Academic literature on the topic 'Coumaroyl quinic acid'

Hydroxycinnamoyltransferase activities which catalyze the formation of O-hydroxycinnamoyl- (p-coumaroyl-, feruloyl-, and sinapoyl-)-glucaric acids via the corresponding 1-O-hydroxycinnamoyl- β-glucoses, and O-(p-coumaroyl)-quinic acid and O-(p-coumaroyl)-shikimic acid both via p-coumaroyl-CoA thioester have been isolated from leaves of Cestrum elegáns D. F. L. v. Schlechtendal. The enzymic activities involved could be classified as 1-O-hydroxycinnamoyl-βglucose : glucaric acid hydroxycinnamoyltransferase (EC 2.3.1.- ) and p-coumaroyl-CoA : quinic acid/shikimic acid hydroxycinnamoyltransferase (EC 2.3.1. - ). This is the first time that both the O-glucoside- and the S-CoA-dependent activities in phenolic acid-ester formation were found to be present in the same plant

Parasitaxus usta (Podocarpaceae) is the only parasitic gymnosperm and endemic to New Caledonia. In this survey, 11 flavonoids and 6 phenolic compounds were isolated from the aerial parts. As for flavonoids, six flavones, apigenin 7- O-glucoside (1), luteolin (2), luteolin 7- O-glucoside (3), chrysoeriol (4), chrysoeriol 7- O-glucoside (5) and tricetin 3′- O-glucoside (6), one C-glycosylflavone, orientin (7), one flavonol, quercetin 3- O-glucoside (8), one anthocyanin, cyanidin 3- O-glucoside (9), and two biflavones, isoginkgetin (10) and agathisflavone (11) were identified by UV, liquid chromatograph–mass spectra (LC-MS), acid hydrolysis, NMR and/or HPLC comparisons with authentic samples. On the other hand, six phenolic compounds were identified as 5- O- E- p-coumaroyl quinic acid (12), 5- O- Z- p-coumaroyl quinic acid (13), 5- O- E- p-coumaroyl quinic acid methyl ester (14), 5- O- Z- p-coumaroyl quinic acid methyl ester (15), E-caffeic acid methyl ester 3- O-β-glucopyranoside (16), and Z-caffeic acid methyl ester 3- O-β-glucopyranoside (17) by UV, LC-MS and NMR. Chemical components of P usta were reported in this survey for the first time. Their chemical characters were chemotaxonomically compared with those of other Podocarpaceae species.

Vitiligo is a stubborn multifactorial skin disease with a prevalence of approximately 1% in the global population. Kaliziri, the seeds of Vernonia anthelmintica (L.) Willd., is a well-known traditional Uyghur medicine for the treatment of vitiligo. Kaliziri injections is a Chinese-marketed treatment approved by the China Food and Drug Administration for the treatment of vitiligo. The significant effects of Kaliziri injection have been thoroughly studied. However, chemical components studies and plasma quantification studies are lacking for Kaliziri injection. Ultra-high-performance liquid chromatography coupled with hybrid quadrupole orbitrap mass spectrometry was employed to comprehensively characterize the caffeoyl quinic acid derivatives present in Kaliziri injection. Based on accurate mass measurements, key fragmental ions and comparisons with reference standards, 60 caffeoyl quinic acid derivatives were identified in Kaliziri injections, including caffeoyl quinic acids, coumaroyl caffeoyl quinic acids, dicaffeoyl quinic acids, feruloyl caffeoyl quinic acids, and dicaffeoyl quinic acid hexosides. Moreover, an HPLC-MS/MS method was developed and validated for the quantitative analysis of 5-caffeoyl quinic acid, 4-caffeoyl quinic acid, 1,3-dicaffeoyl quinic acid, 3,4-dicaffeoyl quinic acid, 3,5-dicaffeoyl quinic acid and 4,5-dicaffeoyl quinic acid in beagle plasma. The quantitative HPLC-MS/MS method was applied to quantify these six major caffeoyl quinic acids in beagle plasma after the subcutaneous administration of Kaliziri injection. All of the six analytes reached their peak plasma of concentrations within 30 min.

The metabolite profile of ten traditional apple cultivars grown in the Piedmont region (Italy) was studied by means of nuclear magnetic resonance spectroscopy, identifying an overall number of 36 compounds. A more complete assignment of the proton nuclear magnetic resonance (1H NMR) resonances from hydroalcoholic and organic apple extracts with respect to literature data was reported, identifying fructose tautomeric forms, galacturonic acid, γ-aminobutyric acid (GABA), p-coumaroyl moiety, phosphatidylcholine, and digalactosyldiacylglycerol. The chemical profile of each apple cultivar was defined by thorough quantitative NMR analysis of four sugars (fructose, glucose, sucrose, and xylose), nine organic acids (acetic, citric, formic, citramalic, lactic, malic, quinic, and galacturonic acids), six amino acids (alanine, asparagine, aspartate, GABA, isoleucine, and valine), rhamnitol, p-coumaroyl derivative, phloretin/phloridzin and choline, as well as β-sitosterol, fatty acid chains, phosphatidylcholine, and digalactosyldiacylglycerol. Finally, the application of PCA analysis allowed us to highlight possible differences/similarities. The Magnana cultivar showed the highest content of sugars, GABA, valine, isoleucine, and alanine. The Runsé cultivar was characterized by high amounts of organic acids, whereas the Gamba Fina cultivar showed a high content of chlorogenic acid. A significant amount of quinic acid was detected in the Carla cultivar. The knowledge of apple chemical profiles can be useful for industries interested in specific compounds for obtaining ingredients of food supplements and functional foods and for promoting apple valorization and preservation.

In the present study, nontargeted metabolomics was used to screen the phenolic and polyhydroxy compounds in pepper products. A total of 186 phenolic and polyhydroxy compounds, including anthocyanins, proanthocyanidins, catechin derivatives, flavanones, flavones, flavonols, isoflavones and 3-O-p-coumaroyl quinic acid O-hexoside, quinic acid (polyhydroxy compounds), etc. For the selected 50 types of phenolic compound, except malvidin 3,5-diglucoside (malvin), l-epicatechin and 4′-hydroxy-5,7-dimethoxyflavanone, other compound contents were present in high contents in freeze-dried pepper berries, and pinocembrin was relatively abundant in two kinds of pepper products. The score plots of principal component analysis indicated that the pepper samples can be classified into four groups on the basis of the type pepper processing. This study provided a comprehensive profile of the phenolic and polyhydroxy compounds of different pepper products and partly clarified the factors responsible for different metabolite profiles in ongoing studies and the changes of phenolic compounds for the browning mechanism of black pepper.

Qualitative analysis of the water extract of Mentha x villosa Huds. leaves was performed by liquid chromatography mass spectrometry (LC-MS/MS) and quantitative analysis was made by reverse-phase liquid chromatography coupled with photodiode array detection (LC-DAD). Sixteen phenolic compounds were identified and quantified consisting of 8 phenolic acids/derivatives and 8 flavonoid glycosides (quinic acid, chlorogenic acid, coumaroyl-hexoside, caffeic acid, coumaroylquinic acid, lithospermic acid, rosmarinic acid, salvianolic acid A, luteolin-7- O-glucuronide, luteolin-7- O-glucoside, luteolin-7- O-rutinoside, eriodictyol-7- O-rutinoside, apigenin-7- O-glucuronide, kaempferol-3- O-glucuronide, chrysoeriol-7- O-rutinoside, and hesperetin-7- O-rutinoside). Luteolin-7- O-rutinoside (25.6 ± 0.7 mg/g dry extract) and rosmarinic acid (17.9 ± 0.4 mg/g dry extract) were the most abundant. High antioxidant activity of this phenolic-rich water extract was confirmed in vitro by DPPH and ABTS tests and ex vivo in the ischemia-reperfusion injured rat superior mesenteric artery. Thus, the water extract of M. x villosa leaves seems to be a promising agent in prevention of tissue injury caused by oxidative stress.

Since early ancient period human being are searching for new drugs with better therapeutic potentials. Traditional medicines are very important because it provide the right direction to the researcher to discover new plant based products against some specific problem and the knowledge has been passed through generation after generation. Curculigo orchioides Gaertn.and Asparagus racemosus Willd. both plants have immune stimulatory properties and are widely used by traditional healers for the treatment of various diseases. The main aim of the present study is to identify the secondary metabolites found in methanolic root extracts of C. orchioides and A. racemosus. Extraction was carried out through standard procedures and the analysis of plant extracts was carried out by using LC-ESI-MS/MS technique in positive and/or negative ionization mode. LC MS study tentatively identified 15 and 19 secondary metabolites from Curculigo orchioides and Asparagus racemosus respectively. Amongst these some were simple phenolic acids such as caffeic acid, quinic acid, p-coumaric acid, sinapic acid, protocatechuic acid, p-hydroxybenzoic acid and vanillic acid. Some others were phenolic acid esters such as chlorogenic acid, di caffeoylquinic acid, p-coumaroyl quinic acid and some flavonoids such as quercetin, rutin, kaempferol, catechin and apigenin were also tentatively identified. Two phenolics caffeic acid and caffeoyl hexoside were further confirmed by MS MS study. This study supports the ethnobotanical claims done by traditional healers of Purulia and Midnapore districts. Characterized phytochemicals were mainly phenolic and flavonoid compounds. Assured levels of phenolics along with other plant constituents in the studied plants supports the ethnobotanical claim done by traditional healers. Further research is needed on structural analysis and bioactivity assay of the identified compounds.

I metaboliti secondari sono composti organici non direttamente coinvolti nella crescita e nello sviluppo della pianta. Queste sostanze sono spesso prodotte e accumulate dopo stress biotici e abiotici, ma le loro precise funzioni in vivo sono ancora poco chiare. Le colture cellulari in vitro possono essere utilizzate al fine di chiarire il ruolo biologico di specifici metaboliti secondari dopo un particolare tipo di stress. In una precedente tesi di dottorato, uno stress termico di 1 ora a 44°C è stato applicato ad una linea cellulare di carota chiamata R3M, una linea pigmentata, in grado di accumulare derivati della cianidina e degli acidi idrossicinnamici, molecole appartenenti alla classe dei fenilpropanoidi. Il trattamento termico causava la comparsa di strutture circolari citoplasmatiche dopo 24 ore di recupero dallo stress, ed è stato dimostrato che le cellule mostranti queste strutture erano destinate ad una lenta morte cellulare, con caratteristiche tipiche di una morte cellulare programmata. Somministrando alle cellule R3M alcuni precursori molecolari (approccio chimico), quali gli acidi idrossicinnamici, prima del trattamento termico, si è osservata una riduzione del numero di cellule con strutture circolari citoplasmatiche e una riduzione del numero di cellule morte. Questo progetto ha come obiettivo la caratterizzazione dei danni morfologici causati dallo stress termico, al fine di chiarire il possibile ruolo biologico di specifici fenilpropanoidi accumulati nella coltura R3M. Inoltre, un tentativo per valutare la possibilità di sfruttare l'approccio chimico, ovvero di somministrare i precursori molecolari in pianta per osservare l’eventuale assorbimento e modificazione degli stessi in piante intere, è stato provato. La doppia colorazione con fluoresceina di acetato e ER tracker blue white delle cellule stressate al calore, ha permesso di investigare la natura di queste strutture circolari citoplasmatiche, rivelando che esse sono circondate dal reticolo endoplasmatico. Questa organizzazione è tipica degli autofagosomi, strutture coinvolte nel processo di macroautofagia e spesso indotte da uno stress. Ulteriori analisi di microscopia hanno mostrato come queste strutture circolari citoplasmatiche contengano anche gocce lipidiche e organelli, per esempio cromoplasti, supportando fortemente l'ipotesi che queste strutture circolari siano autofagosomi. La colorazione con il marcante di endocitosi “FM 1-43” ha permesso di osservare che, nelle cellule stressate, l'arresto dei movimenti endocellulari avveniva immediatamente dopo l’esposizione allo stress termico e che, anche dopo due ore di recupero, la ripresa dei movimenti vescicolari non avveniva. Questo risultato ha suggerito che il citoscheletro, o qualche componente implicato nel trasporto vescicolare, poteva essere stato danneggiato dal calore. Dato che il citoscheletro è formato da diverse strutture, due tossine, colchicina e citocalasina D, agenti contro i microtubuli e microfilamenti, sono state addizionate alla coltura cellulare di carota per provare a mimare i danni causati dallo stress termico. Solo la citocalasina D perfettamente fenocopiava, in una parte della popolazione cellulare, la morfologia stressata, suggerendo che uno dei target dello stress termico erano i microfilamenti, i quali, una volta danneggiati, determinavano, direttamente o indirettamente, la comparsa di putativi autofagosomi nelle cellule stressate. Poiché l'approccio di somministrazione degli acidi idrossicinnamici determinava l'aumento di specifiche antocianine e derivati di acidi idrossicinnamici, prevenendo parzialmente la comparsa di putativi autofagosomi nelle cellule stressate, è stato concluso che questi fenilpropanoidi agiscono contro lo stress termico, prevenendo la morte cellulare programmata, probabilmente mediante un effetto protettivo, non caratterizzato, sui microfilamenti. Rispetto a molte pubblicazioni scientifiche che suggeriscono il ruolo dei metaboliti secondari sulla base di una correlazione tra accumulo/diminuzione di gruppi/classi di metaboliti e uno specifico stress, questo lavoro dimostra chiaramente che alcune molecole specifiche, in particolare la cianidina acilata con acido caffeico e l’acido cumarico coniugato con l’acido quinico, hanno un ruolo biologico di protezione contro lo stress termico in questa linea cellulare carota, risultando in una diminuzione della morte cellulare. Infine, la somministrazione di precursori molecolari è stata condotta su piante intere, rivelando che le piantine di Arabidopsis thaliana sono in grado di assorbire precursori molecolari e convertirli in altri prodotti. Questo risultato dimostra che l’approccio chimico può essere eseguito non solo in colture cellulari in vitro, ma anche in piante intere, permettendo future indagini sui ruoli biologici dei metaboliti secondari.
Secondary metabolites are organic compounds not directly involved in growth and development. These substances are often produced by plants after biotic and abiotic stresses, but their precise in vivo functions are still unclear. In vitro cell culture can be used in order to clarify the role of certain secondary metabolites after stress. In a previous work, a heat stress (1 hour at 44°C) was applied to R3M carrot cell line, a purple pigmented line that is able to accumulate cyanidin derivatives and hydroxycinnamic acid derivatives, molecules belonging to the phenylpropanoid class. The heat treatment caused the appearance of cytoplasmic circular structures after 24 hours of recovery. It has been shown that cells developing these structures were committed to a slow cell death, which showed some morphological markers of a programmed cell death. Feeding R3M cells with hydroxycinnamic acids before the heat treatment caused a reduction of the number of cells with cytoplasm circular structures and a reduction of cell death. The aim of this project is the characterization of the morphological damages caused by heat stress in order to clarify the possible biological role of specific phenylpropanoids accumulated in R3M cells. Finally, an effort to evaluate the possibility to exploit the feeding chemical approach in in vitro whole plants has been pursuit. The double staining of the heat stressed cells with fluorescein di-acetate and ER tracker blue-white allowed at observing the appearance of cytoplasmic circular structures surrounded by endoplasmic reticulum. This organization is typical of autophagosomes, structures involved during the macroautophagy process, which are often stress induced. Further microscope investigations revealed that these circular structures included lipid droplets and also organelles, for instance chromoplasts, strongly supporting that these structures are autophagosomes. The staining of the heat stressed cells with the endocytosis tracker FM 1-43 allowed to observe the arrest of endocellular movements just after heat stress, suggesting that cytoskeleton could have been damaged by heat. Toxins towards microtubules and microfilaments were used in order to phenocopy the damages induced by the heat treatment, but only Cytochalasin D, an anti-microfilament agent, caused the formation of structures similar to the heat induced putative-autophagosomes. Since the feeding approach determined the increase of anthocyanins and hydroxycinnamic acid derivatives, thus partially preventing the putative autophagosome-containing cell phenotype after heat stress, it can be concluded that these phenylpropanoids prevent programmed cell death possibly through an uncharacterized protective effect on microfilaments. Respect to other public researches that show the correlations between groups or classes of molecules and stresses, this work clearly demonstrates that specific molecules, i.e. the cyanidin acylated with caffeic acid and coumaroyl quinic acid, have a protective role against heat stress in this carrot cell line. Finally, the administration of molecular precursors has been investigated on in vitro whole plants revealing that Arabidopsis thaliana seedlings are able to absorb molecular precursors and immediately convert them in other plant products. This finding demonstrates that the chemical approach can be performed also in whole plants, allowing future investigations on secondary metabolite biological roles.