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Antidiabetic, antioxidant, molecular docking and HPTLC analysis of miquelianin isolated from Euphorbia schimperi C. Presl.

ABSTRACT: 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 were quantified by validated HPTLC method. Antioxidant activity was determined by chemical means in terms of ABTS radical cation and DPPH radical scavenging activity. Compound 1 showed significant scavenging activity in both ABTS and DPPH assays as compared to standard BHA. In ABTS method IC50 values of compound 1 and standard BHA is found to be 58.90?±?3.40?µg/mL and 28.70?±?5.20?µg/mL respectively while in DPPH assay IC50 values of Compound 1 and standard BHA is 47.20?±?4.90?µg/mL and 34.50?±?6.20?µg/mL respectively. Antidiabetic effect was studied through ?-amylase and ?-glucosidase inhibitory activity. The mechanistic approach through molecular modelling also support the strong binding sites of compound 1 which showed significant ?-amylase and ?-glucosidase inhibitory activities with IC50 values 128.34?±?12.30 and 89.20?±?9.20?µg/mL respectively as compared to acarbose 64.20?±?5.60 and 52.40?±?4.60?µg/mL respectively. The results of validated RP-HPTLC analyses revealed the concentration of compound 1 found to be 16.39?µg/mg and for compound 2 and compound 3 as 3.92 and 14.98?µg/mg of dried extract, respectively.

SUBMITTER: Ahmed S

PROVIDER: S-EPMC6598219 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Antidiabetic, antioxidant, molecular docking and HPTLC analysis of miquelianin isolated from Euphorbia schimperi C. Presl.

Ahmed Sarfaraz S Al-Rehaily Adnan J AJ Alam Perwez P Alqahtani Ali S AS Alqahtani Ali S AS Hidayatullah Syed S Rehman Md Tabish MT Mothana Ramzi A RA Abbas Syed Sadiq SS Khan M U MU Khalid Jamal M JM Siddiqui Nasir A NA

Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society 20190319 5

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 were quantified by validated HPTLC method. Antioxidant activity was determined by chemical me ...[more]

PMID: 31297020

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Project description:IntroductionNatural products are among the most useful sources for the discovery of new drugs against various diseases. Keeping in view the ethnobotanical relevance ethnopharmacological significance of Polygonaceae family in diabetes, the current study was designed to isolate pure compounds from Persicaria hydropiper L. leaves and evaluate their in vitro and in silico antidiabetic potentials.MethodsSix compounds were isolated from the chloroform-ethyl acetate fractions using gravity column chromatography and were subjected to structure elucidation process. Structures were confirmed using 1H-NMR, 13C-NMR, and mass spectrometry techniques. Isolated phytochemicals were subjected to in vitro antidiabetic studies, including α-glucosidase, α-amylase inhibition, and DPPH, and ABTS antioxidant studies. Furthermore, the in silico binding mode of these compounds in the target enzymes was elucidated via MOE-Dock software.ResultsThe isolated compounds revealed concentration-dependent inhibitions against α-glucosidase enzyme. Ph-1 and Ph-2 were most potent with 81.84 and 78.79% enzyme inhibitions at 1000 µg·mL-1, respectively. Ph-1 and Ph-2 exhibited IC50s of 85 and 170 µg·mL-1 correspondingly. Likewise, test compounds showed considerable α-amylase inhibitions with Ph-1 and Ph-2 being the most potent. Tested compounds exhibited considerable antioxidant potentials in both DPPH and ABTS assays. Molecular simulation studies also revealed top-ranked confirmations for the majority of the compounds in the target enzymes. Highest observed potent compound was Ph-1 with docking score of -12.4286 and formed eight hydrogen bonds and three H-pi linkages with the Asp 68, Phe 157, Phe 177, Asn 241, Glu 276, His 279, Phe 300, Glu 304, Ser 308, Pro 309, Phe 310, Asp 349, and Arg 439 residues of α-glucosidase binding packets. Asp 68, Glu 276, Asp 349, and Arg 439 formed polar bonds with the 3-ethyl-2-methylpentane moiety of the ligand.ConclusionsThe isolated compounds exhibited considerable antioxidant and inhibitory potentials against vital enzymes implicated in T2DM. The docking scores of the compounds revealed that they exhibit affinity for binding with target ligands. The enzyme inhibition and antioxidant potential of the compounds might contribute to the hypoglycemic effects of the plant and need further studies.

Project description:BackgroundOxidative stress and diabetes are medical conditions that have a growing prevalence worldwide, significantly impacting our bodies. Thus, it is essential to develop new natural antioxidant and antidiabetic agents. Dypsis pembana (H.E.Moore) Beentje & J.Dransf (DP) is an ornamental palm of the family Arecaceae. This study aimed to broaden the understanding of this plant's biological properties by evaluating its in vitro antioxidant and antidiabetic activities.MethodsThe in vitro antioxidant activities of the crude extract, fractions, and selected isolates were evaluated by DPPH method. While the in vitro antidiabetic activities of these samples were evaluated by assessing the degree of inhibition of α-glucosidase. Additionally, molecular docking analysis was performed to investigate the interactions of tested compounds with two potential targets, the cytochrome c peroxidase and alpha glucosidase.ResultsThe crude extract displayed the highest antioxidant activity (IC50 of 11.56 µg/ml), whereas among the fractions, the EtOAc fraction was the most potent (IC50 of 14.20 µg/ml). Among tested compounds, isoquercetrin (10) demonstrated the highest potency, with an IC50 value of 3.30 µg/ml, followed by rutin (8) (IC50 of 3.61 µg/ml). Regarding antidiabetic activity, the EtOAc (IC50 of 60.4 µg/ml) and CH2Cl2 fractions (IC50 of 214.9 µg/ml) showed activity, while the other fractions did not demonstrate significant antidiabetic effects. Among tested compounds, kaempferol-3-O-neohesperidoside (9) showed the highest antidiabetic activity, with an IC50 value of 18.38 µg/ml, followed by kaempferol (4) (IC50 of 37.19 µg/ml). These experimental findings were further supported by molecular docking analysis, which revealed that isoquercetrin and kaempferol-3-O-neohesperidoside exhibited strong enzyme-binding affinities to the studied enzyme targets. This analysis provided insights into the structure-activity relationships among the investigated flavonol-O-glycosides.ConclusionThe biological and computational findings revealed that isoquercetrin and kaempferol-3-O-neohesperidoside have potential as lead compounds for inhibiting cytochrome c peroxidase and alpha glucosidase enzymes, respectively.

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Antidiabetic, antioxidant, molecular docking and HPTLC analysis of miquelianin isolated from Euphorbia schimperi C. Presl.

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Antidiabetic, antioxidant, molecular docking and HPTLC analysis of miquelianin isolated from <i>Euphorbia schimperi</i> C. Presl.

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