Insights into an α-Glucosidase Inhibitory Profile of 4,4-Dimethylsterols by Multispectral Techniques and Molecular Docking

Xie, Li; Karrar, Emad; Zheng, Liyou; Xie, Dan; Jin, Jun; Chang, Ming; Wang, Xingguo; Jin, Qingzhe

doi:10.1021/acs.jafc.1c06347

Cited by 17 publications

(11 citation statements)

References 51 publications

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“…For instance, PS as a dietary supplement could decrease TC and LDL, whereas TA from Shea butter or rice bran oil did not significantly reduce TC and LDL (Sierksma et al, 1999; Trautwein et al, 2002). The inhibitory activity of TA on α‐glucosidase was higher than that of PS, which could be used as a potential α‐glucosidase inhibitor to improve blood glucose levels in patients with diabetes (Nair et al, 2020; Xie et al, 2021). Therefore, the separation of these two classes of substances rather than the individual separation was also of sufficient commercial value.…”

Section: Resultsmentioning

confidence: 99%

Purification, characterization, and cellular antioxidant activity of 4,4‐dimethylsterols and 4‐desmethylsterols

Xie

Wang

Karrar

et al. 2022

J Americ Oil Chem Soc

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A mixture of 4,4-dimethylsterols (TA) and 4-desmethylsterols (PS) was produced as valuable byproducts during the large-scale production of ferulic acid by γ-oryzanol. However, the utilization of both byproducts is impeded by this mixed form. This study has developed a novel method for separating TA and PS through a one-step separation procedure using flash chromatography. The optimal conditions were as follows: mobile phase of hexane-ethyl acetate (9:1, vol/vol), the flow rate of 40 ml/min, loading volume of 20 ml, run time of 20 min. Under optimized conditions, TA with a yield of 41.8% AE 2.8% with a purity of 93.4% AE 0.4% was obtained, and 36.8% AE 1.7% and 98.2% AE 0.8% for that of PS. Their chemical structures were further confirmed by ultraviolet spectroscopy (UV), Fourier-transform infrared spectroscopy (FT-IR), and gas chromatography-mass spectrometry (GC-MS). The time-fluorescence value curve indicated that TA and PS had inhibitory effects on peroxyl radicalinduced 2 0 ,7 0 -dichlorofluorescin (DCFH) oxidation. The results showed that TA had higher cellular antioxidant activity (CAA) than PS. TA was more suitable as a potential natural antioxidant. The present study provides a convenient method for high-purity TA and PS production, which will improve the valueadded byproducts from the large-scale production of ferulic acid. K E Y W O R D S 4,4-dimethylsterols, 4-desmethylsterols, cellular antioxidant activity, flash chromatography, GC-MS Liangliang Xie and Tao Zhang contributed equally to this work and should be considered co-first authors.

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Section: Resultsmentioning

confidence: 99%

Purification, characterization, and cellular antioxidant activity of 4,4‐dimethylsterols and 4‐desmethylsterols

Xie

Wang

Karrar

et al. 2022

J Americ Oil Chem Soc

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“…We investigated the binding mode of the active site using Maestro software to simulate the binding of α ‐glucosidase to compounds 1 – 9 , 12 – 13 . Three‐dimensional (3D) structures of α ‐glucosidase [34] (PDB id: 3A4A) and urease (PDB id: 3LA4) from the Protein Data Bank, and the protein structure and ligands were optimized by the Protein Preparation Wizard and the LigPrep module. Then the binding sites were defined as 20×20×20 Å cubic boxes using the software Setmap module.…”

Section: Methodsmentioning

confidence: 99%

Phytoconstituents of Selaginella effusa Alston and Their α‐Glucosidase as well as Urease Inhibitory Activities

Sun

Luo

et al. 2023

Chemistry & Biodiversity

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Three new compounds (1–2, 14), as well as 22 known compounds (3–13, 15–25), were extracted for the first time from the Selaginella effusa Alston (S. effusa). For the unknown compounds, the planar configurations were determined via NMR and by high‐resolution mass spectrometry, while their absolute configurations were determined by calculated electronic circular dichroism (ECD), and the configuration of the stereogenic center of biflavones 4–5 were established for the first time. The pure compounds (1–25) were tested in vitro to determine the inhibitory activity of the enzyme‐catalyzed reactions. Compounds 1–9 inhibited α‐glucosidase with IC50 values ranging from 0.30±0.02 to 4.65±0.04 μM and kinetic analysis of enzyme inhibition indicated that biflavones 1–3 were mixed‐type α‐glucosidase inhibitors. Compounds 12–13 showed excellent inhibitory activity against urease, with compound 12 (IC50=4.38±0.31 μM) showing better inhibitory activity than the positive control drug AHA (IC5013.52±0.61 μM). In addition, molecular docking techniques were used to simulate inhibitor‐enzyme binding and to estimate the binding posture of the α‐glucosidase and urease catalytic sites.

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“…The α−glucosidase inhibitory activity assay method of A. tenuissimum flower flavonoids was slightly modified based on previous studies [ 22 , 23 , 24 ]. A 96−well plate was used for preparing the mixture consisting of 0.1 M PBS (pH 6.8), 1.0 mg/mL sample solution, and 2 U/mL α−glucosidase, which were incubated at 37 °C for 10 min.…”

Section: Methodsmentioning

confidence: 99%

Exploring Active Ingredients, Beneficial Effects, and Potential Mechanism of Allium tenuissimum L. Flower for Treating T2DM Mice Based on Network Pharmacology and Gut Microbiota

et al. 2022

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Forty compounds were isolated and characterized from A. tenuissimum flower. Among them, twelve flavonoids showed higher α−glucosidase inhibition activities in vitro than acarbose, especially kaempferol. The molecular docking results showed that the binding of kaempferol to α−glucosidase (GAA) could reduce the hydrolysis of substrates by GAA and reduce the glucose produced by hydrolysis, thus exhibiting α−glucosidase inhibition activities. The in vivo experiment results showed that flavonoids−rich A. tenuissimum flower could decrease blood glucose and reduce lipid accumulation. The protein expression levels of RAC−alpha serine/threonine−protein kinase (AKT1), peroxisome proliferator activated receptor gamma (PPARG), and prostaglandin G/H synthase 2 (PTGS2) in liver tissue were increased. In addition, the Firmicutes/Bacteroidetes (F/B) ratio was increased, the level of gut probiotics Bifidobacterium was increased, and the levels of Enterobacteriaceae and Staphylococcus were decreased. The carbohydrate metabolism, lipid metabolism, and other pathways related to type 2 diabetes mellitus were activated. This study indicating flavonoids−rich A. tenuissimum flower could improve glycolipid metabolic disorders and inflammation in diabetic mice by modulating the protein expression and gut microbiota.

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Insights into an α-Glucosidase Inhibitory Profile of 4,4-Dimethylsterols by Multispectral Techniques and Molecular Docking

Cited by 17 publications

References 51 publications

Purification, characterization, and cellular antioxidant activity of 4,4‐dimethylsterols and 4‐desmethylsterols

Purification, characterization, and cellular antioxidant activity of 4,4‐dimethylsterols and 4‐desmethylsterols

Phytoconstituents of Selaginella effusa Alston and Their α‐Glucosidase as well as Urease Inhibitory Activities

Exploring Active Ingredients, Beneficial Effects, and Potential Mechanism of Allium tenuissimum L. Flower for Treating T2DM Mice Based on Network Pharmacology and Gut Microbiota

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