Synthesis of Chromen-1-phenylpropen-1-one Derivatives and their Antidepressant/Anticonvulsant Activities

2021 ◽  
Vol 18 ◽  
Author(s):  
Shan-Shan Zhang ◽  
Wei-Hua Liu ◽  
Zhi-Wen He ◽  
Qiu-Wan Tan ◽  
Li-Ping Guan
Keyword(s):  
Biological Activities ◽  
Serotonin Level ◽  
Maximal Electroshock ◽  
Dependent Manner ◽  
Plant Metabolites ◽  
Maximal Electroshock Seizure ◽  
High Biological Activity ◽  
Secondary Plant Metabolites ◽  
Antidepressant Effects ◽  
Immobility Time

Background: Coumarin and chalcone are important secondary plant metabolites that exhibit a range of biological activities. Accordingly, the synthetic derivatives and analogs of these molecules have attracted attention as potential pharmacological agents Objective: This study aims to study new antidepressants with high biological activity and low side effects, and to provide a basis for the treatment of epilepsy and depression. Method: In this study, a series of chalcone derivatives containing a coumarin moiety (2a–2s) was designed, synthesized, and evaluated using classic antidepressant and anticonvulsant mouse models. Results: Forced swimming test results revealed that all but one of the compounds tested significantly decrease immobility time at a dose of 10 mg/kg and exhibit some antidepressant activity. Furthermore, compounds 2a, 2c, 2h, and 2k exhibit relatively high antidepressant effects in a dose-dependent manner from 10 to 30 mg/kg. Maximal electroshock seizure tests showed that compounds 2a, 2b, 2c, 2h, 2l, 2r, and 2s exhibit anticonvulsant activity at a dose of 30 mg/kg. Conclusion: Accordingly, compounds 2a, 2c, and 2h show promise as antidepressant adjunct therapy agents for treating depression in patients with epilepsy. Chromatographic neurochemical analysis of the mouse brain tissue revealed that the antidepressant effects of the compounds may be mediated by an increase in serotonin level.

scholarly journals Volatile terpenoids as potential drug leads in Alzheimer’s disease

2017 ◽  
Vol 15 (1) ◽  
pp. 332-343 ◽  
Author(s):  
Karolina A. Wojtunik-Kulesza ◽  
Katarzyna Targowska-Duda ◽  
Katarzyna Klimek ◽  
Grażyna Ginalska ◽  
Krzysztof Jóźwiak ◽  
...  
Keyword(s):  
Alzheimer’S Disease ◽  
Alzheimer's Disease ◽  
Mtt Assay ◽  
Inhibitory Activity ◽  
Biological Activities ◽  
Plant Metabolites ◽  
Secondary Plant Metabolites ◽  
Docking Simulations ◽  
Ache Inhibitory Activity ◽  
Volatile Terpenoids

AbstractAlzheimer’s disease (AD) is by far the most prevalent of all known forms of dementia. Despite wide-spread research, the main causes of emergence and development of AD have not been fully recognized. Natural, low-molecular, lipophilic terpenoids constitute an interesting group of secondary plant metabolites, that exert biological activities of possible use in the prevention and treatment of AD. In order to identify secondary metabolites possessing both antioxidant activity and the potential to increase the level of acetylcholine, selected terpenoids have been screened for possible acetylcholinesterase inhibitory activity by use of two methods, namely Marston (chromatographic assay) and Ellman (spectrophotometric assay). In order to describe the interaction between terpenes and AChE active gorge, molecular docking simulations were performed. Additionally, all analyzed terpenes were also evaluated for their cytotoxic properties against two normal cell lines using MTT assay. The obtained results show that: carvone (6), pulegone (8) and γ-terpinene (7) possess desirable AChE inhibitory activity. MTT assay revealed low or lack of cytotoxicity of these metabolites. Thus, among the investigated terpenes, carvone (6), pulegone (8) and y-terpinene (7) can be recognized as compounds with most promising activities in the development of multi-target directed ligands.

The effect of different partitions of seaweed Sargassum plagyophylum on depression behavior in mice model of despair

2019 ◽  
Vol 16 (4) ◽  
Author(s):  
Azadeh Mesripour ◽  
Neda Rabian ◽  
Afsaneh Yegdaneh
Keyword(s):  
Single Dose ◽  
Biological Activities ◽  
Food Resource ◽  
Control Group ◽  
Mice Model ◽  
Antidepressant Effects ◽  
Immobility Time ◽  
Term Administration ◽  
Swimming Test

Abstract Background Seaweeds are a famous traditional food resource in some countries containing different types of secondary metabolites. These marine organisms have shown different biological activities. The aim of this study was to investigate the effects of hexane and methanol extracts of Sargassum plagyophylum on depression. Methods Sargassum plagyophylum was collected from Persian Gulf. The plant was extracted by maceration with methanol-ethyl acetate solvent. The extract was evaporated and partitioned by hexane and methanol solvents. The two partitions were administered i.p. to male mice either a single dose or for 7 days. Depression was evaluated by the forced swimming test (FST) which higher immobility time indicates depressive-like behavior. Results The immobility time during FST decreased significantly by all the doses of the hexane partitions (notably 40 mg/kg; 10 s ± 2 vs. 114 s ± 12 control group). However, only the lowest dose (20 mg/kg) of the methanol partition reduced immobility time during FST (23 s ± 8, p<0.001). Following the long term administration both of the partitions reduced the immobility time in FST (hexane 27 s ± 11, methanol 70 s ± 14, p<0.05 vs. control 140 s ± 14). Conclusion The hexane partition showed antidepressant effects not only by long-term administration but also by the single dose during FST. The 7 days therapy with methanol partition also induced antidepressant behavior, but only the lowest single dose reduced immobility in FST. The methanol partitions possibly have certain substance that interfered with behavior in the FST. Therefore, S. plagyophylum should be considered for further antidepressant studies.

scholarly journals Approach to Optimization of FRAP Methodology for Studies Based on Selected Monoterpenes

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5267
Author(s):  
Karolina A. Wojtunik-Kulesza
Keyword(s):  
Biological Activities ◽  
Tween 20 ◽  
Plant Metabolites ◽  
Frap Assay ◽  
Antioxidant Power ◽  
Secondary Plant Metabolites ◽  
Reduction Activity ◽  
High Volatility ◽  
Ferric Reducing Antioxidant Power ◽  
Analgesic Activities

Terpenes, wide-spread secondary plant metabolites, constitute important parts of many natural compounds that hold various biological activities, including antioxidant, calming, antiviral, and analgesic activities. Due to their high volatility and low solubility in water, studies of compounds based on terpenes are difficult, and methodologies must be adjusted to their specific characteristics. Considering the significant influence of iron ions on dementia development, the activity of terpenes in reducing Fe3+ represents an important area to be determined. Previously obtained results were unreliable because ferric-reducing antioxidant power (FRAP) methodology was not adjusted regarding studying terpenes. Taking this fact into account, the aim of this study was to optimize the method for monoterpene assessment. The study included three modifications, namely, (1) slightly adjusting the entire FRAP procedure, (2) replacing methanol with other solvents (heptane, butanone, or ethyl acetate), and (3) adding Tween 20. Additionally, a thin layer chromatography (TLC) -FRAP assay was performed. The obtained results revealed significant improvement in the reduction activity of selected terpenes (linalool, α-phellandrene, and α-terpinene) in studies with Tween 20, whereas replacing methanol with other solvents did not show the expected effects.

scholarly journals Chemical Composition and Insecticide Activity of Essential Oil of Mesosphaerum suaveolens Against Nauphoeta cinerea

2020 ◽  
Vol 8 (2) ◽  
pp. 352
Author(s):  
José Weverton Almeida Bezerra ◽  
Francisco Alves Grangeiro Neto ◽  
Jacques Tavares Pereira Filho ◽  
Adrielle Rodrigues Costa ◽  
Arycelle Alves de Oliveira ◽  
...  
Keyword(s):  
Essential Oil ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Chemical Characterization ◽  
Positive Control ◽  
Plant Metabolites ◽  
Secondary Plant Metabolites ◽  
Nauphoeta Cinerea ◽  
Insecticide Activity ◽  
Insecticidal Action

Essential oils are compounds produced by secondary plant metabolites and are found in leaf trichomes, moreover, they are characteristic because they present strong odors and present biological activities. Thus, the objective of this work was to evaluate the insecticidal action of Mesosphaerum suaveolens essential oil against nymphs of Nauphoeta cinerea as well as to characterize the chemical constituents present in it. The EO was extracted by means of hydrodistillation and its chemical characterization was done by Gas Chromatography coupled to Mass Spectrometry (GC/MS). For the biological assay against cockroaches, nymphs of 20 days old were selected for which they were submitted to different concentrations (50 - 1000 μg/mL oil per air) and mortality was evaluated over 48 hours of EO exposure. As a positive control, ethanol (C2H6O) was used. Have been identified 44 compounds in EO, with β-Caryophyllene (18.57%), sabinene (15.94%) and spatulenol (11.09%) being the major compounds of EO. This showed no activity against the nymphs at any of the concentrations, whereas the positive control caused mortality at all concentrations tested. Thus, the essential oil of M. suaveolens does not present insecticidal properties in low concentrations against the cockroach.

scholarly journals Anticonvulsant profile of 2-ethylthio-7-methyl-4-(4-methylphenyl)pyrazolo[1,5-a][1,3,5]triazine

2014 ◽  
Vol 50 (1) ◽  
pp. 73-81
Author(s):  
Martín Hermógenes Estrada ◽  
Henry Insuasty ◽  
Luis Enrique Cuca ◽  
Mariel Marder ◽  
Angélica Fierro ◽  
...  
Keyword(s):  
Maximal Electroshock ◽  
Dependent Manner ◽  
Maximal Electroshock Seizure ◽  
Gaba A ◽  
Mao B ◽  
Plus Maze ◽  
Marble Burying ◽  
One Step ◽  
Dose Dependent ◽  
Benzodiazepine Site

This work evaluates the central nervous effects in ICR strain mice of 2-ethylthio-7-methyl-4-(4-methylphenyl)pyrazolo[1,5-a][1,3,5]triazine (MH4b1), a compound obtained by an efficient one-step reaction of S,S-diethyl 4-methylbenzoylimidodithiocarbonate with 5-amino-3-methyl-1H-pyrazole, in order to assess its neuro-pharmacological profile. The tests applied were: maximal electroshock seizure (MES), pentylenetetrazole (PTZ) seizures, forced swimming, plus maze, marble burying, sleeping time, rota-rod and catalepsy. In addition, MH4b1 binding to the benzodiazepine site of the GABA-A receptor and MH4b1 inhibition of monoamine oxidase (MAO) subtypes A and B were evaluated. MH4b1 showed anticonvulsant effects in a dose dependent manner (30-300 mg/kg, p.o.) against MES and inhibition of MAO-B (IC50: 24.5 µM) without activity at the benzodiazepine site. These data suggest that MH4b1 has anticonvulsant properties related to MAO-B inhibition.

scholarly journals Synthesis, Characterization and Anti-epileptic Activity of Thiohydantoin Derivatives

2020 ◽  
Vol 11 (4) ◽  
pp. 6490-6494
Author(s):  
Prakash G ◽  
Mohan S ◽  
Sundararajan N ◽  
Senthil Kumar C ◽  
Karpakavalli M
Keyword(s):  
Biological Activities ◽  
Biological Properties ◽  
Epileptic Activity ◽  
Hypolipidemic Activity ◽  
Activity Relationship ◽  
Maximal Electroshock ◽  
Maximal Electroshock Seizure ◽  
Vast Number ◽  
Structural Activity Relationship ◽  
Benzilic Acid

A vast number of biological properties have been recognised to Thiohydantoin derivatives, have attracted continuing interest because of their various biological activities, namely anticonvulsant, hypolipidemic activity, anti-thyroidal activity, and anti-microbial actions. In this look upon, multiple numbers of Thiohydantoin derivatives are synthesised besides anti-epileptic mechanisms have been investigated. A series of 3-substituted 2-thiohydantoin Derivatives were synthesised from Benzil via Benzil-Benzilic Acid Rearrangement, characterised and evaluated for their anti-epileptic activity by Maximal Electroshock Seizure (MES) model for the anti-epileptic activity of synthesised compounds was less when compared to standard. Among the activity, synthesised compounds 1 indicated more anti-epileptic activity. With this confirmation, we revised integrated a series of innovative 3-substituted 2-thiohydantoin derivatives with a different substituent on the construction and studied the structural activity relationship. The outcomes indicated with the purpose of all the tested compounds have displayed evident anti-epileptic activity. Among the series compounds, 1 shows more anti-epileptic activity than other synthesised compounds.

scholarly journals Antibacterial, Antifungal, Antimycotoxigenic, and Antioxidant Activities of Essential Oils: An Updated Review

Molecules ◽  
2020 ◽  
Vol 25 (20) ◽  
pp. 4711
Author(s):  
Aysegul Mutlu-Ingok ◽  
Dilara Devecioglu ◽  
Dilara Nur Dikmetas ◽  
Funda Karbancioglu-Guler ◽  
Esra Capanoglu
Keyword(s):  
Essential Oils ◽  
Environmental Conditions ◽  
Review Paper ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Edible Films ◽  
Edible Coatings ◽  
Plant Metabolites ◽  
Secondary Plant Metabolites ◽  
Chemical Preservatives

The interest in using natural antimicrobials instead of chemical preservatives in food products has been increasing in recent years. In regard to this, essential oils—natural and liquid secondary plant metabolites—are gaining importance for their use in the protection of foods, since they are accepted as safe and healthy. Although research studies indicate that the antibacterial and antioxidant activities of essential oils (EOs) are more common compared to other biological activities, specific concerns have led scientists to investigate the areas that are still in need of research. To the best of our knowledge, there is no review paper in which antifungal and especially antimycotoxigenic effects are compiled. Further, the low stability of essential oils under environmental conditions such as temperature and light has forced scientists to develop and use recent approaches such as encapsulation, coating, use in edible films, etc. This review provides an overview of the current literature on essential oils mainly on antifungal and antimycotoxigenic but also their antibacterial and antioxidant activities. Additionally, the recent applications of EOs including encapsulation, edible coatings, and active packaging are outlined.

scholarly journals Antidepressant Effect ofTetragonia tetragonoides (Pall.) KuntzeExtract on Serotonin Turnover

2019 ◽  
Vol 2019 ◽  
pp. 1-7 ◽  
Author(s):  
Hyun Yang ◽  
Hye Jin Kim ◽  
Eui-Ju Hong ◽  
Bo-Jeong Pyun ◽  
Byung-Seob Ko ◽  
...  
Keyword(s):  
Serum Level ◽  
Forced Swimming Test ◽  
Forced Swimming ◽  
Female Rats ◽  
Serotonin Level ◽  
Mrna Levels ◽  
Dependent Manner ◽  
Ovx Rats ◽  
Immobility Time ◽  
Swimming Test

Tetragonia tetragonoides (Pall.) Kuntze(TTK) is a groundcover found along coastal areas of the Korean peninsula. TTK is traditionally used to improve women’s health and treat gastrointestinal diseases. Use of herbal medicines in the treatment of mood disorders has recently been suggested as an alternative therapeutic strategy. In the present study, we determined that consumption of TTK extract ameliorated progression of depressive-like symptoms in ovariectomized (OVX) rats and further examined the mechanisms involved, i.e., synthesis, release, and reuptake(s) of serotonin (also known as 5-HT). We assessed the mRNA expression levels of tryptophan hydroxylases (TPH-1 and TPH-2) and serotonin transporter (SERT) as well as the reuptake activity of serotonin in RBL-2H3 cells. We also determined whether or not TTK extract regulates the serum level of serotonin and improves depressive-like symptoms in 0.5, 1, and 2% TTK-fed OVX female rats in a forced swimming test. Our results show that the mRNA levels of TPH-1 and SERT were significantly reduced, whereas the mRNA level of TPH-2 was dose-dependently elevated by TTK (50 and 100μg/mL) in RBL-2H3 cells. TTK significantly inhibited LPS- (lipopolysaccharide-) induced serotonin uptake in RBL-2H3 cells in a dose-dependent manner. The serum level(s) of serotonin was elevated by 1% and 2% TTK treatment in OVX female rats. Moreover, immobility time in the forced swimming test was reduced by 1% and 2% TTK treatment but not altered by 0.5% TTK treatment in OVX female rats. Taken together, these results indicate that TTK may significantly inhibit depressive-like symptoms due to upregulation of serotonin level(s) and regulation of serotonin reuptake activity. Thus, TTK may exert beneficial effects on depression during pre- or/and postmenopausal periodsviamodulation of serotonin synthesis and metabolism.

scholarly journals Nanoencapsulation of Plant Volatile Organic Compounds to Improve Their Biological Activities

Planta Medica ◽  
2020 ◽  
Author(s):  
Hakmin Mun ◽  
Helen E. Townley
Keyword(s):  
Volatile Organic Compounds ◽  
Organic Compounds ◽  
Biological Activities ◽  
Biological Properties ◽  
Anticancer Activities ◽  
Plant Metabolites ◽  
Secondary Plant Metabolites ◽  
Plant Volatile ◽  
Synthetic Chemicals ◽  
Volatile Organic

AbstractPlant volatile organic compounds (volatiles) are secondary plant metabolites that play crucial roles in the reproduction, defence, and interactions with other vegetation. They have been shown to exhibit a broad range of biological properties and have been investigated for antimicrobial and anticancer activities. In addition, they are thought be more environmentally friendly than many other synthetic chemicals 1. Despite these facts, their applications in the medical, food, and agricultural fields are considerably restricted due to their volatilities, instabilities, and aqueous insolubilities. Nanoparticle encapsulation of plant volatile organic compounds is regarded as one of the best strategies that could lead to the enhancement of the bioavailability and biological activity of the volatile compounds by overcoming their physical limitations and promoting their controlled release and cellular absorption. In this review, we will discuss the biosynthesis and analysis of plant volatile organic compounds, their biological activities, and limitations. Furthermore, different types of nanoparticle platforms used to encapsulate the volatiles and the biological efficacies of nanoencapsulated volatile organic compounds will be covered.

scholarly journals Chemical Composition and Antimicrobial Activity of Artemisia herba-alba and Origanum majorana Essential Oils from Morocco

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4021 ◽  
Author(s):  
Amor ◽  
Caputo ◽  
La Storia ◽  
De Feo ◽  
Mauriello ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Chemical Composition ◽  
Essential Oils ◽  
Biological Activities ◽  
Vanillyl Alcohol ◽  
Dependent Manner ◽  
Plant Metabolites ◽  
Concentration Dependent Manner ◽  
Main Components ◽  
Origanum Majorana

Essential oils (EOs) are one of the most important groups of plant metabolites responsible for their biological activities. This study was carried out to study the chemical composition and the antimicrobial effects of Artemisia herba-alba and Origanum majorana essential oils against some Gram-positive and Gram-negative bacteria, and a fungal strain isolated from spoiled butter. The plants were collected in the region Azzemour of South West Morocco and the EOs, extracted by hydrodistillation, were analyzed by GC-MS. The antimicrobial activity was determined using the agar paper disc method. The main components of A. herba-alba EO were cis-thujone, trans-thujone and vanillyl alcohol; in O. majorana EO terpinen-4-ol, isopulegol and β-phellandrene predominated. Both essential oils exhibited growth inhibiting activities in a concentration-dependent manner on several microorganism species. Our results demonstrated that O. majorana and A. herba-alba EOs could be effective natural antibacterial agents in foods.

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