Academic literature on the topic 'Caffeoyl derivative'

Abstract The caffeoyl derivatives of Stachys leaves (Labiateae) were identified as chlorogenic acid, verbascoside and stachyoside. The latter compound, reported here for the fist time, was shown to be a verbascoside derivative containing an extra glucose residue attached to C-2, C-3 or C-4 of rhamnose. Cotyledonary leaves of Stachys accumulate high levels (8 -16 μmol/g dry tissue) of the three caffeoyl derivatives; all of which decrease significantly in amount during plant growth. Intact organs of the seedling were shown to efficiently incorporate the label from different precursors into caffeoyl derivatives. The biosynthesis of both verbascoside and stachyoside from labelled precursors revealed that the caffeoyl moiety was exclusively labelled from phenylalanine or cinnamic acid, whereas the 3,4-dihydroxyphenylethanol moiety was labelled from tyrosine, and better from tyramine.

Abstract The first total synthesis of plantamajoside (1), 2-(3′,4′-dihydroxylphenyl)ethyl-4-O-caffeoyl-3-O-(β-D-glucopyranosyl)-β-D-glucopyranoside, which is one of the dihydroxyphenylethyl glycosides (caffeic acid sugar esters), is described. Key intermediate 2, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-β-D-glucopyranoside was glycosylated with trichloroacetoimidoyl 2,3,4,6-tetra-O-acetyl-α-D-glycopyranoside (3) to afford plantamajoside derivative 4a, 2-[3′,4′-bis(O-benzyl)phenyl]ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside, in 39% yield. Plantamajoside derivative 4a was successfully converted into the target compound, plantamajoside (1), through a series of de-protective procedures. 1H- and 13C nuclear magnetic resonance (NMR) spectral data of the synthesized plantamajoside (1) were identical to those of the natural compound.

Bioassay-directed fractionation of an antioxidant methanol extract of the leaves of Chrozophora senegalensis using DPPH assay led to the isolation of three new flavonoid glycosides, quercetin 3-O-(6″-caffeoyl)-β-D-glucopyranoside-3′-O-β-D-glucopyranoside (1), quercetin 3-methyl ether-7-O-α-L-rhamnopyranosyl-(1→6)-(2″-p-coumaroyl)-β-D-glucopyranoside (2), acacetin 7-O-(6″-p-coumaroyl)-β-D-glucopyranoside (3), along with five known flavonoids, one phenolic derivative, and three megastigmane glycosides. Their structures were established on the basis of detailed spectral analysis. All isolated compounds were tested for their antioxidant activity on DPPH stable radical, superoxide anion, metal chelating activity, and DNA cleavage induced by the photolysis of H2O2. Quercetin 3-O-(6″-caffeoyl)-β-D-glucopyranoside-3′-O-β-D-glucopyranoside (1), quercetin 3′-methyl ether-3-O-α-L-rhamnopyranoside (4), and 4″'-methyl ether amenthoflavone (9) exhibited the highest antioxidant capacity being also able to modulate hydroxyl radical formation more efficiently than other compounds acting as direct hydroxyl radical scavengers and chelating iron.

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

Kaempferol is a well-known antioxidant found in many plants and plant-based foods. In plants, kaempferol is present mainly in the form of glycoside derivatives. In this work, we focused on determining the effect of kaempferol and its glycoside derivatives on the expression level of genes related to the reduction of oxidative stress—NFE2L2, NQO1, SOD1, SOD2, and HO-1; the enzymatic activity of superoxide dismutases; and the level of glutathione. We used HL-60 acute promyelocytic leukemia cells, which were incubated with the anticancer drug etoposide and kaempferol or one of its three glycoside derivatives isolated from the aerial parts of Lens culinaris Medik.—kaempferol 3-O-[(6-O-E-caffeoyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P2), kaempferol 3-O-[(6-O-E-p-coumaroyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P5), and kaempferol 3-O-[(6-O-E-feruloyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P7). We showed that none of the tested compounds affected NFE2L2 gene expression. Co-incubation with etoposide (1 µM) and kaempferol (10 and 50 µg/mL) leads to an increase in the expression of the HO-1 (9.49 and 9.33-fold at 10 µg/mL and 50 µg/mL, respectively), SOD1 (1.68-fold at 10 µg/mL), SOD2 (1.72-fold at 10–50 µg/mL), and NQO1 (1.84-fold at 50 µg/mL) genes in comparison to cells treated only with etoposide. The effect of kaempferol derivatives on gene expression differs depending on the derivative. All tested polyphenols increased the SOD activity in cells co-incubated with etoposide. We observed that the co-incubation of HL-60 cells with etoposide and kaempferol or derivative P7 increases the level of total glutathione in these cells. Taken together, our observations suggest that the antioxidant activity of kaempferol is related to the activation of antioxidant genes and proteins. Moreover, we observed that glycoside derivatives can have a different effect on the antioxidant cellular systems than kaempferol.

The outer layer of purple sweet potato is removed during processing; however, this layer serves as a potential source of phenolics, especially anthocyanins. Herein, the phenolic composition and antioxidant activity were determined for the inner and outer layers of five purple sweet potato cultivars (‘Sinjami’, ‘Jami’, ‘Danjami’, ‘Yeonjami’, and ‘Borami’) harvested in Korea. Anthocyanins were identified using ultra-high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometer (UHPLC-(ESI)-qTOF-MS) and ultra-high-performance liquid chromatography-linear ion trap mass spectrometer (UHPLC-Ion trap-MS), and their composition was quantified using HPLC-coupled with diode array detector (DAD). Non-anthocyanin phenolic compounds (phenolic acids and flavonols) were quantified using UHPLC-(ESI)-triple quadrupole (QqQ). A total of 20 anthocyanins, including non-acylated or acylated peonidin, cyanidin, and pelargonidin glycosides, were identified. Peonidin 3-caffeoyl-p-hydroxybenzoyl sophoroside-5-glucoside was the major anthocyanin, with the highest level in the ‘Sinjami’ cultivar (outer; 12,366 mg/kg DW, inner; 14,832 mg/kg DW). Additionally, 12 phenolic acids and 6 flavonols (quercetin derivatives) were identified, with the outer layers of all cultivars displaying higher total levels than the inner layers. ‘Sinjami’ and ‘Jami’ had higher phenolic acid and quercetin derivative content and antioxidant activities than the other three cultivars (p < 0.05). Thus, the outer layers of ‘Sinjami’ and ‘Jami’ cultivars could be potential sources of anthocyanins and other phenolics.

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.

Le syndrome métabolique (SMet) se caractérise par une obésité abdominale qui induit un cercle pernicieux auto-entretenu, dans lequel un état inflammatoire de bas grade et un stress oxydatif vont favoriser l'insulino-résistance pour conduire à terme au diabète de type II. Pour tenter d’empêcher ces troubles physiologiques, un régime alimentaire et une activité physique régulière sont proposés aux personnes à risque. Souvent, le traitement médicamenteux s’avère indispensable et expose le patient à une poly médication prolongée et a ces effets préjudiciables à long terme. Ce travail de thèse consiste à étudier une voie alternative par une médecine douce ciblée consistant en une prise régulière d’une boisson infusée d’Astéracées amères choisies pour leur richesse en sesquiterpènes lactones et en dérivés caffeoyls. Les premiers sont connus pour leur activité anti-inflammatoire et les seconds pour leurs effets à la fois antioxydant/anti-inflammatoire et insulino-sensibilisant. Une étude in vivo sur des rats « syndrome métabolique induit » a été conduite avec pour objectif de tester la pertinence d’une infusion d’Astéracées riche en dérivés caffeoyls dans la prévention du SMet. L’expérimentation a été menée sur le modèle de rat « fructose », un modèle nutritionnel prédisposant au SMet en quatre semaines. La comparaison des paramètres physiologiques de la cohorte d’animaux "témoin" nourris avec une alimentation normale et la cohorte d’animaux nourris avec une alimentation "riche en fructose" supplémentée ou non par l'infusion, nous a permis de montrer des effets patents de l’infusion sur la sensibilité à l’insuline et sur le poids des animaux. Par ailleurs, nous avons recherché de nouvelles substances naturelles toujours plus efficaces dans la lutte contre le stress oxydatif. Pour cela, nous avons procédé à un criblage cellulaire sur 8 extraits hydro alcooliques d’Astéracées amères visant à évaluer leurs effets protecteurs contre un stress oxydatif généré par H2O2. L’extrait de feuille de bardane présentait l’activité protectrice la plus puissante et a été retenu pour un fractionnement séquentiel visant à purifier et à identifier la molécule bioactive par RMN. Une analyse RT-qPCR et une approche d’amarrage moléculaire ont permis d’identifier la cible responsable de l’effet de protection. L’ensemble des résultats à conduit à l’identification d’un nouveau sesquiterpène lactone activateur de la glucose-6-phosphodeshydrogenase
Metabolic syndrome (MetS) is characterised by abdominal obesity that induces a self-perpetuating pernicious cycle in which low-grade inflammation and oxidative stress promote insulin resistance and ultimately lead to type II diabetes. In order to prevent these physiological disorders, diet and regular physical activity are recommended for patients at risk. Often, medical treatment is essential and exposes the patient to prolonged poly-drug therapy and its undermining consequences in the long term. This thesis work consists in studying an alternative way of targeted alternative medicine consisting in a regular intake of a drink infused with bitter Asteraceae chosen for their richness in sesquiterpene lactones and caffeoyl derivatives. The former are known for their anti-inflammatory activity and the latter for their antioxidant/anti-inflammatory and insulin-sensitising effects. An in vivo study on "induced metabolic syndrome" rats was conducted with the aim of testing the relevance of an infusion of Asteraceae rich in caffeoyl derivatives in the prevention of MetS. The experiment was conducted on the "fructose" rat model, a nutritional model predisposing to SMet in four weeks. The comparison of physiological parameters of the cohort of "control" animals fed with a normal diet and the cohort of animals fed with a "high fructose" diet supplemented or not by the infusion, allowed us to show clear effects of the infusion on the insulin sensitivity and on the weight of animals. In addition, we have researched new natural substances that are more effective in the fight against oxidative stress. To do this, we carried out a cellular screening on 8 hydroalcoholic extracts of bitter Asteraceae in order to evaluate their protective effects against oxidative stress generated by H2O2. The burdock leaf extract shows the most potent protective activity and was selected for a sequential fractionation aimed at purifying and identifying the bioactive molecule by NMR. RT-qPCR analysis and a molecular docking approach were used to identify the target responsible for the protective effect. The results led to the identification of a new sesquiterpene lactone that activates glucose-6-phosphodeshydrogenase

Le syndrome métabolique comme le diabète de type 2 sont des pathologies chroniques souvent étroitement liées. Le syndrome métabolique via des dysfonctionnements physiologiques qui s'auto-entretiennent et s'amplifient conduira au diabète de type 2. Les dysfonctionnement majeurs sont l'obésité abdominale, l'inflammation et le stress oxydant tissulaire et enfin l'insulino-résistance des tissus sensibles à l'insuline. Il convient donc de lutter efficacement contre ces dysfonctionnements afin de lutter contre ces pathologies chroniques. Les travaux de l'équipe dans laquelle j'ai effectué ma thèse ont permis de mettre en évidence les effets pléiotropes de substances de la famille des dérivés caffeoyls. Ces dérivés largement reconnus comme substances antioxydantes ont des effets insulino-sensibilisants (augmentent le captage de glucose sous stimulus insulinique) et aussi insulino-stimulants (augmentent la capacité sécrétrice de la cellule -pancréatique). Les plantes qui produisent ces dérivés caffoyls sont donc des sources intéressantes de nouveaux aliments santé, d'allégations ou encore de boissons infusées aptes à lutter contre le syndrome métabolique. Les Astéracées semblent disposer de ces substances bénéfiques.Durant ma thèse, j'ai pu montré l'effet antidiabétique d'un extrait de racine de chicorée sauvage (NCRAE), riche en acide chicorique (CRA) et en dérivés caffeoyl-quinic acides (CQAs). L'analyse de l'extrait par LC-MS a permis de déterminer le ratio CRA/CQAs de 70/30. Nous avons montré qu'un mélange d'acide chicorique et d'acide chlorogénique (70/30) mime l' effet antidiabétique de NCRAE. Nous démontrons pour la première fois le bénéfice antidiabétique d'un mélange de dérivés caffeoylsDe nombreuses Astéracées produisent des mélanges divers de dérivés caffeoyls. Afin de mieux comprendre les effets de mélanges caffeoyls nous avons décidé de réaliser une évaluation des effets biologiques in vitro d'extraits riches en caffeoyls issus de dix Astéracées. Nous voulons ensuite réaliser une analyse corrélative entre leurs contenus et leurs effets. L'analyse LC-MS est en cours actuellement.Enfin, deux plantes exotiques (du Congo Kinshasa) bien connues pour leur vertu antidiabétique par les tradipraticiens ont été étudiées. Bien que faisant parties d'autres familles botaniques, celles-ci contiennent également des dérivés caffeoyls. Il était donc intéressant d'appliquer nos critères d'évaluation in vitro du potentiel antidiabétique d'une plante afin d'envisager ou non l'implication des dérivés caffeoyls.Mon travail soutien l'usage en mélanges des dérivés caffoyls afin de lutter contre le syndrome métabolique et le diabète de type 2
Metabolic syndrome and type 2 diabetes are considered as chronic pathologies. The metabolic syndrome via physiological dysfunctions that self-sustain and expand will lead to type 2 diabetes. The major dysfunctions are abdominal obesity, inflammation and tissue oxidative stress and finally tissue insulin resistance. insulin sensitive. It is therefore necessary to fight effectively against these dysfunctions in order to fight against these chronic pathologies. The work of the team in which I carried out my thesis made it possible to highlight the pleiotropic effects of substances of the family of caffeoyls derivatives. These derivatives widely recognized as antioxidant substances have insulin-sensitizing effects (increase glucose uptake insulin stimulus) and also insulin-stimulating (increase the insulin secretion capacity of the -pancreatic cell). The plants that produce these caffoyl derivatives are therefore interesting sources of new health foods, claims or beverages infused to oppose the metabolic syndrome. Asteraceae seem to have these beneficial substances.During my thesis, I was able to show the antidiabetic effect of wild chicory root extract (NCRAE), rich in chicoric acid (CRA) and caffeoyl-quinic acid derivatives (CQAs). Analysis of the extract by LC-MS determined the CRA / CQAs ratio of 70/30. We have shown that a mixture of chicoric acid and chlorogenic acid (70/30) mimics the antidiabetic effect of NCRAE. We demonstrate for the first time the antidiabetic benefit of a mixture of caffeoyl derivativesMany Asteraceae produce various mixtures of caffeoyl derivatives. In order to better understand the effects of caffeoyl mixtures, we decided to carry out an evaluation of the in vitro biological effects of caffeoyl rich extracts from ten Asteraceae. We then want to carry out a correlative analysis between their contents and their effects. LC-MS analysis is ongoing.Finally, two exotic plants (Congo Kinshasa) well known for their antidiabetic properties by traditional "healers" were studied. Although belonging to other botanical families, these also contain caffeoyl derivatives. It was therefore interesting to apply our criteria of in vitro evaluation of the antidiabetic potential of a plant in order to envisage or not the implication of the caffeoyls derivatives.My work supports the use in mixtures of caffoyl derivatives to fight against metabolic syndrome and type 2 diabetes