Natural Dibenzo[b,d]Pyran-6-Ones: Structural Diversity and Biological Activity

Garazd, Ya. L.; Garazd, M. M.

doi:10.1007/s10600-016-1536-4

Cited by 41 publications

(21 citation statements)

References 138 publications

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“…Their presence in plants and animal and human intestines is probably a result of bacterial metabolism of ellagic acid [3]. Various dibenzo [b,d]pyran-6-ones detected in extracts of medicinal plants were described by Y. L. Garazd and M. M. Garazd [4], while those produced by fungi were described by Mao et al [3]. Some of these compounds are toxic to humans and animals (mycotoxins), while the others show a number of beneficial health effects (antioxidant, antiallergic, antimicrobial, anti-inflammatory, antiproliferative, etc.)…”

Section: Introductionmentioning

confidence: 99%

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Ellagic Acid-Derived Urolithins as Modulators of Oxidative Stress

Djedjibegović

Marjanović

Panieri³

et al. 2020

Oxidative Medicine and Cellular Longevity

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Oxidative stress is a state of excess of prooxidative species relative to the antioxidant defenses (enzymatic and nonenzymatic) in a living organism. The consequence of this imbalance is damage of the major cellular macromolecules (carbohydrates, lipids, proteins, and DNA), which further leads to a gradual loss of tissue and organ function. It has been shown that oxidative stress plays an important role in the pathogenesis of many chronic diseases (cardiovascular, metabolic, and neurodegenerative diseases and cancer) and in the process of aging. Thus, many strategies to combat oxidative stress have been proposed and tested. In this context, food rich in antioxidants has received great attention. Pomegranate, berries, and walnuts have been recognized as “superfood” particularly for their cardioprotective effects. The common characteristic of these foods is the high content of ellagitannins. Since tannins are not bioavailable, they have been neglected in nutrition science and even considered antinutrients for a long time. However, this view has changed dramatically once it was recognized that ellagic acid, released from ellagitannins in the gastrointestinal system, is further metabolized by colonic microbiota to bioavailable compounds—known as urolithins. Thus, urolithins (3,4-benzocoumarin derivatives) have emerged as novel natural bioactive compounds and are now the focus of extensive investigations. So far, urolithins were shown to be powerful modulators of oxidative stress and agents with potential anti-inflammatory, antiproliferative, and antiaging properties. Furthermore, a few synthetic derivatives of urolithins were recognized as lead compounds for new drug development. Available data on urolithin synthesis, physicochemical and pharmacokinetic characteristics, biological activity, and safety will be presented in this review.

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Section: Introductionmentioning

confidence: 99%

“…Some of these compounds are toxic to humans and animals (mycotoxins), while the others show a number of beneficial health effects (antioxidant, antiallergic, antimicrobial, anti-inflammatory, antiproliferative, etc.) [3,4].…”

Section: Introductionmentioning

confidence: 99%

Ellagic Acid-Derived Urolithins as Modulators of Oxidative Stress

Djedjibegović

Marjanović

Panieri³

et al. 2020

Oxidative Medicine and Cellular Longevity

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“…This compound was given the name of urolithin‐A (Uro‐A) 15 years after its isolation from the renal calculus of sheep suffering from clover stone disease . Since then, this and other related compounds were reported to be naturally occurring constituents of plants, lichens, and fungi . In 1980, Doyle and Griffiths demonstrated that Uro‐A was produced from EA by the rat microbiota both in vitro and in vivo and that this was not produced when EA was given to germ‐free rats.…”

Section: Introductionmentioning

confidence: 99%

“…In this case, the review described their reported toxicity, cytotoxicity, and phytotoxicity, as well as antioxidant, antiallergic, antimicrobial, antimalarial, antinematodal, estrogenic/antiestrogenic, and acetylcholinesterase inhibitor effects. In a very similar way, a more recent review, with focus on natural dibenzo[ b,d ]pyran‐6‐ones, also covered the compounds present in plants, fungi, lichens, and animal wastes, and described their chemistry, occurrence, and biological effects (cytotoxicity and effects on cancer cells; antioxidant, antimicrobial, anti‐inflammatory, and estrogenic effects, among others) .…”

Section: Introductionmentioning

confidence: 99%

Urolithins, the rescue of “old” metabolites to understand a “new” concept: Metabotypes as a nexus among phenolic metabolism, microbiota dysbiosis, and host health status

Tomás-Barberán

González‐Sarrías

Garcı́a-Villalba

et al. 2016

Molecular Nutrition Food Res

359

384

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Urolithins are dibenzo[b,d]pyran-6-one derivatives that are produced by the human gut microbiota from ellagitannins and ellagic acid (EA). These metabolites are much better absorbed than their precursors and have been suggested to be responsible for the health effects attributed to ellagitannins and EA that occur in food products as berries and nuts. In the present review, the role and potential of urolithins in human health are critically reviewed, and a perspective of the research approach needed to demonstrate these health effects is presented, based on the existing knowledge. The analytical methods available for urolithin analysis, their occurrence in different tissues and biological fluids, and their metabolism by human gut microbiota are considered. In addition, the interindividual variability observed for the production of urolithins (metabotypes) and its relationship with health status and dysbiosis are also reviewed. The potential mechanisms of action of urolithins are also critically discussed, paying attention to the concentration and the type of metabolites used in the in vitro and in vivo assays and the physiological significance of the results obtained. The gut microbiota metabolism of EA to urolithins and that of daidzein to equol, their individual variations, and the effects on health are also compared.

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“…Among them, benzo[c]coumarins (1; Fig. 1) have emerged as privileged structures in drug discovery (Garazd & Garazd, 2016;Mao et al, 2014). Relevant examples include mycotoxin alternariol (2), (Solfrizzo, 2017) antioxidant and anticancer ellagic acid (3), (Ceci et al, 2018) synthetic cannabinoid agonists cannabilactones (4), (Khanolkar et al, 2007) antimalarial dioncolactone (5) (François et al, 2016) and the glucoside derivatives with antitumor properties gilvocarcins (6), (Tomita, Takahashi & Tamaoki, 1982) chrysomycins (7), (Matson et al, 1989) and ravidomycins (8; Fig.…”

Section: Introductionmentioning

confidence: 99%

Direct multicomponent synthesis of benzocoumarins

Bornadiego

Dı́az

Marcos

2019

PeerJ Organic Chemistry

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A straightforward and versatile protocol for the synthesis of dibenzo[b,d]pyran-6-ones from readily available 3-carbonylcoumarins is reported. Our strategy is based on a reaction cascade of successive [4+1] and [4+2] cycloadditions that occur in one single operation. This work illustrates the unprecedented use of a multicomponent reaction of isocyanides for the preparation of this biologically relevant type of compounds. Notably, in this highly convergent and atom-economic process, one new single and two new double carbon-carbon bonds are formed in a simple synthetic operation.

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Natural Dibenzo[b,d]Pyran-6-Ones: Structural Diversity and Biological Activity

Cited by 41 publications

References 138 publications

Ellagic Acid-Derived Urolithins as Modulators of Oxidative Stress

Ellagic Acid-Derived Urolithins as Modulators of Oxidative Stress

Urolithins, the rescue of “old” metabolites to understand a “new” concept: Metabotypes as a nexus among phenolic metabolism, microbiota dysbiosis, and host health status

Direct multicomponent synthesis of benzocoumarins

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