Hydroxytyrosol-Derived Compounds: A Basis for the Creation of New Pharmacological Agents for Cancer Prevention and Therapy

Bernini, Roberta; Montani, Maria Saveria Gilardini; Merendino, Nicolò; Romani, Annalisa; Velotti, Francesca

doi:10.1021/acs.jmedchem.5b00669

Cited by 82 publications

(68 citation statements)

References 108 publications

(236 reference statements)

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“…The highest cytotoxic activity was found by the ethers with the longest alkyl chain [40]. Similarly, these lipophilic derivatives inhibit both monocyte and macrophage pro-tumorigenic inflammatory activities and platelet function in a more effective way than HT [41], which reflects the broad applicability and importance of these type of molecules.…”

Section: Discussionmentioning

confidence: 99%

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: Discussionmentioning

confidence: 99%

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

et al. 2016

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“…On a positive note, it was noted that HT is a ‘safe’ compound and can be administered at higher doses without signs of any genotoxic or mutagenic effects (38; 39). Recently, there has been an interest in synthesis of HT-derivatives with a focus on improving the overall efficacy (40). A novel ester of hydroxytyrosol and alpha-lipoic acid was reported to enhance potency in colorectal cancer cells (41) through the induction of cell cycle arrest.…”

Section: Discussionmentioning

confidence: 99%

Hydroxytyrosol Induces Apoptosis and Cell Cycle Arrest and Suppresses Multiple Oncogenic Signaling Pathways in Prostate Cancer Cells

Zubair

Bhardwaj

Ahmad

et al. 2017

Nutrition and Cancer

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Scope: Hydroxytyrosol (HT), a polyphenol from olives, is a potential anticancer agent. This study was designed to evaluate the anticancer activity of HT against prostate cancer cells, and the mechanism thereof. Methods and Results: Treatment of LNCaP and C4–2 prostate cancer cells with HT resulted in a dose-dependent inhibition of proliferation. This was in contrast to HT’s ineffectiveness against normal prostate epithelial cells RWPE1 and PWLE2, suggesting cancer cells-specific effect. HT induced G1/S cell cycle arrest, with inhibition of cyclins D1/E and cdk2/4, and induction of inhibitory p21/p27. HT also induced apoptosis, as confirmed by flow cytometry, caspase activation, PARP cleavage and BAX/Bcl-2 ratio. It inhibited the phosphorylation of Akt / STAT3, and induced cytoplasmic retention of NF-κB, which may explain its observed effects. Finally, HT inhibited AR expression and the secretion of AR-responsive prostate-specific antigen. Conclusion: Castration-resistant prostate cancers retain AR signaling and are often marked by activated Akt, NF-κB and STAT3 signaling. Our results establish a pleiotropic activity of HT against these oncogenic signaling pathways. Combined with its non-toxic effects against normal cells, our results support further testing of HT for prostate cancer therapy.

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“…Tocopherols are present in olive oil in the forms α, β, γ, and δ, with 90% being found in the most biologically active α form, vitamin E [5]. Experimental evidence has demonstrated that the phenolic compounds present in EVOO possess numerous biological properties and are, at least partly, responsible for the beneficial effects arising from the consumption of EVOO [8,9,10]. …”

Section: Introductionmentioning

confidence: 99%

Analytical Evaluation and Antioxidant Properties of Some Secondary Metabolites in Northern Italian Mono- and Multi-Varietal Extra Virgin Olive Oils (EVOOs) from Early and Late Harvested Olives

Trombetta

Smeriglio

Marcoccia

et al. 2017

IJMS

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The antioxidant activity and the phenolic and α-tocopherol content of 10 Northern Italian mono- and multi-varietal extra virgin olive oils (EVOOs), after early and late olive harvests, was analyzed. A hierarchical cluster analysis was used to evaluate sample similarity. Secoiridoids (SIDs), lignans and flavonoids were the most abundant phenolic compounds identified. The organic Casaliva (among mono-cultivar) and the organic multi-varietal (among blended oils) EVOOs had the higher total phenol content both in early (263.13 and 326.19 mg/kg, respectively) and late harvest (241.88 and 292.34 mg/kg, respectively) conditions. In comparison to late harvest EVOOs, early harvest EVOOs, in particular the organic mono-cultivar Casaliva, showed both higher antioxidant capacity (up to 1285.97 Oxygen Radicals Absorbance Capacity/ORAC units), probably due to the higher SID fraction (54% vs. 40%), and higher α-tocopherol content (up to 280.67 mg/kg). Overall, these results suggest that SIDs and α-tocopherol mainly contribute to antioxidant properties of the studied EVOOs. In light of this, the authors conclude that early harvest, organic mono-cultivar Casaliva EVOO represents the most interesting candidate to explicate healthy effects ascribed to these functional constituents, particularly regarding oxidative stress-related pathologies.

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Hydroxytyrosol-Derived Compounds: A Basis for the Creation of New Pharmacological Agents for Cancer Prevention and Therapy

Cited by 82 publications

References 108 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

Hydroxytyrosol Induces Apoptosis and Cell Cycle Arrest and Suppresses Multiple Oncogenic Signaling Pathways in Prostate Cancer Cells

Analytical Evaluation and Antioxidant Properties of Some Secondary Metabolites in Northern Italian Mono- and Multi-Varietal Extra Virgin Olive Oils (EVOOs) from Early and Late Harvested Olives

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