Ellagic acid inhibits iron-mediated free radical formation

Dalvi, Luana Taquette; Moreira, Daniel C.; Andrade, Roberto G.; Ginani, Janini Selva; Alonso, Antônio; Hermes‐Lima, Marcelo

doi:10.1016/j.saa.2016.10.034

Cited by 38 publications

(30 citation statements)

References 31 publications

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“…The presence of a catechol group in the former was identified as being responsible for iron chelation (▶ Fig. 2) [75]. Finally, Galano et al [55] concluded that after deprotonation, ellagic acid is also capable of chelating copper in aqueous solution, yielding stable complexes.…”

Section: Ellagic Acid As An Antioxidant Agentmentioning

confidence: 99%

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A Pharmacological Update of Ellagic Acid

et al. 2018

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Ellagic acid is a common metabolite present in many medicinal plants and vegetables. It is present either in free form or as part of more complex molecules (ellagitannins), which can be metabolized to liberate ellagic acid and several of its metabolites, including urolithins. While ellagic acidʼs antioxidant properties are doubtless responsible for many of its pharmacological activities, other mechanisms have also been implicated in its various effects, including its ability to reduce the lipidemic profile and lipid metabolism, alter pro-inflammatory mediators (tumor necrosis factor-α, interleukin-1β, interleukin-6), and decrease the activity of nuclear factor-κB while increasing nuclear factor erythroid 2-related factor 2 expression. These events play an important role in ellagic acidʼs anti-atherogenic, anti-inflammatory, and neuroprotective effects. Several of these activities, together with the effect of ellagic acid on insulin, glycogen, phosphatases, aldose reductase, sorbitol accumulation, advanced glycation end-product formation, and resistin secretion, may explain its effects on metabolic syndrome and diabetes. In addition, results from recent research have increased the interest in ellagic acid, both as a potential protective agent of the liver and skin and as a potential anticancer agent, due to the specific mechanisms affecting cell proliferation, apoptosis, DNA damage, and angiogenesis and its aforementioned anti-inflammatory properties. Taken together, these effects make ellagic acid a highly interesting compound that may contribute to different aspects of health; however, more studies are needed, especially on the compoundʼs pharmacokinetic profile. In this review, we selected papers published from 2005 to the present.

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Section: Ellagic Acid As An Antioxidant Agentmentioning

confidence: 99%

“…2 Effect of ellagic acid on different metals. Proposal mechanism of chelation (adapted from Dalvi et al [75]). translocation of Nrf2 [85].…”

Section: Ellagic Acid As An Antioxidant Agentmentioning

confidence: 99%

A Pharmacological Update of Ellagic Acid

et al. 2018

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“…Previous studies reported that phenolic compounds are highly correlated with metal-chelating abilities. Dalvi et al [ 15 ] reported that ellagic acid has high iron-chelating activity. Jaén et al [ 16 ] studied gallic and ellagic acids in Cistus ladanifer extracts, which have good Fe 2+ -chelating activities because of the three hydroxyl groups of the benzene ring of gallic acid and the four hydroxyl groups attached to the structure of ellagic acid.…”

Section: Resultsmentioning

confidence: 99%

Metal Chelating, Inhibitory DNA Damage, and Anti-Inflammatory Activities of Phenolics from Rambutan (Nephelium lappaceum) Peel and the Quantifications of Geraniin and Corilagin

Li²,

Hou

et al. 2018

Molecules

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Whereas the preparation and biological properties of rambutan peel phenolics (RPP) were explored in our previous studies, the metal chelating, inhibitory DNA damage, and anti-inflammatory activities of RPP were evaluated and the important phenolics of RPP quantified in this study. Results showed that RPP had high Fe2+ and Cu2+-chelating activities with EC50 of 0.80 mg/mL and 0.13 mg/mL, respectively. RPP effectively decreased the production of hydroxyl radical with IC50 of 62.4 μg/mL. The protective effects of RPP against AAPH-induced DNA damage were also explored. RPP efficiently inhibited peroxyl radical-induced plasmid DNA strand breakage. The anti-inflammatory effects of RPP were determined using a lipopolysaccharide (LPS)-induced RAW 264.7 cell model. RPP significantly inhibited the production of nitric oxide (NO) and controlled the levels of inducible NO synthase mRNA in LPS-induced RAW 264.7 cells. The inhibitory activity increased in a dose-dependent manner. The above bioactivity of RPP was associated with its phenolic content and phenolic profiles. Furthermore, the contents of geraniin and corilagin in RPP were determined by an ultra-high performance liquid chromatography coupled with triple quadruple mass spectrometry (UPLC-QQQ-MS), showing 140.02 and 7.87 mg/g extract dry weight. Thus, RPP has potential applications as a novel nutraceutical and functional food in health promotion.

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“…Among the identified compounds, ellagic acid was reported to be able to form complexes with several metal ions and to produce antioxidative effects through reducing the iron-mediated free radical formation by chelating mechanisms [45]. Also, the free radical scavenging effects of rutin and the inhibition of lipid peroxidation were ascribed to its ability to chelate iron ions, thus leading to the formation of metal-complexes that slightly promote free-radical reactions [46][47].…”

Section: Iron Chelating Activitymentioning

confidence: 99%

Hypoglycemic, Antiglycation and Cytoprotective Properties of A Phenol Rich Extract from Waste Peel of <i>Punica Granatum</i> L. Var. Dente Di Cavallo DC2

Sotto¹,

Locatelli²,

Macone³

et al. 2019

Preprint

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Pomegranate peel is a natural source of phenolics, claimed to possess healing properties, among which antioxidant and antidiabetic. In line with this evidence, the ethyl acetate PGE extract, obtained by Soxhlet from the peel of Dente di cavallo DC2 variety and characterized by a 4% amount of ellagic acid, has been studied for its hypoglycemic, antiglycation and antioxidative cytoprotective properties, in order to support a possible further nutraceutical interest. The α-amylase and α-glucosidase enzyme inhibition, interference with advanced glycation end-products (AGE) formation and metal chelating abilities were evaluated as hypoglycemic mechanisms. Also, considering that oxidative stress is associated with hyperglycemia complications, PGE antioxidant cytoprotective properties under hyperglycemic conditions were assayed. Phenolic profile was characterized by integrated chromatographic and spectrophotometric methods. Under our experimental conditions, PGE strongly inhibited the tested enzymes, especially α-glucosidase, and exerted chelating and antiglycation properties. Also, it reduced both ROS and GSH levels under hyperglycemic conditions, thus suggesting its ability to support cell functions by counteracting intracellular oxidative stress. Along with ellagic acid, rutin was the major identified flavonoid (about 4 %) of PGE. Present results suggest PGE to be a possible remedy for hyperglycemia management and encourage further studies to exploit its promising properties.

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Ellagic acid inhibits iron-mediated free radical formation

Cited by 38 publications

References 31 publications

A Pharmacological Update of Ellagic Acid

A Pharmacological Update of Ellagic Acid

Metal Chelating, Inhibitory DNA Damage, and Anti-Inflammatory Activities of Phenolics from Rambutan (Nephelium lappaceum) Peel and the Quantifications of Geraniin and Corilagin

Hypoglycemic, Antiglycation and Cytoprotective Properties of A Phenol Rich Extract from Waste Peel of <i>Punica Granatum</i> L. Var. Dente Di Cavallo DC2

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