Design, Synthesis, andIn VitroAntiplatelet Aggregation Activities of Ferulic Acid Derivatives

Zhang, Peng-Xuan; Lin, Hang; Qu, Cheng; Tang, Yuping; Li, Nian‐Guang; Kai, Jun; Shang, Guanxiong; Li, Baoquan; Zhang, Li; Yan, Hui; Liu, Pei; Duan, Jin‐Ao

doi:10.1155/2015/376527

Cited by 13 publications

(14 citation statements)

References 35 publications

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“…[16]. Ferulic acid has been used to treat thrombosis [17], [18]. Here, ferulic acid found to inhibit platelet aggregation induced by both collagen and ADP with IC50 values estimated to 1.17 and 0.75 mM (Table I) respectively.…”

Section: Resultsmentioning

confidence: 97%

Evaluation of Antiplatelet Activity of Phenolic Compounds by Flow Cytometry

Kyriakidis

Vartholomatos

Μαρκόπουλος

2021

EJMED

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Platelets play a pivotal role in coagulation, or clot formation, resulting in haemostasis, after endothelium injury. Disturbance of platelet activation may lead to pathologic thrombosis. Platelet activation and aggregation are common factors in atherothrombotic events, critical in the atherothrombotic process, and cardiovascular diseases. Several drugs are being used for antiplatelet therapy to prevent and/or treat atherosclerosis and cardiovascular diseases. Synthetic antiplatelet drugs hold possible undesired health consequences (cardiovascular diseases, carcinogenicity, etc.), advocating their replacement with natural, effective, and non-toxic compounds. Many phenolic compounds are created as secondary metabolites of plants, are found in many fruits and vegetables, and constitute a wide family of high-added-value molecules. Their biological activities include antioxidant, anti-platelet, and anti-inflammatory action. Based on the above, we examined five phenolic compounds (ellagic acid, ferulic acid, gallic acid, quercetin, and kaempferol) for their effect on platelet reactivity in whole blood samples using flow cytometry. Quantification of activated platelet marker CD62-P by flow cytometry showed that all five compounds inhibited platelet activation in vitro, induced by adenosine diphosphate (ADP) and collagen. Interestingly, based on the IC50 values obtained for expression of CD62-P, among ellagic, ferulic, and gallic acid, gallic acid showed significantly higher inhibition than the other two. Kaempferol found to be a more potent inhibitor than quercetin, following previously reported results from aggregometry. Results obtained from our flow cytometry screening indicate antiplatelet activity from novel phenolic compounds and their potential use as drugs for thrombosis and cardiovascular diseases.

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Section: Resultsmentioning

confidence: 97%

Evaluation of Antiplatelet Activity of Phenolic Compounds by Flow Cytometry

Kyriakidis

Vartholomatos

Μαρκόπουλος

2021

EJMED

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“…Compounds (5)(6)(7)(8), each displayed three prominent signals, attributed to three NH groups of the thiosemicarbazide derivatives, as follow: (C=O) NH, NHNH-(C=S) and (C=S)-NH-ph: at δ=10.38, 9.69, 9,18 for compound 5; δ=10.53, 9.92, 9.25 for compound 6; δ=10.52, 9.90, 9.25 for compound 7; and δ=10.33 , 9.57, and 9.08 ppm for compound 8, respectively. Also, compounds (9 &10), each recorded the following signals for the three NH groups at δ= 10.49, 9.79, 9.19 for compound 9 and 10.52, 9.91 and 9.24 ppm for compound 10.…”

Section: Chemistrymentioning

confidence: 99%

“…The coagulation system consists of intrinsic and extrinsic pathways the typical final mediated of this system is thrombin, that trigger production of factors (V, VIII, and IX), activation of platelet and cleavage of fibrinogen to fibrin where it remains active after binds to fibrin 6 , many approaches for protection or treatment of thromboembolic events depend on inhibition of thrombin formation or block its activity. While the main antiplatelet mechanisms are; first, cycloxygenase-1 (COX-1) inhibitor, likes aspirin, by inhibition of (COX-1), aspirin will reduce the extent of thromboxane A2 formation, and consequently the aggregation of platelets 7 , like most NSAIDs, its use is associated with the induce of asthma, gastrointestinal (GIT) disorder, and reduce the number of white cells and platelet 8 . Second, adenosine diphosphate (ADP) antagonist as clopidogrel, which acts by preventing (ADP) stimulates platelet's purinergic receptor P 2 Y 12 , it has more considerable role in treatment of pathological conditions associated with high platelet reactivity, as acute coronary syndrome (ACS), and coronary artery disease (CAD), also its uses associated with GIT adverse effect 9 .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Docking Study and Antiplatelet Evaluation of New Thiosemicarbazide Derivatives Derived from Captopril

2019

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A series of thiosemicarbazide derivatives of captopril, a well-known angiotensin-converting enzyme inhibitor ACEI, have been synthesized by reaction of hydrazide of captopril with different phenylisothiocyanate substituents. The synthesized compounds were characterized using FTIR, 1HNMR and CHNS analysis. The final derivatives were tested for antiplatelet activity using multiplate analyzer and adenosine diphosphate (ADP), arachidonic acid (AA), and collagen, as platelet aggregation inducers. Among tested compounds, derivative 7 and 10 were the most potent inhibitors of platelet aggregation induced by arachidonic acid, with percent inhibition (97.14±0 and 95.71±2.02) and IC50 (2.7 and 1.21μgml), respectively. Molecular docking study was performed using purino receptor P2Y12, COX-1, and glycoprotein llbllla as the target protein, compound 7 has a potential to become as a lead molecule for COX-1 inhibitor with binding energy (-10.67) Kcal/mol. Also, compound 6 was found as the best inhibitor for the glycoprotein IIa/IIIb with percent inhibition (83.9±2.8), and binding energy (-10.05) Kcal/mol.

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“…Ferulic acid has been reported to have antiplatelet activity by indirectly inhibiting P2Y12 receptor activity (Yang et al, 2013;Zhang et al, 2015). However, a major inconvenience of FA is its disfavored solubility in both oil and aqueous media constraining its application in formulations proposed for pharmaceutical products (Antonopoulou et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

The Temperature Effect on Ultrasonic-assisted of Synthesis Methyl Ferulate and Its Antiplatelet Assay

et al. 2019

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Ferulic acid (FA) has been reported to have antiplatelet activity through indirectly inhibiting P2Y12 receptor. In order to increase the activity of FA, by improving its lipophilicity, so that it is easier to enter the cell, synthesis methyl ferulate was conducted through Fisher esterification. Ultrasonic waves were utilized as source of energy emitted through water as the medium at two various of temperature, i.e., 55 °C and 65 °C. The purposes of this study are to produce methyl ferulate and to determine the reaction constant rate (k) and its energy activation (Ea), at temperature of 55 °C and 65 °C. Moreover, the biological activity as antiplatelet was investigated at dose 20 mg/kg BW. The antiplatelet assay was conducted by clotting time and bleeding time methods. The results were analyzed by one way ANOVA program (P<0.05). The yield of methyl ferulate are 50.3% and 67.1% at 55 °C and 65 °C, respectively. The k value at 55°C is 4x10-5 cons-1min-1, while that of at 65 °C is 9x10-5 cons-1min-1. The clotting time and bleeding time of methyl ferulate obtained were 265 sec and 175 sec, respectively. The antiplatelet activity of methyl ferulate is better than ferulic acid.

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Design, Synthesis, andIn VitroAntiplatelet Aggregation Activities of Ferulic Acid Derivatives

Cited by 13 publications

References 35 publications

Evaluation of Antiplatelet Activity of Phenolic Compounds by Flow Cytometry

Evaluation of Antiplatelet Activity of Phenolic Compounds by Flow Cytometry

Design, Synthesis, Docking Study and Antiplatelet Evaluation of New Thiosemicarbazide Derivatives Derived from Captopril

The Temperature Effect on Ultrasonic-assisted of Synthesis Methyl Ferulate and Its Antiplatelet Assay

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