- 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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- 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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