Bioavailability of Glucosyl Hesperidin in Rats

Yamada, Mika; Tanabe, Fujimi; Arai, Norie; Mitsuzumi, Hitoshi; Miwa, Yoshikatsu; Kubota, Michio; Chaen, Hiroto; Kibata, Masayoshi

doi:10.1271/bbb.50657

Cited by 122 publications

(105 citation statements)

References 30 publications

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“…GH has about 10000-times greater solubility in water than that of hesperidin. 16,17) In this study, we found that GH prevents influenza virus replication in vitro by inhibition of the viral sialidase activity but not by receptor binding inhibition. The results suggest that GH is useful for preventing IAV infection.…”

mentioning

confidence: 61%

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

Saha

Takahashi

Suzuki

2009

Biological & Pharmaceutical Bulletin

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Hesperidin, a flavonoid obtained from citrus fruits, is known to have multiple biological activities and antimicrobial activities for human viruses; however, hesperidin has very low solubility in water and the target molecule of hesperidin for influenza virus remains unknown. A water-soluble derivative of hesperidin, glucosyl hesperidin (GH), which was synthesized by regioselective transglycosylation with cyclodextrin glucanotransferase, has been reported to have biological activities that are as or stronger than those of hesperidin. To determine the inhibitory effect of GH on influenza A virus (IAV) infection, Madin-Darby canine kidney (MDCK) cells were treated with GH before, at the same time as, and after IAV inoculation. GH treatment before IAV inoculation had no effect on virus replication, whereas, treatment with GH at the same time as or after IAV inoculation induced distinct reduction in IAV replication. Inhibition analysis of GH against two surface glycoprotein spikes of IAV revealed that GH prevents IAV replication by inhibition of viral sialidase activity that is involved in the entry and release stages on IAV infection but not by receptor binding inhibition. GH had no cytotoxic effects on MDCK cells in a dose range of 0-25 mM. Our results provide useful information for the development of novel sialidase inhibitors for influenza prevention.

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mentioning

confidence: 61%

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

Saha

Takahashi

Suzuki

2009

Biological & Pharmaceutical Bulletin

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“…On the other hand, it is also known that the glycosides linked with various sugars in plant foods enhance the absorption of dietary flavonoids in the gut (Hollman et al, 1999). The results of the pharmacokinetic parameters, such as the maximum concentration that a drug achieves after dosing (C max ) and the values for the area under the plasma concentration-time curve (AUC) in serum, revealed that glycosylated purarin or hesperidin were absorbed more rapidly and efficiently than their aglycones (Yamada et al, 2006;Jiang et al, 2008 indicates that flavonoid absorption in the gut can be occurred through active transport in the intestine. Baicalein and baicalin have been shown to exhibit antiinflammatory activity in vivo and in vitro (Lin and Shieh, 1996;Kim et al, 2009a).…”

Section: Discussionmentioning

confidence: 99%

Synthesis and biological evaluation of a novel baicalein glycoside as an anti-inflammatory agent

Kim¹,

Park²,

Park³

et al. 2014

European Journal of Pharmacology

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“…Previous studies have reported that one or more glucuronidation sites predominate. For instance, after the oral administration of hesperetin and hesperidin to rats it was observed that hesperetin-3 0 -O-glucuronide and hesperetin-7-O-glucuronide were present [65,71]. In the case of naringenin, the major metabolites detected in rat urine after oral administration of naringenin or naringin [72] and in human plasma and urine after ingestion of grapefruit juice [72,73] were naringenin-4 0 -Oglucuronide and naringenin-7-O-glucuronide.…”

Section: Stereospecific Pharmacokinetics Of Hesperetin Naringenin Anmentioning

confidence: 99%

Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices

Yáñez

Remsberg

Miranda

et al. 2007

Biopharm & Drug Disp

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The majority of pharmacokinetic studies of individual flavonoids or after ingestion of foodstuffs have overlooked the chirality of some of these xenobiotics. In order to characterize for the first time the stereoselective pharmacokinetics of three flavonoids, hesperetin, naringenin and eriodictyol were intravenously administered (20 mg/kg) to male Sprague-Dawley rats, and their stereospecific content was assessed in various fruit juices. Concentrations in serum, urine and fruit juices were characterized via HPLC and verified by LC/MS. Short half-lives (3-7 h) in serum were observed, while a better estimation of half-life (12-48 h) and the other pharmacokinetic parameters was observed using urinary data. The three flavonoids are predominantly excreted via non-renal routes (fe values of 3-7%), and undergo rapid and extensive phase II metabolism. The (2S)-epimers of the flavonoid glycosides and the S(-)-enantiomers of the aglycones were predominant and in some instances the organic fruit juices had higher concentrations than the conventional fruit juices. This study reports for the first time the stereospecific pharmacokinetics of three chiral flavonoids and their stereospecific content in fruit juices. It also reports for the first time the stereospecific pharmacokinetics of flavonoids employing urine as a more reliable biological matrix.

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Bioavailability of Glucosyl Hesperidin in Rats

Cited by 122 publications

References 30 publications

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

Synthesis and biological evaluation of a novel baicalein glycoside as an anti-inflammatory agent

Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices

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