Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection

Grasso, S.; Siracusa, Laura; Spatafora, Carmela; Renis, Marcella; Tringali, Corrado

doi:10.1016/j.bioorg.2006.09.003

Cited by 137 publications

(129 citation statements)

References 35 publications

Supporting

Mentioning

114

Contrasting

Order By: Relevance

“…Enzymatic esterification of HT and homovanillyl alcohol (Grasso et al, 2007) The order of the scavenging activities toward the ABTS radical was hydroxytyrosyl esters ≥ -tocopherol > hydroxytyrosol > tyrosyl >tyrosyl esters  BHT. In a similar trend, comparison of FRAP values obtained for the free hydroxytyrosol and tyrosol with the corresponding esters revealed that while hydroxytyrosyl esters showed a significantly higher reducing activity than their precursor, all the tyrosyl esters showed a lower antioxidant activity than that of tyrosol.…”

Section: Antioxidant Activitymentioning

confidence: 95%

“…Studies on olive polyphenols have shown the importance of the lipophilicity of the antioxidants on the cell uptake and membrane crossing, and on the substrate to be protected (membrane constituents or LDL), (Grasso et al, 2007). These facts explain the efforts made in the development of new synthetic analogues with increased lipophilicity.…”

Section: Lipophilic Hydroxytyrosol Estersmentioning

confidence: 99%

“…Synthesis of hydroxytyrosyl acetate via benzylation of phenolic hydroxyls A two-step procedure involving the reaction of methyl orthoformate-protected hydroxytyrosol with acetyl chloride, and hydrolytic deprotection in phosphate buffer under very mild conditions (pH=7.2) to get hydroxytyrosyl acetate (87% overall yield) (Scheme 3) was also described as a successful procedure for the preparation of HT-derived esters (Gambacorta et al, 2007 In order to overcome the problems associated to the protection and deprotection steps of the phenolic hydroxyl groups, different methods for the preparation of hydroxytyrosyl esters by reaction of hydroxytyrosol with various acylating agents have been described, such as esterification with free acids (Appendino et al, 2002), transesterification with methyl or ethyl esters (Alcudia et al, 2004;Trujillo et al, 2006), acyl chlorides (Torregiani et al, 2005) and the use of enzymatic methodologies (Grasso et al, 2007;Mateos et al, 2008;Torres de Pinedo et al, 2005;Buisman, 1998).…”

Section: Protection Of Phenolic Hydroxyl Groupsmentioning

confidence: 99%

“…The use of enzymes, like lipases, as catalysts in non-aqueous solvents to prepare lipophilic derivatives directly from HT has been widely described in the last few years (Grasso et al, 2007;Torres de Pinedo et al, 2005;Mateos et al, 2008;Buisman et al, 1998). This procedure avoids the use of toxic reagents and allows mild reaction conditions.…”

Section: Lipase-catalyzed Transesterificationmentioning

confidence: 99%

“…Different enzymes have been tested on hydroxytyrosol (Grasso et al, 2007) . niger, C. cylindracea, M. javanicus, P. cepacia, M. miehei, C. viscosum, P. fluorescens, R. arrhizus, R. niveus, C. antarctica, porcine pancreas and wheat germ, using vinyl acetate as reagent and tert-butyl methyl ether as solvent.…”

Section: Lipase-catalyzed Transesterificationmentioning

confidence: 99%

See 4 more Smart Citations

Biological Properties of Hydroxytyrosol and Its Derivatives

Fernandez‐Bolanos¹,

López²,

López-García³

et al. 2012

Olive Oil - Constituents, Quality, Health Properties and Bioconversions

View full text Add to dashboard Cite

Section: Antioxidant Activitymentioning

confidence: 95%

Section: Lipophilic Hydroxytyrosol Estersmentioning

confidence: 99%

Section: Protection Of Phenolic Hydroxyl Groupsmentioning

confidence: 99%

Section: Lipase-catalyzed Transesterificationmentioning

confidence: 99%

Section: Lipase-catalyzed Transesterificationmentioning

confidence: 99%

See 3 more Smart Citations

Biological Properties of Hydroxytyrosol and Its Derivatives

Fernandez‐Bolanos¹,

López²,

López-García³

et al. 2012

Olive Oil - Constituents, Quality, Health Properties and Bioconversions

View full text Add to dashboard Cite

Valorization of antioxidants extracted from olive mill wastewater

Aissa

Kharrat

Aloui

et al. 2017

Biotech and App Biochem

View full text Add to dashboard Cite

Antioxidants are highly important gradients used to preserve cosmetic products and reduce the effect of oxidative stress on the skin. The present work explores the possibility of using phenolic compounds of olive mill wastewater (OMW) as effective alternatives to the commercial antioxidants used in cosmetic formulations deemed by their allergic and carcinogenic effects. Esterification of tyrosol and hydroxytyrosol extracted from OMW with various fatty acids was conducted using Novozyme 435 lipase as a biocatalyst. Upon synthesis, butyrate, caprate, laurate, and palmitate tyrosyl and hydroxytyrosyl esters were isolated and evaluated for their antioxidant and antibacterial activities. Results showed that laurate derivatives are the most efficient in preventing lipid oxidation and inhibiting growth of pathogenic strains. In the prospective of industrial use, laurate tyrosyl and hydroxytyrosyl derivatives were incorporated in a formulation of moisturizer to substitute the commercial antioxidant butylated hydroxyltoluene. Oleuropein, extracted from olive leaves powder, was also tested as an antiaging ingredient in cosmetic formulations. The evaluation of physicochemical, microbiological, and sensorial properties of the new cosmetic products indicated that oleuropein and lipophilic derivatives do not affect the properties of the standard formulation. Oleuropein and lipophilic derivatives can be added as active ingredients to stabilize cosmetic preparations.

show abstract

Chemoenzymatic Cascade Reaction for the Valorization of the Lignin Depolymerization Product G−C2‐Dioxolane Phenol

et al. 2023

View full text Add to dashboard Cite

Combining solid acid catalysts with enzyme reactions in aqueous environments is challenging because either very acidic conditions inactivate the enzymes, or the solid acid catalyst is neutralized. In this study, Amberlyst‐15 encapsulated in polydimethylsiloxane (Amb‐15@PDMS) is used to deprotect the lignin depolymerization product G−C2 dioxolane phenol in a buffered system at pH 6.0. This reaction is directly coupled with the biocatalytic reduction of the released homovanillin to homovanillyl alcohol by recombinant horse liver alcohol dehydrogenase, which is subsequently acylated by the promiscuous acyltransferase/hydrolase PestE_I208A_L209F_N288A in a one‐pot system. The deprotection catalyzed with Amb‐15@PDMS attains up to 97 % conversion. Overall, this cascade enables conversions of up to 57 %.

show abstract

Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection

Cited by 137 publications

References 35 publications

Biological Properties of Hydroxytyrosol and Its Derivatives

Biological Properties of Hydroxytyrosol and Its Derivatives

Valorization of antioxidants extracted from olive mill wastewater

Chemoenzymatic Cascade Reaction for the Valorization of the Lignin Depolymerization Product G−C2‐Dioxolane Phenol

Contact Info

Product

Resources

About