Design, synthesis, and antifungal activity of 14-aryloxy/amide substituted andrographolide derivatives

preprint OA: closed CC-BY-4.0
📄 Open PDF Full text JSON View at publisher

Abstract

Abstract In order to find more compounds with antifungal activities, a series of new compounds were designed and synthesized using the natural product of diterpenoid lactones, andrographolide, as the parent nucleus. Target compounds were identified by 1 H NMR, 13 C NMR and/or HR-MS. The results of antifungal activity showed that the antifungal activities of 4d against 6 tested fungi were all more than 60% at 100 μg/mL, and the inhibitory activity of 4d against the 6 tested fungi than the positive control Kresoxim-methyl. SEM test showed that 4d could damage the mycelia of P. piricola. obviously. Moreover, 4d had no effect on cowpea seed germination, showing high safety.
Full text 13,306 characters · extracted from preprint-html · click to expand
Design, synthesis, and antifungal activity of 14-aryloxy/amide substituted andrographolide derivatives | 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 Design, synthesis, and antifungal activity of 14-aryloxy/amide substituted andrographolide derivatives Zhuyun Liu, Shanshan Yang, Jieru Ma, Yunying Sha, Yuyan Zhou, and 2 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7031196/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 25 Nov, 2025 Read the published version in Scientific Reports → Version 1 posted 11 You are reading this latest preprint version Abstract In order to find more compounds with antifungal activities, a series of new compounds were designed and synthesized using the natural product of diterpenoid lactones, andrographolide, as the parent nucleus. Target compounds were identified by 1 H NMR, 13 C NMR and/or HR-MS. The results of antifungal activity showed that the antifungal activities of 4d against 6 tested fungi were all more than 60% at 100 μg/mL, and the inhibitory activity of 4d against the 6 tested fungi than the positive control Kresoxim-methyl. SEM test showed that 4d could damage the mycelia of P. piricola. obviously. Moreover, 4d had no effect on cowpea seed germination, showing high safety. Biological sciences/Biochemistry Biological sciences/Biotechnology Biological sciences/Drug discovery Biological sciences/Microbiology Biological sciences/Plant sciences Full Text Additional Declarations No competing interests reported. Supplementary Files Supportinginformation.pdf Cite Share Download PDF Status: Published Journal Publication published 25 Nov, 2025 Read the published version in Scientific Reports → Version 1 posted Editorial decision: Revision requested 30 Sep, 2025 Reviews received at journal 21 Sep, 2025 Reviewers agreed at journal 12 Sep, 2025 Reviews received at journal 11 Sep, 2025 Reviewers agreed at journal 07 Sep, 2025 Reviewers agreed at journal 22 Aug, 2025 Reviewers invited by journal 21 Aug, 2025 Editor assigned by journal 21 Aug, 2025 Editor invited by journal 06 Aug, 2025 Submission checks completed at journal 09 Jul, 2025 First submitted to journal 09 Jul, 2025 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. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. 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-7031196","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Article","associatedPublications":[],"authors":[{"id":506068101,"identity":"299ee581-1ec9-41d4-bd31-300f95f75760","order_by":0,"name":"Zhuyun Liu","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAv0lEQVRIiWNgGAWjYBACPnYwZWPHz8x8+AFRWtiYwVRasmQ7W5oBKVoOM244z6MgQaQW9sefeduYmY0P8zAYMNTYRBNjS4Ixbxsbn9lh3gMPGI6l5TYQoeVAMm8bD7PZYb4EA8aGw8RoASrjbZNg3NzMYyBBpBZmxmbeNgPGDczEawHaM+dcQrLEYWAgJxDjF3729scf3pT9t+PvP3z4wYcaG8JaQICJlw3KSiBGOQgw/vhDrNJRMApGwSgYkQAAkHo0xJoVgkoAAAAASUVORK5CYII=","orcid":"","institution":"Taizhou Polytechnic College","correspondingAuthor":true,"prefix":"","firstName":"Zhuyun","middleName":"","lastName":"Liu","suffix":""},{"id":506068102,"identity":"edd5fbb2-21c3-44d4-8385-b0af4baf3a12","order_by":1,"name":"Shanshan Yang","email":"","orcid":"","institution":"Taizhou Polytechnic College","correspondingAuthor":false,"prefix":"","firstName":"Shanshan","middleName":"","lastName":"Yang","suffix":""},{"id":506068103,"identity":"5362acc0-2926-4300-9d1f-c70ad8ef268e","order_by":2,"name":"Jieru Ma","email":"","orcid":"","institution":"Taizhou Polytechnic College","correspondingAuthor":false,"prefix":"","firstName":"Jieru","middleName":"","lastName":"Ma","suffix":""},{"id":506068104,"identity":"73a9a9ba-9c2b-45f1-975c-e4293d3e54da","order_by":3,"name":"Yunying Sha","email":"","orcid":"","institution":"Taizhou Polytechnic College","correspondingAuthor":false,"prefix":"","firstName":"Yunying","middleName":"","lastName":"Sha","suffix":""},{"id":506068105,"identity":"a4c15ebb-9caf-48ca-868a-6e7900f497bc","order_by":4,"name":"Yuyan Zhou","email":"","orcid":"","institution":"Taizhou Polytechnic College","correspondingAuthor":false,"prefix":"","firstName":"Yuyan","middleName":"","lastName":"Zhou","suffix":""},{"id":506068107,"identity":"398ab305-423d-4dd8-846b-c4b1d8496fef","order_by":5,"name":"Zhuqing Liu","email":"","orcid":"","institution":"Taizhou People’s Hospital","correspondingAuthor":false,"prefix":"","firstName":"Zhuqing","middleName":"","lastName":"Liu","suffix":""},{"id":506068109,"identity":"8d8aa2c6-ac3a-49e2-a7b7-37e91881b2f7","order_by":6,"name":"Lizhong Wang","email":"","orcid":"","institution":"Taizhou Polytechnic College","correspondingAuthor":false,"prefix":"","firstName":"Lizhong","middleName":"","lastName":"Wang","suffix":""}],"badges":[],"createdAt":"2025-07-02 16:08:18","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-7031196/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-7031196/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1038/s41598-025-25907-3","type":"published","date":"2025-11-25T15:58:06+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":97178470,"identity":"c4802c20-6b40-48a1-b9cc-21ea17b9f096","added_by":"auto","created_at":"2025-12-01 16:10:24","extension":"pdf","order_by":1,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":1176026,"visible":true,"origin":"","legend":"","description":"","filename":"Manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-7031196/v1_covered_52760236-66fa-4d67-a76c-ee0fde0d62a6.pdf"},{"id":90152414,"identity":"c6d82a3d-b190-4d86-bec2-5ba9b8658247","added_by":"auto","created_at":"2025-08-29 07:27:06","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"supplement","size":4900448,"visible":true,"origin":"","legend":"","description":"","filename":"Supportinginformation.pdf","url":"https://assets-eu.researchsquare.com/files/rs-7031196/v1/cc1daee17551f8771dfa36e6.pdf"}],"financialInterests":"No competing interests reported.","formattedTitle":"Design, synthesis, and antifungal activity of 14-aryloxy/amide substituted andrographolide derivatives","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":false,"isPdf":true,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"","lastPublishedDoi":"10.21203/rs.3.rs-7031196/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-7031196/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"In order to find more compounds with antifungal activities, a series of new compounds were designed and synthesized using the natural product of diterpenoid lactones, andrographolide, as the parent nucleus. Target compounds were identified by 1 H NMR, 13 C NMR and/or HR-MS. The results of antifungal activity showed that the antifungal activities of 4d against 6 tested fungi were all more than 60% at 100 μg/mL, and the inhibitory activity of 4d against the 6 tested fungi than the positive control Kresoxim-methyl. SEM test showed that 4d could damage the mycelia of P. piricola. obviously. Moreover, 4d had no effect on cowpea seed germination, showing high safety.","manuscriptTitle":"Design, synthesis, and antifungal activity of 14-aryloxy/amide substituted andrographolide derivatives","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-08-29 07:27:01","doi":"10.21203/rs.3.rs-7031196/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-09-30T08:13:52+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-09-21T20:13:07+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"179621490668360876729658949002881848871","date":"2025-09-12T17:57:42+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-09-11T09:31:35+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"40418574321243597714145010857558843691","date":"2025-09-07T12:03:28+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"294922543557221414538053997085034410588","date":"2025-08-23T00:01:39+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-08-21T11:32:57+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-08-21T06:48:20+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"","date":"2025-08-06T06:36:25+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-07-09T04:05:49+00:00","index":"","fulltext":""},{"type":"submitted","content":"Scientific Reports","date":"2025-07-09T04:04:33+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"e1b75636-daf2-4c74-bfaa-9e6a33f2f43a","owner":[],"postedDate":"August 29th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[{"id":53755011,"name":"Biological sciences/Biochemistry"},{"id":53755012,"name":"Biological sciences/Biotechnology"},{"id":53755013,"name":"Biological sciences/Drug discovery"},{"id":53755014,"name":"Biological sciences/Microbiology"},{"id":53755015,"name":"Biological sciences/Plant sciences"}],"tags":[],"updatedAt":"2025-12-01T16:03:09+00:00","versionOfRecord":{"articleIdentity":"rs-7031196","link":"https://doi.org/10.1038/s41598-025-25907-3","journal":{"identity":"scientific-reports","isVorOnly":false,"title":"Scientific Reports"},"publishedOn":"2025-11-25 15:58:06","publishedOnDateReadable":"November 25th, 2025"},"versionCreatedAt":"2025-08-29 07:27:01","video":"","vorDoi":"10.1038/s41598-025-25907-3","vorDoiUrl":"https://doi.org/10.1038/s41598-025-25907-3","workflowStages":[]},"version":"v1","identity":"rs-7031196","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-7031196","identity":"rs-7031196","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}

Text is read by the "Ask this paper" AI Q&A widget below. Extraction quality varies by source — PMC NXML preserves structure cleanly, OA-HTML may include some navigation residue, and OA-PDF can have broken hyphenation. The publisher copy (via DOI) is the canonical version.

My notes (saved in your browser only)

Ask this paper AI returns verbatim quotes from the full text · source: preprint-html

Answers must be backed by verbatim quotes from this paper's full text. Hallucinated quotes are dropped automatically; if no verbatim passage answers the question, we say so. How this works

Citation neighborhood (no data yet)

We don't have any in-corpus citations linked to this paper yet. This is a recent paper (2025) — citers typically take a year or two to land, and the OpenAlex reference graph may still be filling in.

Source provenance

europepmc
last seen: 2026-05-20T01:45:00.602351+00:00
unpaywall
last seen: 2026-05-22T02:00:06.705733+00:00
License: CC-BY-4.0