The antioxidant hydroxytyrosol: biotechnological production challenges and opportunities

Achmon, Yigal; Fishman, Ayelet

doi:10.1007/s00253-014-6310-6

Cited by 47 publications

(44 citation statements)

References 79 publications

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“…Tv CAR readily reduced 3,4‐dihydroxyphenylacetic acid (DOPAC, 3 a ) (Table ). We previously investigated the reduction of 3 a to the antioxidant 3‐hydroxytyrosol (3‐HT, 3 c ) using a whole cell biocatalyst, because the antioxidant 3‐HT was in the spotlight of numerous studies to uncover its beneficial effects on human health . 3‐HT is abundant in olives (Olea europaea) and olive oil, and the health‐promoting Mediterranean diet is partly ascribed to this compound.…”

Section: Resultsmentioning

confidence: 99%

“…Due to its anticarcinogenic, anti‐inflammatory, antiapoptotic and neuroprotective activities, 3‐HT is already used in foods and cosmetics . The high cost of purified 3 c , however, limits its availability on the market and is the bottleneck for its use . The first generation catalyst for 3 c preparation harbored bacterial type I CAR from Nocardia iowensis ( Ni CAR) as the key enzyme.…”

Section: Resultsmentioning

confidence: 99%

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Characterization of Type IV Carboxylate Reductases (CARs) for Whole Cell‐Mediated Preparation of 3‐Hydroxytyrosol

et al. 2019

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Fragrance and flavor industries could not imagine business without aldehydes. Processes for their commercial production raise environmental and ecological concerns. The chemical reduction of organic acids to aldehydes is challenging. To fulfill the demand of a mild and selective reduction of carboxylic acids to aldehydes, carboxylic acid reductases (CARs) are gaining importance. We identified two new subtype IV fungal CARs from Dichomitus squalens CAR (DsCAR) and Trametes versicolor CAR (Tv2CAR) in addition to literature known Trametes versicolor CAR (TvCAR). Expression levels were improved by the co‐expression of GroEL‐GroES with either the trigger factor or the DnaJ‐DnaK‐GrpE system. Investigation of the substrate scope of the three enzymes revealed overlapping substrate‐specificities. Tv2CAR and DsCAR showed a preferred pH range of 7.0 to 8.0 in bicine buffer. TvCAR showed highest activity at pH 6.5 to 7.5 in MES buffer and slightly reduced activity at pH 6.0 or 8.0. TvCAR appeared to tolerate a wider pH range without significant loss of activity. Type IV fungal CARs optimal temperature was in the range of 25–35 °C. TvCAR showed a melting temperature (Tm) of 55 °C indicating higher stability compared to type III and the other type IV fungal CARs (Tm 51–52 °C). Finally, TvCAR was used as the key enzyme for the bioreduction of 3,4‐dihydroxyphenylacetic acid to the antioxidant 3‐hydroxytyrosol (3‐HT) and gave 58 mM of 3‐HT after 24 h, which correlates to a productivity of 0.37 g L−1 h−1.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Characterization of Type IV Carboxylate Reductases (CARs) for Whole Cell‐Mediated Preparation of 3‐Hydroxytyrosol

et al. 2019

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“…It is considered the strongest antioxidant of olive oil and one of the main antioxidants in nature [133]. It acts as a powerful scavenger of free radicals, as a radical chain breaker and as metal chelator [134].…”

Section: Single Nutrients and Bioactive Compoundsmentioning

confidence: 99%

Dietary Strategies Implicated in the Prevention and Treatment of Metabolic Syndrome

Iglesia

Loria-Kohen

Zulet

et al. 2016

IJMS

130

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Metabolic syndrome (MetS) is established as the combination of central obesity and different metabolic disturbances, such as insulin resistance, hypertension and dyslipidemia. This cluster of factors affects approximately 10%–50% of adults worldwide and the prevalence has been increasing in epidemic proportions over the last years. Thus, dietary strategies to treat this heterogenic disease are under continuous study. In this sense, diets based on negative-energy-balance, the Mediterranean dietary pattern, n-3 fatty acids, total antioxidant capacity and meal frequency have been suggested as effective approaches to treat MetS. Furthermore, the type and percentage of carbohydrates, the glycemic index or glycemic load, and dietary fiber content are some of the most relevant aspects related to insulin resistance and impaired glucose tolerance, which are important co-morbidities of MetS. Finally, new studies focused on the molecular action of specific nutritional bioactive compounds with positive effects on the MetS are currently an objective of scientific research worldwide. The present review summarizes some of the most relevant dietary approaches and bioactive compounds employed in the treatment of the MetS to date.

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“…A biocatalytic strategy for its production is desira ble as it prevents fluctuating yields often encountered in hydroxytyrosol recovery strategies from olives and olive-processing wastewater [62]. In addition, hydroxy tyrosol can be produced from multiple starting materials and biocatalysts, which should allow the development of an economically feasible process, preferably using inexpensive substrates [43,63]. Family shuffling generated a new variant of nitrobenzene dioxygenase with three substitutions-F222C, F251L, and G253S-which allowed the oxidation of 3-nitrophenethyl alcohol, a lower-cost choice com pared to the mostly used substrate tyrosol [63], to the antioxidant hydroxytyrosol 375-fold better than wild type and with very high regioselectivity, reducing the production of unwanted side product [43].…”

Section: Protein Engineering For the Production Of Specific Chemicalsmentioning

confidence: 99%

Application of Aromatic Hydrocarbon Dioxygenases

Tan

Parales

2016

Green Biocatalysis

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c h a p t e r 1 7 INTRODUCTIONThe first reported aromatic hydrocarbon dioxygenase, toluene dioxygenase, was identified to catalyze cis-dihydroxylation of benzene and toluene in Pseudomonas putida F1 [1, 2]. Since then, many more dioxygenases have been studied, and the crys tal structures of several have been determined [3]. This group of enzymes plays an important role in the initial step in the biodegradation of both naturally occurring and man-made aromatic compounds, including aromatic acids, polycyclic aromatic hydrocarbons, polychlorinated biphenyls, and nitroaromatic, aminoaromatic and halogenated aromatic compounds [4,5]. Dioxygenases are nonheme Rieske-type NAD(P)H-dependent enzymes that intro duce both atoms of molecular oxygen into their substrates. The multicomponent enzyme systems are composed of a catalytic oxygenase component and one-or two-electron trans fer proteins, including a flavoprotein reductase, and in some cases a ferredoxin that medi ates electron transfer from the reductase to the oxygenase component ([3]; Figure 17.1).In general, Rieske dioxygenases are capable of oxidizing a broad range of substrates, well beyond the range of compounds that serves as growth substrates for the host bacterium [4,5,7]. For example, toluene dioxygenase from P. putida F1 facilitates the oxidation of over 200 different substrates [7], and naphthalene dioxygenase from Pseudomonas sp. NCIB 9816-4 has been documented to oxidize over 60 different substrates [8]. In addition, these enzymes catalyze diverse types of reactions, including cisdihydroxylations, O-and N-dealkylations, desaturations, and the formation of chiral sulfoxides from sulfides ([7-9]; Figure 17.2). In many cases the products are chiral com pounds that are high in enantiomeric purity [8,10,11]. For the aforementioned reasons, dioxygenases are attractive biocatalysts for bioremediation and industrial applications. CHALLENGES IN AROMATIC HYDROCARBON DIOXYGENASE APPLICATIONSThe practical use of dioxygenases in industry is generally limited to the use of whole-cell biocatalysts due to several challenges. The catalytic activity of dioxygenases is dependent on reducing equivalents provided by NADH or NADPH, which require regeneration by electron transfer proteins [12,13]. The regeneration process is typically a limiting step

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The antioxidant hydroxytyrosol: biotechnological production challenges and opportunities

Cited by 47 publications

References 79 publications

Characterization of Type IV Carboxylate Reductases (CARs) for Whole Cell‐Mediated Preparation of 3‐Hydroxytyrosol

Characterization of Type IV Carboxylate Reductases (CARs) for Whole Cell‐Mediated Preparation of 3‐Hydroxytyrosol

Dietary Strategies Implicated in the Prevention and Treatment of Metabolic Syndrome

Application of Aromatic Hydrocarbon Dioxygenases

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