eugenia extracts. Phytochemical profile was assessed by mass spectrometry.ResultsEx vivo, EA and EP (1000 μg/mL) reduced cell adhesion and degranulation, respectively. NET release was inhibited by EA and EP. Anti-inflammatory activities occurred in the absence of cytotoxicity. In vivo, both EA as EP inhibited neutrophil migration. The phytochemical profile revealed that EA contains myricitrin, rutin, quinic acid and quercetin derivatives. EP presents gallic acid, quercetin derivatives, syringic acid, ellagic acid, monogalloyl-glucose, glycosyringic acid, mudanoside B, HHDP glucose isomer and digalloylglucose isomer. EA and EP inhibit neutrophil migration by different pathways.ConclusionDifferent chemical compositions may explain the anti-inflammatory effects described herein for EA and EP. Both extracts inhibit NET release but only EA reduces cell adhesion whereas EP decreases elastase secretion. This work contributes to the elucidation of cellular mechanisms related to the anti-inflammatory activity for leaves of E. aurata and E. punicifolia HBK.

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Section: Resultsmentioning

confidence: 99%

Eugenia aurata and Eugenia punicifolia HBK inhibit inflammatory response by reducing neutrophil adhesion, degranulation and NET release

Costa

Jesus

Lopes

et al. 2016

BMC Complement Altern Med

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“…During ESI negative, flavonoid fragmentation patterns can be predicted without the use of authentic standards. For instance, the removal of O- glycosylated sugar can happen through either heterolytic cleavage with hydrogen migration or hemolytic sugar cleavage to produce an aglycone product ion Y 0 − or an aglycone radical ion [Y 0 -H] − , respectively [ 20 ]. In the past, the ratio of [Y 0 -H] − / Y 0 − has been used with great success in determining the original sugar position before fragmentation [ 21 ].…”

Section: Resultsmentioning

confidence: 99%

The Effect of Temperature on Pressurised Hot Water Extraction of Pharmacologically Important Metabolites as Analysed by UPLC‐qTOF‐MS and PCA

Khoza

Chimuka

Mukwevho

et al. 2014

Evidence-Based Complementary and Alternative Medicine

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Metabolite extraction methods have been shown to be a critical consideration for pharmacometabolomics studies and, as such, optimization and development of new extraction methods are crucial. In the current study, an organic solvent-free method, namely, pressurised hot water extraction (PHWE), was used to extract pharmacologically important metabolites from dried Moringa oleifera leaves. Here, the temperature of the extraction solvent (pure water) was altered while keeping other factors constant using a homemade PHWE system. Samples extracted at different temperatures (50, 100, and 150°C) were assayed for antioxidant activities and the effect of the temperature on the extraction process was evaluated. The samples were further analysed by mass spectrometry to elucidate their metabolite compositions. Principal component analysis (PCA) evaluation of the UPLC-MS data showed distinctive differential metabolite patterns. Here, temperature changes during PHWE were shown to affect the levels of metabolites with known pharmacological activities, such as chlorogenic acids and flavonoids. Our overall findings suggest that, if not well optimised, the extraction temperature could compromise the “pharmacological potency” of the extracts. The use of MS in combination with PCA was furthermore shown to be an excellent approach to evaluate the quality and content of pharmacologically important extracts.

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“…For maximum data output, the analysis was carried out using optimized parameters [ 14 ]. Here, only negative data were analyzed using similar optimized parameters, for reasons of better predictability without need for use of authentic standards [ 14 , 30 ]. Representative single ion monitoring (SIM) chromatograms for target molecules were generated using their m/z values.…”

Section: Methodsmentioning

confidence: 99%

The effect of temperature and methanol–water mixture on pressurized hot water extraction (PHWE) of anti-HIV analogoues from Bidens pilosa

Gbashi

Njobeh

Steenkamp

et al. 2016

Chemistry Central Journal

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BackgroundPressurized hot water extraction (PHWE) technique has recently gain much attention for the extraction of biologically active compounds from plant tissues for analytical purposes, due to the limited use of organic solvents, its cost-effectiveness, ease-of-use and efficiency. An increase in temperature results in higher yields, however, issues with degradation of some metabolites (e.g. tartrate esters) when PHWE is conditioned at elevated temperatures has greatly limited its use. In this study, we considered possibilities of optimizing PHWE of some specific functional metabolites from Bidens pilosa using solvent compositions of 0, 20, 40 and 60 % methanol and a temperature profile of 50, 100 and 150 °C.ResultsThe extracts obtained were analyzed using UPLC-qTOF-MS/MS and the results showed that both temperature and solvent composition were critical for efficient recovery of target metabolites, i.e., dicaffeoylquinic acid (diCQA) and chicoric acid (CA), which are known to possess anti-HIV properties. It was also possible to extract different isomers (possibly cis-geometrical isomers) of these molecules. Significantly differential (p ≤ 0.05) recovery patterns corresponding to the extraction conditions were observed as recovery increased with increase in methanol composition as well as temperature. The major compounds recovered in descending order were 3,5-diCQA with relative peak intensity of 204.23 ± 3.16 extracted at 50 °C and 60 % methanol; chicoric acid (141.00 ± 3.55) at 50 °C and 60 % methanol; 4,5-diCQA (108.05 ± 4.76) at 150 °C and 0 % methanol; 3,4-diCQA (53.04 ± 13.49) at 150 °C and 0 % methanol; chicoric acid isomer (40.01 ± 1.14) at 150 °C and 20 % methanol; and cis-3,5-diCQA (12.07 ± 5.54) at 100 °C and 60 % methanol. Fitting the central composite design response surface model to our data generated models that fit the data well with R2 values ranging from 0.57 to 0.87. Accordingly, it was possible to observe on the response surface plots the effects of temperature and solvent composition on the recovery patterns of these metabolites as well as to establish the optimum extraction conditions. Furthermore, the pareto charts revealed that methanol composition had a stronger effect on extraction yield than temperature.ConclusionUsing methanol as a co-solvent resulted in significantly higher (p ≤ 0.05) even at temperatures as low as 50 °C, thus undermining the limitation of thermal degradation at higher temperatures during PHWE.

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Screening of Terpene Lactones and Flavonoid Glycosides in <i>gingko biloba</i> Capsule by UPLC- Orbitrap High Resolution MS, with Emphasis on Isomer Differentiation

Cited by 10 publications

References 18 publications

Eugenia aurata and Eugenia punicifolia HBK inhibit inflammatory response by reducing neutrophil adhesion, degranulation and NET release

Eugenia aurata and Eugenia punicifolia HBK inhibit inflammatory response by reducing neutrophil adhesion, degranulation and NET release

The Effect of Temperature on Pressurised Hot Water Extraction of Pharmacologically Important Metabolites as Analysed by UPLC‐qTOF‐MS and PCA

The effect of temperature and methanol–water mixture on pressurized hot water extraction (PHWE) of anti-HIV analogoues from Bidens pilosa

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