Merck
  • Home
  • Search Results
  • Synthesis and antioxidant activity of nitrohydroxytyrosol and its acyl derivatives.

Synthesis and antioxidant activity of nitrohydroxytyrosol and its acyl derivatives.

Journal of agricultural and food chemistry (2014-09-30)
Mariana Trujillo, Elena Gallardo, Andrés Madrona, Laura Bravo, Beatriz Sarriá, José A González-Correa, Raquel Mateos, José Luis Espartero
ABSTRACT

A series of nitroderivatives has been synthesized from hydroxytyrosol, the natural olive oil phenol, to increase the assortment of compounds with putative effects against Parkinson's disease. Nitrohydroxytyrosyl esters were obtained from nitrohydroxytyrosol using a chemoselective one-step, high-yield, transesterification procedure. The antioxidant activity of these new series of nitrocatechols was evaluated using FRAP, ABTS, and ORAC assays and compared to that of free hydroxytyrosol. The nitro functional group induced a significant increase in the antioxidant activity of nitrohydroxytyrosol compared to hydroxytyrosol. Regarding nitroester derivatives, variable antioxidant activity was observed depending on the acyl side-chain length; shorter chains maintained or even enhanced the antioxidant activity compared to nitrohydroxytyrosol, decreasing the activity with longer side chains in keeping with their lipophilic nature. Therefore, it may be concluded that nitroester derivatives of hydroxytyrosol, which may be obtained by a simple, high-yield reaction, have elevated antioxidant activity and thus present potential bioactivity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium acetate trihydrate, meets USP testing specifications
Sigma-Aldrich
Potassium phosphate monobasic, ReagentPlus®
Sigma-Aldrich
Sodium acetate trihydrate, BioXtra, ≥99.0%
Sigma-Aldrich
Sodium phosphate dibasic, BioReagent, suitable for cell culture, suitable for insect cell culture, ≥99.0%
Sigma-Aldrich
Potassium phosphate monobasic, for molecular biology, ≥98.0%
Sigma-Aldrich
Potassium phosphate monobasic, powder, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture, ≥99.0%
Sigma-Aldrich
Sodium phosphate dibasic, for molecular biology, ≥98.5% (titration)
Millipore
Bifido Selective Supplement B, suitable for microbiology
Supelco
5α-Androstan-17β-ol-3-one, VETRANAL®, analytical standard
Supelco
Acetone solution, certified reference material, 2000 μg/mL in methanol: water (9:1)
Sigma-Aldrich
Sodium phosphate dibasic, ≥99.5%
Sigma-Aldrich
Sodium nitrite, 99.999% trace metals basis
Sigma-Aldrich
5α-Androstan-17β-ol-3-one, ≥97.5%
Sigma-Aldrich
Dimethyl sulfoxide, sterile-filtered, BioPerformance Certified, meets EP, USP testing specifications, suitable for hybridoma
Sigma-Aldrich
Ethyl acetate, ACS reagent, ≥99.5%
Sigma-Aldrich
Ethyl acetate, anhydrous, 99.8%
Sigma-Aldrich
Dimethyl sulfoxide, anhydrous, ≥99.9%
Sigma-Aldrich
Dimethyl sulfoxide, BioUltra, for molecular biology, ≥99.5% (GC)
Sigma-Aldrich
Potassium phosphate monobasic, 99.99% trace metals basis
Sigma-Aldrich
Sodium phosphate dibasic, 99.95% trace metals basis
Sigma-Aldrich
Sodium phosphate dibasic, BioUltra, for molecular biology, ≥99.5% (T)
Sigma-Aldrich
5α-Androstan-17β-ol-3-one, purum, ≥99.0% (TLC)
Supelco
Dimethyl sulfoxide, analytical standard
Sigma-Aldrich
Fluorescein, for fluorescence, free acid
Supelco
Nitrite ion standard solution, 0.1 M NO2-, for ion-selective electrodes
Sigma-Aldrich
Sodium acetate trihydrate, BioUltra, ≥99.5% (NT)
Sigma-Aldrich
Ethyl acetate, ReagentPlus®, ≥99.8%
Sigma-Aldrich
Potassium phosphate monobasic, BioUltra, for molecular biology, anhydrous, ≥99.5% (T)
Sigma-Aldrich
Potassium phosphate monobasic, tested according to Ph. Eur., anhydrous
Sigma-Aldrich
Sodium phosphate dibasic, purum p.a., anhydrous, ≥98.0% (T)