Effects of dietary virgin olive oil polyphenols: hydroxytyrosyl acetate and 3, 4-dihydroxyphenylglycol on DSS-induced acute colitis in mice

Sánchez-Fidalgo, Susana; Villegas, Isabel; Aparicio‐Soto, Marina; Cárdeno, Ana; Rosillo, María Ángeles; González-Benjumea, Alejandro; Marset, Azucena; López, Óscar; Maya, Inés; Fernández-Bolaños, José G.; Lastra, Catalina Alarcón de la

doi:10.1016/j.jnutbio.2014.12.001

Cited by 63 publications

(86 citation statements)

References 51 publications

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“…2B122) and an aliphatic alcohol as solvent (MeOH). The transesterification reaction was completely chemoselective in the phenolic positions, and gave a monoacetylated derivative in the aliphatic position (compound 3, [22] as depicted in Fig 1, a natural compound present in extra virgin olive oil [23]).…”

Section: Resultsmentioning

confidence: 99%

“…However, despite of the many advances in organic synthesis during the last decades, the conventional chemical synthesis of mono acylated derivatives of polyphenols presents serious difficulties due to the high density of very similar functional groups, which requires extensive protection and deprotection sequences [10]. Thus, although some chemical approaches have been developed for accessing partially acylated polyphenols in a chemoselective way [11–13], most of such procedures are pure chemical synthesis, and involve the use of hazardous reagents or non-green conditions. As an alternative, the biotech industries have traditionally produced compounds of commercial interest by microbial fermentation, or by fermentation followed by subsequent chemical modification to improve specific properties, such as activity, solubility, absorption, pharmacokinetics or stability.…”

Section: Introductionmentioning

confidence: 99%

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A Straightforward Access to New Families of Lipophilic Polyphenols by Using Lipolytic Bacteria

et al. 2016

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The chemical synthesis of new lipophilic polyphenols with improved properties presents technical difficulties. Here we describe the selection, isolation and identification of lipolytic bacteria from food-processing industrial wastes, and their use for tailoring a new set of compounds with great interest in the food industry. These bacteria were employed to produce lipolytic supernatants, which were applied without further purification as biocatalysts in the chemoselective and regioselective synthesis of lipophilic partially acetylated phenolic compounds derived from olive polyphenols. The chemoselectivity of polyphenols acylation/deacylation was analyzed, revealing the preference of the lipases for phenolic hydroxyl groups and phenolic esters. In addition, the alcoholysis of peracetylated 3,4-dihydroxyphenylglycol resulted in a series of lipophilic 2-alkoxy-2-(3,4-dihydroxyphenyl)ethyl acetate through an unexpected lipase-mediated etherification at the benzylic position. These new compounds are more lipophilic and retained their antioxidant properties. This approach can provide access to unprecedented derivatives of 3,4-dihydroxyphenylglycol with improved properties.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Straightforward Access to New Families of Lipophilic Polyphenols by Using Lipolytic Bacteria

et al. 2016

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“…DHPG has important implications as a biomarker and has been shown to fluctuate in concentration in rat testis after methamphetamine intake, which may result in male reproductive dysfunction [41]. DHPG was also shown to have some antioxidant activity [40, 42]. …”

Section: Introductionmentioning

confidence: 99%

Understanding the link between antimicrobial properties of dietary olive phenolics and bacterial ATP synthase

Amini

Liu

Ahmad

2017

International Journal of Biological Macromolecules

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The naturally occurring olive phenolics tyrosol, hydroxytyrosol, dihydroxyphenylglycol (DHPG), and oleuropein are known to have antioxidant, antitumor, and antibacterial properties. In the current study, we examined whether the antimicrobial properties of tyrosol, hydroxytyrosol, DHPG, and oleuropein were linked to the inhibition of bacterial ATP synthase. Tyrosol, hydroxytyrosol, DHPG, and oleuropein inhibited Escherichia coli wild-type and mutant membrane-bound F1Fo ATP synthase to variable degrees. The growth properties of wild-type, null, and mutant strains in presence of above olive phenolics were also abrogated to variable degrees on limiting glucose and succinate. Tyrosol and oleuropein synergistically inhibited the wild-type enzyme. Comparative wild-type and mutant F1Fo ATP synthase inhibitory profiles suggested that αArg-283 is an important residue and olive phenolics bind at the polyphenol binding pocket of ATP synthase. Growth patterns of wild-type, null, and mutant strains in the presence of tyrosol, hydroxytyrosol, DHPG, and oleuropein also hint at the possibility of additional molecular targets. Our results demonstrated that ATP synthase can be used as a molecular target and the antimicrobial properties of olive phenolics in general and tyrosol in particular can be linked to the binding and inhibition of bacterial ATP synthase.

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“…A significant beneficial effect in chronic DSS-induced colitis was also exerted by HT acetate, sharing the same mechanism of action as HT. 123 There is strong evidence in vitro that oleocanthal also is an effective anti-inflammatory agent. In fact, it can efficiently inhibit COX-2 enzyme expression and activity, which is implicated in the pathogenesis of several cancers.…”

Section: Anti-inflammatory Effectmentioning

confidence: 99%

Modulation of intestinal epithelium homeostasis by extra virgin olive oil phenolic compounds

2018

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Dietary habits have been strongly linked to the maintenance of intestinal epithelium homeostasis, whose alteration may contribute to the pathogenesis of inflammatory diseases and cancer. Polyphenols are among those dietary components suggested to be beneficial for gut health. Within a balanced Mediterranean type diet, a good portion of ingested polyphenols comes from olives and extra virgin olive oil (EVOO). Most of them reach the intestine, where they may be directly absorbed or metabolized under absorption. Others undergo an extensive gastrointestinal biotransformation, producing various metabolites that retain the potential beneficial effect of the parent compounds, or exert a more efficient biological action themselves. Ingested EVOO polyphenols (EVOOP) and their metabolites will be particularly concentrated in the intestinal lumen, where they might exert a significant local action. In this review we summarize the few studies that investigated the effect of EVOOP at the intestinal level, focusing on the possible mechanism of action in relation to their interaction with the microbiota, and their ability to potentially modulate the oxidative status of the intestinal epithelial layer, inflammation and immune response.

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Effects of dietary virgin olive oil polyphenols: hydroxytyrosyl acetate and 3, 4-dihydroxyphenylglycol on DSS-induced acute colitis in mice

Cited by 63 publications

References 51 publications

A Straightforward Access to New Families of Lipophilic Polyphenols by Using Lipolytic Bacteria

A Straightforward Access to New Families of Lipophilic Polyphenols by Using Lipolytic Bacteria

Understanding the link between antimicrobial properties of dietary olive phenolics and bacterial ATP synthase

Modulation of intestinal epithelium homeostasis by extra virgin olive oil phenolic compounds

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