Untitled

Buisman, G.J.H.; Helteren, C.T.W. van; Kramer, G.F.H.; Veldsink, J.W.; Derksen, J.T.P.; Cuperus, F.P.

doi:10.1023/a:1005368222340

Cited by 112 publications

(17 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The results from the free radical scavenging activity (DPPH) assay demonstrated that all flavonoids esters maintained at least same level of activity in comparison to their parent flavonoids, which are in line with the findings in studies for other polyphenolic esters (Buisman et al, 1998). The results suggest the esterification does not hamper the antioxidant activity of the parent molecules ( Figure 8 ).…”

Section: Resultssupporting

confidence: 87%

“…This biotransformation created a novel ascorbic ester with much improved lipophilic solubility with equivalent antioxidant activity as ascorbic acid. Since then, a number of polyphenols derivatives have been made enzymatically (Guyot et al, 1997; Buisman et al, 1998; Stamatis et al, 2001), all of which proved to have different physical properties while maintaining the original bioactivities (Riva et al, 1998; de Pinedo et al, 2005, 2007; Burham et al, 2009). …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities

et al. 2017

View full text Add to dashboard Cite

Enzymatic conjugation with fatty acids including omega-3 polyunsaturated fatty acids (ω-3 PUFAs) derived from fish oil to three citrus fruit-derived flavonoids: grapefruit extract, naringin, and neohesperidin dihydrochalcone were investigated. The conversions were achieved over 85% under the catalysis of lipase Novozyme 435 in acetone at 45°C at semi-preparative scale. The conjugates were purified via solvent partition and silica gel chromatography and achieved 90–98% in purity. The NMR analysis of the conjugates confirmed that the fatty acid carbon chain was linked onto the primary –OH group on the glucose moiety of the flavonoids. The purified flavonoid conjugates alongside their original flavonoids were analyzed for antioxidant activities via 2,2-diphenyl-1-picrylhydrazyl scavenging assay, and anti-peroxidation test via peroxide values measured during a 1-week fish oil storage trial. Vascular endothelial growth factor (VEGF) assay was conducted with 1, 10, and 100 μM of naringin and grapefruits and their conjugates, respectively, and total VEGF levels were measured at 24 and 48 h, respectively, using ELISA and dot blot analysis. The results from these functionality experiments demonstrated that flavonoid FA conjugates have at least comparable (if not higher) antioxidant activity, anti-peroxidation activity, and anti-angiogenic activity.

show abstract

Section: Resultssupporting

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities

et al. 2017

View full text Add to dashboard Cite

show abstract

“…49 Since a biocatalytic approach appeared especially appealing to us, we have tried to repeat the experimental protocol reported for the esterifcation of functionalized phenols with Candida antarctica lipase (CAL-B) 49 using thymol and propanoic acid as substrates and tert-butyl methyl ether and hexane as solvents. However, although no reaction occurred in our hands, the biocatalytic approach deserves further investigation within the recent trends of green chemistry methodologies.…”

Section: Chemical Synthesismentioning

confidence: 99%

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Lazarević

Kolarević

Stojanović

et al. 2017

ACSi

View full text Add to dashboard Cite

Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.

show abstract

“…Concomitantly with the natural origin of the being esterified molecule, lipase-catalyzed reactions are believed as economically and ecologically more advantageous [5]. Indeed, lipases are explored for racemic mixture resolution, fat transformation and also for the synthesis of molecules with moisturizing or antioxidant activities allowing the control of human skin integrity [6,7].…”

Section: Introductionmentioning

confidence: 99%

Hydroxytyrosol Acyl Esters: Biosynthesis and Activities

Bouallagui

Bouaziz

Lassoued

et al. 2010

Appl Biochem Biotechnol

View full text Add to dashboard Cite

We previously reported the production of high yields of hydroxytyrosol through the bioconversion of tyrosol. In the present work, hydroxytyrosol was subjected to the lipase catalyzed acylation aiming for the recovery of more lipophilic esters that might be easily incorporated in cosmetic and food preparations. Hydroxytyrosyl acetate and hydroxytyrosyl oleate were produced with respective molar esterification yields of 98% and 78%. DPPH free radical quenching potency demonstrated that the acylation of hydroxytyrosol did not alter its antioxidant activity. The acylated esters were shown to be more effective than the natural antioxidant: caffeic acid and two synthetic ones as BHA and BHT. Antiproliferative activity on human cervical cells (HeLa) resulted in IC(50) values of 0.46, 0.42 and 0.33 mM for hydroxytyrosol and its acetyl and oleyl esters, respectively. Additionally, when used at a non-cytotoxic concentration (100 μM), these compounds showed significant effectiveness in preventing iron-induced oxidative stress, resulting in a reduction of 30%, 36% and 38% in thiobarbituric acid-reactive substance production, respectively.

show abstract

Untitled

Cited by 112 publications

References 9 publications

Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities

Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Hydroxytyrosol Acyl Esters: Biosynthesis and Activities

Contact Info

Product

Resources

About