Study of the effects of selected flavonoid compounds on sphingomyelin monolayers via the Langmuir method with Brewster angle microscopy

Study of the effects of selected flavonoid compounds on sphingomyelin monolayers via the Langmuir method with Brewster angle microscopy | 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 Article Study of the effects of selected flavonoid compounds on sphingomyelin monolayers via the Langmuir method with Brewster angle microscopy Katarzyna Karwowska, Paulina Laszuk, Wiesław Urbaniak, Aneta D. Petelska This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7214916/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract This study aimed to investigate the effects of selected flavonoids (myricetin and kaempferol) on sphingomyelin monolayers. We used the Langmuir method combined with Brewster angle microscopy in these studies. We described the interactions between the tested compounds. Using mathematical equations, we established that the examined flavonoids formed complexes with sphingomyelin at a 1:1 ratio, characterized by high stability constants. We derived the parameters characterizing pure and mixed monolayers (thermodynamic parameters) and the formed complexes (physicochemical parameters). During the formation of the tested monolayers, we also described the phase transitions that occur. The use of model biological membranes, such as Langmuir monolayers, enables various methods to determine several parameters, including the influence of bioactive components on the membrane surface, the surface compressibility modulus, the changes in the excess free energy, the excess surface area per molecule, and the specific surface area of the complex formed. The data presented in this work, obtained through mathematical derivation and confirmed experimentally, are highly important for interpreting phenomena that occur in lipid membranes. A quantitative description of equilibria between sphingomyelin and flavonoids enables us to understand the processes on the membrane surface. As shown in this work, flavonoids are incorporated into the lipid monolayer, significantly modifying its physicochemical properties. Biological sciences/Biochemistry Biological sciences/Biophysics Physical sciences/Chemistry lipid monolayer π-A isotherm flavonoids sphingomyelin kaempferol myricetin complex formation equilibria Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Full Text Additional Declarations No competing interests reported. Table 1 and 2 are available in the Supplementary Files section. Supplementary Files ListofTables.docx Table legends: Table 1. Summary of the measurement results for single-component monolayers. Table 2. Summary of the specific surface areas and durability constant values of the tested systems. Cite Share Download PDF Status: Posted Version 1 posted 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. 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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-7214916","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Article","associatedPublications":[],"authors":[{"id":523830880,"identity":"a3f8d51e-b41e-4b27-9381-64fc8cd52b2b","order_by":0,"name":"Katarzyna Karwowska","email":"","orcid":"","institution":"University of Bialystok","correspondingAuthor":false,"prefix":"","firstName":"Katarzyna","middleName":"","lastName":"Karwowska","suffix":""},{"id":523830881,"identity":"2802c30b-4745-4f40-a81e-3d514376685c","order_by":1,"name":"Paulina Laszuk","email":"","orcid":"","institution":"University of Bialystok","correspondingAuthor":false,"prefix":"","firstName":"Paulina","middleName":"","lastName":"Laszuk","suffix":""},{"id":523830885,"identity":"2e22dc4c-9f5c-4f2c-beca-193345dd127f","order_by":2,"name":"Wiesław Urbaniak","email":"","orcid":"","institution":"Kazimierz Wielki University","correspondingAuthor":false,"prefix":"","firstName":"Wiesław","middleName":"","lastName":"Urbaniak","suffix":""},{"id":523830886,"identity":"a21cbfa0-fd23-42f0-b79d-2dce6dfd174c","order_by":3,"name":"Aneta D. Petelska","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAvElEQVRIiWNgGAWjYNCCCgYGAyAlAcQyxKhnbGA4g9DCQ5wWxjZStPDPbj7+4Oe8w4nbGZgP3uZhuENYi8SdY4mNvdsOJ+5sYEu25mF4RoTDbuQYNvBuO5y74QCPmTQPw2HCWuRv5H9s/DsHpIX/G3FaDG7kMDbzNoBtYSNOi+GNNMPZMsfS63c2sxlbzjEgwi9yN5IffHxTY21szt788MabijtyBLUgADPYnQdI0AEFZGgZBaNgFIyCYQ8AYa09VMgxn2kAAAAASUVORK5CYII=","orcid":"","institution":"University of Bialystok","correspondingAuthor":true,"prefix":"","firstName":"Aneta","middleName":"D.","lastName":"Petelska","suffix":""}],"badges":[],"createdAt":"2025-07-25 13:53:19","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-7214916/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-7214916/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":92713443,"identity":"51e4b0be-ae49-4d94-9940-5e2d9caa25a8","added_by":"auto","created_at":"2025-10-03 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11:34:15","extension":"html","order_by":24,"title":"","display":"","copyAsset":false,"role":"acdc-reference","size":135504,"visible":true,"origin":"","legend":"","description":"","filename":"earlyproof.html","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/afbefa13694186963a0b4c16.html"},{"id":92712508,"identity":"0119a996-5a95-4cdb-8296-f9b3119b9891","added_by":"auto","created_at":"2025-10-03 11:34:14","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":40716,"visible":true,"origin":"","legend":"\u003cp\u003eIsotherms of the tested compounds: sphingomyelin, kaempferol, and myricetin (a) and the compressibility coefficients Cs\u003csup\u003e-1 \u003c/sup\u003e(b) calculated on their basis as a function of surface pressure π.\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/51dae90ad6c6df7633c60803.png"},{"id":92712509,"identity":"3c95c083-31b7-427e-8517-657f26aaaae0","added_by":"auto","created_at":"2025-10-03 11:34:14","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":90742,"visible":true,"origin":"","legend":"\u003cp\u003eIsotherms of monolayers of SM-K mixtures with different molar ratios (a) and the compressibility coefficients Cs\u003csup\u003e-1 \u003c/sup\u003e(b) calculated on their basis as a function of surface pressure π.\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/98a9d46b529821127cd34e70.png"},{"id":92713654,"identity":"8e8873f0-7649-40ed-8d36-c03543f3bff4","added_by":"auto","created_at":"2025-10-03 11:50:14","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":93342,"visible":true,"origin":"","legend":"\u003cp\u003eIsotherms of monolayers of SM-M mixtures with different molar ratios (a) and the compressibility coefficients Cs\u003csup\u003e-1\u003c/sup\u003e (b) calculated on their basis as a function of surface pressure π.\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/b0d7c9528db71b47461b4604.png"},{"id":92713655,"identity":"6122d144-5f6d-4a99-a164-9de60d7f0af5","added_by":"auto","created_at":"2025-10-03 11:50:15","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":76735,"visible":true,"origin":"","legend":"\u003cp\u003eMean molecular area (A\u003csub\u003e12\u003c/sub\u003e) vs. mixed monolayer composition plots for mixtures of K (a, x\u003csub\u003eK\u003c/sub\u003e) and M (b, x\u003csub\u003eM\u003c/sub\u003e) with SM at different constant surface pressures.\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/9ba9fddc83e0096f74f7add9.png"},{"id":92713445,"identity":"8a0d0849-c209-4686-8169-e7493a2db559","added_by":"auto","created_at":"2025-10-03 11:42:14","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":54510,"visible":true,"origin":"","legend":"\u003cp\u003eDependencies of the excess free enthalpy of mixing ΔG\u003csup\u003eexc\u003c/sup\u003e on the mole fractions of kaempferol (a) and myricetin (b) in a sphingomyelin monolayer at different surface pressures.\u003c/p\u003e","description":"","filename":"5.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/c2db5ff2aa79b05f9b48beff.png"},{"id":92712521,"identity":"0f4abd9f-d440-4126-969a-9fbfd37f2dca","added_by":"auto","created_at":"2025-10-03 11:34:15","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":192585,"visible":true,"origin":"","legend":"\u003cp\u003eBAM images taken for SM at surface pressure: (a) ~1 mN/m, (b) ~10 mN/m, (c) 20 mN/m, (d) π\u003csub\u003ecoll\u003c/sub\u003e.\u003c/p\u003e","description":"","filename":"6.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/951149d6ade478d34f2bad40.png"},{"id":92713451,"identity":"0a4d1c9d-b090-4123-838f-aeb117bf08ab","added_by":"auto","created_at":"2025-10-03 11:42:15","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":376614,"visible":true,"origin":"","legend":"\u003cp\u003eBAM images taken for SM-K (1:1) at surface pressure: (a) ~5.0 mN/m, (b) ~10 mN/m, (c) ~20 mN/m, (d) π\u003csub\u003ecoll \u003c/sub\u003eand for SM-M (1:1) at surface pressure: (e) ~5.0 mN/m, (f) ~10 mN/m, (g) ~20 mN/m, (h) π\u003csub\u003ecoll\u003c/sub\u003e.\u003c/p\u003e","description":"","filename":"7.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/662e7c6a39aa8cb6885a5daa.png"},{"id":92713447,"identity":"32d120fb-416a-4aae-8a2f-ca93d9b0a0b4","added_by":"auto","created_at":"2025-10-03 11:42:15","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":35790,"visible":true,"origin":"","legend":"\u003cp\u003eDependence of the total surface concentrations of SM (C\u003csub\u003eSM\u003c/sub\u003e) and K (C\u003csub\u003eK\u003c/sub\u003e) on the mole fraction of K (graph 8a) and the dependence of the total surface concentrations of SM (C\u003csub\u003eSM\u003c/sub\u003e) and M (C\u003csub\u003eM\u003c/sub\u003e) on the mole fraction of M (graph 8b).\u003c/p\u003e","description":"","filename":"8.png","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/fa6b1934618ca221419ff389.png"},{"id":93659924,"identity":"32439ce3-dc38-4067-8854-d4f3c32f3175","added_by":"auto","created_at":"2025-10-16 07:54:25","extension":"pdf","order_by":1,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":857940,"visible":true,"origin":"","legend":"","description":"","filename":"reviewedmanuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1_covered_af93a5e4-9424-4312-9e5e-21fdf945f958.pdf"},{"id":92712512,"identity":"b3830733-fec6-4e93-a240-5a76e5ead6cc","added_by":"auto","created_at":"2025-10-03 11:34:14","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":17083,"visible":true,"origin":"","legend":"\u003cp\u003eTable legends:\u003c/p\u003e\n\u003cp\u003eTable 1. Summary of the measurement results for single-component monolayers.\u003c/p\u003e\n\u003cp\u003eTable 2. Summary of the specific surface areas and durability constant values of the tested systems.\u003c/p\u003e","description":"","filename":"ListofTables.docx","url":"https://assets-eu.researchsquare.com/files/rs-7214916/v1/287981638bd3a2f3547362a9.docx"}],"financialInterests":"\u003cp\u003eNo competing interests reported.\u003c/p\u003e\n\u003cp\u003eTable 1 and 2 are available in the Supplementary Files section.\u003c/p\u003e","formattedTitle":"Study of the effects of selected flavonoid compounds on sphingomyelin monolayers via the Langmuir method with Brewster angle microscopy","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":true,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"lipid monolayer, π-A isotherm, flavonoids, sphingomyelin, kaempferol, myricetin, complex formation equilibria","lastPublishedDoi":"10.21203/rs.3.rs-7214916/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-7214916/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThis study aimed to investigate the effects of selected flavonoids (myricetin and kaempferol) on sphingomyelin monolayers. We used the Langmuir method combined with Brewster angle microscopy in these studies. We described the interactions between the tested compounds. Using mathematical equations, we established that the examined flavonoids formed complexes with sphingomyelin at a 1:1 ratio, characterized by high stability constants. We derived the parameters characterizing pure and mixed monolayers (thermodynamic parameters) and the formed complexes (physicochemical parameters). During the formation of the tested monolayers, we also described the phase transitions that occur. The use of model biological membranes, such as Langmuir monolayers, enables various methods to determine several parameters, including the influence of bioactive components on the membrane surface, the surface compressibility modulus, the changes in the excess free energy, the excess surface area per molecule, and the specific surface area of the complex formed. The data presented in this work, obtained through mathematical derivation and confirmed experimentally, are highly important for interpreting phenomena that occur in lipid membranes. A quantitative description of equilibria between sphingomyelin and flavonoids enables us to understand the processes on the membrane surface. As shown in this work, flavonoids are incorporated into the lipid monolayer, significantly modifying its physicochemical properties.\u003c/p\u003e","manuscriptTitle":"Study of the effects of selected flavonoid compounds on sphingomyelin monolayers via the Langmuir method with Brewster angle microscopy","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-10-03 11:34:10","doi":"10.21203/rs.3.rs-7214916/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"5deac0ea-c902-47ac-9f03-1bff0e5337c0","owner":[],"postedDate":"October 3rd, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[{"id":55675885,"name":"Biological sciences/Biochemistry"},{"id":55675886,"name":"Biological sciences/Biophysics"},{"id":55675887,"name":"Physical sciences/Chemistry"}],"tags":[],"updatedAt":"2025-10-16T07:54:01+00:00","versionOfRecord":[],"versionCreatedAt":"2025-10-03 11:34:10","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-7214916","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-7214916","identity":"rs-7214916","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}