Synthesis of naringin 6"-ricinoleate using immobilized lipase
Abstract Background Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to...
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ftdoajarticles:oai:doaj.org/article:737fefda52764dafaaeaf77e42cb6a6c 2023-05-15T13:50:25+02:00 Synthesis of naringin 6"-ricinoleate using immobilized lipase Almeida Verônica M Branco Carla RC Assis Sandra A Vieira Ivo JC Braz-Filho Raimundo Branco Alexsandro 2012-05-01T00:00:00Z https://doi.org/10.1186/1752-153X-6-41 https://doaj.org/article/737fefda52764dafaaeaf77e42cb6a6c EN eng BMC http://journal.chemistrycentral.com/content/6/1/41 https://doaj.org/toc/1752-153X doi:10.1186/1752-153X-6-41 1752-153X https://doaj.org/article/737fefda52764dafaaeaf77e42cb6a6c Chemistry Central Journal, Vol 6, Iss 1, p 41 (2012) Chemistry QD1-999 article 2012 ftdoajarticles https://doi.org/10.1186/1752-153X-6-41 2022-12-31T08:27:55Z Abstract Background Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to the flavonoid sugar unit using immobilized lipase. However, there is limited research regarding hydroxylation of unsaturated fatty acids as an answer to the low solubility challenge. In this work, we describe the reaction of naringin with castor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica . Analysis of the 1 H and 13 C NMR (1D and 2D) spectra and literature comparison were used to characterise the obtained acyl derivative. Results After allowing the reaction to continue for 120 hours (in acetone media, 50°C), the major product obtained was naringin 6″-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6″-ricinoleate was determined using NMR analysis, including bidimensional (2D) experiments. Conclusion Using immobilized lipase from C. antarctica , the best conversion reaction was observed using castor oil containing ricinoleic acid as the acylating agent rather than an isolated fatty acid. Graphical abstract <display-formula><graphic file="1752-153X-6-41-i1.gif"/></display-formula> Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Chemistry Central Journal 6 1 |
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Chemistry QD1-999 |
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Chemistry QD1-999 Almeida Verônica M Branco Carla RC Assis Sandra A Vieira Ivo JC Braz-Filho Raimundo Branco Alexsandro Synthesis of naringin 6"-ricinoleate using immobilized lipase |
topic_facet |
Chemistry QD1-999 |
description |
Abstract Background Naringin is an important flavanone with several biological activities, including antioxidant action. However, this compound shows low solubility in lipophilic preparations, such as is used in the cosmetic and food industries. One way to solve this problem is to add fatty acids to the flavonoid sugar unit using immobilized lipase. However, there is limited research regarding hydroxylation of unsaturated fatty acids as an answer to the low solubility challenge. In this work, we describe the reaction of naringin with castor oil containing ricinoleic acid, castor oil's major fatty acid component, using immobilized lipase from Candida antarctica . Analysis of the 1 H and 13 C NMR (1D and 2D) spectra and literature comparison were used to characterise the obtained acyl derivative. Results After allowing the reaction to continue for 120 hours (in acetone media, 50°C), the major product obtained was naringin 6″-ricinoleate. In this reaction, either castor oil or pure ricinoleic acid was used as the acylating agent, providing a 33% or 24% yield, respectively. The chemical structure of naringin 6″-ricinoleate was determined using NMR analysis, including bidimensional (2D) experiments. Conclusion Using immobilized lipase from C. antarctica , the best conversion reaction was observed using castor oil containing ricinoleic acid as the acylating agent rather than an isolated fatty acid. Graphical abstract <display-formula><graphic file="1752-153X-6-41-i1.gif"/></display-formula> |
format |
Article in Journal/Newspaper |
author |
Almeida Verônica M Branco Carla RC Assis Sandra A Vieira Ivo JC Braz-Filho Raimundo Branco Alexsandro |
author_facet |
Almeida Verônica M Branco Carla RC Assis Sandra A Vieira Ivo JC Braz-Filho Raimundo Branco Alexsandro |
author_sort |
Almeida Verônica M |
title |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_short |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_full |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_fullStr |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_full_unstemmed |
Synthesis of naringin 6"-ricinoleate using immobilized lipase |
title_sort |
synthesis of naringin 6"-ricinoleate using immobilized lipase |
publisher |
BMC |
publishDate |
2012 |
url |
https://doi.org/10.1186/1752-153X-6-41 https://doaj.org/article/737fefda52764dafaaeaf77e42cb6a6c |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Chemistry Central Journal, Vol 6, Iss 1, p 41 (2012) |
op_relation |
http://journal.chemistrycentral.com/content/6/1/41 https://doaj.org/toc/1752-153X doi:10.1186/1752-153X-6-41 1752-153X https://doaj.org/article/737fefda52764dafaaeaf77e42cb6a6c |
op_doi |
https://doi.org/10.1186/1752-153X-6-41 |
container_title |
Chemistry Central Journal |
container_volume |
6 |
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1 |
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1766253487166849024 |