Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica
The p -methoxycinnamic acid ( p -MCA) is one of the most popular phenylpropanoids, the beneficial impact of which on the human health is well documented in the literature. This compound has shown many valuable activities including anticancer, antidiabetic, and neuro- and hepatoprotective. However, i...
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ftdoajarticles:oai:doaj.org/article:25b121312b654dc696e1c3ae39e33088 2023-05-15T13:35:02+02:00 Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica Magdalena Rychlicka Anna Gliszczyńska 2020-10-01T00:00:00Z https://doi.org/10.3390/catal10101181 https://doaj.org/article/25b121312b654dc696e1c3ae39e33088 EN eng MDPI AG https://www.mdpi.com/2073-4344/10/10/1181 https://doaj.org/toc/2073-4344 doi:10.3390/catal10101181 2073-4344 https://doaj.org/article/25b121312b654dc696e1c3ae39e33088 Catalysts, Vol 10, Iss 1181, p 1181 (2020) egg-yolk phosphatidylcholine p -methoxycinnamic acid lipase-catalyzed interesterification Novozym 435 methoxy derivatives of phenolic acids Chemical technology TP1-1185 Chemistry QD1-999 article 2020 ftdoajarticles https://doi.org/10.3390/catal10101181 2022-12-31T09:45:53Z The p -methoxycinnamic acid ( p -MCA) is one of the most popular phenylpropanoids, the beneficial impact of which on the human health is well documented in the literature. This compound has shown many valuable activities including anticancer, antidiabetic, and neuro- and hepatoprotective. However, its practical application is limited by its low bioavailability resulting from rapid metabolism in the human body. The latest strategy, aimed at overcoming these limitations, is based on the production of more stability in systemic circulation bioconjugates with phospholipids. Therefore, the aim of this research was to develop the biotechnological method for the synthesis of phospholipid derivatives of p -methoxycinnamic acid, which can play a role of new nutraceuticals. We developed and optimized enzymatic interesterification of phosphatidylcholine (PC) with ethyl p -methoxycinnamate (E p -MCA). Novozym 435 and a binary solvent system of toluene/chloroform 9:1 (v/v) were found to be the effective biocatalyst and reaction medium for the synthesis of structured p -MCA phospholipids, respectively. The effects of the other reaction parameters, such as substrate molar ratio, enzyme dosage, and reaction time, on the degree of incorporation of p -MCA into PC were evaluated by use of an experimental factorial design method. The results showed that substrate molar ratio and biocatalyst load have significant effects on the synthesis of p -methoxycinnamoylated phospholipids. The optimum conditions were: Reaction time of three days, 30% (w/w) of Novozym 435, and 1/10 substrate molar ratio PC/E p -MCA. Under these parameters, p -methoxycinnamoylated lysophosphatidylcholine ( p -MCA-LPC) and p -methoxycinnamoylated phosphatidylcholine ( p -MCA-PC) were obtained in isolated yields of 32% and 3% (w/w), respectively. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Catalysts 10 10 1181 |
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English |
topic |
egg-yolk phosphatidylcholine p -methoxycinnamic acid lipase-catalyzed interesterification Novozym 435 methoxy derivatives of phenolic acids Chemical technology TP1-1185 Chemistry QD1-999 |
spellingShingle |
egg-yolk phosphatidylcholine p -methoxycinnamic acid lipase-catalyzed interesterification Novozym 435 methoxy derivatives of phenolic acids Chemical technology TP1-1185 Chemistry QD1-999 Magdalena Rychlicka Anna Gliszczyńska Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica |
topic_facet |
egg-yolk phosphatidylcholine p -methoxycinnamic acid lipase-catalyzed interesterification Novozym 435 methoxy derivatives of phenolic acids Chemical technology TP1-1185 Chemistry QD1-999 |
description |
The p -methoxycinnamic acid ( p -MCA) is one of the most popular phenylpropanoids, the beneficial impact of which on the human health is well documented in the literature. This compound has shown many valuable activities including anticancer, antidiabetic, and neuro- and hepatoprotective. However, its practical application is limited by its low bioavailability resulting from rapid metabolism in the human body. The latest strategy, aimed at overcoming these limitations, is based on the production of more stability in systemic circulation bioconjugates with phospholipids. Therefore, the aim of this research was to develop the biotechnological method for the synthesis of phospholipid derivatives of p -methoxycinnamic acid, which can play a role of new nutraceuticals. We developed and optimized enzymatic interesterification of phosphatidylcholine (PC) with ethyl p -methoxycinnamate (E p -MCA). Novozym 435 and a binary solvent system of toluene/chloroform 9:1 (v/v) were found to be the effective biocatalyst and reaction medium for the synthesis of structured p -MCA phospholipids, respectively. The effects of the other reaction parameters, such as substrate molar ratio, enzyme dosage, and reaction time, on the degree of incorporation of p -MCA into PC were evaluated by use of an experimental factorial design method. The results showed that substrate molar ratio and biocatalyst load have significant effects on the synthesis of p -methoxycinnamoylated phospholipids. The optimum conditions were: Reaction time of three days, 30% (w/w) of Novozym 435, and 1/10 substrate molar ratio PC/E p -MCA. Under these parameters, p -methoxycinnamoylated lysophosphatidylcholine ( p -MCA-LPC) and p -methoxycinnamoylated phosphatidylcholine ( p -MCA-PC) were obtained in isolated yields of 32% and 3% (w/w), respectively. |
format |
Article in Journal/Newspaper |
author |
Magdalena Rychlicka Anna Gliszczyńska |
author_facet |
Magdalena Rychlicka Anna Gliszczyńska |
author_sort |
Magdalena Rychlicka |
title |
Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica |
title_short |
Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica |
title_full |
Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica |
title_fullStr |
Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica |
title_full_unstemmed |
Interesterification of Egg-Yolk Phosphatidylcholine with p -Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica |
title_sort |
interesterification of egg-yolk phosphatidylcholine with p -methoxycinnamic acid catalyzed by immobilized lipase b from candida antarctica |
publisher |
MDPI AG |
publishDate |
2020 |
url |
https://doi.org/10.3390/catal10101181 https://doaj.org/article/25b121312b654dc696e1c3ae39e33088 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Catalysts, Vol 10, Iss 1181, p 1181 (2020) |
op_relation |
https://www.mdpi.com/2073-4344/10/10/1181 https://doaj.org/toc/2073-4344 doi:10.3390/catal10101181 2073-4344 https://doaj.org/article/25b121312b654dc696e1c3ae39e33088 |
op_doi |
https://doi.org/10.3390/catal10101181 |
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Catalysts |
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