- Effect of weakly basic conditions on the separation and purification of flavonoids and glycosides from chrysanthemum morifolium tea
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Tea brewed from chrysanthemum flowers has been widely used in Chinese medicine. The possibly medicinal compounds in Chrysanthemum morifolium tea can be purified by preparative high performance liquid chromatography (HPLC), but this is usually done with acidic conditions, which leads to the hydrolysis of glycosides. In hopes of avoiding this hydrolysis, we explored the effect of weakly basic conditions on the separation and purification of flavonoids and glycosides from Chrysanthemum morifolium. We also explored the effects of weakly basic conditions on chlorogenic acid (3-CQA) and apigenin-7-O-glucoside (A7G). Our results show that the concentration of the weakly basic ammonium hydrogen carbonate and time had no significant effect on A7G, p 0.01, but it had a significant effect on 3-CQA, p 0.01. HPLC and ultraviolet (UV) analysis showed that the structure of 3-CQA is destroyed in weakly basic conditions. Caffeic acid, quinic acid, and 3,4-dihydroxymandelic acid, which is a hydrolysate of 3-CQA, were identified by ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The results showed that weakly basic conditions could be used for the purification of flavonoids and glycosides but not for caffeoylquinic acids. Moreover, our work clarified the hydrolysis behaviour of caffeoylquinic acids, which can be helpful for research into their functional aspects.
- Wang, Yuxiao,Xu, Zhenzhen,Wu, Yue,Li, Mo,Pang, Sicheng,Liang, Zhe,Ni, Yuanying
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- Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium
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Three new caffeoylquinic acid derivatives, chrysanthemorimic acids A-C (1-3), and 11 known compounds (4-14) were isolated and characterized from the flowers of Chrysanthemum morifolium. Their structures were confirmed by spectroscopic data as well as by comparison of the experimental and calculated electronic circular dichroism spectra. Chrysanthemorimic acids A-C possess a rare 8-oxa-bicyclo[3.2.1]oct-3-en-2-one ring that is formed through a [5+2] cycloaddition of caffeoylquinic acid with a d-glucose derivative. Compounds 1-3, 6-8, 12, and 13 displayed significant effects against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells at 10 μM.
- Yang, Peng-Fei,Feng, Zi-Ming,Yang, Ya-Nan,Jiang, Jian-Shuang,Zhang, Pei-Cheng
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p. 1028 - 1033
(2017/05/05)
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- Preferential alkali metal adduct formation by cis geometrical isomers of dicaffeoylquinic acids allows for efficient discrimination from their trans isomers during ultra-high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry
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Rationale Caffeoylquinic acid (CQA) derivatives are a group of structurally diverse phytochemicals that have attracted attention due to their many health benefits. The structural diversity of these molecules is due in part to the presence of regio- A nd geometrical isomerism. This structural diversity hampers the accurate annotation of these molecules in plant extracts. Mass spectrometry (MS) is successfully used to differentiate between the different regioisomers of the CQA derivatives; however, the accurate discrimination of the geometrical isomers of these molecules has proven to be an elusive task. Methods UV-irradiated methanolic solutions of diCQA were analyzed using an ultra-high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UHPLC/QTOFMS) method in negative ionisation mode. An in-source collision-induced dissociation (ISCID) method was optimized by varying both the capillary and cone voltages to achieve differential fragmentation patterns between UV-generated geometrical isomers of the diCQAs during MS analyses. Results Changes in the capillary voltage did not cause a significant difference to the fragmentation patterns of the four geometrical isomers, while changes in the cone voltage resulted in significant differences in the fragmentation patterns. The results also show, for the first time, the preferential formation of alkali metal (Li+, Na+ and K+) adducts by the cis geometrical isomers of diCQAs, compared to their trans counterparts. Conclusions Optimized QTOFMS-based methods may be used to differentiate the geometrical isomers of diCQAs. Finally, additives such as metal salts to induce adduct formation can be applied as an alternative method to differentiate closely related isomers which could have been difficult to differentiate under normal MS settings.
- Makola, Mpho M.,Steenkamp, Paul. A,Dubery, Ian A.,Kabanda, Mwadham M.,Madala, Ntakadzeni E.
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p. 1011 - 1018
(2016/04/01)
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- Thermal stability of 5-o-caffeoylquinic acid in aqueous solutions at different heating conditions
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Chlorogenic acid is a naturally occurring phenolic compound found in all higher plants. This component, being the ester of caffeic acid with quinic acid, is an important biosynthetic intermediate and plays an important role in the plant's response to stress. Potential uses of chlorogenic acid are suggested in pharmaceuticals, foodstuffs, feed additives, and cosmetics due to its recently discovered biomedical activity. This finding caused new interest in chlorogenic acid properties, its isomers, and its natural occurrence. It has been found that as many as nine compounds (chlorogenic acid derivatives and its reaction product with water) can be formed from 5-o-caffeoylquinic acid during the heating of its water solution. Three of them, two hydroxylated 5-o-caffeoylquinic acid derivatives and 4,5-dicaffeoylquinic acid, have been not reported, yet. The amount of each formed component depends on the heating time and temperature. The presented results are important for researchers investigating plant metabolism and looking for new plant components. The transformation product can be mistakenly treated as a new component, not found before in the examined plant, or can be a cause of erroneous quantitative estimations of plant composition.
- Dawidowicz, Andrzej L.,Typek, Rafal
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experimental part
p. 12578 - 12584
(2011/10/30)
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- Antioxidant constituents of almond [Prunus dulcis (Mill.) D.A. Webb] hulls
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Almond hulls (Nonpareil variety) were extracted with methanol and analyzed by reversed phase HPLC with diode array detection. The extract contained 5-O-caffeoylquinic acid (chlorogenic acid), 4-O-caffeoylquinic acid (cryptochlorogenic acid), and 3-O-caffe
- Takeoka, Gary R.,Dao, Lan T.
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p. 496 - 501
(2007/10/03)
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- First efficient syntheses of 1-, 4-, and 5-caffeoylquinic acid
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Efficient synthesis of 1-, 4-, and 5-caffeoylquinic acid was achieved in three or four steps with suitably protected quinic acid precursors, in overall yields of 41%, 36%, and 60% [from quinic acid (1)]. 1-Caffeoylquinic acid was prepared by esterificatio
- Sefkow, Michael,Kelling, Alexandra,Schilde, Uwe
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p. 2735 - 2742
(2007/10/03)
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- Rapid and easy identification of isomers of coumaroyl- and caffeoyl-D-quinic acid by gas chromatography/mass spectrometry
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The 3-O-, 4-O- and 5-O-isomers of caffeoyl-D-quinic acid and the corresponding ethyl esters were separated by high-performance liquid chromatography and the structures were verified by NMR spectrometry. Trimethylsilylation of the compounds allowed a rapid
- Fuchs, Claus,Spiteller, Gerhard
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p. 602 - 608
(2007/10/03)
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