Design, Synthesis, and Vasorelaxant and Platelet Antiaggregatory Activities of Coumarin—Resveratrol Hybrids.

Vilar, Santiago; Quezada, Elías; Santana, Lourdes; Uriarte, Eugenio; Yáñez, Matilde; Fraiz, Nuria; Alcaide, Carlos; Cano, Ernesto; Orallo, Francisco

doi:10.1002/chin.200616140

Cited by 23 publications

(37 citation statements)

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“…1 A wide variety of bioactivities of these heterocyclic compounds have been revealed, including antimicrobial, 2 antioxidant, 3 antinocipeptive, 4 antitumour, 5 anti-inflammatory, 6 antiasthmatic, 7 antiviral, 8 and vasorelexant. 9 Natural coumarins such as geiparvarin 10 and properly modified natural coumarins, have also been characterised as potent and selective monoamine oxidase (MAO-B and MAO-A) isoforms inhibitors. 11 Reactive oxygen species (ROS) are highly reactive molecules that originate mainly from cell metabolism.…”

Section: Introductionmentioning

confidence: 99%

“…, 1H),9.05 (br, 2H);13 C NMR (75 MHz, DMSO-d 6 ): d 16.5, 115.2, 116.25, 117.5, 118.4, 121.28, 122.3, 124.89, 127.36, 128.09, 133.73, 144.81, 145.37, 146.19, 150.97, 159.51; HRMS calcd for C 16 H 11 BrO 4 : m/z: 346.9913, found: 346.9904.4.2.2. 6,8-Dibromo-3-(3,4-dihydroxy-phenyl)-4-methylchromen-2-one (6)Prepared following the general procedure starting from 0.44 mmol (200 mg) of 6,8-dibromo-3-(3,4-dimethoxy-phenyl)-4-methyl-chromen-2-one (3) and 7.04 mmol of BBr 3 (7.04 ml BBr 3…”

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confidence: 97%

“…Interaction% with DPPH, %inhibition of LP induced by AAPH and inhibition of soybean lipoxygenase (LOX) (IC 50 )/% at 100 lM for compounds I,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] …”

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confidence: 99%

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Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity

Roussaki

Zelianaios

Kavetsou

et al. 2014

Bioorganic & Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

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confidence: 97%

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Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity

Roussaki

Zelianaios

Kavetsou

et al. 2014

Bioorganic & Medicinal Chemistry

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“…Resveratrol has been reported to possess a wide range of pharmacological effects, including anti-inflammatory, anticarcinogenic, antioxidant, estrogenic, antiplatelet, and antimicrobial properties. [1][2][3][4][5][6][7] Resveratrol in red wine has been suggested to be responsible for the "French paradox", decreased risk for coronary artery disease in France.…”

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confidence: 99%

The Effects of Chronic Resveratrol Treatment on Vascular Responsiveness of Streptozotocin-Induced Diabetic Rats

Silan

2008

Biological & Pharmaceutical Bulletin

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Resveratrol (3,4Ј,5-trihydroxystilbene) (RSV) is found in dietary plants, and it is a phytoalexin substantially present in grapes and wines, especially in red wines. Resveratrol has been reported to possess a wide range of pharmacological effects, including anti-inflammatory, anticarcinogenic, antioxidant, estrogenic, antiplatelet, and antimicrobial properties. [1][2][3][4][5][6][7] Resveratrol in red wine has been suggested to be responsible for the "French paradox", decreased risk for coronary artery disease in France.8) The beneficial effects of these compounds seem to be due to their antioxidant/antiradical activities protecting the vascular walls from oxidation, inflammation, platelet aggregation, and thrombus formation. 9)Several reports point to protective acute effects of resveratrol on vascular bed, most indicating its vasodilator effects through direct and/or endothelium dependent mechanisms. [10][11][12] The key regulators of the vasomotor function are vasodilatator nitride oxide (NO) and the vasoconstrictor endothelin-1 (ET-1). Alnaeb et al. demonstrated the number of ET-1 receptors was significantly higher whereas, the expression of endothelial NO synthase (eNOS) was significantly lower when comparing aortas from normal rabbits with these from diabetics ones.13) eNOS expression in aorta was significantly lower in insulin-resistant and diabetes mellitus (DM) rats compared with normal control rats and the decrease was more pronounced in DM rats.14) Resveratrol significantly increased the expression of the gene encoding eNOS, which synthesis the vasodilator molecule NO, and decreased expression of the potent vasoconstrictor, endothelin-1 (ET-1). 15)Resveratrol reduces the generation of H 2 O 2 and normalizes the levels of oxidized glutathione reductase and myeloperoxidase (MPO) activities. By normalization of the reductive oxygen species (ROS) levels, resveratrol limits the oxidative stress, which inhibits NO synthesis by eNOS necessary for vasorelaxation.9) Resveratrol inhibits ET-1 promoter activity, ET-1 mRNA level and strain induced ET-1 secretion. Furthermore, resveratrol inhibits ET-1 surproduction and cytosolic phospholipase A 2 activity stimulated by oxidative stress. 9)Diabetes mellitus is an important health problem and mortality from cardiovascular complications is almost three fold higher in the diabetic population than in the general population.16,17) Oxidative stress is a major factor in the genesis of both macroangiopathy and microangiopathy in diabetes. 18)Unlike single angiogenic factor antagonists, resveratrol has therapeutic value (even at very low concentrations of 1-2.5 mM), as it blocks multiple angiogenic pathways including protein kinase C, vascular endothelial growth factor and cyclooxygenase.9) Resveratrol might have a protective effect on diabetic vascular degeneration with its vasorelaxant, antiangiogenic and hypoglycemic features.The purpose of this study was to investigate the chronic effects of resveratrol on diabetes and vascular response in streptozotocin (STZ) induced ...

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“…Coumarins are also described as antiviral, vasorelaxant, antioxidant, antimicrobial, anticancer, anti-inflammatory and enzymatic inhibitors [22][23][24][25][26][27][28][29][30][31][32][33], but limited data is available concerning their antioxidant activity [22,30,[34][35][36].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and electrochemical study of new 3-(hydroxyphenyl)benzo[f]coumarins

Matos

Janeiro

Santana

et al. 2014

Journal of Electroanalytical Chemistry

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Design, Synthesis, and Vasorelaxant and Platelet Antiaggregatory Activities of Coumarin—Resveratrol Hybrids.

Cited by 23 publications

References 1 publication

Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity

Structural modifications of coumarin derivatives: Determination of antioxidant and lipoxygenase (LOX) inhibitory activity

The Effects of Chronic Resveratrol Treatment on Vascular Responsiveness of Streptozotocin-Induced Diabetic Rats

Synthesis and electrochemical study of new 3-(hydroxyphenyl)benzo[f]coumarins

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