Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors

Sadeghian, Hamid; Seyedi, Seyed Mohammad; Saberi, Mohammad Reza; Arghiani, Zahra; Riazi, A. Mehdi

doi:10.1016/j.bmc.2007.10.016

Cited by 73 publications

(70 citation statements)

References 33 publications

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“…Considering our previous work on eugenol and esters [14], we tested the inhibitory properties of eugenol, methyl eugenol, methyl isoeugenol and 2,5-dimethoxyallylbenzene on SLO (substrate: linoleic acid) to study the effect of the methoxy group position on the inhibitory activity. The results showed half maximal inhibitory concentration (IC 50 ) of 34.1 ± 2.1, 96.1 ± 3.3, 138.9 ± 3.1 and 93.1 ± 2.9 µM for the above mentioned compounds, respectively (Table I).…”

Section: Resultsmentioning

confidence: 99%

“…There is reasonable homology between SLO and the human LO [14]. This homology becomes more identical (50%) within 8Å of the active site pocket.…”

Section: Introductionmentioning

confidence: 85%

“…This method has been previously shown to produce bonding models similar to the experimentally observed models [14,[28][29][30]. The torsion angles of the ligands were identified, hydrogens were added to the macromolecule, bond distances were edited and solvent parameters were added to the enzyme 3D structure.…”

Section: Molecular Dockingmentioning

confidence: 97%

“…We suggested that the inhibitory activity of these molecules largely depends on the orientation of the allyl group rESEarCH artICLE Synthesis and SAR comparative studies of 2-allyl-4-methoxy-1-alkoxybenzenes as 15-lipoxygenase inhibitors toward the chelated Fe 3+ -OH and the molecular volume of the carboxylate moiety in the active site pocket of the enzyme without hydroperoxidation of allylic carbons [14]. In this paper we report the results of a comparative study on the 15-LO inhibitory activities of 2-alkoxy derivatives of 5-methoxyallylbenzene.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and SAR comparative studies of 2-allyl-4-methoxy-1-alkoxybenzenes as 15-lipoxygenase inhibitors

Sadeghian

Seyedi

Attaran

et al. 2010

Journal of Enzyme Inhibition and Medicinal Chemistry

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Section: Resultsmentioning

confidence: 99%

“…There is reasonable homology between SLO and the human LO [14]. This homology becomes more identical (50%) within 8Å of the active site pocket.…”

Section: Introductionmentioning

confidence: 85%

Section: Molecular Dockingmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and SAR comparative studies of 2-allyl-4-methoxy-1-alkoxybenzenes as 15-lipoxygenase inhibitors

Sadeghian

Seyedi

Attaran

et al. 2010

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…DOI: 10.3109/13880209.2015.1037003 oil of Eugenia caryophyllata, which contains eugenol as the main constituent, exhibited strong inhibitory activity against COX-2 and 15-LOX enzymes. Moreover, eugenol derivatives have been evaluated as potential inhibitors of 15-LOX through molecular docking studies (Sadeghian et al, 2008). Previous studies have been carried out on the anti-inflammatory activity of eugenol with different methods and mechanisms, and showed a significant activity.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Chemical composition and biological activities of essential oil ofBeilschmiedia pulverulenta

Salleh

Ahmad

Khong

et al. 2015

Pharmaceutical Biology

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Context: The ethnopharmacological study of Beilschmiedia indicates that several species are used for the treatment of various ailments. Objective: This is the first study of the chemical composition of Beilschmiedia pulverulenta Kosterm (Lauraceae) essential oil and its antioxidant, antimicrobial, antityrosinase, antiinflammatory, and anticholinesterase activities. Materials and methods: The antioxidant activities were evaluated by b-carotene, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, ferric-reducing antioxidant power (FRAP), and phenolic content at different concentrations. The antimicrobial activities against Gram-positive and Gram-negative bacteria and fungi were revealed by disk diffusion and microdilution. The antityrosinase and anti-inflammatory activities were assayed against mushroom tyrosinase and lipoxygenase enzymes. The anticholinesterase activity was analyzed using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Results: Forty-two components were detected in B. pulverulenta oil with eugenol (45.3%) being the major component. The oil phenolic content and the FRAP were 660.1 mg gallic acid/g and 604.0 mg ascorbic acid/g, respectively. The oil gave an IC 50 value of 94.5 mg/mL and an inhibition of 93.9% in DPPH and b-carotene, respectively. The antimicrobial activity showed that the oil had strong activity against all Gram-positive bacteria with an minimum inhibitory concentration (MIC) value each of 62.5 mg/mL and moderate against all fungi with MIC and minimum bactericidal concentration (MBC) values each of 125 mg/mL. The oil showed significant antityrosinase and anti-inflammatory activities with 67.6 and 62.5% inhibition, respectively. In addition, the oil had moderate AChE (56.5%) and BChE (48.2%) activities. Discussion and conclusion: The results show that the oil could potentially be used for nutraceutical industries, food manufactures, and therapeutic agents against various diseases such as inflammation and rheumatism.

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On the Importance of CH/π and CH⋅⋅⋅HC Interactions in the Solid State Structure of 15‐Lipoxygenase Inhibitors Based on Eugenol Derivatives

et al. 2015

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In this manuscript the X-ray structures of two potent and known inhibitors of 15-lipoxygenase, that is, 4-allyl-2-methoxyphenyl-1-admantanecarboxylate (1) and allyl-2-methoxyphenyl-1-cyclohexanecarboxylate (2), are reported. Their solid-state architectures show that they have a strong ability to establish C-H/π and C-H⋅⋅⋅H-C interactions. For the former interaction, the adamantane or cyclohexane moieties are the C-H donors and the electron-rich methoxyphenyl ring is the π system. For the latter, the C-H bonds belong to the aliphatic rings of the inhibitors. Interestingly, the active site of lipoxygenase enzyme family is rich in isoleucine and leucine amino acids that participate in the binding of the unsaturated fatty acid substrate by means of multiple hydrophobic C-H⋅⋅⋅H-C interactions. By means of theoretical calculations, we analyze the ability of compounds 1 and 2 to establish C-H/π and C-H⋅⋅⋅H-C interactions in the solid state.

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Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors

Cited by 73 publications

References 33 publications

Synthesis and SAR comparative studies of 2-allyl-4-methoxy-1-alkoxybenzenes as 15-lipoxygenase inhibitors

Synthesis and SAR comparative studies of 2-allyl-4-methoxy-1-alkoxybenzenes as 15-lipoxygenase inhibitors

Chemical composition and biological activities of essential oil ofBeilschmiedia pulverulenta

On the Importance of CH/π and CH⋅⋅⋅HC Interactions in the Solid State Structure of 15‐Lipoxygenase Inhibitors Based on Eugenol Derivatives

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