Impact of Wines and Wine Constituents on Cyclooxygenase-1, Cyclooxygenase-2, and 5-Lipoxygenase Catalytic Activity

Kutil, Zsófia; Temml, Veronika; Maghradze, D.; Pribylova, Marie; Dvořáková, Marcela; Schuster, Daniela; Vaněk, Tomáš; Landa, Přemysl

doi:10.1155/2014/178931

Cited by 50 publications

(36 citation statements)

References 35 publications

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“…Two of the main targets of resveratrol are known to be cyclooxygenase isoforms (COX-1 and COX-2), which metabolize arachidonic acid to generate prostaglandins (PG) and thromboxanes (Tx) both implicated in inflammatory response. The interaction of resveratrol with COX-1 and COX-2 leads to pro-inflammatory factors suppression [55,56]. Notably the inhibition of COX-1 in the arachidonic acid pathway, via suppression of thromboxanes TxA2, was found to be responsible for the anti-thrombotic activity along with the blockade of the mitogen-activated protein kinase (MAPK) signaling and the enhancement of the nitric oxide/cGMP pathway [57,58].…”

Section: Pharmacodynamic Properties Of Resveratrolmentioning

confidence: 99%

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Resveratrol in Cancer Patients: From Bench to Bedside

Berretta

Bignucolo

Francia

et al. 2020

IJMS

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Resveratrol (3,5, is a natural phytoalexin that accumulates in several vegetables and fruits like nuts, grapes, apples, red fruits, black olives, capers, red rice as well as red wines. Being both an extremely reactive molecule and capable to interact with cytoplasmic and nuclear proteins in human cells, resveratrol has been studied over the years as complementary and alternative medicine (CAM) for the therapy of cancer, metabolic and cardiovascular diseases like myocardial ischemia, myocarditis, cardiac hypertrophy and heart failure. This review will describe the main biological targets, cardiovascular outcomes, physico-chemical and pharmacokinetic properties of resveratrol in preclinical and clinical models implementing its potential use in cancer patients.properties of resveratrol are, however, marked by a pharmacokinetic profile and by an unfavorable oral bioavailability, which requires a thorough analysis. To date, to the best of our knowledge, scientific papers and reviews summarizing multiple characteristics of resveratrol, its pharmacokinetic, pharmacodynamic profiles and potential drug interaction in oncology are lacking in literature. Therefore, this review aimed to describe the potential use of resveratrol in cancer management presenting the main biochemical pathways involved, issues and potential uses in cancer patients. Moreover, the involvement of resveratrol in cardioncology, its potential use for risk reduction of myocardial ischemia, myocarditis, cardiac hypertrophy as well as heart failure are also discussed. To endorse this review, we made a comprehensive search on PubMed, Web of Science and SciFinder. The search terms were "resveratrol" combined with "cardioncology" or "cancer" or "drug-food" or "cardiology" or "pharmacokinetic" or "pharmacodynamic". Physico-Chemical and Pharmacokinetic Properties of ResveratrolResveratrol is a low molecular weight phyto-polyphenol of 228 Da that appears as an off-white powder with lipophilic properties (octanol/water partition coefficient, log Kow = 3.1). Its melting point is between 253 and 255 • C, and its solubility in water is very low (3 mg/100 mL) [8]. The ethylene bridge due to a limited degree of freedom generates two geometric isomers: cis-resveratrol and trans-resveratrol ( Figure 1) [5]. These isoforms co-exist in resveratrol extracts even if a greater biological activity and stability are attributed to trans-resveratrol. Comparing to the geometric isomers, the nearly planar structure of trans-resveratrol is less flexible than the non-planar structure of cis-resveratrol, but it possesses a lower repulsive energy that ensures it, albeit small, higher stability. Isomerization of trans-resveratrol to cis-resveratrol occurs via molecule breakdown when trans-resveratrol is exposed to UV radiation at a wavelength of 254 or 366 nm, to high pH conditions or in plants during fermentation processes [5,9]. In analyzing some physical-chemical aspects of resveratrol, Zupancic et al. showed how trans-resveratrol is rapidly degradable in high-pH solutions. In par...

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Section: Pharmacodynamic Properties Of Resveratrolmentioning

confidence: 99%

“…Antioxidant Copper-chelant [44,45,49] Activation p38-MAPK [52] Inhibition QR2 [48] Up-regulation SOD [47] Anti-Inflammatory Inhibition COX 1 [55,56,58] Inhibition COX 2 [55,56,58] Blocked TxA 2 [57,58] Blocked MAPK [57,58] Activation…”

Section: Effect Pathway Referencementioning

confidence: 99%

Resveratrol in Cancer Patients: From Bench to Bedside

Berretta

Bignucolo

Francia

et al. 2020

IJMS

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“…Truly, a vast number of natural compounds have been assessed regarding their capability to inhibit the enzymes of AA metabolism (reviewed in ) and valuable multitargeting leads were described among natural products . In these analyses, many phytochemicals were then identified as dual COX/5‐LOX inhibitors (Table ) . Moreover, plant extracts have been used in traditional medicine for ages and many have been described to impair the AA metabolism through both COX and 5‐LOX pathways .…”

Section: Identification Of Novel Targets In the Arachidonic Acid Cascadementioning

confidence: 99%

Nonsteroidal Anti‐Inflammatory Therapy: A Journey Toward Safety

Pereira-Leite

Nunes

Jamal

et al. 2016

Medicinal Research Reviews

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The efficacy of nonsteroidal anti-inflammatory drugs (NSAIDs) against inflammation, pain, and fever has been supporting their worldwide use in the treatment of painful conditions and chronic inflammatory diseases until today. However, the long-term therapy with NSAIDs was soon associated with high incidences of adverse events in the gastrointestinal tract. Therefore, the search for novel drugs with improved safety has begun with COX-2 selective inhibitors (coxibs) being straightaway developed and commercialized. Nevertheless, the excitement has fast turned to disappointment when diverse coxibs were withdrawn from the market due to cardiovascular toxicity. Such events have once again triggered the emergence of different strategies to overcome NSAIDs toxicity. Here, an integrative review is provided to address the breakthroughs of two main approaches: (i) the association of NSAIDs with protective mediators and (ii) the design of novel compounds to target downstream and/or multiple enzymes of the arachidonic acid cascade. To date, just one phosphatidylcholine-associated NSAID has already been approved for commercialization. Nevertheless, the preclinical and clinical data obtained so far indicate that both strategies may improve the safety of nonsteroidal anti-inflammatory therapy.

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“…An intensive literature search revealed that the identified compounds 5, 6, 7, 20, and 21 are also reported to inhibit 5-LO in a low micromolar range with IC 50 values of 8.40 [32], 6.60 [33], 3.47 [34], 3.29 [35], and 2.25 µM [35], respectively. Our findings, together with published literature data, suggest that S. sediforme bears anti-inflammatory potential.…”

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confidence: 99%

Phytochemical Profile of the Aerial Parts of Sedum sediforme and Anti-inflammatory Activity of Myricitrin

Winekenstädde

Angelis

Waltenberger

et al. 2015

Natural Product Communications

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The aim of this study was to investigate the phytochemical profile of the methanol extract of the aerial parts of Sedum sediforme and to identify its secondary metabolites. By means of chromatographic separation and enrichment of compounds, HPLC-ESI-MS, HRMS, 1D-, 2D-NMR and/or comparison with reference compounds, three triterpenes, two sterols, ten flavonoids and twelve phenolic compounds were identified, together with two new compounds, i.e. (2R * , 3R *)-5,7-dihydroxy-2,3-dimethyl-4-chromanone-7-O-ß-D-glucoside (27) and butan-2-O-rutinoside (28). Out of the 29 identified secondary metabolites, 18 are described as ingredients of S. sediforme herein for the first time. Furthermore, myricitrin, one of the major constituents, was tested for its ability to inhibit different enzymes within the arachidonic acid cascade in order to determine its anti-inflammatory properties. Whereas there was only either weak or no inhibition of the microsomal prostaglandin E 2 synthase-1 (mPGES-1) and the soluble epoxide hydrolase (sEH), myricitrin showed strong inhibition of 5-lipoxygenase (5-LO), with an IC 50 of 7.8 ± 0.2 µM.

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Impact of Wines and Wine Constituents on Cyclooxygenase-1, Cyclooxygenase-2, and 5-Lipoxygenase Catalytic Activity

Cited by 50 publications

References 35 publications

Resveratrol in Cancer Patients: From Bench to Bedside

Resveratrol in Cancer Patients: From Bench to Bedside

Nonsteroidal Anti‐Inflammatory Therapy: A Journey Toward Safety

Phytochemical Profile of the Aerial Parts of Sedum sediforme and Anti-inflammatory Activity of Myricitrin

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