Displaying publications 61 - 80 of 114 in total

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  1. Fulltext Synthesis, In Vitro Evaluation and Molecular Docking of the 5-Acetyl-2-aryl-6-hydroxybenzo[b]furans against Multiple Targets Linked to Type 2 Diabetes
    Mphahlele MJ, Choong YS, Maluleka MM, Gildenhuys S
    Biomolecules, 2020 03 07;10(3).
    PMID: 32156083 DOI: 10.3390/biom10030418
    The 5-acetyl-2-aryl-6-hydroxybenzo[b]furans 2a-h have been evaluated through in vitro enzymatic assay against targets which are linked to type 2 diabetes (T2D), namely, α-glucosidase, protein tyrosine phosphatase 1B (PTP1B) and β-secretase. These compounds have also been evaluated for antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging method. The most active compounds against α-glucosidase and/or PTP1B, namely, 4-fluorophenyl 2c, 4-methoxyphenyl 2g and 3,5-dimethoxyphenyl substituted 2h derivatives were also evaluated for potential anti-inflammatory properties against cyclooxygenase-2 activity. The Lineweaver-Burk and Dixon plots were used to determine the type of inhibition on compounds 2c and 2h against α-glucosidase and PTP1B receptors. The interactions were investigated in modelled complexes against α-glucosidase and PTP1B via molecular docking.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/chemistry*
  2. Fulltext Synthesis, Structure, Carbohydrate Enzyme Inhibition, Antioxidant Activity, In Silico Drug-Receptor Interactions and Drug-Like Profiling of the 5-Styryl-2-Aminochalcone Hybrids
    Mphahlele MJ, Agbo EN, Choong YS
    Molecules, 2021 May 04;26(9).
    PMID: 34064448 DOI: 10.3390/molecules26092692
    The 2-amino-5-(3/4-fluorostyryl)acetophenones were prepared and reacted with benzaldehyde derivatives to afford the corresponding 5-styryl-2-aminochalcone hybrids. The trans geometry of the styryl and α,β-unsaturated carbonyl arms, and the presence of NH…O intramolecular hydrogen bond were validated using 1H-NMR and X-ray data. The 2-amino-5-styrylacetophenones and their 5-styryl-2-aminochalcone derivatives were screened in vitro for their capability to inhibit α-glucosidase and/or α-amylase activities. Their antioxidant properties were evaluated in vitro through the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide (NO) free radical scavenging assays. Kinetic studies of the most active derivatives from each series against α-glucosidase and/or α-amylase activities have been performed supported by molecular docking studies to determine plausible protein-ligand interactions on a molecular level. The key aspects of the pharmacokinetics of these compounds, i.e., absorption, distribution, metabolism, and excretion have also been simulated at theoretical level. The most active compounds from each series, namely, 2a and 3e, were evaluated for cytotoxicity against the normal monkey kidney cells (Vero cells) and the adenocarcinomic human epithelial (A549) cell line to establish their safety profile at least in vitro.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/pharmacology; Glycoside Hydrolase Inhibitors/chemistry
  3. Fulltext Antidiabetic and In Vitro Enzyme Inhibition Studies of Methanol Extract of Ocimum tenuiflorum Linn Leaves and Its Fractions
    Mousavi L, Salleh RM, Murugaiyah V
    Trop Life Sci Res, 2020 Apr;31(1):141-158.
    PMID: 32963716 DOI: 10.21315/tlsr2020.31.1.9
    The current study aimed to determine the best dose of methanol extract of Ocimum tenuiflorum L. leaves extract, and it is a fraction to blood-glucose-lowering in diabetic rats, and evaluated the α-amylase, α-glucosidase inhibitors and insulin level of diabetic rats used to achieve greater control over hyperglycemia. The result of the antihyperglycaemic of oral administration of a different dose of methanol extract in streptozotocin-induced rats showed that the highest dose of methanol extract significantly reduced the blood glucose level compared to another dose. Also, the result of repeated administration of methanol fractions indicates that ethyl acetate-butanol fraction exhibited a stronger antihyperglycemic effect than chloroform and ethanol-water fractions. Moreover, the result showed that effect of methanol extract and its fraction on α-glucosidase and α-amylase enzymes activities and its insulin level by in vitro study, ethyl acetate-butanol fraction could control with low concentration compared to other fractions and acarbose that used as a positive control. From the result of insulin level, methanol extract and fraction did not show any significant. These findings indicated that the active crude extract (methanol) and its active fractions (ethyl acetate/butanol) could exert significant glucose-lowering effect due to the presence of polyphenolics active constituents. In conclusion, isolation of the active components of Ocimum tenuiflorum L. may pave the way to the development of new agents for the treatment of diabetes and its complications.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  4. Anti-acetylcholinesterase, anti-α-glucosidase, anti-leishmanial and anti-fungal activities of chemical constituents of Beilschmiedia species
    Mollataghi A, Coudiere E, Hadi AH, Mukhtar MR, Awang K, Litaudon M, et al.
    Fitoterapia, 2012 Mar;83(2):298-302.
    PMID: 22119096 DOI: 10.1016/j.fitote.2011.11.009
    Phytochemical investigation of Beilschmiedia alloiophylla has resulted in the isolation of one new alkaloid, 2-hydroxy-9-methoxyaporphine (1), and ten known natural products, laurotetanine (2), liriodenine (3), boldine (4), secoboldine (5), isoboldine (6), asimilobine (7), oreobeiline (8), 6-epioreobeiline (9), β-amyrone (10), and (S)-3-methoxynordomesticine (11). Chemical studies on the bark of B. kunstleri afforded compounds 2 and 4 along with one bisbenzylisoquinoline alkaloid, N-dimethylphyllocryptine (12). Structures of compounds 1-12 were elucidated on the basis of spectroscopic methods. All of these isolates were evaluated for their anti-acetylcholinesterase (AChE), anti-α-glucosidase, anti-leishmanial and anti-fungal activities. Compounds 1-12 exhibited strong to moderate bioactivities in aforementioned bioassays.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  5. α-Glucosidase Inhibitory Activity of Selected Malaysian Plants
    Mohd Bukhari DA, Siddiqui MJ, Shamsudin SH, Rahman MM, So'ad SZM
    J Pharm Bioallied Sci, 2017 Jul-Sep;9(3):164-170.
    PMID: 28979070 DOI: 10.4103/jpbs.JPBS_35_17
    Diabetes is a common metabolic disease indicated by unusually high plasma glucose level that can lead to major complications such as diabetic neuropathy, retinopathy, and cardiovascular diseases. One of the effective therapeutic managements of the disease is to reduce postprandial hyperglycemia through inhibition of α-glucosidase, a carbohydrate-hydrolyzing enzyme to retard overall glucose absorption. In recent years, a plenty of research works have been conducted looking for novel and effective α-glucosidase inhibitors (AGIs) from natural sources as alternatives for the synthetic AGI due to their unpleasant side effects. Plants and herbs are rich with secondary metabolites that have massive pharmaceutical potential. Besides, studies showed that phytochemicals such as flavonoids, alkaloids, terpenoids, anthocyanins, glycosides, and phenolic compounds possess significant inhibitory activity against α-glucosidase enzyme. Malaysia is a tropical country that is rich with medicinal herbs. In this review, we focus on eight Malaysian plants with the potential as AGI to develop a potential functional food or lead compounds against diabetes.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  6. Fulltext Potent α-glucosidase and α-amylase inhibitory activities of standardized 50% ethanolic extracts and sinensetin from Orthosiphon stamineus Benth as anti-diabetic mechanism
    Mohamed EA, Siddiqui MJ, Ang LF, Sadikun A, Chan SH, Tan SC, et al.
    BMC Complement Altern Med, 2012;12:176.
    PMID: 23039079 DOI: 10.1186/1472-6882-12-176
    In the present study, we tested a 50% ethanolic extract of Orthosiphon stamineus plants and its isolated bioactive compound with respect to their α-glucosidase and α-amylase inhibitory activities.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors*
  7. Fulltext Evaluation of α-Glucosidase Inhibitory Effect of 50% Ethanolic Standardized Extract of Orthosiphon stamineus Benth in Normal and Streptozotocin-Induced Diabetic Rats
    Mohamed EA, Ahmad M, Ang LF, Asmawi MZ, Yam MF
    Evid Based Complement Alternat Med, 2015;2015:754931.
    PMID: 26649063 DOI: 10.1155/2015/754931
    In the present study, a 50% ethanolic extract of Orthosiphon stamineus was tested for its α-glucosidase inhibitory activity. In vivo assays of the extract (containing 1.02%, 3.76%, and 3.03% of 3'hydroxy-5,6,7,4'-tetramethoxyflavone, sinensetin, and eupatorin, resp.) showed that it possessed an inhibitory activity against α-glucosidase in normal rats loaded with starch and sucrose. The results showed that 1000 mg/kg of the 50% ethanolic extract of O. stamineus significantly (P < 0.05) decreased the plasma glucose levels of the experimental animals in a manner resembling the effect of acarbose. In streptozotocin-induced diabetic rats, only the group treated with 1000 mg/kg of the extract showed significantly (P < 0.05) lower plasma glucose levels after starch loading. Hence, α-glucosidase inhibition might be one of the mechanisms by which O. stamineus extract exerts its antidiabetic effect. Furthermore, our findings indicated that the 50% ethanolic extract of O. stamineus can be considered as a potential agent for the management of diabetes mellitus.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  8. Fulltext Antidiabetic and antioxidant properties of Ficus deltoidea fruit extracts and fractions
    Misbah H, Aziz AA, Aminudin N
    BMC Complement Altern Med, 2013;13:118.
    PMID: 23718315 DOI: 10.1186/1472-6882-13-118
    Diabetes is a serious metabolic disorder affecting the metabolism of carbohydrate, protein and fat. A number of studies have shown that diabetes mellitus is associated with oxidative stress, leading to an increased production of reactive oxygen species. Ficus deltoidea is traditionally used in Malaysia for regulating blood sugar, blood pressure and cholesterol levels. The use of F. deltoidea as an alternative medicinal herb is increasingly gaining popularity with the sale of F. deltoidea tea bags and capsules in the local market. The present study was undertaken to investigate the antidiabetic and antioxidant activities of the fruits from different varieties of F. deltoidea, employing in vitro methods.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  9. Fulltext Isolation of Antidiabetic Withanolides from Withania coagulans Dunal and Their In Vitro and In Silico Validation
    Maher S, Choudhary MI, Saleem F, Rasheed S, Waheed I, Halim SA, et al.
    Biology (Basel), 2020 Jul 30;9(8).
    PMID: 32751610 DOI: 10.3390/biology9080197
    Withania coagulans (W. coagulans) is well-known in herbal medicinal systems for its high biological potential. Different parts of the plant are used against insomnia, liver complications, asthma, and biliousness, as well as it is reported to be sedative, emetic, diuretic, antidiabetic antimicrobial, anti-inflammatory, antitumor, hepatoprotective, antihyperglycemic, cardiovascular, immuno-suppressive and central nervous system depressant. Withanolides present in W. coagulans have attracted an immense interest in the scientific field due to their diverse therapeutic applications. The current study deals with chemical and biological evaluation of chloroform, and n-butanol fractions of W. coagulans. The activity-guided fractionation of both extracts via multiple chromatographic steps and structure elucidation of pure isolates using spectroscopies (NMR, mass spectrometry, FTIR and UV-Vis) led to the identification of a new withanolide glycoside, withacogulanoside-B (1) from n-butanol extract and five known withanolides from chloroform extract [withanolid J (2), coagulin E (3), withaperuvin C (4), 27-hydroxywithanolide I (5), and ajugin E (6)]. Among the tested compounds, compound 5 was the most potent α-glucosidase inhibitor with IC50 = 66.7 ± 3.6 µM, followed by compound 4 (IC50: 407 ± 4.5 µM) and compound 2 (IC50: 683 ± 0.94 µM), while no antiglycation activity was observed with the six isolated compounds. Molecular docking was used to predict the binding potential and binding site interactions of these compounds as α-glucosidase inhibitors. Consequently, this study provides basis to discover specific antidiabetic compounds from W. coagulans.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  10. Fulltext In vitro inhibitory potential of selected Malaysian plants against key enzymes involved in hyperglycemia and hypertension
    Loh SP, Hadira O
    Malays J Nutr, 2011 Apr;17(1):77-86.
    PMID: 22135867 MyJurnal
    This study was conducted to determine the inhibitory potential of selected Malaysian plants against key enzymes related to type 2 diabetes and hypertension.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  11. Fulltext In vitro antioxidant capacities and antidiabetic properties of phenolic extracts from selected citrus peels
    Lim, S.M., Loh, S.P.
    International Food Research Journal, 2016;23(1):211-219.
    MyJurnal
    This study aims to determine the antioxidant capacities (AC) and antidiabetic properties of
    phenolic extracts (free and bound) from white Tambun pomelo peels, kaffir lime peels, lime
    peels and calamansi peels. AC, total phenolic content (TPC) and antidiabetic properties of
    selected citrus peels extracts were determined spectrophotometrically using 2,2-Diphenyl-1-
    picrylhydrazyl free radical (DPPH) scavenging, ferric-reducing antioxidant power (FRAP),
    Folin-Ciocalteu (FC) and α-amylase and α-glucosidase inhibition assay, respectively. This
    study found that the methanolic extract of kaffir lime showed the best AC with the lowest
    IC50 value of DPPH radical (7.51 ± 0.50 mg/ml) and highest FRAP value [369.48 ± 20.15
    mM Fe (II) E/g DW]. TPC of free phenolic extracts of all citrus peels were significantly (p<
    0.05) higher compared to the bound phenolic extracts with extract of calamansi showed the
    highest TPC. Free- and bound phenolic extract of calamansi also had the highest α-amylase
    inhibition activity (61.79 ± 4.13%; 45.30 ± 5.35%) respectively. The highest inhibitory effect in
    α-glucosidase inhibition assay of free- and bound phenolic extracts were white Tambun pomelo
    (41.06 ± 10.94%) and calamansi (43.99 ± 22.03%) respectively. Hence, the citrus peels could
    be furthered study for their potential in management and/or prevention of diabetes.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors
  12. In vitro and in silico evaluations of diarylpentanoid series as α-glucosidase inhibitor
    Leong SW, Abas F, Lam KW, Yusoff K
    Bioorg Med Chem Lett, 2018 02 01;28(3):302-309.
    PMID: 29292226 DOI: 10.1016/j.bmcl.2017.12.048
    A series of thirty-four diarylpentanoids derivatives were synthesized and evaluated for their α-glucosidase inhibitory activity. Eleven compounds (19, 20, 21, 24, 27, 28, 29, 31, 32, 33 and 34) were found to significantly inhibit α-glucosidase in which compounds 28, 31 and 32 demonstrated the highest activity with IC50 values ranging from 14.1 to 15.1 µM. Structure-activity comparison shows that multiple hydroxy groups are essential for α-glucosidase inhibitory activity. Meanwhile, 3,4-dihydroxyphenyl and furanyl moieties were found to be crucial in improving α-glucosidase inhibition. Molecular docking analyses further confirmed the critical role of both 3,4-dihydroxyphenyl and furanyl moieties as they bound to α-glucosidase active site in different mode. Overall result suggests that diarylpentanoids with both five membered heterocyclic ring and polyhydroxyphenyl moiety could be a new lead design in the search of novel α-glucosidase inhibitor.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/chemical synthesis; Glycoside Hydrolase Inhibitors/pharmacology*; Glycoside Hydrolase Inhibitors/chemistry
  13. Fulltext Antioxidants and α-glucosidase inhibitors from Neptunia oleracea fractions using 1H NMR-based metabolomics approach and UHPLC-MS/MS analysis
    Lee SY, Mediani A, Ismail IS, Maulidiani, Abas F
    BMC Complement Altern Med, 2019 Jan 07;19(1):7.
    PMID: 30616569 DOI: 10.1186/s12906-018-2413-4
    BACKGROUND: Neptunia oleracea is a plant cultivated as vegetable in Southeast Asia. Previous works have revealed the potential of this plant as a source of natural antioxidants and α-glucosidase inhibitors. Continuing our interest on this plant, the present work is focused in identification of the bioactive compounds from different polarity fractions of N. oleracea, namely hexane (HF), chloroform (CF), ethyl acetate (EF) and methanol (MF).

    METHODS: The N. oleracea fractions were obtained using solid phase extraction (SPE). A metabolomics approach that coupled the use of proton nuclear magnetic resonance (1H NMR) with multivariate data analysis (MVDA) was applied to distinguish the metabolite variations among the N. oleracea fractions, as well as to assess the correlation between metabolite variation and the studied bioactivities (DPPH free radical scavenging and α-glucosidase inhibitory activities). The bioactive fractions were then subjected to ultra-high performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) analysis to profile and identify the potential bioactive constituents.

    RESULTS: The principal component analysis (PCA) discriminated EF and MF from the other fractions with the higher distributions of phenolics. Partial least squares (PLS) analysis revealed a strong correlation between the phenolics and the studied bioactivities in the EF and the MF. The UHPLC-MS/MS profiling of EF and MF had tentatively identified the phenolics present. Together with some non-phenolic metabolites, a total of 37 metabolites were tentatively assigned.

    CONCLUSIONS: The findings of this work supported that N. oleracea is a rich source of phenolics that can be potential antioxidants and α-glucosidase inhibitors for the management of diabetes. To our knowledge, this study is the first report on the metabolite-bioactivity correlation and UHPLC-MS/MS analysis of N. oleracea fractions.

    Matched MeSH terms: Glycoside Hydrolase Inhibitors/analysis*; Glycoside Hydrolase Inhibitors/chemistry
  14. Synthesis and molecular docking studies of potent α-glucosidase inhibitors based on biscoumarin skeleton
    Khan KM, Rahim F, Wadood A, Kosar N, Taha M, Lalani S, et al.
    Eur J Med Chem, 2014 Jun 23;81:245-52.
    PMID: 24844449 DOI: 10.1016/j.ejmech.2014.05.010
    In our effort directed toward the discovery of new anti-diabetic agent for the treatment of diabetes, a library of biscoumarin derivative 1-18 was synthesized and evaluated for α-glucosidase inhibitory potential. All eighteen (18) compounds displayed assorted α-glucosidase activity with IC50 values 16.5-385.9 μM, if compared with the standard acarbose (IC50 = 906 ± 6.387 μM). In addition, molecular docking studies were carried out to explore the binding interactions of biscoumarin derivatives with the enzyme. This study has identified a new class of potent α-glucosidase inhibitors.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/chemical synthesis; Glycoside Hydrolase Inhibitors/pharmacology*; Glycoside Hydrolase Inhibitors/chemistry
  15. Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of new thiazole derivatives
    Khan KM, Qurban S, Salar U, Taha M, Hussain S, Perveen S, et al.
    Bioorg Chem, 2016 10;68:245-58.
    PMID: 27592296 DOI: 10.1016/j.bioorg.2016.08.010
    Current study based on the synthesis of new thiazole derivatives via "one pot" multicomponent reaction, evaluation of their in vitro α-glucosidase inhibitory activities, and in silico studies. All synthetic compounds were fully characterized by (1)H NMR, (13)C NMR and EIMS. CHN analysis was also performed. These newly synthesized compounds showed activities in the range of IC50=9.06±0.10-82.50±1.70μM as compared to standard acarbose (IC50=38.25±0.12μM). It is worth mentioning that most of the compounds such as 1 (IC50=23.60±0.39μM), 2 (IC50=22.70±0.60μM), 3 (IC50=22.40±0.32μM), 4 (IC50=26.5±0.40μM), 6 (IC50=34.60±0.60μM), 7 (IC50=26.20±0.43μM), 8 (IC50=14.06±0.18μM), 9 (IC50=17.60±0.28μM), 10 (IC50=27.16±0.41μM), 11 (IC50=19.16±0.19μM), 12 (IC50=9.06±0.10μM), 13 (IC50=12.80±0.21μM), 14 (IC50=11.94±0.18μM), 15 (IC50=16.90±0.20μM), 16 (IC50=12.60±0.14μM), 17 (IC50=16.30±0.29μM), and 18 (IC50=32.60±0.61μM) exhibited potent inhibitory potential. Molecular docking study was performed in order to understand the molecular interactions between the molecule and enzyme. Newly identified α-glucosidase inhibitors except few were found to be completely non-toxic.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/chemical synthesis; Glycoside Hydrolase Inhibitors/pharmacology*; Glycoside Hydrolase Inhibitors/chemistry
  16. Fulltext Discovery of Amide-Functionalized Benzimidazolium Salts as Potent α-Glucosidase Inhibitors
    Khan IA, Ahmad M, Ashfaq UA, Sultan S, Zaki MEA
    Molecules, 2021 Aug 06;26(16).
    PMID: 34443347 DOI: 10.3390/molecules26164760
    α-Glucosidase inhibitors (AGIs) are used as medicines for the treatment of diabetes mellitus. The α-Glucosidase enzyme is present in the small intestine and is responsible for the breakdown of carbohydrates into sugars. The process results in an increase in blood sugar levels. AGIs slow down the digestion of carbohydrates that is helpful in controlling the sugar levels in the blood after meals. Among heterocyclic compounds, benzimidazole moiety is recognized as a potent bioactive scaffold for its wide range of biologically active derivatives. The aim of this study is to explore the α-glucosidase inhibition ability of benzimidazolium salts. In this study, two novel series of benzimidazolium salts, i.e., 1-benzyl-3-{2-(substituted) amino-2-oxoethyl}-1H-benzo[d]imidazol-3-ium bromide 9a-m and 1-benzyl-3-{2-substituted) amino-2-oxoethyl}-2-methyl-1H-benzo[d] imidazol-3-ium bromide 10a-m were screened for their in vitro α-glucosidase inhibitory potential. These compounds were synthesized through a multistep procedure and were characterized by 1H-NMR, 13C-NMR, and EI-MS techniques. Compound 10d was identified as the potent α-glucosidase inhibitor among the series with an IC50 value of 14 ± 0.013 μM, which is 4-fold higher than the standard drug, acarbose. In addition, compounds 10a, 10e, 10h, 10g, 10k, 10l, and 10m also exhibited pronounced potential for α-glucosidase inhibition with IC50 value ranging from 15 ± 0.037 to 32.27 ± 0.050 µM when compared with the reference drug acarbose (IC50 = 58.8 ± 0.12 μM). A molecular docking study was performed to rationalize the binding interactions of potent inhibitors with the active site of the α-glucosidase enzyme.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/metabolism; Glycoside Hydrolase Inhibitors/pharmacology*; Glycoside Hydrolase Inhibitors/chemistry*
  17. Correlation of chemical profiles obtained from 1 H-NMR and LC-MS metabolomics with α-glucosidase inhibition activity for varietal selections of Ficus deltoidea
    Kasim N, Afzan A, Mediani A, Low KH, Ali AM, Mat N, et al.
    Phytochem Anal, 2022 Dec;33(8):1235-1245.
    PMID: 36192845 DOI: 10.1002/pca.3175
    INTRODUCTION: Ficus deltoidea Jack (Moraceae) is a plant used in Malaysia to treat various ailments, including diabetes. The presence of several varieties raises essential questions regarding which is the potential bioactive variety and what are the bioactive metabolites.

    OBJECTIVES: Here, we explored the phytochemical diversity of the seven varieties from Peninsular Malaysia using Nuclear Magnetic Resonance (NMR) and Liquid Chromatography-Mass Spectrometry (LC-MS) analyses and correlated it with the α-glucosidase inhibitory activity.

    METHODOLOGY: The Nuclear Overhauser Effect Spectroscopy (NOESY) One-Dimensional (1D)-NMR and LC-MS data were processed, annotated, and correlated with in vitro α-glucosidase inhibitory using multivariate data analysis.

    RESULTS: The α-glucosidase results demonstrated that different varieties have varying inhibitory effects, with the highest inhibition rate being F. deltoidea var. trengganuensis and var. kunstleri. Furthermore, diverse habitats and plant ages could also influence the inhibitory rate. The heat map from NMR and LC-MS profiles showed unique patterns according to varying levels of α-glucosidase inhibition rate. The Partial Least Squares (PLS) model constructed from both NMR and LC-MS further confirmed the correlation between the α-glucosidase inhibition rate of F. deltoidea varieties and its metabolite profiles. The Variable Influence on Projection (VIP) and correlation coefficient (p(corr)) values values were used to determine the highly relevant metabolites for explaining the anticipated inhibitory action.

    CONCLUSION: NMR and LC-MS annotations allow the identification of flavan-3-ols and proanthocyanidins as the key bioactive factors. Our current results demonstrated the value of multivariate data analysis to predict the quality of herbal materials from both biological and chemical aspects.

    Matched MeSH terms: Glycoside Hydrolase Inhibitors/pharmacology; Glycoside Hydrolase Inhibitors/chemistry
  18. Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs
    Javid MT, Rahim F, Taha M, Rehman HU, Nawaz M, Wadood A, et al.
    Bioorg Chem, 2018 08;78:201-209.
    PMID: 29597114 DOI: 10.1016/j.bioorg.2018.03.022
    α-Glucosidase is a catabolic enzyme that regulates the body's plasma glucose levels by providing energy sources to maintain healthy functioning. 2-Amino-thiadiazole (1-13) and 2-amino-thiadiazole based Schiff bases (14-22) were synthesized, characterized by 1H NMR and HREI-MS and screened for α-glucosidase inhibitory activity. All twenty-two (22) analogs exhibit varied degree of α-glucosidase inhibitory potential with IC50 values ranging between 2.30 ± 0.1 to 38.30 ± 0.7 μM, when compare with standard drug acarbose having IC50 value of 39.60 ± 0.70 μM. Among the series eight derivatives 1, 2, 6, 7, 14, 17, 19 and 20 showed outstanding α-glucosidase inhibitory potential with IC50 values of 3.30 ± 0.1, 5.80 ± 0.2, 2.30 ± 0.1, 2.70 ± 0.1, 2.30 ± 0.1, 5.50 ± 0.1, 4.70 ± 0.2, and 5.50 ± 0.2 μM respectively, which is many fold better than the standard drug acarbose. The remaining analogs showed good to excellent α-glucosidase inhibition. Structure activity relationship has been established for all compounds. The binding interactions of these compounds were confirmed through molecular docking.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/chemical synthesis; Glycoside Hydrolase Inhibitors/pharmacology*; Glycoside Hydrolase Inhibitors/chemistry
  19. Chemical profiling and biological properties of Neolitsea kedahense Gamble essential oils
    Jani NA, Sirat HM, Ahmad F, Mohamad Ali NA, Jamil M
    Nat Prod Res, 2017 Dec;31(23):2793-2796.
    PMID: 28278643 DOI: 10.1080/14786419.2017.1294172
    Hydrodistillation of the fresh stem and leaf of Neolitsea kedahense Gamble, collected from Gunung Jerai, Malaysia followed by the GC-FID and GC-MS analysis revealed the detection of a total of 47 constituents of which 28 (86.4%) from the stem and 31 (96.4%) constituents from the leaf. δ-Cadinene (17.4%), 1-epi-cubenol (11.8%), cyperotundone (9.0%), cis-cadin-4-en-7-ol (7.7%), τ-cadinol (7.1%) and α-cadinol (7.1%) were the principle constituents in the stem oil, whereas β-caryophyllene (18.9%), bicyclogermacrene (18.6%) and trans-muurola-4(14),5-diene (9.8%) were the major constituents in the leaf oil. Among the identified constituents, three constituents namely 7-epi-α-selinene, junenol and cis-cadin-4-en-7-ol have not been found previously from Neolitsea oils. The stem and leaf oils were screened for their α-glucosidase inhibitory and antibacterial activities. Both oils displayed potential α-glucosidase inhibitory activity, while the stem oil possessed weak antibacterial activity against Bacillus subtilis.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/pharmacology*; Glycoside Hydrolase Inhibitors/chemistry
  20. Synthesis, bioactivity and binding energy calculations of novel 3-ethoxysalicylaldehyde based thiosemicarbazone derivatives
    Ishaq M, Taslimi P, Shafiq Z, Khan S, Ekhteiari Salmas R, Zangeneh MM, et al.
    Bioorg Chem, 2020 07;100:103924.
    PMID: 32442818 DOI: 10.1016/j.bioorg.2020.103924
    In recent decade, the entrance of α-N-heterocyclic thiosemicarbazones derivates (Triapne, COTI-2 and DpC) in clinical trials for cancer and HIV-1 has vastly increased the interests of medicinal chemists towards this class of organic compounds. In the given study, a series of eighteen new (3a-r) 3-ethoxy salicylaldehyde-based thiosemicarbazones (TSC), bearing aryl and cycloalkyl substituents, were synthesized and assayed for their pharmacological potential against carbonic anhydrases (hCA I and hCA II), cholinesterases (AChE and BChE) and α-glycosidase. The hCA I isoform was inhibited by these novel 3-ethoxysalicylaldehyde thiosemicarbazone derivatives (3a-r) in low nanomolar levels, the Ki of which differed between 144.18 ± 26.74 and 454.92 ± 48.32 nM. Against the physiologically dominant isoform hCA II, the novel compounds demonstrated Kis varying from 110.54 ± 14.05 to 444.12 ± 36.08 nM. Also, these novel derivatives (3a-r) effectively inhibited AChE, with Ki values in the range of 385.38 ± 45.03 to 983.04 ± 104.64 nM. For BChE was obtained with Ki values in the range of 400.21 ± 35.68 to 1003.02 ± 154.27 nM. For α-glycosidase the most effective Ki values of 3l, 3n, and 3q were with Ki values of 12.85 ± 1.05, 16.03 ± 2.84, and 19.16 ± 2.66 nM, respectively. Moreover, the synthesized TCSs were simulated using force field methods whereas the binding energies of the selected compounds were estimated using MM-GBSA method. The findings indicate the present novel 3-ethoxy salicylaldehyde-based thiosemicarbazones to be excellent hits for pharmaceutical applications.
    Matched MeSH terms: Glycoside Hydrolase Inhibitors/chemical synthesis; Glycoside Hydrolase Inhibitors/pharmacology; Glycoside Hydrolase Inhibitors/chemistry*
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