A Comparative Study of Hesperetin, Hesperidin and Hesperidin Glucoside: Antioxidant, Anti-Inflammatory, and Antibacterial Activities In Vitro

Abstract

The antioxidant, anti-inflammatory and antibacterial activities of hesperetin, hesperidin and hesperidin glucoside with different solubility were compared in vitro. Hesperetin was prepared by enzymatic hydrolysis from hesperidin, and hesperidin glucoside composed of hesperidin mono-glucoside was prepared from hesperidin through enzymatic transglycosylation. Solubility of the compounds was different: the partition coefficient (log P) was 2.85 ± 0.02 for hesperetin, 2.01 ± 0.02 for hesperidin, and −3.04 ± 0.03 for hesperidin glucoside. Hesperetin showed a higher effect than hesperidin and hesperidin glucoside on radical scavenging activity in antioxidant assays, while hesperidin and hesperidin glucoside showed similar activity. Cytotoxicity was low in the order of hesperidin glucoside, hesperidin, and hesperetin in murine macrophage RAW264.7 cells. Treatment of the cells with each compound reduced the levels of inflammatory mediators, nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6). Hesperetin was most effective at relatively low concentrations, however, hesperidin glucoside was also effective at higher concentration. Hesperetin showed higher antibacterial activity than hesperidin in both Gram-positive and -negative bacteria, and hesperidin glucoside showed similarly higher activity with hesperetin depending on the bacterial strain. In conclusion, hesperetin in the form of aglycone showed more potent biological activity than hesperidin and hesperidin glucoside. However, hesperidin glucoside, the highly soluble form, has been shown to increase the activity compared to poorly soluble hesperidin.

Effects of hesperidin combined with synephrine on the capture of acrolein in a mouse model, or in humans by citrus consumption

“…Structurally, it is a flavonoid glycoside comprising hesperetin (HESP) and disaccharides. 22 Increasing number of studies have reported that HES exhibits a broad range of biological activities, like antibacterial, antioxidant, anti-inflammatory, 23 and antithrombotic functions. 24 In particular, HES has been confirmed using the RNase A-MGO assay model system as well to inhibit the generation of advanced glycation end products by capturing methylglyoxal (MGO, an RCS).…”

Egyptian propolis extract for functionalization of cellulose nanofiber/poly(vinyl alcohol) porous hydrogel along with characterization and biological applications

“…As illustrated in Table 1 , hesperetin, chlorogenic acid, and caffeic acid were reported as three compounds from PE with high concentrations. Hesperetin was obtained from the enzymatic hydrolysis of hesperidin and evaluated for antimicrobial activity against Gram-positive and Gram-negative bacteria, the results revealed that hesperetin more effectively inhibited the model microbes than hesperidin and hesperidin glucoside 46 . Yen et al 47 .…”

Hesperetin—Between the Ability to Diminish Mono- and Polymicrobial Biofilms and Toxicity

“…Previous study of hesperetin has indicated its low inhibitory potential towards S. aureus (MIC > 1 mg/mL) [ 17 ], as confirmed also in this study (MIC > 4 mg/mL). Moreover, stronger antibacterial potential for hesperetin was noticed in the study of Choi et al [ 18 ], who determined MIC at 0.125 mg/mL, and in the study of Ivanov et al [ 19 ], with MIC 0.5 mg/mL, both towards S. aureus . In this previous study [ 19 ] hesperetin exhibited identical antibacterial potential as its glycoside hesperidin, suggesting that sugar moiety does not have impact on antibacterial properties of this flavonoid.…”