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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...
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... 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. ...
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Citations
... Clove also contains tetraethylammonium chloride, gallic acid, phenolic acids, polyphenols, and flavonol glycosides with free radical scavenging/antioxidant activity [89]. Isoeugenol has proven to be beneficial for T2DM management, owing to its inhibitory effects against α-glycosidase and α-amylase [93]. ...
Diabetes mellitus (DM) comprises a range of metabolic disorders characterized by high blood glucose levels caused by defects in insulin release, insulin action, or both. DM is a widespread condition that affects a substantial portion of the global population, causing high morbidity and mortality rates. The prevalence of this major public health crisis is predicted to increase in the forthcoming years. Although several drugs are available to manage DM, these are associated with adverse side effects, which limits their use. In underdeveloped countries, where such drugs are often costly and not widely available, many people continue to rely on alternative traditional medicine, including medicinal plants. The latter serves as a source of primary healthcare and plant-based foods in many low-and middle-income countries. Interestingly, many of the phytochemicals they contain have been demonstrated to possess antidiabetic activity such as lowering blood glucose levels, stimulating insulin secretion, and alleviating diabetic complications. Therefore, such plants may provide protective effects that could be used in the management of DM. The purpose of this article was to review the medicinal plant-based foods traditionally used for the management of DM, including their therapeutic effects, pharmacologically active phytoconstituents, and antidiabetic mode of action at the molecular level. It also presents future avenues for research in this field.
... These compounds possess antifungal, antibacterial, antioxidant, anti-diabetic, anticancer, and anti-inflammatory properties (Kalaivani et al., 2012, Gopinath et al., 2013. From the prior reports, it was established that quercetin (Kim et al., 2017), isoeugenol (Topal 2019), isorhamnetine (Shibano et al., 2008, and Isovanillic acid (Choi et al., 2020) Table 4 Docking score compounds in the active site of a-Glc. ...
Due to the presence of various phenolic compounds in D.sophia, this plant may have an inhibitory effect on α-Glc and ultimately diabetes control. Therefore, this work aims to scrutinize total phenolic, flavonoid contents, antioxidant capacity, and α-Glc inhibitory activity in aerial parts of methanolic D.sophia extract. The methanolic flower extracts were selected from among aerial parts for the experimental study of anti-diabetic effects by α-Glc inhibitory assays. The flower extracts were also studied by GC/MS to detect the compounds. The total phenolic and flavonoid contents were 21.38 ± 0.93 GAE/g and 96.2 ± 0.20 QE/g, respectively. The IC50 value of flower extract for α-Glc inhibition with mixed (Competitive/non-competitive) mode was found to be 20.34 ± 0.11 mg/ml. Furthermore, in-vivo studies showed that the blood glucose level reduced after consumption of flower extract compared to the control group. Twenty-one compounds were identified by GC/MS technique. These compounds were assessed for high docking scores against α-Glc in silico. Docking score calculations exhibited that the DES-α-Glc complex had a significantly higher binding energy (-6.13 Kcal/mol) than other compounds. The DES-α-Glc complex which displayed a higher docking energy value than the ACR was subjected to MDs studies. The findings of this study suggest that the flower extract of D.sophia can be used as a suitable additive in syrups or foods with anti-diabetic capacity.
... 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]. ...
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. ...
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. ...
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. ...
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). ...
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]. ...
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. ...
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. ...
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.
