Relationship between Hydrophobicity and Antioxidant Ability of “Phenolipids” in Emulsion: A Parabolic Effect of the Chain Length of Rosmarinate Esters

Laguerre, Mickaël; Giraldo, Luis Javier López; Lecomte, Jérôme; Figueroa-Espinoza, María-Cruz; Baréa, Bruno; Weiß, Jochen; Decker, Eric A.; Villeneuve, Pierre

doi:10.1021/jf904119v

Cited by 208 publications

(190 citation statements)

References 35 publications

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“…In vitro studies showed that the antioxidant capacity of RA alkyl derivatives could be higher than RA [32], and further work is in progress to more thoroughly characterize the methylated form of RA and to verify whether its production is a result of genuine biosynthesis or artifactual methylation during methanol extraction.…”

Section: Cads Quantificationmentioning

confidence: 99%

Rosmarinic acid content in basil plants grown in vitro and in hydroponics

et al. 2011

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The accumulation of selected caffeic acid derivatives (CADs), in particular rosmarinic acid (RA), was investigated in different tissues (leaves, roots and plantlet shoots) of sweet basil (Ocimum basilicum L.) plants grown either in vitro or in hydroponic culture (floating system) under greenhouse conditions. Two cultivars with green leaves (Genovese and Superbo) and one with purple leaves (Dark Opal) were tested. The content of CADs in HCl-methanol extracts was determined by HPLC. LC-MS and LC-MS-MS were used to confirm the identification of the metabolites of interest. Apart from rosmarinic acid (RA) and a methylated form of this substance, no other CADs were detected at significant level in any of the analyzed samples. The content of RA ranged approximately from 4 to 63 mg/g DW, depending on the growing system. The highest RA content was found during the in vitro multiplication, in the acclimatized plants and in the roots of hydroponically-grown seedlings at full bloom. In vitro, 6-benzyladenine reduced the accumulation of RA in purple-leaf Dark Opal cultivar, but an opposite effect of this growth regulator was observed in the green-leaf genotypes. Our findings suggest the possibility to scale-up RA production by means of in vitro or hydroponic culture of sweet basil.

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Section: Cads Quantificationmentioning

confidence: 99%

Rosmarinic acid content in basil plants grown in vitro and in hydroponics

et al. 2011

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“…Thus, the results lead to the conclusion that lipophilization with medium chain fatty acids is a promising way to increase the antioxidant activity [16]. However, the results obtained with chlorogenate and rosmarinate esters have also led to the suggestion that the exact location of antioxidants in the discontinuous phase, interfacial layer or oil droplets, is important for the activity of the antioxidants [11,16]. In addition, a study on lipophilized dihydrocaffeic acids and their antioxidative effect in o/w emulsions reported by Sørensen et al [17] suggested that lipophilized dihydrocaffeic acid tended to follow the newly suggested cut-off effect in relation to the alkyl chain length attached although only two chain lengths were evaluated.…”

Section: Introductionmentioning

confidence: 95%

“…The current work in this area has been summarized by Shahidi and Zhong [15]. Laguerre et al [11,16] have recently reported on the antioxidative effect of lipohilized chlorogenic and rosmarinic acids. For chlorogenic acid the antioxidant capacity increased as the alkyl chain length was increased from 1 to 12 carbon atoms, whereas further increase of the chain length resulted in a drastic decrease in the antioxidant capacity.…”

Section: Introductionmentioning

confidence: 99%

“…For rosmarinate esters, the octyl rosmarinate improved the antioxidative effect eight times compared to rosmarinic acid. Thus, the results lead to the conclusion that lipophilization with medium chain fatty acids is a promising way to increase the antioxidant activity [16]. However, the results obtained with chlorogenate and rosmarinate esters have also led to the suggestion that the exact location of antioxidants in the discontinuous phase, interfacial layer or oil droplets, is important for the activity of the antioxidants [11,16].…”

Section: Introductionmentioning

confidence: 99%

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The antioxidative effect of lipophilized rutin and dihydrocaffeic acid in fish oil enriched milk

Sørensen

Petersen

Diego

et al. 2012

Euro J Lipid Sci & Tech

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The antioxidative effect of phenolipids was evaluated in fish oil enriched milk emulsions as a model for a complex food system. Two different phenolipids modified from dihydrocaffeic acid (with C8 or C18:1) and rutin (with C12 or C16) were evaluated. Both dihydrocaffeate esters and rutin laurate showed significantly better antioxidant properties in milk emulsion compared with the original phenolics. However, rutin palmitate only performed slightly better as antioxidant than rutin. The results with rutin indicated that a cut‐off effect exists in relation to the alkyl chain length with respect to optimal antioxidant activity in milk emulsions. Thus, the optimal alkyl chain length is at least below 16 carbon atoms, and maybe even less for rutin esters. For dihydrocaffeate esters it was not possible to conclude on a cut‐off effect in relation to alkyl chain length and antioxidative effect due to the almost similar antioxidant effect of the two phenolipids. However, there was a tendency towards octyl dihydrocaffeate being slightly more efficient than oleyl dihydrocaffeate.Practical application: The finding that phenolipids are better antioxidants in milk emulsions than the original phenolic acid provides new knowledge that can be used to develop new antioxidant strategies to protect foods against lipid oxidation. However, the results indicate that both optimization of alkyl chain length for each type of phenolic, and optimization for each type of emulsion will be necessary in order to get the best oxidative stability of an emulsion with these phenolipids. Use of efficient antioxidants may lower the amount of antioxidant needed to protect against lipid oxidation and may in addition decrease the costs.

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“…In that sense, the lipophilization reactions are particularly advantageous and effective, and may be seen as a vectorization key unlocking the lipid barrier encountered by the bioactive molecule while maintaining its original functional properties. In the case of phenolic acids, the methods commonly used consists in attaching on the reactive carboxyl group, either a single or double tail lipophilic domain (usually an aliphatic with a different carbon backbone) resulting in new molecule with emulsifying properties, and often greatly improved antioxidant activity (Durand et al, 2015;Laguerre et al, 2010). This reaction can be performed on simple phenolic acids derived from benzoic acid (hydroxybenzoic acids), cinnamic (hydroxycinnamic acids) or more complex polyphenolic acids such as chlorogenic acid and rosmarinic acid with single or double tail (Fig.…”

Section: Lttm a New Family Of Promising Green Mediamentioning

confidence: 99%

Are emerging deep eutectic solvents (DES) relevant for lipase-catalyzed lipophilizations?

Durand

Lecomte

Villeneuve

2015

OCL

Self Cite

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-With the recent interest on green chemistry, the scientists have focused on developing new and more efficient solvents to carry out enzymatic-catalyzed reactions with emphasis on reduced costs, risks and toxicity while improving biodegradability. Among the new available solvents, the multimolecular-based liquids (such as ionic liquids and eutectic solvents) have been the subject of most recent studies. Currently, and mainly due to its environmental and economic features, DES are arousing much interest and curiosity. Regarding the biotransformations with lipases, the so-called "lipophilization" reactions are of major interest. However, they are complex to implement mainly because it is difficult to find a suitable reaction medium. Thus, this review aimed at providing a presentation of these multimolecularbased solvents with general overview of the recent studies dealing with lipase-catalyzed reactions in DES. In addition, emphasis was placed on their strengths and weaknesses, especially with the perspective to be use as efficient and green medium to implement complex and valuable biotransformation such as lipase-catalyzed lipophilizations.Keywords: Low transition temperature mixtures / deep eutectic solvents / Lipase / Lipophilization Résumé -Solvants de type eutectiques profonds : milieux réactionnels adaptés aux réactions de lipophilisation biocatalysées par les lipases ? Depuis le début des années 1990 et l'émergence de la « chimie verte », il est indispensable de concevoir des nouveaux procédés, en particulier enzymatiques, qui mettent l'accent sur la réduction des coûts, des risques et de la toxicité tout en améliorant la biodégradabilité. Les nouveaux solvants de type « liquides multimoléculaires » (tels que les liquides ioniques et les solvants eutectiques) ont fait l'objet de la plupart des études récentes. Actuellement, et principalement en raison de ses atouts environnementaux et économiques, les solvants eutectiques suscitent beaucoup plus d'intérêt et de curiosité. Concernant les biotransformations lipasiques, les réactions dites « de lipophilisation » présentent de nombreux avantages. Cependant, ces réactions sont complexes à mettre en oeuvre, principalement parce qu'il est difficile de trouver un milieu réactionnel adapté. Ainsi, cette revue a pour objectif de fournir une présentation de ces milieux réactionnels avec un aperçu des travaux récents portant sur les réactions lipasiques dans des solvants eutectiques. En outre, l'accent a été mis sur leurs forces et leurs faiblesses, avec la perspective d'être utilisés comme milieu réactionnel « vert » pour mettre en oeuvre des biotransformations complexes telles que les réactions de lipophilisation biocatalysées par les lipases. Mots clés :Mélanges à faible transition de température / solvants eutectiques profonds / lipase / lipophilisation

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Relationship between Hydrophobicity and Antioxidant Ability of “Phenolipids” in Emulsion: A Parabolic Effect of the Chain Length of Rosmarinate Esters

Cited by 208 publications

References 35 publications

Rosmarinic acid content in basil plants grown in vitro and in hydroponics

Rosmarinic acid content in basil plants grown in vitro and in hydroponics

The antioxidative effect of lipophilized rutin and dihydrocaffeic acid in fish oil enriched milk

Are emerging deep eutectic solvents (DES) relevant for lipase-catalyzed lipophilizations?

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