High Resolution Mass Spectrometric Analysis of Secoiridoids and Metabolites as Biomarkers of Acute Olive Oil Intake—An Approach to Study Interindividual Variability in Humans

Silva, S.; Garcia-Aloy, Mar; Figueira, Maria Eduardo; Combet, Emilie; Mullen, William; Bronze, Maria Rosário

doi:10.1002/mnfr.201700065

Cited by 28 publications

(49 citation statements)

References 60 publications

(98 reference statements)

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“…In the current study, we can confirm that they were direct metabolites of OLC. In another study [25], the hydrated metabolite was also identified in plasma samples after the ingestion of EVOO. These results are consistent with the work of Garcia-Villalba et al [24], who studied the urinary excretion of phenolic compounds after olive oil intake in humans.…”

Section: Phase I Metabolismmentioning

confidence: 94%

Section: Phase I Metabolismmentioning

confidence: 94%

“…The hydrogenated metabolites were found in a glucuronidated form in plasma but not in the lumen. Even when considering the differences between rat and human microsomal activity, hydrogenation seems to be an important phase I metabolic route for secoiridoids [25]. This reduction reaction is catalysed by NADPH-dependent aldo-keto reductases (AKR) located in the small intestine epithelium and can occur because OLC contains an open dialdehydic form of the attached elenolic acid molecule.…”

Section: Phase I Metabolismmentioning

confidence: 99%

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Absorption and Intestinal Metabolic Profile of Oleocanthal in Rats

et al. 2020

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Oleocanthal (OLC), a phenolic compound of extra virgin olive oil (EVOO), has emerged as a potential therapeutic agent against a variety of diseases due to its anti-inflammatory activity. The aim of the present study is to explore its in vivo intestinal absorption and metabolism. An in situ perfusion technique in rats was used, involving simultaneous sampling from the luminal perfusate and mesenteric blood. Samples were analysed by UHPLC–MS–MS for the presence of oleocanthal (OLC) and its metabolites. OLC was mostly metabolized by phase I metabolism, undergoing hydration, hydrogenation and hydroxylation. Phase II reactions (glucuronidation of hydrogenated OLC and hydrated metabolites) were observed in plasma samples. OLC was poorly absorbed in the intestine, as indicated by the low effective permeability coefficient (2.23 ± 3.16 × 10−5 cm/s) and apparent permeability coefficient (4.12 ± 2.33 × 10−6 cm/s) obtained relative to the values of the highly permeable reference compound levofloxacin (LEV). The extent of OLC absorption reflected by the area under the mesenteric blood-time curve normalized by the inlet concentration (AUC) was also lower than that of LEV (0.25 ± 0.04 vs. 0.64 ± 0.03, respectively). These results, together with the observed intestinal metabolism, suggest that OLC has a moderate-to-low oral absorption; but higher levels of OLC are expected to reach human plasma vs. rat plasma.

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Section: Phase I Metabolismmentioning

confidence: 94%

Section: Phase I Metabolismmentioning

confidence: 94%

Section: Phase I Metabolismmentioning

confidence: 99%

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Absorption and Intestinal Metabolic Profile of Oleocanthal in Rats

et al. 2020

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“…In fact, Romero et al verified that OLE was stable in gastric acid conditions at 37 • C for 4 h [70]. Although it has been postulated that OLE is mainly metabolized by Phase I (hydrogenation, hydroxylation, and hydration) [71,72], some hydrogenated metabolites pass to Phase II of metabolism as glucoronidated forms [54], whereas methylated or sulfate forms of OLE have not been detected in any study in humans to date [71,72]. The report published by García-Villalba et al revealed that OLE and several secoiridoids metabolites were excreted in human urine between 2 and 6 h after olive oil ingestion [72].…”

Section: Pharmacokinetics Of Secoiridoids From the Olive Treementioning

confidence: 99%

Potential Protective Role Exerted by Secoiridoids from Olea europaea L. in Cancer, Cardiovascular, Neurodegenerative, Aging-Related, and Immunoinflammatory Diseases

et al. 2020

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Iridoids, which have beneficial health properties, include a wide group of cyclopentane [c] pyran monoterpenoids present in plants and insects. The cleavage of the cyclopentane ring leads to secoiridoids. Mainly, secoiridoids have shown a variety of pharmacological effects including anti-diabetic, antioxidant, anti-inflammatory, immunosuppressive, neuroprotective, anti-cancer, and anti-obesity, which increase the interest of studying these types of bioactive compounds in depth. Secoiridoids are thoroughly distributed in several families of plants such as Oleaceae, Valerianaceae, Gentianaceae and Pedialaceae, among others. Specifically, Olea europaea L. (Oleaceae) is rich in oleuropein (OL), dimethyl-OL, and ligstroside secoiridoids, and their hydrolysis derivatives are mostly OL-aglycone, oleocanthal (OLE), oleacein (OLA), elenolate, oleoside-11-methyl ester, elenoic acid, hydroxytyrosol (HTy), and tyrosol (Ty). These compounds have proved their efficacy in the management of diabetes, cardiovascular and neurodegenerative disorders, cancer, and viral and microbial infections. Particularly, the antioxidant, anti-inflammatory, and immunomodulatory properties of secoiridoids from the olive tree (Olea europaea L. (Oleaceae)) have been suggested as a potential application in a large number of inflammatory and reactive oxygen species (ROS)-mediated diseases. Thus, the purpose of this review is to summarize recent advances in the protective role of secoiridoids derived from the olive tree (preclinical studies and clinical trials) in diseases with an important pathogenic contribution of oxidative and peroxidative stress and damage, focusing on their plausible mechanisms of the action involved.

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“…However, it is necessary to underline that HT, homovanillic alcohol, and its derivative homovanillic acid are also endogenously formed by the oxidative metabolism of dopamine, and therefore low concentrations of these metabolites can always be found in biological matrices (Rodriguez-Morato et al 2016). Glucuronidated metabolites have also been observed for minor components such as luteolin, pinoresinol, and ferulic acid (Silva et al 2018).…”

Section: Extra Virgin Olive Oilmentioning

confidence: 99%

Antioxidants in Diets and Food

Smeriglio¹,

Cornara²,

Trombetta³

2019

Handbook of Dietary Phytochemicals

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Nowadays, the society looks with increasing interest in the diet, which is no longer simply a means by which to take the necessary nutrients but has become a means by which it is possible to preserve the health state. German philosopher Ludwig Feuerbach once said: "We are what we eat." This statement is even truer today because of the hectic life, people often tend to eat frugal, fast, and often very fat and unhealthy meals. Today, there is a very high attention both from the social point of view and by the scientific community to the so-called functional foods. These foods, which contain several bioactive compounds, exert innumerable biological properties and therefore can help to preserve the health state. In addition, the use of nutraceuticals has taken the upper hand, unfortunately, often also to the detriment of functional foods, which unlike the former still remain foods and, as such, with a certainly better efficacy-safety profile. The term nutraceutical, indeed, does not refer to a food but rather to a formulation containing one or more compounds isolated from plant extracts or one or more titrated plant extracts. Moreover, some formulations (capsules, tablets, powders, etc.) are rarely studied before being commercialized, and their effectiveness remains rather doubtful in light of a very lax regulation in many countries worldwide. Keywords Diet • Antioxidants • Phytochemicals • Extra virgin olive oil • Edible berries • Grapes and wine • Pomegranate • Tree nuts • Brassicaceae vegetables • Herbs and spices "Let food be thy medicine and medicine be thy food." Hippocrates (400 BC).

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High Resolution Mass Spectrometric Analysis of Secoiridoids and Metabolites as Biomarkers of Acute Olive Oil Intake—An Approach to Study Interindividual Variability in Humans

Cited by 28 publications

References 60 publications

Absorption and Intestinal Metabolic Profile of Oleocanthal in Rats

Absorption and Intestinal Metabolic Profile of Oleocanthal in Rats

Potential Protective Role Exerted by Secoiridoids from Olea europaea L. in Cancer, Cardiovascular, Neurodegenerative, Aging-Related, and Immunoinflammatory Diseases

Antioxidants in Diets and Food

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