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Indole-3-acetic acid (IAA), one of tryptophan metabolites from gut microbiota, is critical for gut health through mechanisms such as activating aryl hydrocarbon receptor. Delivery of IAA to colon is beneficial for treatment of gastrointestinal diseases, and one promising strategy is IAA esterified starch, which is digested by gut microbes in colon and releases loaded IAA. Amylose content is a key structural characteristic that controls the physicochemical properties and digestibility of starch. Methods: In the current study, IAA was esterified with three typical starches with distinct amylose content to obtain indolyl acetylated waxy maize starch (WMSIAA), indolyl acetylated normal maize starch (NMSIAA), and indolyl acetylated high-amylose maize starch (HAMSIAA). The study comparatively analyzed their respective physicochemical properties, how they behave under in vitro digestion conditions, their ability to deliver IAA directly to the colon, and their effects on the properties of the gut microbiota. Results: The new characteristic peak of 1H NMR at 10.83 ppm, as well as the new characteristic peak of FTIR spectra at 1729 cm\u22121, represented the successful esterification of IAA on starch backbone. The following in vitro digestion study further revealed that treatment with indolyl acetylation significantly elevated the resistant starch content in the starch samples. In vivo experimental results demonstrated that WMSIAA exhibited the most significant increase in IAA levels in the stomach, whereas HAMSIAA and NMSIAA demonstrated the most remarkable increases in IAA levels in the small intestine and colon, respectively. The elevated IAA levels in the colon are conducive to promoting the growth of beneficial intestinal bacteria and significantly alleviating DSS-induced colitis. Conclusions: This research presents innovative insights and options for the advancement of colon-specific drug delivery systems aimed at preventing and curing gastrointestinal disorders.<\/jats:p>","DOI":"10.3390\/nu16203446","type":"journal-article","created":{"date-parts":[[2024,10,11]],"date-time":"2024-10-11T08:10:16Z","timestamp":1728634216000},"page":"3446","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Indole-3-Acetic Acid Esterified with Waxy, Normal, and High-Amylose Maize Starches: Comparative Study on Colon-Targeted Delivery and Intestinal Health Impact"],"prefix":"10.3390","volume":"16","author":[{"given":"Qian","family":"Gong","sequence":"first","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinyan","family":"Qu","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yisheng","family":"Zhao","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xingjing","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuhua","family":"Cao","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4236-2483","authenticated-orcid":false,"given":"Xiao","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yingying","family":"Song","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Charles R.","family":"Mackay","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8931-4046","authenticated-orcid":false,"given":"Quanbo","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory for Natural Active Pharmaceutical Constituents Research in Universities of Shandong Province, School of Pharmaceutical Sciences, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,10,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"980","DOI":"10.1016\/j.jaci.2023.10.029","article-title":"High Metabolite Concentrations in Portal Venous Blood as a Possible Mechanism for Microbiota Effects on the Immune System, and Western Diseases","volume":"153","author":"Wang","year":"2024","journal-title":"J. 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