Biological Relevance of Extra Virgin Olive Oil Polyphenols Metabolites
Abstract
:1. Introduction
2. Olive Oil
2.1. Extra-Virgin Olive Oil Polyphenols
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- secoiridoids, where the most abundant are the dialdehydic form of decarboxymethyl elenolic acid linked to HT (3,4-DHPEA) or Tyr (p-HPEA), (3,4-DHPEA-EDA or p-HPEA-EDA), oleacein, oleuropein, an isomer of the oleuropein aglycon (HT linked to elenolic acid) (3,4-DHPEA-EA), and ligstroside aglycon (Tyr linked to elenolic acid) (p-HPEA-EA). p-HPEA-derivates and dialdehydic forms of oleuropein and ligstroside aglycon have also been detected as minor hydrophilic phenols of EVOO [19,24];
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- phenylethanoids, which possess a hydroxyl group attached to an aromatic hydrocarbon group, such as oleocanthal, HT (3,4-dihydroxyphenyl-ethanol or 3,4-DHPEA) and Tyr (p-hydroxyphenyl-ethanol or p-HPEA) [6]. Their concentration is usually low in fresh oils but increases during oil storage due to the hydrolysis of secoiridoids [25];
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- phenolic acids, which can be divided into two subgroups: hydroxybenzoic acid derivatives and hydroxycinnamic acid derivatives, such as gallic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, p- and o-coumaric acid, ferulic acid, and cinnamic acid [24];
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- flavonoids, which contain two benzene rings joined by a linear three carbon chain. Flavonoids are largely planar molecules and their structural variation comes in part from the pattern of modification by hydroxylation, methoxylation, prenylation, or glycosylation. Flavonoid aglycones are subdivided into flavones, flavonols, flavanones, and flavanols depending upon the presence of a carbonyl carbon at C-4, an OH group at C-3, a saturated single bond between C-2 and C-3, and a combination of carbonyl at C-4 with an OH group at C-3, respectively. Luteolin and apigenin are the most concentrated [24];
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- hydroxy-isocromans, a class which consists in only two compounds: 1-phenyl-6,7-dihydroxy-isochroman and 1-(39-methoxy-49-hydroxy) phenyl-6,7-dihydroxy- isochroman [26];
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- lignans, whose structure is not well understood, but it is based on the condensation of aromatic aldehydes. (+)-1-Acetoxypinoresinol and (+)-1-pinoresinol were characterized as the most concentrated lignans in EVOO [27].
2.2. Absorption and Distribution of Polyphenols
2.3. Metabolism of Polyphenols
3. Activity of Polyphenols Metabolites
3.1. Hydroxytyrosol and Tyrosol Glucuronides and Sulfates
3.2. Homovanillic Acid and Homovanillyl Alcohol
3.3. Other Polyphenol Metabolites
4. Conclusions and Future Research
Funding
Acknowledgments
Conflicts of Interest
References
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Compounds | Concentration Tested | In Vitro/In Vivo Model | Outcome | Reference |
---|---|---|---|---|
Mix of metabolites | 10–80 µM | In vitro red blood cells (RBC) | Protection of red blood cells from H2O2-induced oxidative injury | [64] |
10 mg/kg | ApoE−/− mice | Reduction of VCAM-1, ICAM-1, E-selectin and MCP-1 molecules secretion by inhibiting mRNA expression | [67] | |
1–5 μM | Human aortic endothelial cells (HAEC) | Reduction of p38δ, JNK1-3, CREB, AKT3, p53 and P70 S6 kinase phosphorylation, and of lymphocytes adhesion | [67] | |
HT glucuronide | 100 μM | Rat aortic rings | Reduced endothelial dysfunction by blocking superoxide production | [43] |
2.3 µM | DPPH test | Good antioxidant and antiradical capacity | [48] | |
0.01–10 μM | In vitro Cu-induced oxidation of LDL | Loss of antioxidant activity with respect to HT | [61] | |
5–10 μM | Renal LLC-PK1 cells culture model | Protection of renal cells against H2O2-induced lipid peroxidation | [63] | |
10–25 µM | Human hepatocarcinoma HepG2 cells | Inhibition of tunicamycin-induced endoplasmic reticulum (ER) stress | [66] | |
HT sulfate | 91 µM | DPPH test | Poor antioxidant and antiradical capacity | [48] |
2.5–10 µM | Caco-2 intestinal cells monolayers | Counteraction of the oxidizing action of oxidized cholesterol on intestinal cell membranes | [60] | |
10 µM | Neuroblastoma (SH-SY5Y) and dopaminergic (LUHMES) neuronal cells | Protective effects against oxidative stress | [68] | |
Tyr glucuronide | 0.01–10 μM | In vitro Cu-induced oxidation of LDL | Loss of antioxidant activity with respect to Tyr | [61] |
100 µM | Endothelial HUVEC cells monolayers | Prevention of the phosphorylation of NF-κB signaling proteins and of the over-expression of adhesion molecules | [65] | |
0.1–0.5 mg/kg | Carrageenan-induced hind paw oedema in mice | Amelioration of plantar and ear edemas | [65] | |
Tyr sulfate | 2.5–10 µM | Intestinal Caco-2 cells monolayers | Counteraction of the oxidizing action of oxidized cholesterol on intestinal cell membranes | [60] |
0.1–0.5 mg/kg | Carrageenan-induced hind paw oedema in mice | Amelioration of plantar and ear edemas | [65] | |
100 µM | Endothelial HUVEC cells monolayers | Prevention of the phosphorylation of NF-κB signaling proteins and of the over-expression of adhesion molecules | [65] | |
Homovanillic acid | 14.8 µM | DPPH test | Good antioxidant and antiradical capacity | [48] |
Homovanillyl alcohol | 11.4 µM | DPPH test | Good antioxidant and antiradical capacity | [48] |
5.4–146.5 mM | Human clinical study | Reduction of CVD and total mortality risk | [55] | |
0.3–1 µM | Renal LLC-PK1 cell culture model | Protection against H2O2-induced renal epithelial injury through interaction both MAP kinase and PI3 kinase pathways | [70] | |
2–20 µM | Endothelial HUVEC cells monolayers | Inhibition of ICAM-1, VCAM-1 and MCP-1 secretion | [73] | |
5–25 µM | Intestinal Caco-2 cells monolayers | Protection of cell membranes from oxidative damage induced by TBH | [75] | |
0.5–10 mM | Human gastric adenocarcinoma (AGS) cells | Inhibition of NF-kB driven transcription and nuclear translocation | [76] | |
0.5–25 µM | Endothelial HUVEC cells monolayers | Inhibition of cell surface expression of E-selectin, ICAM-1 and VCAM-1 adhesion molecules | [77] | |
1–7.5 µM | Human monocytic cells U937 | Reduced cell adhesion and ICAM-1 expression | [78] | |
10–50 µM | Erythrocytes by blood samples obtained from trisomic patients | Decreased oxidative stress-induced ROS generation | [79] | |
0.25–1 µM | Peripheral mononucleated blood cells (PBMCs) | Inhibition of oxysterols-induced production of proinflammatory cytokines, interleukin-1β, normal T-cell macrophage migration inhibitory factor. Decreased levels of reactive oxygen species (ROS) and phosphorylation of the p38 and JNK MAP kinases | [80] | |
FA glucuronide | 11.42–114.2 µg/kg | Male Swiss mice | Elicitation of vasorelaxation of saphenous and femoral arteries and aortae. Decreased mean arterial pressure | [82] |
IsoFA | 0.5–1 mg/day | Mice infected by intranasal inoculation of influenza virus | Inhibition of the progression of lethal influenza virus pneumonia | [83] |
1–13 μg/mL | In vitro lipid peroxidation, DPPH and ABTS tests | Good antioxidant activity | [84] | |
5.0 mg/kg | Streptozotocin-induced diabetic rats | Inhibition of hepatic gluconeogenesis and increase of the glucose utilization in peripheral tissue to lower plasma glucose | [85] | |
1.25–5 mM | In vitro Glycation of Bovine Serum Albumin (BSA) | Antiglycation properties against fructose and glucose-mediated glycation and oxidation of bovine serum albumin | [86] | |
HydroFA | 0.01–100 μg/mL | In vitro platelet culture | Inhibitor of platelet activation by decreasing P-selectin expression | [87] |
Luteolin sulfate | 40 μM | Macrophages Raw 264.7 cells | Anti-inflammatory activities as inhibition of LPS-stimulated iNOS expression and production of nitric oxide, TNF-α, IL-1β, and IL-6 | [88] |
Luteolin glucuronide | 25–200 μg/mL | Macrophages Raw 264.7 cells | Anti-inflammatory activities as inhibition of LPS-stimulated iNOS expression and production of nitric oxide, TNF-α, IL-1β, and IL-6 | [33] |
40 μM | Macrophages Raw 264.7 cells | Anti-inflammatory activities as inhibition of LPS-stimulated iNOS expression and production of nitric oxide, TNF-α, IL-1β, and IL-6 | [88] | |
50 mM | Macrophages Raw 264.7 cells | Reduction of expression of LPS-stimulated inflammatory genes | [90] | |
Apigenin glucuronide | 25–100 μg/mL | Macrophages Raw 264.7 cells | Inhibition of Ox-LDL uptake and the scavenger receptor CD36 mRNA and protein expression. Enhancement of the expression of scavenger receptor class B type 1, following inhibition of ERK1/2 phosphorylation | [32] |
12.5–100 µM | Macrophages Raw 264.7 cells | Counteraction of prostaglandin E2 (PGE2) production, LPS-induced mRNA expression of iNOS, COX-2 and TNF-α Decrease of the translocation of c-Jun into the nucleus inhibition p38 and ERK phosphorylation | [91] |
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Serreli, G.; Deiana, M. Biological Relevance of Extra Virgin Olive Oil Polyphenols Metabolites. Antioxidants 2018, 7, 170. https://doi.org/10.3390/antiox7120170
Serreli G, Deiana M. Biological Relevance of Extra Virgin Olive Oil Polyphenols Metabolites. Antioxidants. 2018; 7(12):170. https://doi.org/10.3390/antiox7120170
Chicago/Turabian StyleSerreli, Gabriele, and Monica Deiana. 2018. "Biological Relevance of Extra Virgin Olive Oil Polyphenols Metabolites" Antioxidants 7, no. 12: 170. https://doi.org/10.3390/antiox7120170