Synthesis of new multifunctional linolenic acid vanillyl ester and investigation of antioxidant and antibacterial activities

Synthesis of new multifunctional linolenic acid vanillyl ester and investigation of antioxidant and antibacterial activities | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Synthesis of new multifunctional linolenic acid vanillyl ester and investigation of antioxidant and antibacterial activities Jennifer Indra Marvella, Hyung-Kwoun Kim This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4001763/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 22 Apr, 2024 Read the published version in Applied Biochemistry and Biotechnology → Version 1 posted 3 You are reading this latest preprint version 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 developing 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. linolenic acid vanillyl ester antioxidant antibacterial lipase transesterification Full Text Supplementary Files SupplementaryFigure.pptx Cite Share Download PDF Status: Published Journal Publication published 22 Apr, 2024 Read the published version in Applied Biochemistry and Biotechnology → Version 1 posted Reviewers agreed at journal 06 Mar, 2024 Reviewers invited by journal 06 Mar, 2024 First submitted to journal 29 Feb, 2024 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-4001763","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":276658480,"identity":"93749236-e270-49b3-9f2f-de44bfd113ce","order_by":0,"name":"Jennifer Indra Marvella","email":"","orcid":"","institution":"Atma Jaya Catholic University of Indonesia - Semanggi Campus: Universitas Katolik Indonesia Atma Jaya","correspondingAuthor":false,"prefix":"","firstName":"Jennifer","middleName":"Indra","lastName":"Marvella","suffix":""},{"id":276658481,"identity":"3792e137-9888-4530-a715-93a43739eaa4","order_by":1,"name":"Hyung-Kwoun Kim","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA2UlEQVRIiWNgGAWjYBACAx42hgMMFUCWBAPjgQSwGBsxWs4wMPBIMDAQr4WBsQ2qhYEYLeY8xxIP3ZxnJ28v3XzgwIMaBnn+Bra0D/i0WPa2HTicuy3ZsEfmWMKBhGMMhjMOsB2egddh59kbgFoOMPZI5BgcSGxgYNzAwN6M3y9gLXMO2MO02BPWchbksIYDiTAtiRsY2A7j13LmWMLhnGPJyT030kB+kUiecZgtmYCWNOPPOTV2tu0zkg8+/FFjY9vf3maMVws6AMYOM0kaRsEoGAWjYBRgAwBSTU1BnHZx8QAAAABJRU5ErkJggg==","orcid":"https://orcid.org/0000-0002-7685-0904","institution":"The Catholic University of Korea","correspondingAuthor":true,"prefix":"","firstName":"Hyung-Kwoun","middleName":"","lastName":"Kim","suffix":""}],"badges":[],"createdAt":"2024-03-01 02:25:23","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-4001763/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-4001763/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1007/s12010-024-04945-z","type":"published","date":"2024-04-22T23:07:51+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":55691182,"identity":"075499c4-597f-40c6-aea7-831c9d1c0042","added_by":"auto","created_at":"2024-05-01 23:07:59","extension":"pdf","order_by":1,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":584728,"visible":true,"origin":"","legend":"","description":"","filename":"manuscriptABB20240301.pdf","url":"https://assets-eu.researchsquare.com/files/rs-4001763/v1_covered_c5d66b2b-6b86-4f30-89d6-fd99a1cde36c.pdf"},{"id":52314093,"identity":"1334edbc-10c8-4d30-97f7-64a8c037ff70","added_by":"auto","created_at":"2024-03-08 22:51:56","extension":"pptx","order_by":5,"title":"","display":"","copyAsset":false,"role":"supplement","size":167344,"visible":true,"origin":"","legend":"","description":"","filename":"SupplementaryFigure.pptx","url":"https://assets-eu.researchsquare.com/files/rs-4001763/v1/c7ee908d80e0495d4a2ee72e.pptx"}],"financialInterests":"","formattedTitle":"Synthesis of new multifunctional linolenic acid vanillyl ester and investigation of antioxidant and antibacterial activities","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":true,"isPdf":true,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"applied-biochemistry-and-biotechnology","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"abab","sideBox":"Learn more about [Applied Biochemistry and Biotechnology](https://www.springer.com/journal/12010)","snPcode":"12010","submissionUrl":"https://submission.nature.com/new-submission/12010/3","title":"Applied Biochemistry and Biotechnology","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"linolenic acid vanillyl ester, antioxidant, antibacterial, lipase, transesterification","lastPublishedDoi":"10.21203/rs.3.rs-4001763/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-4001763/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eVanillyl 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 developing 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. 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