Efficient transport and biotransformation of dipeptide-like tyrosine/phenylalanine-conjugated phenolic amide esters in THP-1 cells and PBMCs: A potential means for transporting compounds inside monocytes/macrophages

2021 ◽  
Vol 03 ◽  
Author(s):  
Jae B. Park
Keyword(s):  
Methyl Ester ◽  
Biological Activities ◽  
Methyl Esters ◽  
Inflammatory Activity ◽  
Cell Transport ◽  
Ph Dependent ◽  
Efficient Transport ◽  
Anti Inflammatory ◽  
Phenolic Amides

Background: Recent studies suggest that dipeptide-like tyrosine/phenylalanine-conjugated phenolic amide compounds may contain several biological activities including anti-inflammatory activity. However, there is currently no information about their transport and biotransformation in monocytes/macrophages involved in inflammation process. Objective: The objective of this study was to investigate cell transport and biotransformation of the phenolic amides and esters in monocyte/macrophage-like cells. Methods: Cell transport and biotransformation of the phenolic amides and esters (N-coumaroylphenylalanine, N-caffeoylphenylalanine, N-feruloylphenylalanine, N-coumaroyltyrosine, N-caffeoyltyrosine, N-feruloyltyrosine and their O-methyl esters) were investigated in THP-1 cells and PBMCs using HPLC, cellular and kinetics methods Results: In THP-1 cells, the phenolic amides were not transported significantly, but their O-methyl esters were transported significantly (P < 0.02). Also, the transport of the esters was found to be sodium-independent and pH-dependent. Among the tested esters, N-feruloylphenylalanine-O-methyl ester showed the highest uptake (Km of 25 µM), and the uptake was inhibited by PepT1/2 substrate and blocker (GlySar and enalapril) in THP-1 cells. Particularly, enalapril competitively inhibited the uptake with Ki of 560 µM. The data also showed that N-feruloylphenylalanine-O-methyl ester and N-feruloyltyrosine-O-methyl ester could be biotransformed into parent phenolic amides in THP-1 cells. Similarly, the ester compounds were also found to be transported and biotransformed in PBMCs. Conclusion: The data suggest that dipeptide-like tyrosine/phenylalanine-conjugated phenolic amide esters may be transported and biotransformed in THP-1 cells and PBMCs.

Design, Synthesis, Characterization and in silico molecular docking studies and in vivo anti-inflammatory Activity of Pyrazoline clubbed Thiazolinone Derivatives

2020 ◽  
Vol 17 ◽  
Author(s):  
Deepak Kumar Singh ◽  
Mayank Kulshreshtha ◽  
Yogesh Kumar ◽  
Pooja A Chawla ◽  
Akash Ved ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Biological Activities ◽  
Inflammatory Activity ◽  
Standard Drug ◽  
Docking Score ◽  
Chemical Structures ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Cox 1

Background: The pyrazolines give the reactions of aliphatic derivatives, resembling unsaturated compounds in their behavior towards permanganate and nascent hydrogen. This nucleus has been associated with various biological activities including inflammatory. Thiazolinone is a heterocyclic compound that contains both sulfur and nitrogen atom with a carbonyl group in their structure.Thiazolinone and their derivatives have attracted continuing interest because of their various biological activities, such as anti-inflammatory, antimicrobial, anti-proliferative, antiviral, anticonvulsant etc. The aim of the research was to club pyrazoline nucleus with thiazolinone in order to have significantanti-inflammatory activity. The synthesized compounds were chemically characterized for the establishment of their chemical structures and to evaluate as anti-inflammatory agent. Method: In the present work, eight derivatives of substituted pyrazoline (PT1-PT8) were synthesized by a three step reaction.The compounds were subjected to spectral analysis by Infrared, Mass and Nuclear magnetic resonance spectroscopy and elemental analysis data. All the synthesized were evaluated for their in vivo anti-inflammatory activity. The synthesized derivatives were evaluated for their affinity towards target COX-1 and COX-2, using indomethacin as the reference compound molecular docking visualization through AutoDock Vina. Results: Compounds PT-1, PT-3, PT-4 and PT-8 exhibited significant anti-inflammatory activity at 3rd hour being 50.7%, 54.3%, 52.3% and 57% respectively closer to that of the standard drug indomethacin (61.9%).From selected anti-inflammatory targets, the synthesized derivatives exhibited better interaction with COX-1 and COX-2 receptor, where indomethacin showed docking score of -6.5 kJ/mol, compound PT-1 exhibited highest docking score of -9.1 kJ/mol for COX-1 and compound PT-8 having docking score of 9.4 kJ/mol for COX-2. Conclusion: It was concluded that synthesized derivatives have more interaction with COX-2 receptors in comparison to the COX-1 receptors because the docking score with COX-2 receptors were very good. It is concluded that the synthesized derivatives (PT-1 to PT-8) are potent COX-2 inhibitors.

scholarly journals Biosynthesis of resveratrol derivatives and evaluation of their anti-inflammatory activity

2021 ◽  
Vol 64 (1) ◽  
Author(s):  
Yoojin Chong ◽  
Hye Lim Lee ◽  
Jihyeon Song ◽  
Youngshim Lee ◽  
Bong-Gyu Kim ◽  
...  
Keyword(s):  
Biological Activities ◽  
Stilbene Synthase ◽  
Inflammatory Activity ◽  
E Coli ◽  
Prephenate Dehydrogenase ◽  
Coa Ligase ◽  
Final Yield ◽  
Resveratrol Derivatives ◽  
Anti Inflammatory ◽  
Tyrosine Biosynthesis

AbstractResveratrol is a typical plant phenolic compound whose derivatives are synthesized through hydroxylation, O-methylation, prenylation, and oligomerization. Resveratrol and its derivatives exhibit anti-neurodegenerative, anti-rheumatoid, and anti-inflammatory effects. Owing to the diverse biological activities of these compounds and their importance in human health, this study attempted to synthesize five resveratrol derivatives (isorhapontigenin, pterostilbene, 4-methoxyresveratrol, piceatannol, and rhapontigenin) using Escherichia coli. Two-culture system was used to improve the final yield of resveratrol derivatives. Resveratrol was synthesized in the first E. coli cell that harbored genes for resveratrol biosynthesis including TAL (tyrosine ammonia lyase), 4CL (4-coumaroyl CoA ligase), STS (stilbene synthase) and genes for tyrosine biosynthesis such as aroG (deoxyphosphoheptonate aldolase) and tyrA (prephenate dehydrogenase). Thereafter, culture filtrate from the first cell was used for the modification reaction carried out using the second E. coli harboring hydroxylase and/or O-methyltransferase. Approximately, 89.8 mg/L of resveratrol was synthesized and using the same, five derivatives were prepared with a conversion rate of 88.2% to 22.9%. Using these synthesized resveratrol derivatives, we evaluated their anti-inflammatory activity. 4-Methoxyresveratrol, pterostilbene and isorhapontigenin showed the anti-inflammatory effects without any toxicity. In addition, pterostilbene exhibited the enhanced anti-inflammatory effects for macrophages compared to resveratrol.

AN UPDATE ON THE SYNTHESIS OF BENZOXAZOLES

2017 ◽  
Vol 10 (10) ◽  
pp. 48 ◽  
Author(s):  
Jyothi M ◽  
Ramchander Merugu
Keyword(s):  
Central Nervous System ◽  
Nervous System ◽  
Biological Activity ◽  
Biological Activities ◽  
Starting Material ◽  
Bioactive Molecules ◽  
Living Systems ◽  
Inflammatory Activity ◽  
Anti Inflammatory

Benzoxazoles being structurally similar to bases adenine and guanine interact with biomolecules present in living systems. These compounds possess antimicrobial, central nervous system activities, antihyperglycemic potentiating activity, analgesic, and anti-inflammatory activity. It can also be used as starting material for other bioactive molecules. Modifications in structure and the biological profiles of new generations of benzoxazoles were found to be more potent with enhanced biological activity. Considering all these, we have prepared this review and discussed the synthesis and biological activities of benzoxazoles.

A OVERVIEW ON ANTIMICROBIAL AND ANTI-INFLAMMATORY ACTIVITY OF 1, 3, 4-OXADIAZOLES

INDIAN DRUGS ◽  
2020 ◽  
Vol 57 (02) ◽  
pp. 9-17
Author(s):  
Satvir Singh ◽  
Manpreet Kaur ◽  
Divya Bhandari ◽  
Mandeep Kaur ◽  
Monika Gupta
Keyword(s):  
Biological Activities ◽  
Present Review ◽  
Inflammatory Activity ◽  
World Population ◽  
Microbial Infections ◽  
Anti Inflammatory

1, 3, 4-oxadiazoles first came into the lime light about 80 years ago. With the increasing world population, the number of microbial infections has increased all over. To overcome the continuously spreading harmful microbial infections, the need for newer and newer drugs has increased tremendously. 1, 3, 4- oxadiazoles have been researched for the above mention purpose, because this nucleus has proven beneficial in a number of microbial infections from time to time. In the present review, we are highlight the biological activities being shown by the 1, 3, 4- oxadiazoles.

Synthesis, Characterization and Evaluation of some newer Pyrimidine derivatives as Anti-inflammatory Agents

2021 ◽  
pp. 2529-2534
Author(s):  
Kalpana Divekar ◽  
Rekha. S ◽  
Murugan. Vedigounder ◽  
Shivaprakash. H
Keyword(s):  
Biological Activities ◽  
Diclofenac Sodium ◽  
Pyrimidine Derivative ◽  
Inflammatory Activity ◽  
Paw Edema ◽  
Pyrimidine Derivatives ◽  
Anti Inflammatory ◽  
1Hnmr Spectroscopy ◽  
Hydrolysis Of ◽  
Antiparasitic Agents

Pyrimidine is an important baseone of the base formed by hydrolysis of nucleosides. It is an interesting molecule in the medicinal chemistry because of its diversified biological activities. Alloxan which is an oxidation product of Uric acid is also a pyrimidine derivative of interest to a medicinal chemist. Several pyrimidines are reported as antimicrobial, analegesic, anti-inflammatory, antibacterial, and antiparasitic agents. Pyrimidine scaffold is considered as an interesting one due to its various pharmacological properties. In this scheme, an attempt is made to carry out synthesis of some new pyrimidine derivatives. The Starting material Chalcone is synthesized by condensation of various aromatic aldehyde and aromatic ketone. Chalcone is then treated with thiourea and KOH in presence of ethanol to yield pyrimidine derivatives. Then those pyrimidine derivatives were subjected to alkylation and acetylation. The synthesized compounds were characterized and confirmed by IR and 1HNMR spectroscopy and then evaluated for their anti-inflammatory activity. The anti-inflammatory activity of newly synthesized pyrimidine derivatives were carried out by the carrageenan induced rat hind paw edema method by taking Diclofenac sodium as standard.

scholarly journals Inclusion Complexes of β and HPβ-Cyclodextrin with α, β Amyrin and In Vitro Anti-Inflammatory Activity

Biomolecules ◽  
2019 ◽  
Vol 9 (6) ◽  
pp. 241 ◽  
Author(s):  
Walter Ferreira da Silva Júnior ◽  
Danielle Lima Bezerra de Menezes ◽  
Luana Carvalho de Oliveira ◽  
Letícia Scherer Koester ◽  
Patrícia Danielle Oliveira de Almeida ◽  
...  
Keyword(s):  
Inclusion Complexes ◽  
Biological Activities ◽  
Physicochemical Characterization ◽  
Inflammatory Activity ◽  
Scanning Calorimetry ◽  
Promising Alternative ◽  
Wide Range ◽  
Natural Mixture ◽  
Anti Inflammatory

α, β amyrin (ABAM) is a natural mixture of pentacyclic triterpenes that has a wide range of biological activities. ABAM is isolated from the species of the Burseraceae family, in which the species Protium is commonly found in the Amazon region of Brazil. The aim of this work was to develop inclusion complexes (ICs) of ABAM and β-cyclodextrin (βCD) and hydroxypropyl-β-cyclodextrin (HPβCD) by physical mixing (PM) and kneading (KN) methods. Interactions between ABAM and the CD’s as well as the formation of ICs were confirmed by physicochemical characterization in the solid state by Fourier transform infrared (FTIR), scanning electron microscopy (SEM), X-ray diffraction (XRD), thermogravimetry (TG) and differential scanning calorimetry (DSC). Physicochemical characterization indicated the formation of ICs with both βCD and HPβCD. Such ICs were able to induce changes in the physicochemical properties of ABAM. In addition, the formation of ICs with cyclodextrins showed to be an effective and promising alternative to enhance the anti-inflammatory activity and safety of ABAM.

scholarly journals The Essential Oil and Hydrolats from Myristica fragrans Seeds with Magnesium Aluminometasilicate as Excipient: Antioxidant, Antibacterial, and Anti-inflammatory Activity

Foods ◽  
2020 ◽  
Vol 9 (1) ◽  
pp. 37 ◽  
Author(s):  
Inga Matulyte ◽  
Aiste Jekabsone ◽  
Lina Jankauskaite ◽  
Paulina Zavistanaviciute ◽  
Vytaute Sakiene ◽  
...  
Keyword(s):  
Essential Oil ◽  
Biological Activities ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Inflammatory Activity ◽  
Poly I:C ◽  
Bioactive Substances ◽  
Myristica Fragrans ◽  
Anti Inflammatory ◽  
Nutmeg Essential Oil

Nutmeg (Myristica fragrans) essential oil has antimicrobial, antiseptic, antiparasitic, anti-inflammatory, and antioxidant properties. We have recently demonstrated that hydrodistillation of nutmeg essential oil by applying magnesium aluminometasilicate as an excipient significantly increases both the content and amount of bioactive substances in the oil and hydrolats. In this study, we aimed to compare the antioxidant, antimicrobial, and anti-inflammatory activity of hydrolats and essential oil obtained by hydrodistillation in the presence and absence of magnesium aluminometasilicate as an excipient. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method revealed that magnesium aluminometasilicate did not significantly improved antioxidant activity of both essential oil and hydrolat. Antibacterial efficiency was evaluated by monitoring growth of 15 bacterial strains treated by a range of dilutions of the essential oil and the hydrolats. Essential oil with an excipient completely inhibited the growth of E. faecalis, S. mutans (referent), and P. multocida, whereas the pure oil was only efficient against the latter strain. Finally, the anti-inflammatory properties of the substances were assessed in a fibroblast cell culture treated with viral dsRNR mimetic Poly I:C. The essential oil with an excipient protected cells against Poly I:C-induced necrosis more efficiently compared to pure essential oil. Also, both the oil and the hydrolats with aluminometasilicate were more efficient in preventing IL-6 release in the presence of Poly I:C. Our results show that the use of magnesium aluminometasilicate as an excipient might change and in some cases improve the biological activities of nutmeg essential oil and hydrolats.

scholarly journals A Review on the Anti-Inflammatory Activity of Pomegranate in the Gastrointestinal Tract

2013 ◽  
Vol 2013 ◽  
pp. 1-11 ◽  
Author(s):  
Elisa Colombo ◽  
Enrico Sangiovanni ◽  
Mario Dell'Agli
Keyword(s):  
Gastrointestinal Tract ◽  
Clinical Studies ◽  
Intestinal Tract ◽  
Biological Activities ◽  
Inflammatory Activity ◽  
Beneficial Effects ◽  
Anti Inflammatory ◽  
Gastro Intestinal Tract ◽  
Inflammatory Effect

Several biological activities of pomegranate have been widely described in the literature, but the anti-inflammatory effect in the gastrointestinal tract has not been reviewed till now. The aim of the present paper is to summarize the evidence for or against the efficacy of pomegranate for coping with inflammatory conditions of the gastro-intestinal tract. The paper has been organized in three parts: (1) the first one is devoted to the modifications of pomegranate active compounds in the gastro-intestinal tract; (2) the second one considering the literature regarding the anti-inflammatory effect of pomegranate at gastric level; (3) the third part considers the anti-inflammatory effect of pomegranate in the gut.In vivostudies performed on the whole fruit or juice, peel, and flowers demonstrate antiulcer effect in a variety of animal models. Ellagic acid was the main responsible for this effect, although other individual ellagitannins could contribute to the biological activity of the mixture. Different preparations of pomegranate, including extracts from peels, flowers, seeds, and juice, show a significant anti-inflammatory activity in the gut. No clinical studies have been found, thus suggesting that future clinical studies are necessary to clarify the beneficial effects of pomegranate in the gastrointestinal tract.

scholarly journals Antioxidant, Anti-Inflammatory, and Anti-Aging Potential of a Kalmia angustifolia Extract and Identification of Some Major Compounds

Antioxidants ◽  
2021 ◽  
Vol 10 (9) ◽  
pp. 1373 ◽  
Author(s):  
Alexe Grenier ◽  
Jean Legault ◽  
André Pichette ◽  
Lorry Jean ◽  
Audrey Bélanger ◽  
...  
Keyword(s):  
Biological Activities ◽  
Skin Aging ◽  
Inflammatory Activity ◽  
No Production ◽  
Skin Substitutes ◽  
Kalmia Angustifolia ◽  
Isolation And Characterization ◽  
Assembly Method ◽  
Dermal Thickness ◽  
Anti Inflammatory

Skin aging is the most visible element of the aging process, giving rise to a major concern for many people. Plants from the Ericaceae family generally have antioxidant and anti-inflammatory properties, making them potential anti-aging active ingredients. This study aimed to evaluate the safety and anti-aging efficacy of a Kalmia angustifolia extract using reconstructed skin substitutes. The safety evaluation was performed using a 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide (MTT) assay, while the efficacy was determined by assessing antioxidant and anti-inflammatory activity and analyzing skin substitutes reconstructed according to the self-assembly method by histology and immunofluorescence staining (elastin, collagen-1, collagen-3, aquaporin-3). The cell viability assay established the safety of the extract at a concentration up to 200 μg/mL. The Oxygen Radical Absorbance Capacity (ORAC) assay and a cell-based assay using 2’,7’-dichlorofluorescein-diacetate (DCFH-DA) revealed a strong antioxidant activity with an ORAC value of 16 µmol Trolox Equivalent/mg and a half-maximal inhibitory concentration (IC50) of 0.37 ± 0.02 μg/mL, while an interesting anti-inflammatory activity was found in the inhibition of NO production, with an inhibition percentage of NO production of 49 ± 2% at 80 µg/mL. The isolation and characterization of the extract allowed the identification of compounds that could be responsible for these biological activities, with two of them being identified for the first time in K. angustifolia: avicularin and epicatechin-(2β-O-7, 4β-6)-ent-epicatechin. Histological analyses of skin substitutes treated with the extract showed an increase in dermal thickness compared with the controls. K. angustifolia extract enhanced the expression of elastin and collagen-1, which are usually decreased with skin aging. These results suggest that K. angustifolia has promising antioxidant efficacy and anti-aging potential.

scholarly journals Intestinal Anti-Inflammatory Activity of Terpenes in Experimental Models (2010–2020): A Review

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5430
Author(s):  
Maria Elaine Araruna ◽  
Catarina Serafim ◽  
Edvaldo Alves Júnior ◽  
Clelia Hiruma-Lima ◽  
Margareth Diniz ◽  
...  
Keyword(s):  
Gastrointestinal Tract ◽  
Biological Activities ◽  
Structural Diversity ◽  
Experimental Models ◽  
New Drugs ◽  
Inflammatory Activity ◽  
Bowel Diseases ◽  
Inflammatory Bowel ◽  
Anti Inflammatory

Inflammatory bowel diseases (IBDs) refer to a group of disorders characterized by inflammation in the mucosa of the gastrointestinal tract, which mainly comprises Crohn’s disease (CD) and ulcerative colitis (UC). IBDs are characterized by inflammation of the intestinal mucosa, are highly debilitating, and are without a definitive cure. Their pathogenesis has not yet been fully elucidated; however, it is assumed that genetic, immunological, and environmental factors are involved. People affected by IBDs have relapses, and therapeutic regimens are not always able to keep symptoms in remission over the long term. Natural products emerge as an alternative for the development of new drugs; bioactive compounds are promising in the treatment of several disorders, among them those that affect the gastrointestinal tract, due to their wide structural diversity and biological activities. This review compiles 12 terpenes with intestinal anti-inflammatory activity evaluated in animal models and in vitro studies. The therapeutic approach to IBDs using terpenes acts basically to prevent oxidative stress, combat dysbiosis, restore intestinal permeability, and improve the inflammation process in different signaling pathways.

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