Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger
Sunflower and rapeseed meals are agro-industrial coproducts that contain high amount of phenolics (1–4 % dry matter), mostly as esters of caffeic acid (CA) and sinapic acid (SA), respectively. The enzymatic hydrolysis of the ester bonds enables to recover the corresponding free phenolic acids that are bioactive compounds and platform molecules for various applications in green chemistry. Here we aimed to find the best route for producing free CA and SA by applying various fungal carboxylic ester hydrolases from recombinant Aspergillus niger strains either directly on crude meal or on their phenolic extracts obtained by methanolic extraction. Two types of meals were studied: (i) industrial (commercial) meals (I-meals), produced by a process that includes cooking at 95–100 °C and steam desolventizing at 105–107 °C, and (ii) non-industrial meals (NI-meals) obtained at pilot-scale with much milder heat treatment, that offer a higher total phenolic content. CA release through hydrolysis of sunflower meal (SFM) was successfully achieved with A. niger type-B feruloyl esterase (AnFaeB) and chlorogenic acid esterase (ChlE). Maximal amount of free CA released was of 54.0 ± 1.1 to 59.8 ± 2.1 μmol/g defatted dry matter (DDM) from I-SFM (94–100% hydrolysis yield) against 42.0 ± 1.1 to 52.3 ± 0.2 μmol/g DDM (59–73% hydrolysis yield) from NI- SFM in which CA release was hampered by a phenolic oxidation side-reaction, seemingly due to meal endogenous polyphenol oxidase activities. AnFaeB and ChlE hydrolysis of phenolic extracts from NI-SFM increased the CA amount obtained to 55.0–68.1 μmol/g DDM (77–95% hydrolysis yield). In all cases, AnFaeB showed broader specificity towards SFM caffeoyl quinic acid isomers than ChlE. In particular, ChlE did not hydrolyze 3-O-caffeoylquinic acid. The maximal amount of free SA released by AnFaeA hydrolysis was 41.3 ± 0.3 μmol/g DDM from NI-SFM (50% hydrolysis yield) and 32.3 ± 0.4 μmol/g DDM from the phenolic extract (64% hydrolysis yield), with AnFaeA also having sinapine transesterification activity that led to the synthesis of 1,2-di-O-sinapoyl-β-D-glucose. Finally, of all the substrates tested for enzymatic hydrolysis in our conditions, I-RSM and NI-SFM extract showed the best compromise between initial total phenolic content, hydrolysis yields and amounts of CA/SA released.
Main Authors: | , , , , , , , , , , , |
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Format: | article biblioteca |
Language: | eng |
Subjects: | Q51 - Technologie des aliments pour animaux, Q70 - Traitement des déchets agricoles, tourteau de colza, tourteau de tournesol, Aspergillus niger, acide phénolique, hydrolase ester carboxylique, hydrolyse enzymatique, sous-produit d'huilerie, http://aims.fao.org/aos/agrovoc/c_16027, http://aims.fao.org/aos/agrovoc/c_35709, http://aims.fao.org/aos/agrovoc/c_26373, http://aims.fao.org/aos/agrovoc/c_16197, http://aims.fao.org/aos/agrovoc/c_9617, http://aims.fao.org/aos/agrovoc/c_27512, http://aims.fao.org/aos/agrovoc/c_25402, http://aims.fao.org/aos/agrovoc/c_3081, |
Online Access: | http://agritrop.cirad.fr/593311/ http://agritrop.cirad.fr/593311/1/Industrial%20Crops%20and%20Products_2019_139_111579.pdf |
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Q51 - Technologie des aliments pour animaux Q70 - Traitement des déchets agricoles tourteau de colza tourteau de tournesol Aspergillus niger acide phénolique hydrolase ester carboxylique hydrolyse enzymatique sous-produit d'huilerie http://aims.fao.org/aos/agrovoc/c_16027 http://aims.fao.org/aos/agrovoc/c_35709 http://aims.fao.org/aos/agrovoc/c_26373 http://aims.fao.org/aos/agrovoc/c_16197 http://aims.fao.org/aos/agrovoc/c_9617 http://aims.fao.org/aos/agrovoc/c_27512 http://aims.fao.org/aos/agrovoc/c_25402 http://aims.fao.org/aos/agrovoc/c_3081 Q51 - Technologie des aliments pour animaux Q70 - Traitement des déchets agricoles tourteau de colza tourteau de tournesol Aspergillus niger acide phénolique hydrolase ester carboxylique hydrolyse enzymatique sous-produit d'huilerie http://aims.fao.org/aos/agrovoc/c_16027 http://aims.fao.org/aos/agrovoc/c_35709 http://aims.fao.org/aos/agrovoc/c_26373 http://aims.fao.org/aos/agrovoc/c_16197 http://aims.fao.org/aos/agrovoc/c_9617 http://aims.fao.org/aos/agrovoc/c_27512 http://aims.fao.org/aos/agrovoc/c_25402 http://aims.fao.org/aos/agrovoc/c_3081 |
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Q51 - Technologie des aliments pour animaux Q70 - Traitement des déchets agricoles tourteau de colza tourteau de tournesol Aspergillus niger acide phénolique hydrolase ester carboxylique hydrolyse enzymatique sous-produit d'huilerie http://aims.fao.org/aos/agrovoc/c_16027 http://aims.fao.org/aos/agrovoc/c_35709 http://aims.fao.org/aos/agrovoc/c_26373 http://aims.fao.org/aos/agrovoc/c_16197 http://aims.fao.org/aos/agrovoc/c_9617 http://aims.fao.org/aos/agrovoc/c_27512 http://aims.fao.org/aos/agrovoc/c_25402 http://aims.fao.org/aos/agrovoc/c_3081 Q51 - Technologie des aliments pour animaux Q70 - Traitement des déchets agricoles tourteau de colza tourteau de tournesol Aspergillus niger acide phénolique hydrolase ester carboxylique hydrolyse enzymatique sous-produit d'huilerie http://aims.fao.org/aos/agrovoc/c_16027 http://aims.fao.org/aos/agrovoc/c_35709 http://aims.fao.org/aos/agrovoc/c_26373 http://aims.fao.org/aos/agrovoc/c_16197 http://aims.fao.org/aos/agrovoc/c_9617 http://aims.fao.org/aos/agrovoc/c_27512 http://aims.fao.org/aos/agrovoc/c_25402 http://aims.fao.org/aos/agrovoc/c_3081 Laguna, Oscar Odinot, Elise Bisotto, Alexandra Baréa, Bruno Villeneuve, Pierre Sigoillot, Jean-Claude Record, Eric Faulds, Craig B. Fine, Frédéric Lesage-Meesen, Laurence Lomascolo, Anne Lecomte, Jérôme Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger |
description |
Sunflower and rapeseed meals are agro-industrial coproducts that contain high amount of phenolics (1–4 % dry matter), mostly as esters of caffeic acid (CA) and sinapic acid (SA), respectively. The enzymatic hydrolysis of the ester bonds enables to recover the corresponding free phenolic acids that are bioactive compounds and platform molecules for various applications in green chemistry. Here we aimed to find the best route for producing free CA and SA by applying various fungal carboxylic ester hydrolases from recombinant Aspergillus niger strains either directly on crude meal or on their phenolic extracts obtained by methanolic extraction. Two types of meals were studied: (i) industrial (commercial) meals (I-meals), produced by a process that includes cooking at 95–100 °C and steam desolventizing at 105–107 °C, and (ii) non-industrial meals (NI-meals) obtained at pilot-scale with much milder heat treatment, that offer a higher total phenolic content. CA release through hydrolysis of sunflower meal (SFM) was successfully achieved with A. niger type-B feruloyl esterase (AnFaeB) and chlorogenic acid esterase (ChlE). Maximal amount of free CA released was of 54.0 ± 1.1 to 59.8 ± 2.1 μmol/g defatted dry matter (DDM) from I-SFM (94–100% hydrolysis yield) against 42.0 ± 1.1 to 52.3 ± 0.2 μmol/g DDM (59–73% hydrolysis yield) from NI- SFM in which CA release was hampered by a phenolic oxidation side-reaction, seemingly due to meal endogenous polyphenol oxidase activities. AnFaeB and ChlE hydrolysis of phenolic extracts from NI-SFM increased the CA amount obtained to 55.0–68.1 μmol/g DDM (77–95% hydrolysis yield). In all cases, AnFaeB showed broader specificity towards SFM caffeoyl quinic acid isomers than ChlE. In particular, ChlE did not hydrolyze 3-O-caffeoylquinic acid. The maximal amount of free SA released by AnFaeA hydrolysis was 41.3 ± 0.3 μmol/g DDM from NI-SFM (50% hydrolysis yield) and 32.3 ± 0.4 μmol/g DDM from the phenolic extract (64% hydrolysis yield), with AnFaeA also having sinapine transesterification activity that led to the synthesis of 1,2-di-O-sinapoyl-β-D-glucose. Finally, of all the substrates tested for enzymatic hydrolysis in our conditions, I-RSM and NI-SFM extract showed the best compromise between initial total phenolic content, hydrolysis yields and amounts of CA/SA released. |
format |
article |
topic_facet |
Q51 - Technologie des aliments pour animaux Q70 - Traitement des déchets agricoles tourteau de colza tourteau de tournesol Aspergillus niger acide phénolique hydrolase ester carboxylique hydrolyse enzymatique sous-produit d'huilerie http://aims.fao.org/aos/agrovoc/c_16027 http://aims.fao.org/aos/agrovoc/c_35709 http://aims.fao.org/aos/agrovoc/c_26373 http://aims.fao.org/aos/agrovoc/c_16197 http://aims.fao.org/aos/agrovoc/c_9617 http://aims.fao.org/aos/agrovoc/c_27512 http://aims.fao.org/aos/agrovoc/c_25402 http://aims.fao.org/aos/agrovoc/c_3081 |
author |
Laguna, Oscar Odinot, Elise Bisotto, Alexandra Baréa, Bruno Villeneuve, Pierre Sigoillot, Jean-Claude Record, Eric Faulds, Craig B. Fine, Frédéric Lesage-Meesen, Laurence Lomascolo, Anne Lecomte, Jérôme |
author_facet |
Laguna, Oscar Odinot, Elise Bisotto, Alexandra Baréa, Bruno Villeneuve, Pierre Sigoillot, Jean-Claude Record, Eric Faulds, Craig B. Fine, Frédéric Lesage-Meesen, Laurence Lomascolo, Anne Lecomte, Jérôme |
author_sort |
Laguna, Oscar |
title |
Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger |
title_short |
Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger |
title_full |
Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger |
title_fullStr |
Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger |
title_full_unstemmed |
Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger |
title_sort |
release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from aspergillus niger |
url |
http://agritrop.cirad.fr/593311/ http://agritrop.cirad.fr/593311/1/Industrial%20Crops%20and%20Products_2019_139_111579.pdf |
work_keys_str_mv |
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dig-cirad-fr-5933112024-01-29T02:14:00Z http://agritrop.cirad.fr/593311/ http://agritrop.cirad.fr/593311/ Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger. Laguna Oscar, Odinot Elise, Bisotto Alexandra, Baréa Bruno, Villeneuve Pierre, Sigoillot Jean-Claude, Record Eric, Faulds Craig B., Fine Frédéric, Lesage-Meesen Laurence, Lomascolo Anne, Lecomte Jérôme. 2019. Industrial Crops and Products, 139:111579, 13 p.https://doi.org/10.1016/j.indcrop.2019.111579 <https://doi.org/10.1016/j.indcrop.2019.111579> Release of phenolic acids from sunflower and rapeseed meals using different carboxylic esters hydrolases from Aspergillus niger Laguna, Oscar Odinot, Elise Bisotto, Alexandra Baréa, Bruno Villeneuve, Pierre Sigoillot, Jean-Claude Record, Eric Faulds, Craig B. Fine, Frédéric Lesage-Meesen, Laurence Lomascolo, Anne Lecomte, Jérôme eng 2019 Industrial Crops and Products Q51 - Technologie des aliments pour animaux Q70 - Traitement des déchets agricoles tourteau de colza tourteau de tournesol Aspergillus niger acide phénolique hydrolase ester carboxylique hydrolyse enzymatique sous-produit d'huilerie http://aims.fao.org/aos/agrovoc/c_16027 http://aims.fao.org/aos/agrovoc/c_35709 http://aims.fao.org/aos/agrovoc/c_26373 http://aims.fao.org/aos/agrovoc/c_16197 http://aims.fao.org/aos/agrovoc/c_9617 http://aims.fao.org/aos/agrovoc/c_27512 http://aims.fao.org/aos/agrovoc/c_25402 France http://aims.fao.org/aos/agrovoc/c_3081 Sunflower and rapeseed meals are agro-industrial coproducts that contain high amount of phenolics (1–4 % dry matter), mostly as esters of caffeic acid (CA) and sinapic acid (SA), respectively. The enzymatic hydrolysis of the ester bonds enables to recover the corresponding free phenolic acids that are bioactive compounds and platform molecules for various applications in green chemistry. Here we aimed to find the best route for producing free CA and SA by applying various fungal carboxylic ester hydrolases from recombinant Aspergillus niger strains either directly on crude meal or on their phenolic extracts obtained by methanolic extraction. Two types of meals were studied: (i) industrial (commercial) meals (I-meals), produced by a process that includes cooking at 95–100 °C and steam desolventizing at 105–107 °C, and (ii) non-industrial meals (NI-meals) obtained at pilot-scale with much milder heat treatment, that offer a higher total phenolic content. CA release through hydrolysis of sunflower meal (SFM) was successfully achieved with A. niger type-B feruloyl esterase (AnFaeB) and chlorogenic acid esterase (ChlE). Maximal amount of free CA released was of 54.0 ± 1.1 to 59.8 ± 2.1 μmol/g defatted dry matter (DDM) from I-SFM (94–100% hydrolysis yield) against 42.0 ± 1.1 to 52.3 ± 0.2 μmol/g DDM (59–73% hydrolysis yield) from NI- SFM in which CA release was hampered by a phenolic oxidation side-reaction, seemingly due to meal endogenous polyphenol oxidase activities. AnFaeB and ChlE hydrolysis of phenolic extracts from NI-SFM increased the CA amount obtained to 55.0–68.1 μmol/g DDM (77–95% hydrolysis yield). In all cases, AnFaeB showed broader specificity towards SFM caffeoyl quinic acid isomers than ChlE. In particular, ChlE did not hydrolyze 3-O-caffeoylquinic acid. The maximal amount of free SA released by AnFaeA hydrolysis was 41.3 ± 0.3 μmol/g DDM from NI-SFM (50% hydrolysis yield) and 32.3 ± 0.4 μmol/g DDM from the phenolic extract (64% hydrolysis yield), with AnFaeA also having sinapine transesterification activity that led to the synthesis of 1,2-di-O-sinapoyl-β-D-glucose. Finally, of all the substrates tested for enzymatic hydrolysis in our conditions, I-RSM and NI-SFM extract showed the best compromise between initial total phenolic content, hydrolysis yields and amounts of CA/SA released. article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/593311/1/Industrial%20Crops%20and%20Products_2019_139_111579.pdf text Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1016/j.indcrop.2019.111579 10.1016/j.indcrop.2019.111579 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.indcrop.2019.111579 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1016/j.indcrop.2019.111579 |