Quercetin particles with lower inhibitory activity for α-glycosidase and negligible effects on blood clotting

Abstract

Poly(quercetin) (p(QR)) particles was synthesis by using poly(ethylene glycol) diglycidyl ether (PEGGE) crosslinker in a single step via microemulsion system. The morphological, size and functional analysis of the prepared particles were carried by optic microscope, scanning electron microscope (SEM), dynamic light scattering (DLS) measurements and FT-IR spectroscopy. P(QR) particles were found to be in spherical shape with 372±9 nm size range by means of SEM images and DLS measurements. The zeta potential measurements, performed at different pH conditions and potentiometric titration of p(QR) particles were revealed that the isoelectric point and pKa values of as around pH 2.5 and 2.3, respectively. Ferric reducing antioxidant power (FRAP) was determined for QR and p(QR) particles at pH 3.6 and found as 9.4 and 0.43 µg reduced Fe(ll). The effects of QR and p(QR) particles on alfa-glycosidase enzyme activity at pH 6.9 were investigated and found that QR molecules and p(QR) particles were capable of inhibiting the α-glycosidase enzyme 89.3% and 24.7% respectively. The fluorescence spectroscopy of QR and p(QR) in fibrinogen showed that p(QR) particles do not induce clothing of blood.

Keywords

• Quercetin particles
• alpha glucosidase inhibitor
• fibrinogen binding
• antioxidant

References

1. 1. Buchweitz M, Kroon PA, Rich GT, Wilde PJ. Quercetin solubilisation in bile salts: A comparison with sodium dodecyl sulphate. Food Chem 2016 Nov;211:356–64.
2. 2. Leopoldini M, Russo N, Toscano M. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem 2011 Mar;125(2):288–306.
3. 3. Sahiner N. One step poly(quercetin) particle preparation as biocolloid and its characterization. Colloids Surfaces A Physicochem Eng Asp 2014 Jun;452:173–80.
4. 4. Tan L, Zhou X, Wu K, Yang D, Jiao Y, Zhou C. Tannic acid/CaII anchored on the surface of chitin nanofiber sponge by layer-by-layer deposition: Integrating effective antibacterial and hemostatic performance. Int J Biol Macromol 2020 Sep;159:304–15.
5. 5. Terao J. Factors modulating bioavailability of quercetin-related flavonoids and the consequences of their vascular function. Biochem Pharmacol 2017 Sep;139:15–23.
6. 6. Cherubim DJ, Martins CV, Fariña L, Lucca RA. Polyphenols as natural antioxidants in cosmetics applications. J Cosmet Dermatol 2020 Jan 7;19(1):33–7.
7. 7. Wang W, Sun C, Mao L, Ma P, Liu F, Yang J, et al. The biological activities, chemical stability, metabolism and delivery systems of quercetin: A review. Trends Food Sci Technol 2016 Oct;56:21–38.
8. 8. Baldissarelli J, Santi A, Schmatz R, Zanini D, Cardoso AM, Abadalla FH, et al. Quercetin changes purinergic enzyme activities and oxidative profile in platelets of rats with hypothyroidism. Biomed Pharmacother 2016 Dec;84:1849–57.

9. 9. Balasubramaniam V, Mustar S, Mustafa Khalid N, Abd Rashed A, Mohd Noh MF, Wilcox MD, et al. Inhibitory activities of three Malaysian edible seaweeds on lipase and α-amylase. J Appl Phycol 2013 Oct 25;25(5):1405–12.
10. 10. Zaharudin N, Salmeán AA, Dragsted LO. Inhibitory effects of edible seaweeds, polyphenolics and alginates on the activities of porcine pancreatic α-amylase. Food Chem 2018 Apr;245:1196–203.
11. 11. Zhu Y, Liu R, Wu D, Yu Q, Shea KJ, Zhu Q. Engineered polymer nanoparticles incorporating L-amino acid groups as affinity reagents for fibrinogen. J Pharm Anal 2020 Oct; doi:10.1016/j.jpha.2020.10.004
12. 12. Deng L, Qi Y, Liu Z, Xi Y, Xue W. Effect of tannic acid on blood components and functions. Colloid Surface B 2019;184(September):110505.
13. 13. Sahiner N, Sagbas S, Sahiner M, Silan C, Aktas N, Turk M. Biocompatible and biodegradable poly(Tannic Acid) hydrogel with antimicrobial and antioxidant properties. Int J Biol Macromol 2016; 82. 150–9.
14. 14. Sahiner N, Sagbas S, Sahiner M, Aktas N. Degradable natural phenolic based particles with micro-and nano-size range. Recent Patents Mater Sci 2018;11(1). 33-40.
15. 15. Tadapaneni RK, Banaszewski K, Patazca E, Edirisinghe I, Cappozzo J, Jackson L, et al. Effect of high-pressure processing and milk on the anthocyanin composition and antioxidant capacity of strawberry-based beverages. J Agric Food Chem 2012;60(23):5795–802.
16. 16. Firuzi O, Lacanna A, Petrucci R, Marrosu G, Saso L. Evaluation of the antioxidant activity of flavonoids by “ferric reducing antioxidant power” assay and cyclic voltammetry. Biochim Biophys Acta - Gen Subj 2005 Jan;1721(1–3):174–84.
17. 17. Li Y, Ma D, Sun D, Wang C, Zhang J, Xie Y, et al. Total phenolic, flavonoid content, and antioxidant activity of flour, noodles, and steamed bread made from different colored wheat grains by three milling methods. Crop J 2015;3(4):328–34.
18. 18. Sahiner M, Blake DA, Fullerton ML, Suner SS, Sunol AK, Sahiner N. Enhancement of biocompatibility and carbohydrate absorption control potential of rosmarinic acid through crosslinking into microparticles. Int J Biol Macromol 2019;137.
19. 19. Sahiner N, Sagbas S, Sahiner M, Blake DA, Reed WF. Polydopamine particles as nontoxic, blood compatible, antioxidant and drug delivery materials. Colloid Surface B 2018 Dec;172:618–26.
20. 20. Sahiner M, Sahiner N, Sagbas S, Fullerton ML, Blake DA. Fabrication of Biodegradable Poly(naringin) Particles with Antioxidant Activity and Low Toxicity. ACS Omega 2018;3(12).
21. 21. Júnior SD da C, Santos JV de O, Campos LA de A, Pereira MA, Magalhães NSS, Cavalcanti IMF. Antibacterial and antibiofilm activities of quercetin against clinical isolates of Staphyloccocus aureus and Staphylococcus saprophyticus with resistance profile. Int J Environ Agric Biotechnol 2018;3(5):1948–58.
22. 22. Chen C, Zhou J, Ji C. Quercetin: A potential drug to reverse multidrug resistance. Life Sci 2010 Sep;87(11–12):333–8.
23. 23. Wojdyło A, Samoticha J, Chmielewska J. Effect of different pre-treatment maceration techniques on the content of phenolic compounds and color of Dornfelder wines elaborated in cold climate. Food Chem. 2021 Mar;339:127888. doi:10.1016/j.foodchem.2020.127888
24. 24. Dhanaraj T, Mohan M, Arunakaran J. Quercetin attenuates metastatic ability of human metastatic ovarian cancer cells via modulating multiple signaling molecules involved in cell survival, proliferation, migration and adhesion. Arch Biochem Biophys 2021 Feb;108795.
25. 25. Zhao F-Q, Wang G-F, Xu D, Zhang H-Y, Cui Y-L, Wang Q-S. Glycyrrhizin mediated liver-targeted alginate nanogels delivers quercetin to relieve acute liver failure. Int J Biol Macromol 2021 Jan;168:93–104.
26. 26. Hu Q, Zhang Y, Wang C, Xu J, Wu J, Liu Z, et al. Hemocompatibility evaluation in vitro of methoxy polyethyleneglycol-polycaprolactone copolymer solutions. J Biomed Mater Res Part A 2016 Mar;104(3):802–12.