Coumarins of Haplopappus Multifolius and Derivative as Inhibitors of Lox: Evaluation in-Vitro and Docking Studies

Torres, René; Mascayano, Carolina; Núñez, Carolina; Modak, Brenda; Faini, Francesca

doi:10.4067/s0717-97072013000400027

Cited by 6 publications

(3 citation statements)

References 17 publications

(28 reference statements)

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“…3) is a kind of coumarin derivative, with an inhibition of 34.75% at a concentration of 12.7 μM against 15-LOX. 42 In molecular docking study, its bond energy at the bonding site with 15-LOX and 5-LOX was −0.19 and 3.11 kcal mol −1 , respectively, which indicated that this compound has more affinity for human 5-LOX than 15-LOX. This phenomenon could result from the size of the catalytic cavity of 5-LOX being bigger than that of 15-LOX.…”

Section: Inhibitors Obtained By the Modification Of Previously Known mentioning

confidence: 94%

Recent development of lipoxygenase inhibitors as anti-inflammatory agents

2018

Med. Chem. Commun.

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Inflammation is favorable in most cases, because it is a kind of body defensive response to external stimuli; sometimes, inflammation is also harmful, such as attacks on the body's own tissues. It could be that inflammation is a unified process of injury and resistance to injury. Inflammation brings extreme pain to patients, showing symptoms of rubor, swelling, fever, pain and dysfunction. As the specific mechanism is not clear yet, the current anti-inflammatory agents are given priority for relieving suffering of patients. Thus it is emergent to find new anti-inflammatory agents with rapid effect. Lipoxygenase (LOX) is a kind of rate-limiting enzyme in the process of arachidonic acid metabolism into leukotriene (LT) which mediates the occurrence of inflammation. The inhibition of LOX can reduce LT, thereby producing an anti-inflammatory effect. In this review, the LOX inhibitors reported in recent years are summarized, and, in particular, their activities, structure-activity relationships and molecular docking studies are emphasized, which will provide new ideas to design novel LOX inhibitors.

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Section: Inhibitors Obtained By the Modification Of Previously Known mentioning

confidence: 94%

Recent development of lipoxygenase inhibitors as anti-inflammatory agents

2018

Med. Chem. Commun.

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“…To the best of our knowledge, there are no crystal structures containing cocrystallized structures of compounds investigated in this study with soybean lipoxygenase. Therefore, molecular docking was performed on soybean lipoxygenase-Ib (PDB ID: 5T5V) (SRIVASTAVA et al, 2016;TORRES et al, 2013). Initially, the protein was prepared for molecular modelling after being loaded into the UCSF Chimera v1.10.1 software (PETTERSEN et al, 2004) for Linux 64 bit architecture and visually inspected.…”

Section: The Structure Crystal Preparation Soybean Lipoxygenasementioning

confidence: 99%

In vitro and in silico lipoxygenase inhibition studies and antimicrobial activity of pyrazolyl-phthalazine-diones

Milovanović¹,

Petrović²,

Petrović³

et al. 2021

Kragujevac J Science

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The series of pyrazolyl-phthalazine-dione derivatives (PPDs) was subjected to evaluation of their in vitro lipoxygenase (LOX) inhibition and antimicrobial activities. Results obtained for LOX inhibition activities of PPDs showed that all compounds exhibit good to excellent activity, whereby compounds with eudesmic, syringic, vanillic or toluic moiety are the most active. Molecular modelling study was performed to investigate the possible mechanism of action and binding mode of compounds within the LOX active site. Docking results revealed that activity of the examined compounds depends on the functional group ability to create hydrogen bond accepting (HBA) and hydrophobic features (Hy) in the LOX-Ib active site. In addition, all substances were tested for their antibacterial and antifungal activities. The investigated compounds showed better antifungal than antibacterial activity. The highest antifungal activity was on Aspergillus fumigatus ATTC 204305 and Trichoderma viridae ATCC 13233.

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“…In lipoxygenase pathway, undesirable compounds may be formed causing side effects in plants and vegetables by changing color, creating unwanted odors, and changing the antioxidant properties ( Chatterjee and Sharma, 2018 ). Some natural compounds, such as polyphenols (-)-epigallocatechin gallate ( Skrzypczak-Jankun et al, 2003a ), curcumin ( Skrzypczak-Jankun et al, 2003b ), quercetin ( Sadik et al, 2003 ), and coumarins ( Torres et al, 2013 ) can effectively inhibit this enzyme. Previous studies have shown that various synthesized organic compounds can inhibit lipoxygenase: thiazolyl derivatives ( Tsolaki et al, 2018 ) and coumarin derivatives ( Lončarić et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis of Thiazolidine-2,4-dione Derivatives and Their Lipoxygenase Inhibition Activity With QSAR and Molecular Docking Studies

et al. 2022

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Thiazolidinediones are five-membered, heterocyclic compounds that possess a number of pharmacological activities such as antihyperglycemic, antitumor, antiarthritic, anti-inflammatory, and antimicrobial. Conventional methods for their synthesis are often environmentally unacceptable due to the utilization of various catalysts and organic solvents. In this study, deep eutectic solvents were used in the synthesis of thiazolidinedione derivatives that acted as both solvents and catalysts. Initially, a screening of 20 choline chloride-based deep eutectic solvents for thiazolidinedione synthesis, via Knoevenagel condensation, was performed in order to find the most suitable solvent. Deep eutectic solvent, choline chloride, N-methylurea, was proven to be the best for further synthesis of 19 thiazolidinedione derivatives. Synthesized thiazolidinediones are obtained in yields from 21.49% to 90.90%. The synthesized compounds were tested for the inhibition of lipid peroxidation as well as for the inhibition of soy lipoxygenase enzyme activity. The antioxidant activity of the compounds was also determined by the ABTS and DPPH methods. Compounds showed lipoxygenase inhibition in the range from 7.7% to 76.3%. Quantitative structure–activity relationship model (R2 = 0.88; Q2loo = 0.77; F = 33.69) for the inhibition of soybean lipoxygenase was obtained with descriptors Mor29m, G2u, and MAXDP. The molecular docking confirms experimentally obtained results, finding the binding affinity and interactions with the active sites of soybean LOX-3.

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Coumarins of Haplopappus Multifolius and Derivative as Inhibitors of Lox: Evaluation in-Vitro and Docking Studies

Cited by 6 publications

References 17 publications

Recent development of lipoxygenase inhibitors as anti-inflammatory agents

Recent development of lipoxygenase inhibitors as anti-inflammatory agents

In vitro and in silico lipoxygenase inhibition studies and antimicrobial activity of pyrazolyl-phthalazine-diones

Green Synthesis of Thiazolidine-2,4-dione Derivatives and Their Lipoxygenase Inhibition Activity With QSAR and Molecular Docking Studies

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