Antioxidant, α-Glucosidase Inhibitory Activity and Molecular Docking Study of Gallic Acid, Quercetin and Rutin: A Comparative Study

Agus Limanto, Adelina Simamora, Adit Widodo Santoso, Kris Herawan Timotius


Background: Plant-phenolics and flavonoids, including gallic acid, quercetin and rutin, are considered as safe inhibitors for α-glucosidase. This study aimed to compare antioxidant and α-glucosidase inhibitory activities of gallic acid (GA), quercetin (QUE) and rutin (RUT).

Materials and Methods: Pure compounds of GA, QUE, and RUT were used. Their antioxidant and inhibitory activity on α-glucosidase were investigated spectroscopically, including their kinetic analysis and interaction mechanism by docking simulation.

Results: All the tested compounds (GA, QUE, and RUT) showed good antioxidant activity better than the standards ascorbic acid (AA) and butylated hydroxytoluene (BHT), with QUE showing the highest antioxidant activity based on 2,2-diphenyl1-picrylhydrazyl (DPPH) radical scavenging activity. Based on their reducing properties, the activities of the compounds follow the following order: AA > GA > BHT > QUE > RUT. Both GA and RUT induced a competitive type of inhibition, with activities stronger than acarbose (IC50 = 823 μg/mL), whereas QUE inhibited in a mixed type manner. The IC50 of GA, QUE, and RUT were 220.12, 65.52, and 224.55 μg/mL respectively. The results obtained from molecular docking indicate that all compounds have affinity in the active site pocket of α-glucosidase, with the hydrogen bond being the major force involved in each compound binding to the enzyme.

Conclusion: In conclusion, QUE has better antioxidant and α-glucosidase inhibitory activity than GA and RUT. This work provides insights into the interactions between GA, QUE, and RUT and α-glucosidase.

Keywords: docking, gallic acid, α-glucosidase, rutin, quercetin

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Yan J, Zhang G, Pan J, Wang Y. α-Glucosidase inhibition by luteolin: Kinetics, interaction and molecular docking. Int J Biol Macromol. 2014; 64: 213-23, CrossRef.

Peng X, Zhang G, Liao Y, Gong D. Inhibitory kinetics and mechanism of kaempferol on α-glucosidase. Food Chem. 2016; 190: 207-15, CrossRef.

Oboh G, Ogunsuyi OB, Ogunbadejo MD, Adefegha SA. Influence of gallic acid on α-amylase and α-glucosidase inhibitory properties of acarbose. J Food Drug Anal. 2016; 24(3): 627-34, CrossRef.

Zanwar AA, Badole SL, Shende PS, Hegde MV, Bodhankar SL. Role of gallic acid in cardiovascular disorders. In: Watson RR, Preedy VR, Zibadi S, eds. Polyphenols in Human Health and Disease: Amsterdam: Elsevier; 2014. p.1045-7, CrossRef.

Ademiluyi AO, Oboh G, Aragbaiye FP, Oyeleye SI, Ogunsuyi OB. Antioxidant properties and in vitro α-amylase and α-glucosidase inhibitory properties of phenolics constituents from different varieties of Corchorus spp. J Taibah Univ Med Sci. 2015; 10(3): 278-87, CrossRef.

Abdel-Moneim A, El-Twab SMA, Yousef AI, Reheim ESA, Ashour MB. Modulation of hyperglycemia and dyslipidemia in experimental type 2 diabetes by gallic acid and p-coumaric acid: The role of adipocytokines and PPARγ. Biomed Pharmacother. 2018; 105: 1091-7, CrossRef.

Kamiyama O, Sanae F, Ikeda K, Higashi Y, Minami Y, Asano N, et al. In vitro inhibition of α-glucosidases and glycogen phosphorylase by catechin gallates in green tea. Food Chem. 2010; 122(4): 1061-6, CrossRef.

You Q, Chen F, Wang X, Jiang Y, Lin S. Anti-diabetic activities of phenolic compounds in muscadine against alpha-glucosidase and pancreatic lipase. LWT-Food Sci Technol. 2012; 46(1): 164-8, CrossRef.

Benalla W, Bellahcen S, Bnouham M. Antidiabetic medicinal plants as a source of alpha glucosidase inhibitors. Curr Diabetes Rev. 2010; 6(4): 247-54, CrossRef.

Banjarnahor SDS, Artanti N. Antioxidant properties of flavonoids. Med J Indones. 2014; 23(4): 5, CrossRef.

Chen C, Zhou J, Ji C. Quercetin: a potential drug to reverse multidrug resistance. Life Sci. 2010; 87(11-12): 333-8, CrossRef.

Ghorbani A. Mechanisms of antidiabetic effects of flavonoid rutin. Biomed Pharmacother. 2017; 96: 305-12, CrossRef.

Jo S, Ka E, Lee H, Apostolidis E, Jang H, Kwon Y. Comparison of antioxidant potential and rat intestinal a-glucosidases inhibitory activities of quercetin, rutin, and isoquercetin. Int J App Res Nat Prod. 2009; 2(4): 52-60, article.

Shi GJ, Li Y, Cao QH, Wu HX, Tang XY, Gao XH, et al. In vitro and in vivo evidence that quercetin protects against diabetes and its complications: a systematic review of the literature. Biomed Pharmacother. 2019; 109: 1085-99, CrossRef.

Youl E, Bardy G, Magous R, Cros G, Sejalon F, Virsolvy A, et al. Quercetin potentiates insulin secretion and protects INS-1 pancreatic β-cells against oxidative damage via the ERK1/2 pathway. Br J Pharmacol. 2010; 161(4): 799-814, CrossRef.

Li YQ, Zhou FC, Gao F, Bian JS, Shan F. Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of α-glucosidase. J Agric Food Chem. 2009; 57(24): 11463-8, CrossRef.

Timotius KH, Simamora A, Santoso AW. Chemical characteristics and in vitro antidiabetic and antioxidant activities of Premna serratifolia L. leaf infusion and decoction. Pharmacog J. 2018; 10(6): 1114-8, CrossRef.

Simamora A, Paramita L, Mohamad Hamid NAB, Santoso AW, Timotius KH. In vitro antidiabetic and antioxidant activities of aqueous axtract from the leave and fruit of Psidium guajava L. Indones Biomed J 2018; 10(2): 156-64, CrossRef.

Khatoon M, Islam E, Islam R, Rahman AA, Alam AK, Khondkar P, et al. Estimation of total phenol and in vitro antioxidant activity of Albizia procera leaves. BMC Res Notes. 2013; 6(1): 121, CrossRef.

Simamora A, Adit Widodo S, Kris Herawan T. Bioactivities of methanol and ethyl acetate mace extracts of Myristica fragrans Houtt. Pharmacognosy Communications. 2018; 8(3): 103-7, CrossRef.

Niedowicz DM, Daleke DL. The role of oxidative stress in diabetic complications. Cell Biochem Biophys. 2005; 43(2): 289-330, CrossRef.

King GL, Loeken MR. Hyperglycemia-induced oxidative stress in diabetic complications. Histochem Cell Biol. 2004; 122(4): 333-8, CrossRef.

Islam MM. Biochemistry, medicinal and food values of jute (Corchorus capsularis L. and C. olitorius L.) leaf: a review. Int J Enhanc Res Sci Technol Eng. 2013; 2(11): 35-44, article.

Gulcin I, Elmastas M, Aboul-Enein HY. Determination of antioxidant and radical scavenging activity of Basil (Ocimum basilicum L. Family Lamiaceae) assayed by different methodologies. Phytother Res. 2007; 21(4): 354-61, CrossRef.

Çelik H, Arinç E. Evaluation of the protective effects of quercetin, rutin, naringenin, resveratrol and trolox against idarubicin-induced DNA damage. J Pharm Pharm Sci. 2010; 13(2): 231-41, CrossRef.

Heijnen C, Haenen G, Van Acker F, Van der Vijgh W, Bast A. Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups. Toxicol In Vitro. 2001; 15(1): 3-6, CrossRef.

American Diabetes Association.. Diagnosis and classification of diabetes mellitus. Diabetes Care. 2004; 27(Suppl 1): s5-s10, CrossRef.

Zhang BW, Sang YB, Sun WL, Yu HS, Ma BP, Xiu ZL, et al. Combination of flavonoids from Oroxylum indicum seed extracts and acarbose improves the inhibition of postprandial blood glucose: In vivo and in vitro study. Biomed Pharmacother. 2017; 91: 890-8, CrossRef.

Proença C, Freitas M, Ribeiro D, Oliveira EF, Sousa JL, Tomé SM, et al. α-Glucosidase inhibition by flavonoids: an in vitro and in silico structure–activity relationship study. J enzyme inhibit med chem. 2017; 32(1): 1216-28, CrossRef.


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