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Antiviral Activity of Glucosyl Hesperidin Against Feline Calicivirus

by Sung-Sook Choi, Sun-Hyung Lee and Kyung-Ae Lee

Microorganisms 2025, 13(10), 2332; https://doi.org/10.3390/microorganisms13102332 - 10 Oct 2025

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The objective of this study was to evaluate the antiviral activity of glucosyl hesperidin (GH), a water-soluble derivative of hesperidin with known antioxidant and anti-inflammatory properties, in order to explore its potential applications. Antiviral activity was assessed using feline calicivirus (FCV), a surrogate model for human norovirus, a major foodborne pathogen. Cytotoxicity testing in Crandell–Rees feline kidney (CRFK) cells demonstrated that GH exhibited high biocompatibility, maintaining 100% cell viability at concentrations up to 8000 μM. Antiviral efficacy assays revealed that GH inhibited FCV replication in a concentration-dependent manner across the range of 250~8000 μM, with a half-maximal inhibitory concentration (IC₅₀) of 3281 μM. Complete viral inhibition, however, was not achieved at the maximum concentration tested. In conclusion, GH was shown to inhibit FCV while maintaining low cytotoxicity, indicating its potential as a natural, water-soluble candidate for the suppression of norovirus. Full article

(This article belongs to the Special Issue Natural Products for Antimicrobial Therapy)

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14 pages, 2875 KB

Open AccessArticle

Glucosyl Hesperidin Supplementation Prevents Tubulointerstitial Fibrosis and Immune Activation in Diabetic Nephropathy in Mice

by Kotaro Hashimoto, Yuki Yoshida, Mion Kamesawa, Nao Yazawa, Hikaru Tominaga, Rahmawati Aisyah, Siyi Chen, Chanikan Bumrungkit, Seiji Kawamoto, Thanutchaporn Kumrungsee and Noriyuki Yanaka

Nutrients 2025, 17(3), 383; https://doi.org/10.3390/nu17030383 - 21 Jan 2025

Cited by 2 | Viewed by 2028

Abstract

Background: Diabetic nephropathy (DN) is a serious condition that can result in end-stage renal failure. Recent evidence has focused on the dietary effects of polyphenols on blood glucose levels and the complications of diabetes. Objectives: In this study, we investigated the protective effect of glucosyl hesperidin (G-Hes), composed of glucose and hesperidin, against streptozotocin (STZ)-induced nephropathy in mice. Methods: We used an STZ-induced diabetic mouse model to investigate the preventive effect of G-Hes on renal pathology. After G-Hes supplementation for 4 weeks, we investigated the renal gene expression profiles using DNA microarray analysis and renal histology to examine the underlying molecular mechanism. Results: G-Hes suppressed the increase in kidney weight without any change in the blood glucose levels. This study identified 511 genes whose expression levels were substantially increased during DN development but were downregulated by G-Hes supplementation. G-Hes prevented mRNA expression associated with renal tubule injury, fibrosis, and immune responses. Notably, G-Hes supplementation considerably decreased the complement component C3 at the mRNA and protein levels in the glomeruli and ameliorated glomerular and mesangial matrix expansion in diabetic nephropathy. Conclusions: G-Hes supplementation is useful in preventing tubulointerstitial fibrosis and inflammation in a mouse model of DN, without exhibiting a hypoglycemic effect. Full article

(This article belongs to the Section Nutrition and Diabetes)

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17 pages, 2925 KB

Open AccessArticle

Enzymatic Synthesis, Structural Analysis, and Evaluation of Antibacterial Activity and α-Glucosidase Inhibition of Hesperidin Glycosides

by Titaporn Chaisin, Prakarn Rudeekulthamrong and Jarunee Kaulpiboon

Catalysts 2021, 11(5), 532; https://doi.org/10.3390/catal11050532 - 21 Apr 2021

Cited by 17 | Viewed by 4765

Abstract

This study was designed to investigate the structure of synthesized hesperidin glycosides (HGs) and evaluate their antibacterial and α-glucosidase inhibitory activities. The preliminary structure of HG_s was confirmed by glucoamylase treatment and analyzed on thin layer chromatography (TLC). The LC-MS/MS profiles of HGs showed the important fragments at m/z ratios of 345.21 (added glucose to glucose of rutinose in HG₁) and 687.28 (added maltose to glucose of rutinose in HG₂), confirming that the structures of HG₁ and HG₂ were α-glucosyl hesperidin and α-maltosyl hesperidin, respectively. In addition, ¹H and ¹³C-NMR of hesperidin derivatives were performed to identify their α-1,4-glycosidic bonds. The MIC and MBC studies showed that transglycosylated HG₁ and HG₂ had better antibacterial and bactericidal activities than hesperidin and diosmin, and were more active against Staphylococcus aureus than Escherichia coli. Hesperidin, HG₁, HG₂, and diosmin inhibited α-glucosidase with IC₅₀ values of 2.75 ± 1.57, 2.48 ± 1.61, 2.36 ± 1.48, and 2.99 ± 1.23 mg/mL, respectively. The inhibition kinetics of HG₂ shown by a Lineweaver–Burk plot confirmed HG₂ was an α-glucosidase competitive inhibitor with an inhibitor constant, K_i, of 2.20 ± 0.10 mM. Thus, HGs have the potential to be developed into antibacterial drugs and treatments for treating α-glucosidase-associated type 2 diabetes. Full article

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11 pages, 2710 KB

Open AccessArticle

Effect of Alpha-Glucosyl-Hesperidin Consumption on Lens Sclerosis and Presbyopia

by Yosuke Nakazawa, Yuri Doki, Yuki Sugiyama, Ryota Kobayashi, Noriaki Nagai, Naoki Morisita, Shin Endo, Megumi Funakoshi-Tago and Hiroomi Tamura

Cells 2021, 10(2), 382; https://doi.org/10.3390/cells10020382 - 12 Feb 2021

Cited by 14 | Viewed by 4495

Abstract

Presbyopia is characterized by a decline in the ability to accommodate the lens. The most commonly accepted theory for the onset of presbyopia is an age-related increase in the stiffness of the lens. However, the cause of lens sclerosis remains unclear. With age, water microcirculation in the lens could change because of an increase in intracellular pressure. In the lens, the intracellular pressure is controlled by the Transient Receptor Potential Vanilloid (TRPV) 1 and TRPV4 feedback pathways. In this study, we tried to elucidate that administration of α-glucosyl-hesperidin (G-Hsd), previously reported to prevent nuclear cataract formation, affects lens elasticity and the distribution of TRPV channels and Aquaporin (AQP) channels to meet the requirement of intracellular pressure. As a result, the mouse control lens was significantly toughened compared to both the 1% and 2% G-Hsd mouse lens treatments. The anti-oxidant levels in the lens and plasma decreased with age; however, this decrease could be nullified with either 1% or 2% G-Hsd treatment in a concentration- and exposure time-dependent manner. Moreover, G-Hsd treatment affected the TRPV4 distribution, but not TRPV1, AQP0, and AQP5, in the peripheral area and could maintain intracellular pressure. These findings suggest that G-Hsd has great potential as a compound to prevent presbyopia and/or cataract formation. Full article

(This article belongs to the Special Issue Eye Diseases: From Cellular and Molecular Mechanisms to Novel Therapeutic Approaches)

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11 pages, 1957 KB

Open AccessArticle

Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase

by José L. González-Alfonso, Noa Míguez, J. Daniel Padilla, Laura Leemans, Ana Poveda, Jesús Jiménez-Barbero, Antonio O. Ballesteros, Georgina Sandoval and Francisco J. Plou

Molecules 2018, 23(11), 2885; https://doi.org/10.3390/molecules23112885 - 5 Nov 2018

Cited by 25 | Viewed by 5619

Abstract

The regioselective α-glucosylation of hesperetin was achieved by a transglycosylation reaction catalyzed by cyclodextrin glucanotransferase (CGTase) from Thermoanaerobacter sp. using soluble starch as glucosyl donor. By combining mass spectrometry (ESI-TOF) and 2D-NMR analysis, the main monoglucosylated derivative was fully characterized (hesperetin 7-O-α-d-glucopyranoside). In order to increase the yield of monoglucoside, several reaction parameters were optimized: Nature and percentage of cosolvent, composition of the aqueous phase, glucosyl donor, temperature, and the concentrations of hesperetin and soluble starch. Under the optimal conditions, which included the presence of 30% of bis(2-methoxyethyl) ether as cosolvent, the maximum concentration of monoglucoside was approximately 2 mM, obtained after 24 h of reaction. To our knowledge, this is the first report of direct glucosylation of hesperetin employing free enzymes instead of whole cells. Full article

(This article belongs to the Section Natural Products Chemistry)

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