Pyrrole-2-carbaldehydes with neuroprotective activities from Moringa oleifera seeds

Jiang, Yueping; Liu, Rong; Li, Jing; Huang, Qi; Shao, Lei; He, Jia

doi:10.1016/j.phytochem.2022.113451

Cited by 9 publications

(6 citation statements)

References 18 publications

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“…Furthermore, another study by Kondeva-Burdina et al confirmed that pyrrole-based hydrazones could protect isolated rat brain synaptosomes against toxicity induced by 6-OHDA ( 20 ). In another study, it was reported that pyrrole-2-carbaldehydes had a neuroprotective effect against oxygen-glucose deprivation/reperfusion injury in PC12 cells ( 21 ). Similarly, our observations revealed that pre-treatment with synthetic pyrrolic compounds protected PC12 cells against 6-OHDA-induced neurotoxicity.…”

Section: Resultsmentioning

confidence: 99%

Biological Activity of Novel Pyrrole Derivatives as Antioxidant Agents Against 6-OHDA Induced Neurotoxicity in PC12 Cells

Javid,

Saeedian Moghadam,

Farahmandfar

et al. 2023

Iran J Pharm Res

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Background: Neuroinflammation and oxidative stress are critical factors involved in the pathogenesis of Parkinson's disease (PD), the second most common progressive neurodegenerative disease. Additionally, lipid peroxidation end products contribute to inflammatory responses by activating pro-inflammatory genes. Lipid peroxidation occurs as a result of either the overproduction of intracellular reactive oxygen species (ROS) or the reaction of cyclooxygenases (COXs). Objectives: In this study, we examined the role of 1,5-diaryl pyrrole derivatives against the neurotoxic effects of 6-hydroxydopamine (6-OHDA) in a cellular model of PD. Methods: PC12 cells were pre-treated with compounds 2-(4-chlorophenyl)-5-methyl-1-(4-(trifluoromethoxy)phenyl)-1H-pyrrole (A), 2-(4-chlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-pyrrole (B), and 1-(2-chlorophenyl)-2-(4-chlorophenyl)-5-methyl-1H-pyrrole (C), respectively, 24 h before exposure to 6-OHDA. We conducted various assays, including 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazoliumbromide (MTT), ROS, and lipid peroxidation assays, Hoechst staining, Annexin V/PI, Western blotting analysis and ELISA method, to assess the neuroprotective effects of pyrrole derivatives on 6-OHDA-induced neurotoxicity. Results: Our results demonstrated that apoptosis induction was inhibited by controlling the lipid peroxidation process in the in vitro model following pre-treatment with compounds A, B, and, somehow, C. Furthermore, compounds A and C likely act by suppressing the COX-2/PGE2 pathway, a mechanism not attributed to compound B. Conclusions: These findings suggest that the novel synthetic pyrrolic derivatives may be considered promising neuroprotective agents that can potentially prevent the progression of PD.

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Section: Resultsmentioning

confidence: 99%

Biological Activity of Novel Pyrrole Derivatives as Antioxidant Agents Against 6-OHDA Induced Neurotoxicity in PC12 Cells

Javid,

Saeedian Moghadam,

Farahmandfar

et al. 2023

Iran J Pharm Res

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“…Currently, the pyrrole derivative, 3-carboxylic acid pyrroles have been patented as active NRF2 regulators (US2020/0031820A1). Moreover, pyrrole-2-carbaldehydes exert neuroprotective effects against oxygen-glucose deprivation/reperfusion injury by modulating NRF2 and Nuclear Factor kappa B (NF-ĸB) in PC12 cells [ 32 ].…”

Section: Nitrogen Heterocycles As Modulators Of the Nrf2 Pathwaymentioning

confidence: 99%

NRF2 Activation by Nitrogen Heterocycles: A Review

et al. 2023

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Several nitrogen heterocyclic analogues have been applied to clinical practice, and about 75% of drugs approved by the FDA contain at least a heterocyclic moiety. Thus, nitrogen heterocycles are beneficial scaffolds that occupy a central position in the development of new drugs. The fact that certain nitrogen heterocyclic compounds significantly activate the NRF2/ARE signaling pathway and upregulate the expression of NRF2-dependent genes, especially HO-1 and NQO1, underscores the need to study the roles and pharmacological effects of N-based heterocyclic moieties in NRF2 activation. Furthermore, nitrogen heterocycles exhibit significant antioxidant and anti-inflammatory activities. NRF2-activating molecules have been of tremendous research interest in recent times due to their therapeutic roles in neuroinflammation and oxidative stress-mediated diseases. A comprehensive review of the NRF2-inducing activities of N-based heterocycles and their derivatives will broaden their therapeutic prospects in a wide range of diseases. Thus, the present review, as the first of its kind, provides an overview of the roles and effects of nitrogen heterocyclic moieties in the activation of the NRF2 signaling pathway underpinning their antioxidant and anti-inflammatory actions in several diseases, their pharmacological properties and structural–activity relationship are also discussed with the aim of making new discoveries that will stimulate innovative research in this area.

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“…The structures of the unknown Py-2-Cs ( 93 (dahurine F) and 98 ) were determined based on the spectroscopic analyses [ 87 ]. From Moringa oleifera seeds, seven new Py-2-Cs ( 99 – 105 ) and four known Py-2-Cs ( 5 , 10 , 96 , and 106 ) were isolated and the structures of the new compounds were characterized mainly based on NMR spectroscopic analyses and HR-ESI-MS [ 88 ] ( Figure 4 ).…”

Section: Naturally Occurring Pyrrole-2-carbaldehyde Derivativesmentioning

confidence: 99%

“…From Moringa oleifera seeds , seven new Py-2-Cs ( 99 – 105 ) and four known Py-2-Cs ( 5 , 10 , 96 , and 106 ) were isolated and characterized [ 88 ]. An oxygen deprivation experiment was carried out in the presence of 5 , 99 , and 103 at 0.1 μM using PC12 cell lines.…”

Section: Physiological Activities Of Pyrrole-2-carbaldehydesmentioning

confidence: 99%

Pyrrole-2-carboxaldehydes: Origins and Physiological Activities

Matsugo

Nakamura

2023

Molecules

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Pyrrole-2-carboxaldehyde (Py-2-C) derivatives have been isolated from many natural sources, including fungi, plants (roots, leaves, and seeds), and microorganisms. The well-known diabetes molecular marker, pyrraline, which is produced after sequential reactions in vivo, has a Py-2-C skeleton. Py-2-Cs can be chemically produced by the strong acid-catalyzed condensation of glucose and amino acid derivatives in vitro. These observations indicate the importance of the Py-2-C skeleton in vivo and suggest that molecules containing this skeleton have various biological functions. In this review, we have summarized Py-2-C derivatives based on their origins. We also discuss the structural characteristics, natural sources, and physiological activities of isolated compounds containing the Py-2-C group.

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Pyrrole-2-carbaldehydes with neuroprotective activities from Moringa oleifera seeds

Cited by 9 publications

References 18 publications

Biological Activity of Novel Pyrrole Derivatives as Antioxidant Agents Against 6-OHDA Induced Neurotoxicity in PC12 Cells

Biological Activity of Novel Pyrrole Derivatives as Antioxidant Agents Against 6-OHDA Induced Neurotoxicity in PC12 Cells

NRF2 Activation by Nitrogen Heterocycles: A Review

Pyrrole-2-carboxaldehydes: Origins and Physiological Activities

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