Anti-inflammatory activity of myricetin-3-O-β-D-glucuronide and related compounds

Hiermann, A.; Schramm, Hans-Wolfgang; Laufer, Stefan

doi:10.1007/s000110050355

Cited by 53 publications

(30 citation statements)

References 20 publications

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“…Thus, the own biological activity of the glucuronides should be considered, even though the possibility of hydrolysis into aglycones inside the cells is still under investigation (O'Leary et al, 2001;Shimoi et al, 2001). A few studies have reported antioxidative or anti-inflammatory activity of flavonoid conjugates (Manach et al, 1998;Hiermann et al, 1998;Day et al, 2000;Moon et al, 2001). The intestinal microflora, besides the deglycosylation of narirutin and hesperidin, has also the capacity to degrade the aglycones into phenolic acids such as p-hydroxyphenylpropionic, p-coumaric, and p-hydroxybenzoic acids (Booth et al, 1958;Scheline, 1991;Felgines et al, 2000).…”

Section: Discussionmentioning

confidence: 99%

Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice

Manach¹,

Morand²,

et al. 2003

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Objective: Flavanones are polyphenols specific of citrus fruits, where they are present in high amounts. Although citrus fruits and juices are widely consumed in the world, little information has been published on flavanone bioavailability in humans. The aim of the present study was to determine the nature of the circulating metabolites, the plasma kinetics and the urinary excretion patterns of the flavanones, hesperidin and narirutin. Design: After an overnight fast, five healthy volunteers ingested 0.5 or 1 l of a commercial orange juice providing 444 mg=l hesperidin and 96.4 mg=l narirutin, together with a polyphenol-free breakfast. Blood was sampled at 10 different timepoints over a 24 h period. Urine was collected for 48 h, in five fractions. Results: Flavanones metabolites appeared in plasma 3 h after the juice ingestion, reached a peak between 5 and 7 h, then returned to baseline at 24 h. The peak plasma concentration of hesperetin was 0.46 AE 0.07 mmol=l and 1.28 AE 0.13 mmol=l after the 0.5 and 1 l intake, respectively. It was lower for naringenin: 0.20 AE 0.04 mmol=l after the 1 l dose. The circulating forms of hesperetin were glucuronides (87%) and sulphoglucuronides (13%). For both flavanones, the urinary excretion was nearly complete 24 h after the orange juice ingestion. The relative urinary excretion was similar for hesperetin and naringenin and did not depend on the dose: values ranged from 4.1 AE 1.2 to 7.9 AE 1.7% of the intake. Conclusions: In case of a moderate or high consumption of orange juice, flavanones may represent an important part of the pool of total polyphenols present in plasma.

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Section: Discussionmentioning

confidence: 99%

Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice

Manach¹,

Morand²,

et al. 2003

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“…The highly anti-inflammatory compound 2 (Hiermann et al, 1991(Hiermann et al, , 1998 was present only in minor quantities (0.1-0.3 mg/g) with significant lower amounts at 800 m compared with 1000 and 1500 m.…”

Section: Quantification Of Individual Flavonoidsmentioning

confidence: 97%

“…Rosebay willow-herb shows antioxidative, anti-inflammatory, antimicrobial, antiproliferative, and anti-exudative activities (Hevesi Toth et al, 2009;Kiss et al, 2011;Kosalec et al, 2013;Onar et al, 2012;Stolarczyk et al, 2013b;Vitalone et al, 2001Vitalone et al, , 2003Vogl et al, 2013). The anti-inflammatory activity of E. angustifolium has been closely related to its flavonoids evidenced by the finding of myricetin 3-O-glucuronide as strongly active (4 10-fold more potent than indomethacin) in the rat paw edema test, a model of acute inflammation (Hiermann et al, 1998) and showing an inhibitory effect on prostaglandin biosynthesis (Hiermann et al, 1991). However, for treatment of benign prostate hyperplasia, tannins also seem to play a role as 5a-reductase and aromatase were inhibited by the tannins oenotheins A and B.…”

Section: Introductionmentioning

confidence: 99%

Content of phenolic compounds in wild populations ofEpilobium angustifoliumgrowing at different altitudes

Monschein

Jaindl

Buzimkić

et al. 2015

Pharmaceutical Biology

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Context: Flavonoids are regarded as essential ingredients for the anti-inflammatory activity of Epilobium angustifolium L. (Onagraceae). The metabolic profiles of medicinal plants vary aside from genetic determination due to the influence by external factors. Objectives: This study evaluates the influence of altitudinal variation on the content of flavonoids in E. angustifolium in two consecutive growing periods. Materials and methods: Aerial and herbaceous plant materials were collected at three different altitudes (800, 1000, and 1500 m) during two collection periods. Plant samples (11-13 samples per altitude and year) were extracted with methanol using accelerated solvent extraction (ASE). Identification and quantification of the constituents were achieved by chromatographic means of HPLC-PDA and LC-PDA-MS analyses. Results: Rising concentrations of flavonol 3-O-glycosides could be detected with increasing altitude. The content of the major compound, quercetin 3-O-glucuronide, ranged from 4.4 ± 2.05 (800 m) to 4.9 ± 1.03 (1000 m) and up to 6.6 ± 1.14 mg/g (1500 m). The total amount of flavonol 3-O-glycosides in 73 analyzed samples ranged from 10.7 ± 1.37 up to 17.3 ± 1.99 mg/g. Discussion: Quercetin-3-O-glucuronide can be considered as a potential marker for the increased production of flavonols in herbal parts of E. angustifolium at higher altitudinal levels. Conclusion: The study confirms that environmental factors at higher altitude result in elevated levels of flavonols in aerial plant tissues of E. angustifolium. Specific factors for influencing the flavonoid content have to be clarified in further studies.

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“…Besides anticancer, antiviral, antimicrobial, immunmodulatory and antithrombotic activities, the anti-inflammatory properties, observed in vitro and in vivo, are most recognized. Thus, flavonoids have been shown to inhibit acute or chronic inflammation in various animal models such as rat Freund's adjuvant arthritis [98], [99] and carrageenan-induced mouse paw edema, when given orally [99], [100]. In particular, however, flavonoids showed beneficial effects in AA-induced ear edema, when applied topically (for review see [97]).…”

Section: Inhibitors Of 5-lo Product Synthesis From Plant Originmentioning

confidence: 99%

“…Unfortunately, among those, only for papyriflavonol 20 has the efficacy in intact cells been demonstrated [103]. Although for inhibition of cellular 5-LO, the flavonoid aglycones are generally superior over the corresponding glycosides, the myricetin 3-O-b-D-glucuronide 13 is more efficient than the corresponding aglycone myricetin 12 under comparable assay conditions [99], [109], probably related to more effective cellular uptake of the glycoside by specific transporters. Since conventional flavonoids show only weak efficacy after oral administration, presumably due to poor bioavailability (low absorption) and/or rapid metabolism and elimination, the more lipophilic prenylated derivatives may possess the advantage of facilitated membrane (and skin) penetration in addition to their higher potency as 5-LO inhibitors, suggesting a potential for topical treatment of inflammatory skin diseases [103], [105], [113].…”

Section: Inhibitors Of 5-lo Product Synthesis From Plant Originmentioning

confidence: 99%

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

Werz¹

2007

Planta Med

155

135

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The biosynthesis of leukotrienes (LTs) is initiated by the transformation of free arachidonic acid to LTA 4 by 5-lipoxygenase (5-LO). Subsequent enzymatic conversion of LTA 4 yields LTB 4 and the cysteinyl-LTs C 4 , D 4 and E 4 . LTs have prominent functions in pathophysiology and are connected to numerous disorders including bronchial asthma, allergic rhinitis, inflammatory bowel and skin diseases, rheumatoid arthritis, cancer, osteoporosis and cardiovascular diseases. Pharmacological and genetic interruption of the 5-LO pathway or blockade of LT receptors, serving as means for intervention with LTs, may be of therapeutic value for certain related disorders. Natural or plant-derived substances were among the first 5-LO inhibitors identified in the early 1980 s. To date, a huge number of diverse plant-derived compounds have been reported to interfere with 5-LO product synthesis. However, many investigations have addressed the efficacy of a given compound solely in cellular test systems and analysis of direct interference with 5-LO has been neglected. In the first part of this review, the biology and molecular pharmacology of the 5-LO pathway is summarized in order to understand its overall regulation and complexity as well as to comprehend the possible points of attack of compounds that eventually lead to inhibition of 5-LO product formation in intact cells. In the second part, natural compounds that interfere with 5-LO product formation are compiled and grouped into structural classes, and the underlying molecular mechanisms and structureactivity relationships are discussed.

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Anti-inflammatory activity of myricetin-3-O-β-D-glucuronide and related compounds

Abstract: MGL is a COX-1, COX-2 and 5-LOX inhibitor. In view of the moderate in vitro activity and the very potent in vivo activity an additive mechanism must be involved. Small changes in the molecular structure lead to the loss or reduction of the anti-inflammatory activity.

Cited by 53 publications

References 20 publications

Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice

Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice

Content of phenolic compounds in wild populations ofEpilobium angustifoliumgrowing at different altitudes

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

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