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Synthesis of New Multifunctional Linolenic Acid Vanillyl Ester and Investigation of Antioxidant and Antibacterial Activities

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Abstract

Vanillyl alcohol (VA) possesses potent antioxidant activity, yet its applicability is hindered by its limited solubility in emulsions or non-polar organic solvents. Conversely, long-chain polyunsaturated fatty acids exhibit antibacterial properties. The combination of these compounds offers the prospect of develo** novel phenolic lipid compounds with dual antioxidant and antibacterial activities, alongside enhanced solubility capabilities. In this investigation, linolenic acid vanillyl ester (LAVE) was synthesized from VA and linseed oil (LO) through a transesterification reaction employing immobilized lipase. Optimization of LAVE production was achieved by varying reaction temperature, substrate concentration, and reaction time. LAVE demonstrated efficacy in scavenging both 2,2-diphenyl-1-picryhydrazyl and 2,2'-azino-bis (3-ethylbenthiazoline-6-sulphonic acid) radicals in organic solvents. Antioxidant testing via lipid oxidation analysis revealed that LAVE, when distributed within emulsions, effectively impeded the formation of conjugated dienes and conjugated trienes. Furthermore, LAVE exhibited antibacterial activity against four strains of spoilage bacteria: Bacillus subtilis, Bacillus coagulans, Pseudomonas fluorescens, and Alcaligenes faecalis. Zeta potential analysis substantiated the binding of LAVE to the bacterial cell surface. Propidium iodide uptake assay and fluorescence microscopy further elucidated that LAVE induces cell lysis by augmenting membrane permeability.

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Data Availability

The data that support the findings of this study are available from the corresponding author, [Kim, H. K.], upon reasonable request.

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Funding

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2022R1F1A1062029). This work was also supported by the Research Fund 2023 of The Catholic University of Korea.

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Authors and Affiliations

  1. Division of Biotechnology, the Catholic University of Korea, Bucheon, 420-743, Republic of Korea

    Jennifer Indra Marvella & Hyung Kwoun Kim

  2. Faculty of Biotechnology, Atma Jaya Catholic University of Indonesia, Jalan Jenderal Sudirman 51, Jakarta Selatan, 12930, Indonesia

    Jennifer Indra Marvella

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  1. Jennifer Indra Marvella
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by Jennifer Indra Marvella and Hyung Kwoun Kim. The first draft of the manuscript was written by Jennifer Indra Marvella and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Hyung Kwoun Kim.

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Marvella, J.I., Kim, H.K. Synthesis of New Multifunctional Linolenic Acid Vanillyl Ester and Investigation of Antioxidant and Antibacterial Activities. Appl Biochem Biotechnol (2024). https://doi.org/10.1007/s12010-024-04945-z

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