A Three-Step, Gram-Scale Synthesis of Hydroxytyrosol, Hydroxytyrosol Acetate, and 3,4-Dihydroxyphenylglycol

Kalampaliki, Amalia D.; Giannouli, Vassiliki; Skaltsounis, Alexios‐Léandros; Kostakis, Ioannis K.

doi:10.3390/molecules24183239

Cited by 16 publications

(14 citation statements)

References 65 publications

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“…Indeed, most involve fresh olives [ 34 , 75 , 76 , 77 ], while there were others that used olives intended only for oil production [ 70 , 78 ]. To this date, the content of processed edible olives has been mainly investigated by HPLC-DAD [ 15 , 37 , 73 , 74 , 75 , 76 , 77 ] and MS [ 32 , 56 , 57 , 58 , 59 , 78 ], with NMR coming in a resounding third place [ 60 ]. It is important to note that minor deviations compared with the literature were observed, in some cases, in chemical shifts due to pH or calibration mismatches.…”

Section: Resultsmentioning

confidence: 99%

NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters

et al. 2020

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Edible olive drupes (from Olea europaea L.) are a high-value food commodity with an increasing production trend over the past two decades. In an attempt to prevent fraud issues and ensure quality, the International Olive Council (IOC) issued guidelines for their sensory evaluation. However, certain varieties, geographical origins and processing parameters are omitted. The aim of the present study was the development of a method for the quality assessment of edible olives from the Konservolia, Kalamon and Chalkidikis cultivars from different areas of Greece processed with the Spanish or Greek method. A rapid NMR-based untargeted metabolic profiling method was developed along with multivariate analysis (MVA) and applied for the first time in edible olives’ analysis complemented by the aid of statistical total correlation spectroscopy (STOCSY). Specific biomarkers, related to the classification of olives based on different treatments, cultivars and geographical origin, were identified. STOCSY proved to be a valuable aid towards the assignment of biomarkers, a bottleneck in untargeted metabolomic approaches.

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Section: Resultsmentioning

confidence: 99%

NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters

et al. 2020

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“…Some researchers focus on the possibility of isolating some of the bioactive compounds from EVOO [ 82 ], such as hydroxytyrosol, to enrich the olive oil itself [ 16 ] or even to be used as a natural food additive, taking advantage of their antioxidant and antimicrobial activity to improve the stability of processed foods including processed meats [ 111 , 112 , 113 , 114 , 115 ]. In fact, EFSA confirmed in 2017 that hydroxytyrosol can be extracted from olive sources or produced by chemical synthesis or through the use of microorganisms and added in formulas for dietary supplementation with no difference from the natural compound [ 116 ].…”

Section: Resultsmentioning

confidence: 99%

“…Hydroxytyrosol, which is one of the most studied compounds and to which a great antioxidant capacity is attributed, has not reported toxicity and no adverse effects (NOAEL) have been observed up to 500 mg/kg/day (NOAEL) [80]. Phenolic compounds play a key role in the beneficial effects of EVOO on human health and could act as supplement in the pharmaceutical and nutraceutical industry for the treatment and prevention of oxidative stress such as inflammatory and cardiovascular diseases and cancer [81][82][83].…”

Section: Evoo Phenolics Structure-antioxidant Activity Relationships mentioning

confidence: 99%

Structure–Biological Activity Relationships of Extra-Virgin Olive Oil Phenolic Compounds: Health Properties and Bioavailability

et al. 2020

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Extra-virgin olive oil is regarded as functional food since epidemiological studies and multidisciplinary research have reported convincing evidence that its intake affects beneficially one or more target functions in the body, improves health, and reduces the risk of disease. Its health properties have been related to the major and minor fractions of extra-virgin olive oil. Among olive oil chemical composition, the phenolic fraction has received considerable attention due to its bioactivity in different chronic diseases. The bioactivity of the phenolic compounds could be related to different properties such as antioxidant and anti-inflammatory, although the molecular mechanism of these compounds in relation to many diseases could have different cellular targets. The aim of this review is focused on the extra-virgin olive oil phenolic fraction with particular emphasis on (a) biosynthesis, chemical structure, and influence factors on the final extra-virgin olive oil phenolic composition; (b) structure–antioxidant activity relationships and other molecular mechanisms in relation to many diseases; (c) bioavailability and controlled delivery strategies; (d) alternative sources of olive biophenols. To achieve this goal, a comprehensive review was developed, with particular emphasis on in vitro and in vivo assays as well as clinical trials. This report provides an overview of extra-virgin olive oil phenolic compounds as a tool for functional food, nutraceutical, and pharmaceutical applications.

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“…Therefore, it is not surprising that many chemical efforts have been made to collect pure HTy, either by synthesis or from natural sources [12]. Particularly, HTy can be obtained from Ty chemically, often using costly reactants [13][14][15]; enzymatically [16]; or from tyrosine through three biocatalyzed steps [17].…”

Section: Introductionmentioning

confidence: 99%

“…Antioxidants 2021, 10, x FOR PEER REVIEW 2 of 9 be obtained from Ty chemically, often using costly reactants [13][14][15]; enzymatically [16]; or from tyrosine through three biocatalyzed steps [17]. Moreover, the acetylation of the primary alcohol of Ty and HTy, to give TyAc and HTyAc (Figure 1), respectively, increases their lipophilicity and lipid solubility, modifying their bioavailability [18], stability [19] and antioxidant effect in cosmetic products and food emulsions [20].…”

Section: Introductionmentioning

confidence: 99%

Biocatalyzed Flow Oxidation of Tyrosol to Hydroxytyrosol and Efficient Production of Their Acetate Esters

et al. 2021

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Tyrosol (Ty) and hydroxytyrosol (HTy) are valuable dietary phenolic compounds present in olive oil and wine, widely used for food, nutraceutical and cosmetic applications. Ty and HTy are endowed with a number of health-related biological activities, including antioxidant, antimicrobial and anti-inflammatory properties. In this work, we developed a sustainable, biocatalyzed flow protocol for the chemo- and regio-selective oxidation of Ty into HTy catalyzed by free tyrosinase from Agaricus bisporus in a gas/liquid biphasic system. The aqueous flow stream was then in-line extracted to recirculate the water medium containing the biocatalyst and the excess ascorbic acid, thus improving the cost-efficiency of the process and creating a self-sufficient closed-loop system. The organic layer was purified in-line through a catch-and-release procedure using supported boronic acid that was able to trap HTy and leave the unreacted Ty in solution. Moreover, the acetate derivatives (TyAc and HTyAc) were produced by exploiting a bioreactor packed with an immobilized acyltransferase from Mycobacterium smegmatis (MsAcT), able to selectively act on the primary alcohol. Under optimized conditions, high-value HTy was obtained in 75% yield, whereas TyAc and HTyAc were isolated in yields of up to 80% in only 10 min of residence time.

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A Three-Step, Gram-Scale Synthesis of Hydroxytyrosol, Hydroxytyrosol Acetate, and 3,4-Dihydroxyphenylglycol

Cited by 16 publications

References 65 publications

NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters

NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters

Structure–Biological Activity Relationships of Extra-Virgin Olive Oil Phenolic Compounds: Health Properties and Bioavailability

Biocatalyzed Flow Oxidation of Tyrosol to Hydroxytyrosol and Efficient Production of Their Acetate Esters

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