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Inhibition of a-amylase activity by Acarbose and compound 1. (A) binding of Acarbose at the active site of a-amylase, (B) Interaction of Acarbose with the active site residues of a-amylase, (C) binding of compound 1 at the active site of a-amylase, and (D) Interaction of compound 1 with the active site residues of a-amylase.
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The present study demonstrates the miquelianin or quercetin 3-O-glucuronide (compound 1) isolated from aerial parts of Euphorbia schimperi exhibited significant results for antioxidant and antidiabetic potential. The compound 1 along with kaempferol 3-O-glucuronide (compound 2) and quercetin 3-O-rhamnoside (compound 3) isolated from the same source...
Contexts in source publication
Context 1
... involved in hydrogen bond formation were Trp59, Tyr62, Gln63, Arg195, Glu233, Asp300, and Gly306 (Table 2). It is very exciting to note that Asp300 formed two hydrogen bonds. Moreover, Val163 formed two hydrophobic interactions (Pi-Sigma) with compound 1 while His305 interacted with compound 1 through Pi-Pi (T-shaped) hydrophobic interaction ( Fig. 6; Table 2). Other amino acid residues involved in stabilizing compound 1-a-amylase complex were Trp59, Tyr151, Leu162, Asp197, Ala198, His201, Ile235, His299, etc. The Gibb's free energy for the interaction between compound 1 and a-amylase was estimated to be À8.2 kcal/mol, which corresponded to a binding affinity of 1.03 Â 10 6 M À1 . ...
Context 2
... of compound 1 were comparable to a known inhibitor (Acarbose). Li, 2005). Our molecular docking analysis revealed that compound 1 form hydrogen bonds with two out of the three active site residues (namely Glu233 and Asp300). Moreover, it also interacted through hydrogen bonding with Arg195, one of the residue which binds with the chloride ion (Fig. 6). These results together with the findings of in-vitro a-amylase activity suggest that compound 1 is a potent inhibitor of a-amylase ...
Context 3
... involved in hydrogen bond formation were Trp59, Tyr62, Gln63, Arg195, Glu233, Asp300, and Gly306 (Table 2). It is very exciting to note that Asp300 formed two hydrogen bonds. Moreover, Val163 formed two hydrophobic interactions (Pi-Sigma) with compound 1 while His305 interacted with compound 1 through Pi-Pi (T-shaped) hydrophobic interaction ( Fig. 6; Table 2). Other amino acid residues involved in stabilizing compound 1-a-amylase complex were Trp59, Tyr151, Leu162, Asp197, Ala198, His201, Ile235, His299, etc. The Gibb's free energy for the interaction between compound 1 and a-amylase was estimated to be À8.2 kcal/mol, which corresponded to a binding affinity of 1.03 Â 10 6 M À1 . ...
Context 4
... of compound 1 were comparable to a known inhibitor (Acarbose). Li, 2005). Our molecular docking analysis revealed that compound 1 form hydrogen bonds with two out of the three active site residues (namely Glu233 and Asp300). Moreover, it also interacted through hydrogen bonding with Arg195, one of the residue which binds with the chloride ion (Fig. 6). These results together with the findings of in-vitro a-amylase activity suggest that compound 1 is a potent inhibitor of a-amylase ...
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Citations
... Especially quinic acid, miquelianin (quercetin 3-O-glucuronide), and ellagic acid increased the activity. Quinic acid, miquelianin, and ellagic acid have been reported to be effective in many studies investigating their antioxidant effects and in various antioxidant activity tests [73][74][75]. Species belonging to the genus Alchemilla are used for many purposes in traditional medicine. For this reason, there are many phytochemical analysis studies available. ...
Alchemilla species (Rosaceae) are popularly known as 'Lady's Mantle, Lion's claw' and are used for medicinal purposes as diuretic, laxative, tonic, and wound healing agents. Bioactivities and phenolic content of Alchemilla pseudocartalinica Juz. species have yet to be investigated. Our research focused on assessing the antioxidant characteristics of A. pseudocartalinica methanol (MEAP) and water extracts (WEAP), as well as their inhibitory effects on acetylcholinesterase (AChE), α-glycosidase (α-gly), and human carbonic anhydrase II (hCA II) enzymes. Additionally, we conducted chemical characterization using UPLC-MS/MS and investigated the correlation between major phenolic compounds and enzymes through molecular docking analysis. To assess the antioxidant activities of the MEAP and WEAP, six test systems were employed, including DPPH, ABTS, DMPD, FRAP, CUPRAC, and Fe 3+ reducing assays. The outcome showed that the methanol extract of the plant generally has stronger antioxidant activity. In addition, UPLC-MS/MS analysis indicated, miquelianin (44.095 mg/g), quinic acid (17.054 mg/g), and ellagic acid (6.492 mg/g) were significant in the methanol extract. A molecular docking study revealed a significant affinity for binding between the hCAII enzyme and quinic acid, miquelianin, and AChE/α-gly enzymes. A. pseudocatalinica methanol and water extracts have high antioxidant activity and good inhibition effect against AChE, α-glycosidase, and hCA II enzymes.
... As mentioned in the beginning, Q3G was the most abundant metabolite in non-germinated quinoa seeds, which is in agreement with Dostalikova et al. [29]. This metabolite has been primarily detected in aerial plant parts in various plant species [30][31][32], but research quantifying the content of Q3G in seeds is insufficient. During the germination, Q3G showcased an opposite pattern as RUT with 80% decline in the initial days of germination in 'Besançon' and 'Faro'. ...
Quinoa is a highly nutritious crop with diverse applications in the food industry. The study assessed the impact of various processing techniques, including microwaving, boiling, roasting, steaming, flaking, and germination, on the crude protein content (CP), total phenolic content (TPC), antioxidant activity (AA), and 12 phenolic compounds in quinoa. CP was significantly affected by the heat treatments. Boiled quinoa flakes exhibited the highest average CP, boiling and roasting the lowest. Microwaving strongly enhanced the TPC and the content of six bioactive compounds (CFA, KMP, NAR, QCE, RUT, SA), while boiling and steaming had the most adverse effect. Germination improved the overall nutritional profile of quinoa. The most pronounced increase in the bioactive metabolites occurred between the third and fifth day of germination in a genotype-dependent manner. Six metabolites (NAR, SA, 4BA, IQ, PC, IH) were detected in germinated quinoa for the first time. The results emphasize the substantial influence of processing techniques and type of sample on quinoa nutritional quality and underscore the importance of proper consideration of those factors to obtain nutritionally optimal food products.
... Likewise, many flavonoids and isoflavonoids were identified, as shown in the Table 3, namely 243 apigenin, luteolin, 3-methoxy-5,7,3',4'-tetrahydroxy-flavone, quercetin 3-O-rhamnoside-7-O-244 glucoside, malvidin, astragalin, daidzein, miquelianin, kaempferitrin, taxifolin, afzelin. [56][57][58][59][60][61][62][63][64][65] The 245 basic antioxidant mechanism of flavonoids consists in the oxidation of flavonoids by free radicals, 246 resulting in a more stable, less reactive radicals. [66] In fact, the configuration and number of hydroxyl 247 groups in flavonoids are a great determinant of their antioxidant capacity, more specifically, the high 248 reactivity of hydroxyl groups participate in scavenging free radicals by the following reaction: [67] 249 ...
Sonchus oleraceus(L.) L.(Asteraceae) is an edible wild plant, known for its uses in traditional medicine. The aim of this study is to explore the phytochemical composition of the aerial parts(AP) and roots(R) of aqueous extracts of Sonchus oleraceus L. growing in Tunisia, using liquid chromatography-tandem mass spectrometry(LC-MS/MS), and determine the content of polyphenols and antioxidant activities. Results showed that aqueous extractsof AP and R contained respectively, 195.25±33µg/g and 118.66±14µg/g gallic acid equivalent(GAE), and 52.58±7µg/g and 3.2±0.3µg/g quercetin equivalent. AP and R extractsalso contained tannins, 581.78±33µg/g and 948.44±19µg/g GAE. The AP extract in the1,1-diphenyl-2-picrylhydrazyl(DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid(ABTS) scavenging activities, hydroxyl radical scavenging(OH-)and incupric reducing antioxidant activity(CUPRAC) assays were respectively 0.325±0.036mg/mL, 0.053±0.018mg/mL, 0.696±0.031mg/mL and 60.94±0.004 µMTE/g, while the R extract using the same assays showed, 0.209±0.052mg/mL, 0.034±0.002mg/mL, 0.444± 0.014mg/mL and 50.63±0.006µM Trolox equivalent/g, respectively. A total of 68 compounds were tentatively identified by LC-MS/MS in both extracts in which quinic acid, pyrogallol, osthrutin, piperine, genistic acid, fisetin, luteolin, caffeic acid, gingerol, were the most abundant in the LC-MS/MS spectrum. Many of these metabolites were found for the first time in Tunisian Sonchus oleraceus L. which may take account for the antioxidant activities exhibited by the plant.
... 194 In terms of α-amylase inhibition, all three curated papers confirmed the weak inhibitory potent of quercetagetin (73). [195][196][197] Isorhamnetin (74) is also known as 3'-methoxy quercetin, a methoxyflavonol found in Ginkgo biloba leaf extract. As reported in 10 studies, isorhamnetin (74) demonstrated simultaneous inhibition against α-glucosidase and α-amylase. ...
... Hyperoside (98, hyperin, or quercetin-3-β-D-galactoside) had similar patterns as 97 but was slightly inferior in disaccharide hydrolysis, demonstrated in 13 curated studies. 32,44,57,58,81,172,195,201,206,209,224,234,235 Quercitrin (99), also known as quercetin-3-rhamnoside, appeared to potently inhibit α-glucosidase in a mixed manner, 218 noticeably better than acarbose in more than 12 studies. 38,55,58,78,83,102,133,140,188,217,237,238 However, only one research examined quercitrin as an α-amylase inhibitor, which showed quercitrin as roughly 30 times stronger than acarbose. ...
... Kaempferol-3-O-β-D-glucopyranoside, also known as astragalin (109), potently inhibited α-glucosidase as potent as acarbose, proven by at least eight studies. 124,148,174,189,195,199,226,230 Two out of three studies examined the α-amylase inhibition of 109 as three times weaker than the control agent. 195,233 Nicotiflorin (110) is a 3-rutinoside derivative, exhibiting controversial results in either inhibitory potential or inhibition mechanisms. ...
Diabetes mellitus remains a major global health burden and great attention is directed at natural therapeutics. This systematic review aimed to evaluate the potential of flavonoids as antidiabetic agents through their ability to inhibit α-amylase and α-glucosidase, two key starch digestive enzymes. Six scientific databases were queried up until August 21, 2022, for in vitro studies reporting the IC50 results of purified flavonoids on α-amylase or α-glucosidase, along with the respective data of acarbose control. A total of 339 articles were assessed as eligible and subjected to the data extraction process, resulting in 1643 retrieved flavonoid structures. Chemical structures were then rigorously standardized and curated to 974 unique compounds, in which 177 flavonoids showed both inhibitions against α-amylase and α-glucosidase. Quality assessment was conducted following a modified CONSORT checklist. The structure-activity relationships revealed that a double bond C2=C3 and a keto group C4=O is essential for simultaneous inhibition. The hydroxyl group at C3 is favourable for α-glucosidase inhibition but detrimental to the effect against α-amylase. Further notable features which affect α-glucosidase and α-amylase inhibition were also discussed. Several limitations were considered, including the inconsistency among included studies, language restriction, and the contemporaneity of the review. In conclusion, the systematic review has summarized some crucial findings in the investigation of flavonoids as dual-target inhibitors against α-glucosidase and α-amylase and proposed several orientations for future research.
... Quercetin-3-O-glucuronide (miquelianin) has a variety of health benefits, including anti-inflammatory effects (Derlindati et al., 2012), protective effects against neurotoxicity (Pariyar et al., 2019), and antibreast cancer properties (Yamazaki et al., 2014). It also possesses antioxidant , antidepressant (Juergenliemk et al., 2003), antimelanogenesis (Ha et al., 2021), antidiabetic (Ahmed et al., 2019), and anti-Alzheimer activities (Ho et al., 2013). However, engineered production of miquelianin is hindered by insufficient production of UDP-glucuronic acid in the hosts. ...
Polyphenolic compounds (such as quercetin and resveratrol) possess potential medicinal values due to their various bioactivities, but poor water solubility hinders their health benefits to humankind. Glycosylation is a well-known post-modification method to biosynthesize natural product glycosides with improved hydrophilicity. Glycosylation has profound effects on decreasing toxicity, increasing bioavailability and stability, together with changing bioactivity of polyphenolic compounds. Therefore, polyphenolic glycosides can be used as food additives, therapeutics, and nutraceuticals. Engineered biosynthesis provides an environmentally friendly and cost-effective approach to generate polyphenolic glycosides through the use of various glycosyltransferases (GTs) and sugar biosynthetic enzymes. GTs transfer the sugar moieties from nucleotide-activated diphosphate sugar (NDP-sugar) donors to sugar acceptors such as polyphenolic compounds. In this review, we systematically review and summarize the representative polyphenolic O-glycosides with various bioactivities and their engineered biosynthesis in microbes with different biotechnological strategies. We also review the major routes towards NDP-sugar formation in microbes, which is significant for producing unusual or novel glycosides. Finally, we discuss the trends in NDP-sugar based glycosylation research to promote the development of prodrugs that positively impact human health and wellness.
... The presence of luteolin, -amyrin, scopoletin, and kaempferol in the methanol extract of this plant has been demonstrated. In the course of the phytochemical isolation of this plant, it was discovered that it contained key anti-oxidant substances such as quercetin 3-O-glucuronide and kaempferol 3-Oglucuronide, among other compounds (Ahmed et al., 2019). ...
Historically, skin disorders have received less attention in health management than other life-threatening diseases that occur on a global scale. However, numerous skin problems are reported to primary health care systems worldwide, particularly in tropical locations. While modern physicians often address most skin conditions, it is estimated that over 70% of individuals with skin illnesses do not seek treatment. Traditional medicine dates all the way back to human civilization's inception. Numerous materials are utilized in traditional medicinal remedies, but the use of plants is particularly critical. Saudi Arabia is one of the world's most botanically varied countries, having an extensive folk medicine heritage. While several reviews on the use of plants to cure skin disorders has been published worldwide, very few have been undertaken in Saudi Arabia, much alone a comprehensive one. Thus, the present review identified the most significant and medicinally relevant herbs used in the treatment of various dermatological conditions in Saudi Arabia. A total of 43 plants were identified and described in this study. This investigation omitted publications that lacked detailed data and had only fragmented information regarding the herb's traditional use in topical applications.
... Patel et al., 2007;Semwal et al., 2016;Wang et al., 2019) are reported by flavonoids such as quercetin (24), apigenin (25), kaempferol (26), luteolin (27), myricetin (28) and catechin (29). Flavonoid glucosides such as kaempferol 3-glucuronide (30), quercetin 3-glucuronide (31), isoquercitrin (32), and quercitrin (33) have antioxidant and antidiabetic activity (Ahmed et al., 2019). ...
Etlingera is one of the plant genera from the Zingiberaceae family and is widely distributed in Asia to the Pacific Islands, with various species ranging from 150 to 200 species. The Etlingera are commonly used as spices, vegetables, and traditional medicines. Many pharmacological activities have been reported from this genus, including antioxidants, antibacterials, cholesterol-lowering, anticancer, and others. The phytochemical content of Etlingera reported are phenolics, diarylheptanoids, flavonoids, steroids, alkaloids, and terpenoids. Eight species from Etlingera, namely Etlingera elatior, E. pavieana, E. brevilabrum, E. pyramidosphaera, E. megalocheilos, E. coccinea, E. fimbriobracteata, and E. corneri are reported provided anticancer activity. This review article aims to review the phytochemical screening from Etlingera genus, and its anticancer activity.
... In silico studies The newly synthesized benzoxazole nucleus derivatives (1a, 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5b, 6a, 6b, 7a and 7b) were docked against target Human pancreatic alpha-amylase (PDB ID: 3BAW) [16] using AutoDoc 4.2 platform. The binding energies of the same is tabulated in Table 1. ...
In the present study, a set of different benzoxazole derivatives has been synthesized from ethyl acetoacetate, ethoxymethylene malononitrile, NaNO2, and organic acids. Analytical instruments like proton NMR (1H), carbon NMR (13C), infrared spectroscopy (IR), and LC-MS mass spectrometry were used for structural characterization. Synthesized molecules were evaluated for In-vitro antioxidant property (DPPH assay, Total antioxidant & reducing power method) and anti-diabetic property (alpha-amylase & alpha-glucosidase assay). In silico, studies against Human pancreatic alpha-amylase (PDB ID: 3BAW) have been carried out to get the binding approach of the ligand towards the protein. The results demonstrated that compounds namely 5b, 6b, 3b and 4b had potent antioxidant and anti-diabetic activity compared with ascorbic acid and acarbose. HIGHLIGHTS Anti-oxidant (DPPH assay, Total antioxidant and Reducing power) and Anti-diabetic (alpha-amylase & alpha-glucosidase assay) activities performed for synthesized molecules Sulfonamide substitutions are more potent towards biological activities In silico docking studies correlate with in vitro studies The small three-dimensional, stable structure and its ability to form hydrogen bonding the molecules show good activity towards antioxidant and anti-diabetic GRAPHICAL ABSTRACT
... O-glucunoride (compound 16) is a quercetin derivative consisting of a flavonoid attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage.65 Quercetin 3-Oglucunoride was identified in CBL, CRL, CSB, and CSL. This finding is the first report of the presence of quercetin 3-schimperi C. Presl has been demonstrated in vitro.66 Quercetin 3-O-glucunoride has been shown to inhibit angiotensinconverting enzyme (ACE)59 and was able to promote proliferation and migration of murine neuronal cells in vitro.67 ...
Introduction:
Species of Connaraceae are globally used in traditional medicines. However, several of these have not been studied regarding their chemical composition, and some are even at risk of extinction without proper studies. Therefore, the chemical composition and pharmacological potential of Connarus blanchetii Planch., Connarus nodosus Baker, Connarus regnellii G. Schellenb., and Connarus suberosus Planch., which were previously unknown, were analyzed.
Objective:
This work aims to investigate the pharmacological potential of these four Connarus species. The chemical composition of different extracts was determined by high-resolution mass spectrometry (HRMS), with subsequent analysis by the GNPS platform and competitive fragmentation modeling (CFM).
Materials and methods:
Leaf extracts (C. blanchetii, C. nodosus, C. regnellii, and C. suberosus) and bark extracts (C. regnellii and C. suberosus) were obtained by decoction, infusion, and maceration. LC/HRMS data were submitted to the GNPS platform and evaluated using CFM in order to confirm the structures.
Results:
The HRMS-GNPS/CFM analysis indicated the presence of 23 compounds that were mainly identified as phenolic derivatives from quercetin and myricetin, of which 21 are unedited in the Connarus genus. Thus, from the analyses performed, we can identify different compounds with pharmacological potential, as well as the most suitable forms of extraction.
Conclusion:
Using HRMS-GNPS/CFM, 21 unpublished compounds were identified in the studied species. Therefore, our combination of data analysis techniques can be used to determine their chemical composition.
... The antioxidant property of the test samples was evaluated by percent inhibition of DPPH (2, 2-diphenyl-1-picrylhydrazyl) free radical where ascorbic acid was used as standard (Ahmed et al., 2019). Concentration of the compound that provides 50% inhibition or reduction of DPPH, also known as IC 50 was calculated from the equation of the percentage inhibition versus concentration of the sample logarithmic curve. ...
Five α-D-ribofuranose analogues (2, 3, 4, 5 and 6) were synthesized in good yields from 3-O-benzyl-4-C-(hydroxymethyl)-1, 2-O-isopropylidene-α-D-ribofuranose (1). The synthesized compounds were then subjected to analgesic, anti-inflammatory, antimicrobial and antioxidant assays. Compound 3 demonstrated 79.74% (P <0.001) writhing inhibition and highest reaction time of 2.55 ± 0.13 min (P <0.001) after 30 minutes of oral administration in peripheral and central analgesic assay, respectively, at 50 mg/kg dose. Compound 2 and 6 exhibited significant anti-inflammatory activity at 100 mg/kg dose with paw edema inhibition of 91.15% (P <0.001) and 95.13% (P <0.001), respectively, in 4th hour. The synthesized analogues did not show notable antioxidant and antibacterial properties. Molecular docking study revealed higher binding affinity of -8.1 kcal/mol and -8.9 kcal/mol of compound 3 towards cyclooxygenase-1 and phospholipase A2, respectively, compared to -7.7 and 7.6 kcal/mol respectively for corresponding native ligands. Compound 2 demonstrated binding affinity of -9.1 kcal/mol towards interleukin-1 receptor-associated kinase-4 compared to -8.7 kcal/mol of the native ligand. The molecular properties related to drug likeness of compounds were found to be within acceptable range. Synthesized D-ribofuranose analogues demonstrated promising analgesic and anti-inflammatory activities and further development may lead to new potent analgesic and anti-inflammatory agents.
