Experimental pharmacokinetics of biologically active plant phenolic compounds. I. Pharmacokinetics of mangiferin in the rat

Geodakyan, S. V.; Voskoboinikova, I. V.; Tjukavkina, N. A.; Kolhir, V. K.; Kolesnik, Yu. A.; Zjuzin, V. A.; Glyzin, V. I.; Sokolov, S. J.

doi:10.1002/ptr.2650060611

Cited by 21 publications

(10 citation statements)

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“…11) Mangiferin orally administered to rats or mice exerts biological antitumor, 11) antidiabetic, 12) antioxidant, 13) hepatoprotective 14) and immunomodulative 15) activities. However, the pharmacokinetic studies in rats given oral mangiferin have failed to detect mangiferin in plasma, 16) suggesting poor absorption. On the other hand, appreciable amounts of euxanthone (1,7-dihydroxyxanthone) and its glucuronides are excreted into the urine of rabbits given oral mangiferin, 17) indicating a unique metabolic transformation that involves elimination of a Cglucosyl chain and two phenolic hydroxyl groups.…”

Section: -8)mentioning

confidence: 99%

“…When orally administered, mangiferin has antitumor, antidiabetic, antioxidant, hepatoprotective and immunomodulative activities. [11][12][13][14][15] Owing to poor absorption from the gastrointestinal tract, 16) B. sp. MANG seems to play important roles in the pharmacological actions of mangiferin.…”

Section: Isolation and Characterization Of A Bacterium That Transformmentioning

confidence: 99%

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Isolation of a Human Intestinal Bacterium That Transforms Mangiferin to Norathyriol and Inducibility of the Enzyme That Cleaves a C-Glucosyl Bond

Sanugul

Akao

et al. 2005

Biological & Pharmaceutical Bulletin

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C-Glucosides, which are widely distributed among plants, are more resistant towards acid, alkaline and enzyme hydrolysis than O-glucosides. Even prolonged exposure to acid does not cleave the glucosyl bond of C-glucosides, in which glucose is attached by a carbon-carbon bond to the aglycone, to give the aglycone. 1) However, intestinal bacteria from human feces can cleave C-glucosyl bonds in various C-glucosides such as mangiferin, abrusin 2Љ-O-b-D-apioside, aloeresin A, aloesin, barbaloin, bergenin, homoorientin, puerarin and safflor yellow B. 2-8)Mangiferin (2-b-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone), was originally isolated from Mangifera indica L. (Anacardiaceae). It is distributed among at least sixteen plant families including Anacardiaceae, Iridaceae and Gentianaceae. Studies in vitro have shown that mangiferin has antiviral activity against herpes simplex virus 9) as well as antioxidant, 10) and anti-HIV activity. 11) Mangiferin orally administered to rats or mice exerts biological antitumor, 11) antidiabetic, 12) antioxidant, 13) hepatoprotective 14) and immunomodulative 15) activities. However, the pharmacokinetic studies in rats given oral mangiferin have failed to detect mangiferin in plasma, 16) suggesting poor absorption. On the other hand, appreciable amounts of euxanthone (1,7-dihydroxyxanthone) and its glucuronides are excreted into the urine of rabbits given oral mangiferin, 17) indicating a unique metabolic transformation that involves elimination of a Cglucosyl chain and two phenolic hydroxyl groups. The transformation of mangiferin to norathyriol by human fecal flora in vitro ( Fig. 1) 5) indicates an important role of mangiferinmetabolizing bacteria in the disposition of norathyriol and its subsequent metabolites in vivo, as well as in the pharmacological activities of mangiferin. Norathyriol also exerts antiinflammatory, 18,19) vasorelaxation 20) and antiplatelet 21) activities. Therefore, the biotransformation of mangiferin should be thoroughly investigated.Here, we isolated and characterized a bacterium that transforms mangiferin to norathyriol. Furthermore, the novel enzyme that cleaved C-glucosyl was selectively inducible with mangiferin and apparently differs from a-and b-glucosidases. The C-glucosyl bond of C-glucosides generally tolerates acid and enzymatic hydrolysis. Many C-glucosides are cleaved by human intestinal bacteria. We isolated the specific bacterium involved in the metabolism of mangiferin (2-b b-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone), C-glucosyl xanthone, from a mixture of human fecal bacteria. The anaerobic Bacteroides species named MANG, transformed mangiferin to the aglycone, norathyriol, suggesting cleavage of a C-glucosyl bond. However, B. sp. MANG cleaved C-glucosyl in a dose-and time-dependent manner only when cultivated in the presence of mangiferin. Cleavage was abolished by inhibitors of RNA and protein syntheses, such as rifampicin and chloramphenicol, respectively, indicating that the enzyme that cleaves C-glucosyl is induced by mangiferin....

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Section: -8)mentioning

confidence: 99%

Section: Isolation and Characterization Of A Bacterium That Transformmentioning

confidence: 99%

Isolation of a Human Intestinal Bacterium That Transforms Mangiferin to Norathyriol and Inducibility of the Enzyme That Cleaves a C-Glucosyl Bond

Sanugul

Akao

et al. 2005

Biological & Pharmaceutical Bulletin

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“…The MG stock solution was stored at room temperature (about 23˚C). Buffer supporting electrolyte solutions were prepared by mixing either solutions of KH 2 PO 4 and Na 2 HPO 4 (both from BDH), HCl and KCl (from Fischer scientific international) or CH 3 COOH and CH 3 COONa from Fischer scientific international and BDH respectively. The buffer solutions were used immediately after preparation.…”

Section: Reagents and Chemicalsmentioning

confidence: 99%

“…The modified electrode's active surface area was electrically activated by immersion in 0.5 M HCl solution, followed by five cyclic voltammetric scans from -0.2 V to +1 V. This electrical activation led to the protonation of the amino (-NH 2 ) groups of chitosan to form 3 -NH + groups [40]. Cyclic voltammograms were recorded by transferring the chitosan-CPE either in a phosphate buffer (PB), HCl/KCl or in an acetate buffer (AB) solution containing MG at a given concentration.…”

Section: Electroanalytical Proceduresmentioning

confidence: 99%

“…One of such ingredients that have undergone close scrutiny in recent years is mangiferin (MG), a C-glucosylxanthone (Scheme 1). MG belongs to the class of yellow oxygenated heterocyclics called xanthones, whose role is well-known in medicinal chemistry [3] [4]. The extraction of this promising pharmacological ingredient from various parts of the tropical based Mangifera indica L. by different authors has been reviewed by [5].…”

Section: Introductionmentioning

confidence: 99%

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Adsorptive Stripping Voltammetric Determination of Mangiferin Using an Activated Chitosan Modified Carbon Paste Electrode

Tchieno¹,

Njanja²,

Tapondjou³

et al. 2014

AJAC

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A medium molecular weight powdered chitosan modified carbon paste electrode was used to investigate the electrochemical behaviour by cyclic voltammetry of the pharmacologically-active ingredient mangiferin (MG). An irreversible system was observed, with a peak at +0.55 V (vs Ag/AgCl). The peak current increases about fourfold, at the modified electrode in comparison with that recorded at the chitosan free carbon paste electrode. This allowed the use of adsorptive stripping voltammetry to develop a simple and sensitive electroanalytical method for the determination of MG. The influence of key parameters was investigated, including the electrolysis potential, the preconcentration time, the pH of supporting electrolyte and MG concentration. Upon optimisation of these parameters, the electrode response was found to be directly proportional to the concentration of MG in the range from 2.06 × 10 −6 M to 6.74 × 10 −5 M, leading to a detection limit of 1.84 μM for 240 s preconcentration at −0.1 V. A mechanism was also proposed for the electrochemical oxidation of MG.

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Elucidation of stress‐induced degradation products of mangiferin: Method development and validation

Khurana

Kaur²,

Kaur³

et al. 2017

Biomedical Chromatography

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The degradation behavior of mangiferin, under various ICH Q1A(R2) recommended stress conditions, was studied using an isocratic elution with mobile phase (pH 2.4), composed of acetonitrile and 1% orthophosphoric acid (12:88 v/v) at a flow rate of 1.0 mL/min, with λ 262 nm. It was suitably adapted for LC-MS studies by replacing with 1% acetic acid (ACN-1% acetic acid; 18:82) and the pH was adjusted to 3.0. Extensive degradation was found to occur during alkaline medium stress studies at 2.31 min of retention time at λ of 235 nm. The mass spectrum of mangiferin, 3 h after treatment with 0.1 M NaOH, clearly shows the rupture of the tricyclic ring, indicating that a fragment at m/z - 269 was formed. Furthermore, the results were supported by nuclear magnetic resonance as well. However, no degradation was observed in other stress conditions.

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Experimental pharmacokinetics of biologically active plant phenolic compounds. I. Pharmacokinetics of mangiferin in the rat

Cited by 21 publications

References 2 publications

Isolation of a Human Intestinal Bacterium That Transforms Mangiferin to Norathyriol and Inducibility of the Enzyme That Cleaves a C-Glucosyl Bond

Isolation of a Human Intestinal Bacterium That Transforms Mangiferin to Norathyriol and Inducibility of the Enzyme That Cleaves a C-Glucosyl Bond

Adsorptive Stripping Voltammetric Determination of Mangiferin Using an Activated Chitosan Modified Carbon Paste Electrode

Elucidation of stress‐induced degradation products of mangiferin: Method development and validation

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