Chemical structure of isoeugenol.

Chemical structure of isoeugenol.

Source publication
Article
Full-text available
Isoeugenol (2-methoxy-4-(prop-1-en-1-yl)phenol), a component of from clove (Eugenia caryophylata) oil, is a starting material for both the biotechnological and synthetic production of vanillin and vanillic acid. In this article, the isoeugenol showed excellent inhibitory effects against some metabolic enzymes such as acetylcholinesterase (AChE) enz...

Context in source publication

Context 1
... Evaluation of the effects of the isoeugenol on AChE, α-amylase, and α-glycosidase was an important aim of this article and inhibition findings are represented in Table 4. The chemical structure of isoeugenol is shown in Figure 1. Half maximal inhibition concentration (IC 50 ) is a measure of the potency of a substance in inhibiting a specific biological or biochemical function. ...

Similar publications

Article
Full-text available
Alpha glucosidase is a potential target enzyme in the management of diabetes mellitus. Diabetes mellitus (DM) is a metabolic disorder caused by defect in insulin secretion, insulin action, or both. Insulin deficiency as such results to a chronic hyperglycemia with disturbances of carbohydrate, fat and protein metabolism. The current work studied th...
Article
Full-text available
Elevated free fatty acids (FFAs) are a risk factor for type 2 diabetes. Endothelial dysfunction induced by high levels of FFAs is one of the mechanisms related to the progression of diabetes. In clinical diabetes care, DPP-4 inhibitors have been shown to be effective in reducing glucose levels. In this study, we investigated the molecular mechanism...
Article
Full-text available
Patients with type 2 diabetes mellitus (T2DM) have been reported to have an enhanced risk of bone fracture, however the association between insulin treatment and risk of fracture in patients with T2DM remains to be fully elucidated. The aim of the present meta-analysis was to examine the possible association between insulin treatment and risk of fr...
Article
Full-text available
Alpha glucosidase is a potential target enzyme in the management of diabetes mellitus. Diabetes mellitus (DM) is a metabolic disorder caused by defect in insulin secretion, insulin action, or both. Insulin deficiency as such results to a chronic hyperglycemia with disturbances of carbohydrate, fat and protein metabolism. The current work studied th...

Citations

... The cholinesterase inhibitor, eugenol from S. aromaticum, inhibited the generation of superoxide anion via the suppression of the Raf/MEK/ERK1/2/p47phoxphosphorylation pathway and decreased cytokine concentrations attributed to its antioxidant and anti-inflammatory activities [18,77,78]. Its derivative, isoeugenol, exhibited potent inhibition against AChE, α-amylase, and α-glucosidase at 77.00, 411.5, and 19.25 nM of IC 50 , respectively [48]. ...
Article
Full-text available
Alzheimer’s disease (AD) causes progressive memory loss and cognitive dysfunction. It is triggered by multifaceted burdens such as cholinergic toxicity, insulin resistance, neuroinflammation, and oxidative stress. Syzygium plants are ethnomedicinally used in treating inflammation, diabetes, as well as memory impairment. They are rich in antioxidant phenolic compounds, which can be multi-target neuroprotective agents against AD. This review attempts to review the pharmacological importance of the Syzygium genus in neuroprotection, focusing on anti-cholinesterase, anti-diabetic, anti-inflammatory, and antioxidant properties. Articles published in bibliographic databases within recent years relevant to neuroprotection were reviewed. About 10 species were examined for their anti-cholinesterase capacity. Most studies were conducted in the form of extracts rather than compounds. Syzygium aromaticum (particularly its essential oil and eugenol component) represents the most studied species owing to its economic significance in food and therapy. The molecular mechanisms of Syzygium species in neuroprotection include the inhibition of AChE to correct cholinergic transmission, suppression of pro-inflammatory mediators, oxidative stress markers, RIS production, enhancement of antioxidant enzymes, the restoration of brain ions homeostasis, the inhibition of microglial invasion, the modulation of ß-cell insulin release, the enhancement of lipid accumulation, glucose uptake, and adiponectin secretion via the activation of the insulin signaling pathway. Additional efforts are warranted to explore less studied species, including the Australian and Western Syzygium species. The effectiveness of the Syzygium genus in neuroprotective responses is markedly established, but further compound isolation, in silico, and clinical studies are demanded.
... For example, it has been shown to suppress leukocyte recruitment, oxidative stress, cytokine production, and NF-κB activation in mouse models [213,214] and to have anti-obesity effects by improving energy metabolism in vitro and in vivo [215]. It exerts its anti-diabetic effects either directly by reducing methylglyoxal-induced Neuro-2A cell apoptosis or by inhibiting the metabolic enzymes such as acetylcholinesterase enzymes, α-glycosidase, and α-amylase [216,217]. Thus, VA could be used as a natural health promoter and potential drug candidate but should be investigated further. ...
Article
Full-text available
Cardiovascular and metabolic diseases are a leading cause of death worldwide. Epidemiological studies strongly highlight various benefits of consuming colorful fruits and vegetables in everyday life. In this review, we aimed to revisit previous studies conducted in the last few decades regarding green-colored foods and their bioactive compounds in consideration of treating and/or preventing cardiovascular and metabolic diseases. This review draws a comprehensive summary and assessment of research on the physiological effects of various bioactive compounds, mainly polyphenols, derived from green-colored fruits and vegetables. In particular, their health-beneficial effects, including antioxidant, anti-inflammatory, anti-diabetic, anti-obesity, cardioprotective, and lipid-lowering properties, will be discussed. Furthermore, the bioavailability and significance of action of these bioactive compounds on cardiovascular and metabolic diseases will be discussed in detail.
... The NMR spectra of the aqueous extract reveal that PAE contains xylobiose (Lim et al. 2018), asparagines (Hannou et al. 2018), homoarginine (Citro et al. 2015;Rodionov et al. 2019) and maslinic acid (Lozano-Mena et al. 2014), which exhibit antidiabetic property. The metabolites found in the organic phase of Panchvalkal (Supplementary material, Figure S4 and Table S5) are myrcene, ocimene, isoeugenol (Topal 2019), stigmasterol, b-sitosterol (Xu et al. 2014, ergosterol (Ma et al. 2013;Xiong et al. 2018), squalene (Gab as-Rivera et al. 2014, sphingosine (Tong et al. 2014), betulin (Xie et al. 2017), methyl ferulate (Karama c et al. 2017), neohesperidin (Jia et al. 2015) and cis-jasmone (Kaviya et al. 2019) The metabolites exhibit antioxidant, antidiabetic, anticancer and anti-inflammatory activities. Detection of these phytocompounds in PK formulation may further pave the way for their isolation of compounds and exploration of their pharmacological properties. ...
Article
Panchvalkal kwath (PK) is a bark formulation of five pharmacologically important plants, i.e., Ficus benghalensis, Ficus racemosa, Ficus religiosa, Thespesia populnea, and Ficus lacor. The Ayurvedic formulation is being used since ancient times to cure diabetes, bacterial infections and heal wounds. The present study aims to identify the metabolite profiles of PK which could explain its properties and its mode of action against specific diseases and disorders. The aqueous extract of Panchvalkal is prepared through a hot maceration process. The extract is subjected to preliminary identification of phytoconstituents and FTIR spectroscopy to recognize functional groups. GC-MS analysis reveals that the extract is enriched with 24-Norursa-3,12-diene (25.16%); Lup-20(29)-en-3-one (16.76%); 2-methyl-3-(4-propan-2-ylphenyl) propanal (7.04%); 2-(hydroxymethyl)-2-nitropropane-1,3-diol (11.21%) and 3,5-dihydroxy-6-methyl-2,3-dihydropyran-4-one (4.15%). The presence of three new phytocompounds that are 4-(hydroxymethyl)-7-methyl-1,3-dioxepane-5,6-diol; 1-(4-isopropylphenyl)-2-methylpropylacetate and 4,4,6 A,6B,8A,11,11,14B-octamethyl-1,4,4A,5,6,6A,8,8a,910,11,12,12a,12b,13,14,14a,14b-ctadecahydro-3(2H)-picenone are detected in the extract. Metabolite profiles of the extract also constitute isoeugenol, stigmasterol, ergosterol, ocimene, myrcene, squalene, sphingosine, betulin, methyl ferulate and cis-jasmone, which are unraveled by 1 D ¹H and 2 D ¹H-¹³C HSQC NMR spectroscopy. This article focuses on the presence of different phytocompounds in PK in order to demonstrate its efficacy as a therapeutic formulation for a variety of diseases.
... suberin, has shown its role in anticholinergic and antidiabetic effects. 37 Additionally, the glyceridic ester of the 4-methoxycinnamic acid has been traditionally used in the formulation of UV-B sun screening. 38 4′-Hydroxy acetophenone (piceol) was identified here at suberin from both hybrids. ...
Article
Full-text available
Although extractives have been symbolized as major bioactive pharmacological compounds fromSalix(Salicaceae) bark, we speculated that these pharmaceutical effects cannot be solely attributed to phenolic components and their derivatives, but the long-chain suberin acids also contribute to their therapeutic effects. Hence, isolation and deconstruction of suberin were conducted, for the first time, to enrich our knowledge about the macromolecular components at the cell wall of willow bark. Saponification was adopted to obtain suberin extracts at a yield of approximately 5 wt % based on the bark of the studied hybrids. Gas chromatography–mass spectrometry allowed qualification and quantification of 23 compounds from the released suberin monomers, from which fatty acids represented majority of the isolated suberin, namely, fatty acid methyl esters (C17–C19); mono-carboxylic acid (C7–C16); alpha, omega-dicarboxylic acid (C7–C16); and omega-hydroxy long-chain fatty acids (C16–C22). Additionally, the lipophilic extractive was dominated by piceol, heptacosane, β-sitosterol, and fatty acids (C16–C28) from the studied hybrids. These findings could boost our integrative approach toward full valorization of willow bark.
... Acetylcholinesterase (AChE) is an enzyme that plays a role in the hydrolysis of the neurotransmitter acetylcholine (ACh), found in greater quantities in the healthy human brain than in other tissues in the body (Akincio glu and G€ ulçin, 2020). The increase in AChE activity is one of the factors associated with the development of neurodegenerative diseases (Topal, 2019), such as Alzheimer's Disease (AD) (Işık et al., 2017). ...
Article
Background: Acetylcholinesterase (AChE) acts on cholinergic hydrolysis, whose changes in its functions are related to the development of neurodegenerative diseases. Another important component in these pathologies is oxidative stress, responsible for extensive cellular damage, caused by free radicals. Alkaloids represent an important active source in the search for compounds that act in the treatment of neurodegenerative diseases, having established antioxidant and AChE inhibitory properties. The present study aimed to evaluate the in vitro antioxidant and AChE inhibitory activities of the alkaloid fraction of Cissampelos sympodialis roots (FARCs). Methods: Modified Ellman and DPPH inhibition assays were used, respectively to assess the AChE inhibitory and antioxidant activities of FARCs. Results: Through assessment of the AChE inhibitory activity, FARCs was able to promote clinically relevant inhibition with an IC50 of 25.19 ± 0.02 µg/mL. In addition, FARCs led to a lasting effect, maintaining the levels of inhibition, through readings taken at 15 and 30 min after the reaction. In the antioxidant assay, the FARCs presented an IC50 of 161.2 ± 3.17 µg/mL, similar to that of the control (BHT), with an IC50 of 171.5 ± 4.96 µg/mL. The non-alkaloid fraction did not show any significant activity. Conclusion: These results indicate that FARCs is a source of alkaloids with AChE inhibitory properties and natural antioxidants, in addition, it can be said that the fraction properties are due to the presence of alkaloids, being necessary studies for the isolation and structural determination of these compounds.
... Isoeugenol belongs to the group of phenylpropenes, is found in essential oils of plants such as ylang-ylang (Cananga odorata), and is a component of wood smoke [29,30]. As one of the most important components of natural flavors, isoeugenol (2-methoxy-4-(prop-1-en-1-yl)phenol) has been widely used in perfumes, soaps, detergents, air fresheners, and as a flavoring agent in cosmetics and food additives [31][32][33][34][35]. Because isoeugenol-constituted phenolic groups are known to have antioxidant and antibacterial functions, they can provide oxidation protection and bacterial fouling resistance [36][37][38][39][40]. ...
Article
Full-text available
We synthesized a series of renewable and plant-based isoeugenol-substituted polystyrenes (PIEU#, # = 100, 80, 60, 40, and 20, where # is the molar percent content of isoeugenol moiety), using polymer modification reactions to study their liquid crystal (LC) alignment behavior. In general, the LC cells fabricated using polymer film with a higher molar content of isoeugenol side groups showed vertical LC alignment behavior. This alignment behavior was well related to the surface energy value of the polymer layer. For example, vertical alignments were observed when the polar surface energy value of the polymer was smaller than approximately 3.59 mJ/m2, generated by the nonpolar isoeugenol moiety with long and bulky carbon groups. Good alignment stability at 100 °C and under ultraviolet (UV) irradiation of 15 J/cm2 was observed for the LC cells fabricated using PIEU100 as a LC alignment layer. Therefore, renewable isoeugenol-based materials can be used to produce an eco-friendly vertical LC alignment system.
... Myrtenol, was found to improve asthma by reducing inflammatory cell infiltration and preventing hyperplasia of goblet cells Rajizadeh et al., 2019). Isoeugenol also was detected only in the highest dose level 10.0 kGy it is a promising antidiabetic and it can work against Alzheimer disease because it works as α-glycosidase inhibitor and AChE inhibitor (Topal, 2019). Isolongifolene a tricyclic sesquiterpene which increased by increasing irradiation dose level can help in decreasing rotenone-induced mitochondrial dysfunction and cell apoptosis in SH-SY5Y cells. ...
Article
Full-text available
Celery seed oils can help in detoxification processes of the body as it facilitates the elimination of toxins and other harmful substances out of the body. This study aimed to assess biological activity of essential oils extracted from un-irradiated and irradiated celery seeds by gamma rays. Celery seeds were irradiated with different dose levels of gamma radiation; control, 2.5, 5.0, and 10.0 kGy. The highest increase of essential oil extracted was registered with a dosage level of 10.0 kGy (2.42%). The GC-MS analysis showed that, there were new compounds detected in the irradiated samples and others compounds were increased or decreased. The FTIR spectra showed alterations in functional groups of essential oils extracted from celery seeds upon gammairradiation. Total phenols, total flavonoids and antioxidant activity increased proportional to the increase in the irradiation dose level and the maximum increase obtained in the irradiation dose level 10.0 kGy. This may be an evidence on the biological value, there were anticancer activity against 2 cell lines, breast cancer cell line (MCF-7) and lung cancer cell line (A549). The best IC50 in A549 was 145 μg/ml in sample with irradiation dose level 5.0 kGy while the best IC50 in MCF-7 was 124 μg/ml in irradiated sample with dose 5.0 kGy. Also, the highest inhibition zone of S. aureus , B. subtilis and K. pneumoniae were obtained with the oil extracted from seeds irradiated with 5 kGy dose level, where E. coli and C. albicans were more pronounced for the oil gotten from the seeds irradiated with 10.0 kGy. The irradiation process for celery seeds may be promising for biological value of celery oils.
... Some compounds, such as tannins corilagin and ellagic acid, have been described (Li et al. 2014). Additionally, the isolated compound, isoeugenol, from volatile oils of E. caryophyllata demonstrated α-glucosidase inhibitory activities (Topal 2019). One more study explores the effects of volatile oil from clove buds on α-amylase and α-glucosidase activities. ...
Chapter
One of the major challenges today for research groups on natural products distributed around the world is the discovery of substances that are bioactive, as well as their respective analogues. Thus, plants represent an important study target in the search for these new substances, being considered a promising source of molecular diversity for selective enzymatic inhibitors and synthesis for numerous bioactive compounds. The Brazilian biodiversity is one of the richest on the planet: it encompasses from 15 to 25% of all plant species, with a high rate of biological endemism, dispersed in unique biomes. A wide variety of micro- and macromolecular metabolites have been obtained, and several substances present biological and pharmacological activities with potential for the development of supplements alimentary, pharmaceuticals, and pesticides prototypes. In this context, this chapter documents the enzyme inhibitory potential of Myrtaceae, Lauraceae, and Piperaceae families from Brazilian Flora.
... [14][15][16] One of the most important treatments is to maintain the ACh concentration with AChE inhibitors. [17][18][19] AD is a disease caused by damage or death of these neuron cells. [16] The AChE gene was in living organisms because it was vital to stop AChE nerve conduction. ...
Article
Full-text available
Sesamol (1,3-benzodioxol-5-ol) is found in the oilseed product, sesame. In our study, the inhibitory effects of sesamol compound on acetylcholinesterase and α-glycosidase enzymes were evaluated. Another aim of this study was to compare the inhibitory effects of sesamol to acarbose for α-glycosidase enzyme and tacrine for acetylcholinesterase (AChE). Sesamol exhibited non-competitive inhibition for both metabolic enzymes. IC50 values for AChE and α-glycosidase enzymes were calculated as 86.63 nM and 99.00 nM, respectively. On the other hand, Ki values were calculated as 46.68 nM and 75.33 nM for AChE and α-glycosidase enzymes, respectively. According to the obtained results showed effective inhibition at low concentrations.