Synthesis, Characterization and Free Radical Scavenging Properties of Rosmarinic Acid Fatty Esters

Lecomte, Jérôme; Giraldo, Luis Javier López; Laguerre, Mickaël; Baréa, Bruno; Villeneuve, Pierre

doi:10.1007/s11746-010-1543-8

Cited by 58 publications

(78 citation statements)

References 19 publications

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“…R0 and its alkyl esters were selected as a means of varying hydrophobicity while keeping the AOX portion of the molecule constant. 11 The activity of each antioxidant was tested at 159 μmol because it corresponded to 500 ppm of R0, a concentration typically used by industry for AOX applications. R0 and its alkyl esters naturally fluoresce (blue region of Figure 1), allowing their location to be determined with confocal microscopy without the use of additional probes.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Impact of Hydrophobicity on Antioxidant Efficacy in Low-Moisture Food

Barden

Barouh

Villeneuve

et al. 2015

J. Agric. Food Chem.

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The polarity and partitioning of antioxidants (AOX) in lipid dispersions and bulk oils have a large impact on efficacy, but this has not yet been studied in low-moisture foods. Using a homologous series of rosmarinic esters as AOX in crackers, we determined that efficacy increases with increasing hydrophobicity based on lipid hydroperoxide and hexanal generation. Confocal microscopy was used to determine the location of both lipids and AOX. Hydrophobic rosmarinic esters partitioned more closely with the lipid than rosmarinic acid, presumably placing the hydrophobic AOX at the site of oxidation reactions. Partitioning and efficacy of the intermediate polarity ester were affected by mode of incorporation (e.g., added to the water or to the lipid prior to dough formation). The synthetic AOXs propyl gallate, butylhydroxytoluene, and tert-butylhydroquinone gave similar results with the more hydrophobic BHT and TBHQ being more effective at reducing lipid hydroperoxide and hexanal generation than the more hydrophilic propyl gallate. These results provide important information on which AOX would be most effective in low-moisture foods.

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Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Impact of Hydrophobicity on Antioxidant Efficacy in Low-Moisture Food

Barden

Barouh

Villeneuve

et al. 2015

J. Agric. Food Chem.

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“…Phenolipids" synthesized of RA or chlorogenic acid and a variety of alcohols have been mainly used as antioxidants to prevent lipid oxidation in emulsified systems (22,23). They have been considered safe for use in foods or pharmaceuticals since the ester bond between the phenolic moiety and the lipid carbon chain is readily hydrolyzed under physiological conditions (6).…”

Section: Discussionmentioning

confidence: 99%

“…Recently, a novel class of " phenolipids," esters of phenolic acids and alcohols, have been developed at Centre de Cooperation Internationale en Recherche Agronomique pour le Developpement (CIRAD), Montpellier, France (23). These phenolipids are surface active, i.e., they preferentially adsorb at interfaces.…”

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confidence: 99%

Impact of Fatty Acid Chain Length of Rosmarinate Esters on Their Antimicrobial Activity against Staphylococcus camosus LTH1502 and Escherichia coli K-12 LTH4263

Suriyarak¹,

Bayrasy

Schmidt

et al. 2013

Journal of Food Protection

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The effect of the addition of a newly synthesized series of rosmarinic acid (RA) estes (REs) and alcohols with chain lengths of 1, 4, 8, 10, 12, 16, and 18 carbons (RE1 to 18) on the growth behavior of Staphylococcus carnosus LTH1502 and Escherichia coli K-12 LTH4263 was investigated. An initial microtiter dilution assay indicated activity of compounds against S. carnosus LTH1502, whereas esters with chain lengths, RA, n-methyl rosmarinate (RE1), n-dodecyl rosmarinate (RE12), and n-octadecyl rosmarinate (RE18) were used in a time-kill assay S. carnosus LTH1502. Compounds were added at 0.75 mM in the log phase, 5 mM in the exponential phase, 10 mM in the stationary phase. RA had no effect in the lag and exponential phase but decreased cell counts during the stationary phase. In contrast, RE1 and RE12 decreased cell number in all three phase, will RE12 reducing counts most rapidly. Addition of RE18 did not affect regardless of the growth phase. Appearance and physiological state of S. carnosus LTH1502 cells indicated difference in the way the compounds interacted with and damaged cells. Results were attributed to the different physicochemical properties of RA and its esters.

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“…In that context, one strategy to design surface‐active antioxidants consists in their association via covalent bond with a lipophilic moiety to design a new class of molecule called “phenolipids.” Typically, this approach named “lipophilization” corresponds to a strategy where the hydrophilic/lipophilic balance of a bioactive hydrophilic molecule is adjusted by a covalent grafting of a lipophilic domain, without affecting the functional groups responsible of its chemical reactivity. To date, a multitude of antioxidants have been lipophilized with various lipophilic moieties such as alkyl chains , phospholipids , and diacylglycerol to obtain multifunctional compounds.…”

Section: Introductionmentioning

confidence: 99%

The nonlinear effect of alkyl chain length in the membrane interactions of phenolipids: Evidence by X‐ray diffraction analysis

Durand

Jacob²,

Sherratt³

et al. 2017

Euro J Lipid Sci & Tech

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Despite the evidence supporting a relationship between phenolipid's alkyl chain length and their interaction/affinity with membranes, such a connection has not been directly evaluated. In this study, the membrane interactions of rosmarinic acid, and its corresponding alkyl esters having 4 carbon (RC4), 8 carbon (RC8), 10 carbon (RC10), and 16 carbon (RC16) have been investigated via small angle X-ray scattering (SAXS) approaches in model membrane liposomes. The results of this work show significant differences between the tested phenolipids with respect to their interaction and location within the lipid bilayer. Both membrane affinity and penetration depth follow a nonlinear behavior. They have been shown to increase as a function of increasing alkyl chain length until a threshold is reached for medium alkyl chain, beyond which any lengthening of the chain results in a collapse. RC8 show the highest affinity for the membrane, whereas RC10 constitute a critical chain length from which the penetration depth decreases. The X-ray scattering analyses seem to perfectly correlate with the phenolipids' activities (antioxidant and membranes crossing) previously observed both in biological system and in formulated lipid dispersions. Practical applications: Phenolic compounds are potent antioxidants that may play an important role as well in biological system as in formulated lipid dispersions. However, their activity is often limited by low solubility or bioavailability. Lipophilization of phenolic compounds may increase their solubility in lipophilic matrices, conferring better antioxidant protection for food or nonfood application. In biological system, lipophilization may contribute to easier penetration of antioxidants through lipid bilayer of cell membranes, which can significantly increase their bioavailability. Despite the evidence supporting a relationship between phenolipid's alkyl chain length and their interaction/affinity with membranes, such a relationship has not been directly evaluated. Investigation of membrane interactions between phenolic and its lipophilic derivative, via SAXS approaches in model membrane liposomes, provide new knowledge about this class of compound with the perspective to be used as substances with maintained or improved biological properties for food, cosmetic and pharmaceutical applications. (Résumé d'auteur

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Synthesis, Characterization and Free Radical Scavenging Properties of Rosmarinic Acid Fatty Esters

Cited by 58 publications

References 19 publications

Impact of Hydrophobicity on Antioxidant Efficacy in Low-Moisture Food

Impact of Hydrophobicity on Antioxidant Efficacy in Low-Moisture Food

Impact of Fatty Acid Chain Length of Rosmarinate Esters on Their Antimicrobial Activity against Staphylococcus camosus LTH1502 and Escherichia coli K-12 LTH4263

The nonlinear effect of alkyl chain length in the membrane interactions of phenolipids: Evidence by X‐ray diffraction analysis

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