Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i>
The <i>p</i>-methoxycinnamic acid (<i>p</i>-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 neur...
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MDPI AG
2020-10-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/10/10/1181 |
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| author | Magdalena Rychlicka Anna Gliszczyńska |
| author_facet | Magdalena Rychlicka Anna Gliszczyńska |
| author_sort | Magdalena Rychlicka |
| collection | DOAJ |
| description | The <i>p</i>-methoxycinnamic acid (<i>p</i>-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 <i>p</i>-methoxycinnamic acid, which can play a role of new nutraceuticals. We developed and optimized enzymatic interesterification of phosphatidylcholine (PC) with ethyl <i>p</i>-methoxycinnamate (E<i>p</i>-MCA). Novozym 435 and a binary solvent system of toluene/chloroform 9:1 (<i>v</i>/<i>v</i>) were found to be the effective biocatalyst and reaction medium for the synthesis of structured <i>p</i>-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 <i>p</i>-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 <i>p</i>-methoxycinnamoylated phospholipids. The optimum conditions were: Reaction time of three days, 30% (<i>w</i>/<i>w</i>) of Novozym 435, and 1/10 substrate molar ratio PC/E<i>p</i>-MCA. Under these parameters, <i>p</i>-methoxycinnamoylated lysophosphatidylcholine (<i>p</i>-MCA-LPC) and <i>p</i>-methoxycinnamoylated phosphatidylcholine (<i>p</i>-MCA-PC) were obtained in isolated yields of 32% and 3% (<i>w</i>/<i>w</i>), respectively. |
| first_indexed | 2024-03-10T15:38:14Z |
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| id | doaj.art-25b121312b654dc696e1c3ae39e33088 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T15:38:14Z |
| publishDate | 2020-10-01 |
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| spelling | doaj.art-25b121312b654dc696e1c3ae39e330882023-11-20T17:03:13ZengMDPI AGCatalysts2073-43442020-10-011010118110.3390/catal10101181Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i>Magdalena Rychlicka0Anna Gliszczyńska1Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandThe <i>p</i>-methoxycinnamic acid (<i>p</i>-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 <i>p</i>-methoxycinnamic acid, which can play a role of new nutraceuticals. We developed and optimized enzymatic interesterification of phosphatidylcholine (PC) with ethyl <i>p</i>-methoxycinnamate (E<i>p</i>-MCA). Novozym 435 and a binary solvent system of toluene/chloroform 9:1 (<i>v</i>/<i>v</i>) were found to be the effective biocatalyst and reaction medium for the synthesis of structured <i>p</i>-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 <i>p</i>-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 <i>p</i>-methoxycinnamoylated phospholipids. The optimum conditions were: Reaction time of three days, 30% (<i>w</i>/<i>w</i>) of Novozym 435, and 1/10 substrate molar ratio PC/E<i>p</i>-MCA. Under these parameters, <i>p</i>-methoxycinnamoylated lysophosphatidylcholine (<i>p</i>-MCA-LPC) and <i>p</i>-methoxycinnamoylated phosphatidylcholine (<i>p</i>-MCA-PC) were obtained in isolated yields of 32% and 3% (<i>w</i>/<i>w</i>), respectively.https://www.mdpi.com/2073-4344/10/10/1181egg-yolk phosphatidylcholine<i>p</i>-methoxycinnamic acidlipase-catalyzed interesterificationNovozym 435methoxy derivatives of phenolic acids |
| spellingShingle | Magdalena Rychlicka Anna Gliszczyńska Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i> Catalysts egg-yolk phosphatidylcholine <i>p</i>-methoxycinnamic acid lipase-catalyzed interesterification Novozym 435 methoxy derivatives of phenolic acids |
| title | Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i> |
| title_full | Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i> |
| title_fullStr | Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i> |
| title_full_unstemmed | Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i> |
| title_short | Interesterification of Egg-Yolk Phosphatidylcholine with <i>p</i>-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from <i>Candida Antarctica</i> |
| title_sort | interesterification of egg yolk phosphatidylcholine with i p i methoxycinnamic acid catalyzed by immobilized lipase b from i candida antarctica i |
| topic | egg-yolk phosphatidylcholine <i>p</i>-methoxycinnamic acid lipase-catalyzed interesterification Novozym 435 methoxy derivatives of phenolic acids |
| url | https://www.mdpi.com/2073-4344/10/10/1181 |
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