32719-11-2Relevant academic research and scientific papers
Effect of weakly basic conditions on the separation and purification of flavonoids and glycosides from chrysanthemum morifolium tea
Wang, Yuxiao,Xu, Zhenzhen,Wu, Yue,Li, Mo,Pang, Sicheng,Liang, Zhe,Ni, Yuanying
, (2019)
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.
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
Makola, Mpho M.,Steenkamp, Paul. A,Dubery, Ian A.,Kabanda, Mwadham M.,Madala, Ntakadzeni E.
, p. 1011 - 1018 (2016/04/01)
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.
Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
Oyama, Kin-Ichi,Watanabe, Noriyuki,Yamada, Tomomi,Suzuki, Masako,Sekiguchi, Yukiko,Kondo, Tadao,Yoshida, Kumi
, p. 3120 - 3130 (2015/05/04)
An efficient and versatile synthesis of 5-O-acylquinic acids from commercially available (-)-quinic acid was accomplished. We designed p-methoxybenzyl quinate as a key intermediate, and two problems, the esterification of the sterically hindered 5-OH group for the concise divergent synthesis and the low yield of the final deprotection step, were solved. For the first problem, we improved Tanabe's method, TsCl/NMI-mediated esterification using free carboxylic acids, by the addition of i-Pr2NEt. For the second problem, we established a TFA- or BCl3/C6HMe5-catalyzed deprotection reaction for the final deprotection step. 5-O-Acylquinic acids were synthesized in seven steps with 45-60% overall yield.
Thermal stability of 5-o-caffeoylquinic acid in aqueous solutions at different heating conditions
Dawidowicz, Andrzej L.,Typek, Rafal
experimental part, p. 12578 - 12584 (2011/10/30)
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.
Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)
Regos, Ionela,Urbanella, Andrea,Treutter, Dieter
body text, p. 5843 - 5852 (2010/06/17)
Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phen
Polyphenols are intensively metabolized in the human gastrointestinal tract after apple juice consumption
Kahle, Kathrin,Huemmer, Wolfgang,Kempf, Michael,Scheppach, Wolfgang,Erk, Thomas,Richling, Elke
experimental part, p. 10605 - 10614 (2009/10/02)
Polyphenols are secondary plant compounds showing anticarcinogenic effects both in vitro and in animal experiments and may thus reduce the risk of colorectal cancer in man. The identification of polyphenol metabolites formed via their passage through the small intestine of healthy ileostomy subjects after apple juice consumption is presented. Identification and quantification of polyphenols and their metabolites were performed using HPLC-DAD as well as HPLC-ESI-MS/MS. Total procyanidin content (TPA) was measured, and additionally the mean degree of polymerization (DPm) of the procyanidins was determined in the apple juice and ileostomy effluents. As products of polyphenol metabolism, D-(-)-quinic acid and methyl esters of caffeic acid and p-coumaric acid are liberated from the corresponding hydroxycinnamic acid esters. 1-Caffeoylquinic acid and 3-caffeoylquinic acid were determined as products of isomerization. Phloretin 2′-O-glucoside (phloridzin) and phloretin 2′-O-xyloglucoside were metabolized into the corresponding aglycons phloretin and phloretin 2′-Oglucuronide and all were found in the ileostomy effluent. Ninety percent of the consumed procyanidins were recovered in the ileostomy effluent and therefore would reach the colon under physiologic circumstances. The DPm was reduced (DPm of apple juice = 5.7) and varied depending on the time point of excretion. The gastrointestinal passage seems to play an important role in the colonic availability of apple polyphenols.
Synthesis of designed acylquinic acid derivatives involved in blue color development of hydrangea and their co-pigmentation effect
Toyama-Kato, Yuki,Kondo, Tadao,Yoshida, Kumi
, p. 239 - 254 (2008/03/12)
The blue sepal color of hydrangea may be developed by an unstable stipramolecular metal-complex pigment composed of delphinidin 3-glucoside (1), 5-O-caffeoylquinic acid (2) and 5-O-p-coumaroylquinic acid (3) as co-pigments and Al3+ in aqueous s
Essential structure of co-pigment for blue sepal-color development of hydrangea
Kondo, Tadao,Toyama-Kato, Yuki,Yoshida, Kumi
, p. 6645 - 6649 (2007/10/03)
Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al 3+ in an aqueous
Antioxidant constituents of almond [Prunus dulcis (Mill.) D.A. Webb] hulls
Takeoka, Gary R.,Dao, Lan T.
, p. 496 - 501 (2007/10/03)
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
First efficient syntheses of 1-, 4-, and 5-caffeoylquinic acid
Sefkow, Michael,Kelling, Alexandra,Schilde, Uwe
, p. 2735 - 2742 (2007/10/03)
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
