One-Step Semisynthesis of Oleacein and the Determination as a 5-Lipoxygenase Inhibitor

Vougogiannopoulou, Konstantina; Lémus, Christelle; Halabalaki, Maria; Pergola, Carlo; Werz, Oliver; Smith, Amos B.; Michel, Sylvie; Skaltsounis, Léandros; Deguin, Brigitte

doi:10.1021/np401010x

Cited by 62 publications

(54 citation statements)

References 41 publications

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“…Furthermore, (−)-oleocanthal is known for its anti-oxidant and anti-inflammatory activities (Galvano et al, 2007; Scotece et al, 2012). Reported anti-inflammatory activity of (−)-oleocanthal has been shown to be mediated by inhibition of macrophage inflammatory protein 1-alpha (MIP-1α), interleukin-6 (IL-6) expression and secretion, 5-lipoxygenase, and heat shock protein 90 (Hsp90) (Margarucci et al, 2013; Scotece et al, 2012; 2013; Vougogiannopoulou et al, 2014). …”

Section: Discussionmentioning

confidence: 99%

The olive oil phenolic (-)-oleocanthal modulates estrogen receptor expression in luminal breast cancer in vitro and in vivo and synergizes with tamoxifen treatment

Ayoub

Siddique

Ebrahim

et al. 2017

European Journal of Pharmacology

101

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Luminal breast cancer represents a therapeutic challenge in terms of aggressive disease and emerging resistance to targeted therapy. (−)-Oleocanthal has demonstrated anticancer activity in multiple human cancers. The goal of this study was to explore the effect of (−)-oleocanthal treatment on growth of luminal breast cancer cells and to examine the effect of combination of (−)-oleocanthal with tamoxifen. Results showed that (−)-oleocanthal inhibited growth of BT-474, MCF-7, and T-47D human breast cancer cells in mitogen-free media with IC50 values of 32.7, 24.07, and 80.93 μM, respectively. Similarly, (−)-oleocanthal suppressed growth of BT-474, MCF-7, and T-47D cells in 17β-estradiol-supplemented media with IC50 values of 22.28, 20.77, and 83.91 μM, respectively. Combined (−)-oleocanthal and tamoxifen treatments resulted in a synergistic growth inhibition of BT-474, MCF-7, and T-47D cells with combination index values of 0.65, 0.61, and 0.53 for each cell line, respectively. In-silico docking studies indicated high degree of overlapping for the binding of (−)-oleocanthal and 17β-estradiol to estrogen receptors, while (−)-oleocanthal and tamoxifen have distinguished binding modes. Treatment with 5 mg/kg or 10 mg/kg (−)-oleocanthal resulted in 97% inhibition of tumor growth in orthotopic athymic mice bearing BT-474 tumor xenografts compared to vehicle-treated animals. (−)-Oleocanthal treatment reduced total levels of estrogen receptors in BT-474 cells both in vitro and in vivo. Collectively, (−)-oleocanthal showed a potential beneficial effect in suppressing growth of hormone-dependent breast cancer and improving sensitivity to tamoxifen treatment. These findings provide rational for evaluating the effect of (−)-oleocanthal in combination with endocrine treatments in luminal breast cancer.

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Section: Discussionmentioning

confidence: 99%

The olive oil phenolic (-)-oleocanthal modulates estrogen receptor expression in luminal breast cancer in vitro and in vivo and synergizes with tamoxifen treatment

Ayoub

Siddique

Ebrahim

et al. 2017

European Journal of Pharmacology

101

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“…In a murine model of simultaneous hypertension and diabetes, daily dosage of oleuropein up to 60 mg day −1 produced a significant decrease in systolic blood pressure (Khalili et al, ), reduced renal hypertension (Khalili et al, ; Nekooeian et al, 2014), improved oxidative stress in hypertensive rats (Ivanov et al, ), reduced blood pressure (A.A. Nekooeian, Khalili, & Khosravi, ; A.A. Nekooeian, Khalili, & Khosravi, ; Khalili et al, ), and mitigated the negative effects of angiotensin 2 on epithelial progenitor cells (Vougogiannopoulou et al, ). Angiotensin 2 is a known vasoconstrictor, and it also protected rat hearts from reperfusion injury, which is usually associated with oxidative stress (Bali et al, ; M. Esmailidehaj et al, ; M. Esmailidehaj et al, ; Manna et al, ).…”

Section: Role Of Oleuropein In Treatment Of Metabolic Syndromementioning

confidence: 99%

Oleuropein: A natural antioxidant molecule in the treatment of metabolic syndrome

Ahamad

Toufeeq

Khan

et al. 2019

Phytotherapy Research

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Olive (Olea europaea Linn., Fam. Oleaceae) is commonly known as Zaytoon in Mediterranean region. Its fruits and oil are essential components of Mediterranean diets. Olive tree is a prevalent plant species and one of the important cultivated crops of Mediterranean region. Oleuropein is a phenolic constituents of olive, which, along with its related compounds, has been indicated to be majorly responsible for its beneficial effects. Oleuropein is a secoiridoid type of phenolic compound and consists of three structural subunits: hydroxytyrosol, elenolic acid, and a glucose molecule. It is also reported to be the chemotaxonomic marker of olive. The oleuropein is reported to possess a number of biological activities including action against dyslipidemia, antiobesity, antidiabetic, antioxidant, antiatherogenic, antihypertensive, antiinflammatory, and hepatoprotective actions. The scientific evidence supports the role of oleuropein as a potential agent against metabolic syndrome. The present review discusses chemistry of oleuropein along with potential role of oleuropein with reference to pathophysiology of metabolic syndrome.

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“…For example, hydroxytyrosol appears to be a more potent inhibitor of ADP- or collagen- induced platelet activation than other EVOO-derived phenolics including oleuropein (Petroni et al, 1995), while oleocanthal (the dialdehydic form of decarboxymethyl ligstroside aglycon) has received considerable interest as a COX inhibitor (Beauchamp et al, 2005), and oleacein (the dialdehydic form of decarboxymethyl oleuropein aglycon) has been reported as a 5-LOX inhibitor (Vougogiannopoulou et al, 2014). Since the characterization of specific phenolic profiles in EVOO interventions remains rare, it remains difficult to discriminate in vivo EVOOassociated effects of specific phenolics on the biochemical networks associated with cardiovascular disease initiation and progression.…”

Section: Introductionmentioning

confidence: 99%

Oleocanthal-rich extra virgin olive oil demonstrates acute anti-platelet effects in healthy men in a randomized trial

Agrawal

Melliou

et al. 2017

Journal of Functional Foods

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The phenolic profiles of extra virgin olive oils (EVOOs) may influence their cardiovascular benefits. In a randomized crossover of acute EVOO intake on platelet function, participants (n=9) consumed 40 mL of EVOO weekly. EVOOs were matched for total phenolic content and were either tyrosol-poor with 1:2 oleacein/oleocanthal (D2i0.5), or 2:1 oleacein/oleocanthal (D2i2), or predominantly tyrosol (D2i0). Ibuprofen provided a platelet inhibition control. Blood was collected pre- and 2 hr post-EVOO intake. D2i0.5 and D2i2 reduced 1 µg/mL collagen-stimulated maximum platelet aggregation (Pmax), with effects best correlated to oleocanthal intake (R=0.56, P=0.002). Total phenolic intake was independently correlated to eicosanoid production inhibition, suggesting that cyclooxygenase blockade was not responsible for the Pmax inhibition. Five participants exhibited >25% ΔPmax declines with D2i0.5 and D2i2 intake and plasma metabolomic profiles discriminated subjects by oil responsivity. Platelet responses to acute EVOO intake are associated with oil phenolic composition and may be influenced by diet.

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One-Step Semisynthesis of Oleacein and the Determination as a 5-Lipoxygenase Inhibitor

Cited by 62 publications

References 41 publications

The olive oil phenolic (-)-oleocanthal modulates estrogen receptor expression in luminal breast cancer in vitro and in vivo and synergizes with tamoxifen treatment

The olive oil phenolic (-)-oleocanthal modulates estrogen receptor expression in luminal breast cancer in vitro and in vivo and synergizes with tamoxifen treatment

Oleuropein: A natural antioxidant molecule in the treatment of metabolic syndrome

Oleocanthal-rich extra virgin olive oil demonstrates acute anti-platelet effects in healthy men in a randomized trial

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