Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives

International audience Hydrosoluble sesame oil fatty acid transesters having enhanced antioxidant activities were synthesizedin a two-step process. The key step involved the biocatalyzed (lipase from Candida antarctica)acylation of sesame oil methanolic ester with either vanillyl (VNA) or piperonyl...

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Published in:Journal of Agricultural and Food Chemistry
Main Authors: Alencar, Juliana, Gosset, Gaelle, Robin, Maxime, Pique, Valérie, Culcasi, Marcel, Mercier, Anne, Pietri, Sylvia
Other Authors: Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
Format: Article in Journal/Newspaper
Language:English
Published: HAL CCSD 2009
Subjects:
Online Access:https://amu.hal.science/hal-01142289
https://doi.org/10.1021/jf9010627
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spelling ftunivaixmarseil:oai:HAL:hal-01142289v1 2024-05-12T07:53:47+00:00 Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives Alencar, Juliana Gosset, Gaelle Robin, Maxime Pique, Valérie Culcasi, Marcel Mercier, Anne Pietri, Sylvia Institut de Chimie Radicalaire (ICR) Aix Marseille Université (AMU)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS) 2009-08-04 https://amu.hal.science/hal-01142289 https://doi.org/10.1021/jf9010627 en eng HAL CCSD American Chemical Society info:eu-repo/semantics/altIdentifier/doi/10.1021/jf9010627 hal-01142289 https://amu.hal.science/hal-01142289 doi:10.1021/jf9010627 ISSN: 0021-8561 EISSN: 1520-5118 Journal of Agricultural and Food Chemistry https://amu.hal.science/hal-01142289 Journal of Agricultural and Food Chemistry, 2009, 57, pp.7311-7323. ⟨10.1021/jf9010627⟩ DEPMPO 3T3 fibroblasts UV irradiation spray-dried emulsions antioxidant capacity ESR spin trapping Sesame oil enzymatic transesterification vanillyl alcohol [CHIM]Chemical Sciences info:eu-repo/semantics/article Journal articles 2009 ftunivaixmarseil https://doi.org/10.1021/jf9010627 2024-04-18T00:39:07Z International audience Hydrosoluble sesame oil fatty acid transesters having enhanced antioxidant activities were synthesizedin a two-step process. The key step involved the biocatalyzed (lipase from Candida antarctica)acylation of sesame oil methanolic ester with either vanillyl (VNA) or piperonyl benzylic alcohols, or5-hydroxymethyl resorcinol (5-HMR). These substrates were selected to introduce phenolic orsesamol structurally related frameworks. The VNA and 5-HMR-derived transesters were obtainedwith 20-40% yields and retained the starting proportions of sesame oil linoleic, oleic, and saturatedacids, these fatty acids also being the only constituents of the nonesterified fraction. The VNAderivedtransester showed the best antioxidant capacity in standard assays and was processed asthe unique lipid phase of spray-dried emulsions containing a high level of linoleic acid phenolic ester.These emulsions provided a high degree of protection to UV-irradiated fibroblasts, through thepotential synergy between VNA antioxidant action and replenishment of damaged membranes byunsaturated fatty acids. Article in Journal/Newspaper Antarc* Antarctica Aix-Marseille Université: HAL Journal of Agricultural and Food Chemistry 57 16 7311 7323
institution Open Polar
collection Aix-Marseille Université: HAL
op_collection_id ftunivaixmarseil
language English
topic DEPMPO
3T3 fibroblasts
UV irradiation
spray-dried emulsions
antioxidant capacity
ESR spin trapping
Sesame oil
enzymatic transesterification
vanillyl alcohol
[CHIM]Chemical Sciences
spellingShingle DEPMPO
3T3 fibroblasts
UV irradiation
spray-dried emulsions
antioxidant capacity
ESR spin trapping
Sesame oil
enzymatic transesterification
vanillyl alcohol
[CHIM]Chemical Sciences
Alencar, Juliana
Gosset, Gaelle
Robin, Maxime
Pique, Valérie
Culcasi, Marcel
Mercier, Anne
Pietri, Sylvia
Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives
topic_facet DEPMPO
3T3 fibroblasts
UV irradiation
spray-dried emulsions
antioxidant capacity
ESR spin trapping
Sesame oil
enzymatic transesterification
vanillyl alcohol
[CHIM]Chemical Sciences
description International audience Hydrosoluble sesame oil fatty acid transesters having enhanced antioxidant activities were synthesizedin a two-step process. The key step involved the biocatalyzed (lipase from Candida antarctica)acylation of sesame oil methanolic ester with either vanillyl (VNA) or piperonyl benzylic alcohols, or5-hydroxymethyl resorcinol (5-HMR). These substrates were selected to introduce phenolic orsesamol structurally related frameworks. The VNA and 5-HMR-derived transesters were obtainedwith 20-40% yields and retained the starting proportions of sesame oil linoleic, oleic, and saturatedacids, these fatty acids also being the only constituents of the nonesterified fraction. The VNAderivedtransester showed the best antioxidant capacity in standard assays and was processed asthe unique lipid phase of spray-dried emulsions containing a high level of linoleic acid phenolic ester.These emulsions provided a high degree of protection to UV-irradiated fibroblasts, through thepotential synergy between VNA antioxidant action and replenishment of damaged membranes byunsaturated fatty acids.
author2 Institut de Chimie Radicalaire (ICR)
Aix Marseille Université (AMU)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
format Article in Journal/Newspaper
author Alencar, Juliana
Gosset, Gaelle
Robin, Maxime
Pique, Valérie
Culcasi, Marcel
Mercier, Anne
Pietri, Sylvia
author_facet Alencar, Juliana
Gosset, Gaelle
Robin, Maxime
Pique, Valérie
Culcasi, Marcel
Mercier, Anne
Pietri, Sylvia
author_sort Alencar, Juliana
title Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives
title_short Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives
title_full Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives
title_fullStr Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives
title_full_unstemmed Improving the Stability and Antioxidant Properties of Sesame Oil: Water-Soluble Spray-Dried Emulsions from New Transesterified Phenolic Derivatives
title_sort improving the stability and antioxidant properties of sesame oil: water-soluble spray-dried emulsions from new transesterified phenolic derivatives
publisher HAL CCSD
publishDate 2009
url https://amu.hal.science/hal-01142289
https://doi.org/10.1021/jf9010627
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source ISSN: 0021-8561
EISSN: 1520-5118
Journal of Agricultural and Food Chemistry
https://amu.hal.science/hal-01142289
Journal of Agricultural and Food Chemistry, 2009, 57, pp.7311-7323. ⟨10.1021/jf9010627⟩
op_relation info:eu-repo/semantics/altIdentifier/doi/10.1021/jf9010627
hal-01142289
https://amu.hal.science/hal-01142289
doi:10.1021/jf9010627
op_doi https://doi.org/10.1021/jf9010627
container_title Journal of Agricultural and Food Chemistry
container_volume 57
container_issue 16
container_start_page 7311
op_container_end_page 7323
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