{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T10:32:14Z","timestamp":1785407534907,"version":"3.56.0"},"reference-count":40,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2026,6,13]],"date-time":"2026-06-13T00:00:00Z","timestamp":1781308800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22578149"],"award-info":[{"award-number":["22578149"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"award":["22578149"],"award-info":[{"award-number":["22578149"]}],"id":[{"id":"https:\/\/ror.org\/01h0zpd94","id-type":"ROR","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100020084","name":"Guangzhou Key R&D Programme","doi-asserted-by":"publisher","award":["2024B03J1307"],"award-info":[{"award-number":["2024B03J1307"]}],"id":[{"id":"10.13039\/501100020084","id-type":"DOI","asserted-by":"publisher"}]},{"name":"projects of Zhaoqing University","award":["qn202609"],"award-info":[{"award-number":["qn202609"]}]},{"name":"projects of Zhaoqing University","award":["250031"],"award-info":[{"award-number":["250031"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antioxidants"],"abstract":"<jats:p>Fruit and vegetable processing by-products, such as peels and pomace, are rich in antioxidant polyphenols and represent promising sources of functional ingredients, but how their galloyl-based polyphenols interact with starch remains insufficiently understood. In this study, corilagin with three non-free galloyl moieties and 1,2,3,4,6-O-pentagalloyl glucose with five free galloyl moieties were used as model polyphenols to clarify how galloyl moiety number and accessibility modulate their complexation with high-amylose maize starch (HAMS). Size-exclusion chromatography showed that both polyphenols preferentially complexed with amylose, while FTIR confirmed that complex formation occurred mainly through non-covalent interactions. The two polyphenols induced distinct changes in HAMS structure. Corilagin disrupted short-range order and produced no detectable crystalline structure, whereas 1,2,3,4,6-O-pentagalloyl glucose enhanced molecular order and induced V-type crystallization. Isothermal titration calorimetry revealed more binding sites but weaker affinity for corilagin, with thermodynamic signatures indicating hydrogen bonding and van der Waals interactions. By contrast, 1,2,3,4,6-O-pentagalloyl glucose showed stronger affinity and hydrophobic interaction-dominated binding. Molecular dynamics simulations further confirmed that 1,2,3,4,6-O-pentagalloyl glucose formed a more stable association with the amylose helix than corilagin. These results indicate that galloyl moiety characteristics markedly influence starch\u2013polyphenol interaction mechanisms, providing guidance for the utilization of polyphenol-rich agro-processing by-products in functional starch-based foods.<\/jats:p>","DOI":"10.3390\/antiox15060748","type":"journal-article","created":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T08:22:56Z","timestamp":1781684576000},"page":"748","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Mechanistic Insights into Starch-Polyphenol Complexation: Role of Structural Differences in Galloyl-Based Polyphenols"],"prefix":"10.3390","volume":"15","author":[{"given":"Liang","family":"Wang","sequence":"first","affiliation":[{"name":"Guangdong Provincial Key Laboratory of Food Quality and Safety, College of Food Science, South China Agricultural University, Guangzhou 510642, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leyi","family":"Li","sequence":"additional","affiliation":[{"name":"Guangzhou Dublin International College of Life Sciences and Technology, South China Agricultural University, Guangzhou 510642, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8790-9529","authenticated-orcid":false,"given":"Seda","family":"Arioglu-Tuncil","sequence":"additional","affiliation":[{"name":"Department of Nutrition and Dietetics, Nezahat Kele\u015fo\u011flu Health Sciences Faculty, Necmettin Erbakan University, 42090 Konya, T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ting","family":"He","sequence":"additional","affiliation":[{"name":"Guangdong Provincial Key Laboratory of Food Quality and Safety, College of Food Science, South China Agricultural University, Guangzhou 510642, China"},{"name":"School of Food & Pharmaceutical Engineering, Zhaoqing University, Zhaoqing 526061, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8072-7220","authenticated-orcid":false,"given":"Kai","family":"Wang","sequence":"additional","affiliation":[{"name":"Guangdong Provincial Key Laboratory of Food Quality and Safety, College of Food Science, South China Agricultural University, Guangzhou 510642, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,6,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1016\/j.tifs.2021.04.032","article-title":"Formation, structure and properties of the starch-polyphenol inclusion complex: A review","volume":"112","author":"Deng","year":"2021","journal-title":"Trends Food Sci. Technol."},{"key":"ref_2","first-page":"667","article-title":"Recent advances in the formation, characterization, and applications of starch-polyphenol complexes: A review","volume":"112","author":"Han","year":"2026","journal-title":"Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"121326","DOI":"10.1016\/j.carbpol.2023.121326","article-title":"A comprehensive review on starch: Structure, modification, and applications in slow\/controlled-release fertilizers in agriculture","volume":"322","author":"Salimi","year":"2023","journal-title":"Carbohydr. Polym."},{"key":"ref_4","first-page":"3185","article-title":"Complexation of starch and phenolic compounds during food processing and impacts on the release of phenolic compounds","volume":"22","author":"Wang","year":"2023","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"136624","DOI":"10.1016\/j.foodchem.2023.136624","article-title":"Insoluble dietary fiber from wheat bran retards starch digestion by reducing the activity of alpha-amylase","volume":"426","author":"He","year":"2023","journal-title":"Food Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"12338","DOI":"10.1039\/D1FO02891J","article-title":"Longan seed polyphenols inhibit alpha-amylase activity and reduce postprandial glycemic response in mice","volume":"12","author":"He","year":"2021","journal-title":"Food Funct."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Zagoskina, N.V., Zubova, M.Y., Nechaeva, T.L., Kazantseva, V.V., Goncharuk, E.A., Katanskaya, V.M., Baranova, E.N., and Aksenova, M.A. (2023). Polyphenols in Plants: Structure, Biosynthesis, Abiotic Stress Regulation, and Practical Applications (Review). Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms241813874"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"4202","DOI":"10.1039\/D5FO00855G","article-title":"The interaction between starch and phenolic acids: Effects on starch physicochemical properties, digestibility and phenolic acids stability","volume":"16","author":"Zheng","year":"2025","journal-title":"Food Funct."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"711","DOI":"10.1016\/j.tifs.2021.01.078","article-title":"Update of the concept of type 5 resistant starch (RS5): Self-assembled starch V-type complexes","volume":"109","author":"Tovar","year":"2021","journal-title":"Trends Food Sci. Technol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"118101","DOI":"10.1016\/j.carbpol.2021.118101","article-title":"Pickering emulsions stabilized by spherical cellulose nanocrystals","volume":"265","author":"Dong","year":"2021","journal-title":"Carbohydr. Polym."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"135257","DOI":"10.1016\/j.ijbiomac.2024.135257","article-title":"Research progress on the regulation of starch-polyphenol interactions in food processing","volume":"279","author":"Wu","year":"2024","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"114913","DOI":"10.1016\/j.foodres.2024.114913","article-title":"The influence mechanism of pH and polyphenol structures on the formation, structure, and digestibility of pea starch-polyphenol complexes via high-pressure homogenization","volume":"194","author":"Luo","year":"2024","journal-title":"Food Res. Int."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"110419","DOI":"10.1016\/j.foodhyd.2024.110419","article-title":"Differences in structure, physicochemical properties, and in vitro digestibility of three types of starch complexed with tannic acid","volume":"157","author":"Zuo","year":"2024","journal-title":"Food Hydrocoll."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"137708","DOI":"10.1016\/j.foodchem.2023.137708","article-title":"Interaction of high amylose corn starch with polyphenols: Modulating the stability of polyphenols with different structure against thermal processing","volume":"437","author":"Fan","year":"2024","journal-title":"Food Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"155063","DOI":"10.1016\/j.phymed.2023.155063","article-title":"Inhibitory activities and rules of plant gallotannins with different numbers of galloyl moieties on sucrase, maltase and alpha-amylase in vitro and in vivo","volume":"120","author":"Liu","year":"2023","journal-title":"Phytomedicine"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"123904","DOI":"10.1016\/j.carbpol.2025.123904","article-title":"V-type starch-galloyl-based polyphenol complex stimulates GLP-1 and PYY secretion and improves satiety in mice","volume":"366","author":"Zheng","year":"2025","journal-title":"Carbohydr. Polym."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1186\/s43014-025-00322-3","article-title":"Polyphenol-polysaccharide interactions: Molecular mechanisms and potential applications in food systems\u2014A comprehensive review","volume":"7","author":"Shahidi","year":"2025","journal-title":"Food Prod. Process Nutr."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"129846","DOI":"10.1016\/j.foodchem.2021.129846","article-title":"Number of galloyl moiety and intramolecular bonds in galloyl-based polyphenols affect their interaction with alpha-glucosidase","volume":"367","author":"Cao","year":"2022","journal-title":"Food Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3838","DOI":"10.1039\/C9FO02735A","article-title":"Number of galloyl moieties and molecular flexibility are both important in alpha-amylase inhibition by galloyl-based polyphenols","volume":"11","author":"Cao","year":"2020","journal-title":"Food Funct."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"117537","DOI":"10.1016\/j.carbpol.2020.117537","article-title":"Interaction with longan seed polyphenols affects the structure and digestion properties of maize starch","volume":"256","author":"He","year":"2021","journal-title":"Carbohydr. Polym."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1016\/j.carbpol.2015.03.081","article-title":"Roles of GBSSI and SSIIa in determining amylose fine structure","volume":"127","author":"Wang","year":"2015","journal-title":"Carbohydr. Polym."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2245","DOI":"10.1021\/bm900426n","article-title":"Characterization of starch by size-exclusion chromatography: The limitations imposed by shear scission","volume":"10","author":"Cave","year":"2009","journal-title":"Biomacromolecules"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"112540","DOI":"10.1016\/j.foodhyd.2026.112540","article-title":"Volatility-tuned encapsulation in V-type starch: Phase-dependent efficiency and release kinetics","volume":"175","author":"Lai","year":"2026","journal-title":"Food Hydrocoll."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"129408","DOI":"10.1016\/j.ijbiomac.2024.129408","article-title":"Gallic acid forms V-amylose complex structure with starch through hydrophobic interaction","volume":"260","author":"He","year":"2024","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/j.softx.2015.06.001","article-title":"GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers","volume":"1","author":"Abraham","year":"2015","journal-title":"SoftwareX"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2135","DOI":"10.1002\/jcc.23354","article-title":"CHARMM36 all-atom additive protein force field: Validation based on comparison to NMR data","volume":"34","author":"Huang","year":"2013","journal-title":"J. Comput. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"108285","DOI":"10.1016\/j.foodhyd.2022.108285","article-title":"Molecular encapsulation of cinnamaldehyde in V-type starch: The role of solvent and temperature","volume":"136","author":"Gao","year":"2023","journal-title":"Food Hydrocoll."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"136182","DOI":"10.1016\/j.foodchem.2023.136182","article-title":"Stability of starch-proanthocyanidin complexes to in-vitro amylase digestion after hydrothermal processing","volume":"421","author":"Althawab","year":"2023","journal-title":"Food Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"139191","DOI":"10.1016\/j.foodchem.2024.139191","article-title":"Elucidating the influence and mechanism of different phenols on the properties, food quality and function of maize starch","volume":"449","author":"Chen","year":"2024","journal-title":"Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"117172","DOI":"10.1016\/j.carbpol.2020.117172","article-title":"Inhibition effect of three common proanthocyanidins from grape seeds, peanut skins and pine barks on maize starch retrogradation","volume":"252","author":"Wang","year":"2021","journal-title":"Carbohydr. Polym."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"120737","DOI":"10.1016\/j.carbpol.2023.120737","article-title":"Molecular interactions between apigenin and starch with different amylose\/amylopectin ratios revealed by X-ray diffraction, FT-IR and solid-state NMR","volume":"310","author":"Ma","year":"2023","journal-title":"Carbohydr. Polym."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"108064","DOI":"10.1016\/j.foodhyd.2022.108064","article-title":"Assessment of order of helical structures of retrograded starch by Raman spectroscopy","volume":"134","author":"Lu","year":"2023","journal-title":"Food Hydrocoll."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"320","DOI":"10.1016\/j.tifs.2021.12.011","article-title":"Changes of starch during thermal processing of foods: Current status and future directions","volume":"119","author":"Liu","year":"2022","journal-title":"Trends Food Sci. Technol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"115302","DOI":"10.1016\/j.lwt.2023.115302","article-title":"Effects of acid hydrolysis level prior to heat-moisture treatment on properties of starches with different crystalline polymorphs","volume":"187","author":"Gonzalez","year":"2023","journal-title":"Lwt-Food Sci. Technol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"780","DOI":"10.1080\/10408398.2018.1550739","article-title":"Starch-guest inclusion complexes: Formation, structure, and enzymatic digestion","volume":"60","author":"Tan","year":"2020","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2125","DOI":"10.1080\/10408398.2025.2564215","article-title":"Current understanding of starch-polyphenol complexes and their potential in vivo metabolism, impact on gut microbiota and treating diabetes","volume":"66","author":"Deng","year":"2026","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"106544","DOI":"10.1016\/j.foodhyd.2020.106544","article-title":"Interactions between caffeic acid and corn starch with varying amylose content and their effects on starch digestion","volume":"114","author":"Yu","year":"2021","journal-title":"Food Hydrocoll."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3096","DOI":"10.1021\/bi00514a017","article-title":"Thermodynamics of protein association reactions: Forces contributing to stability","volume":"20","author":"Ross","year":"1981","journal-title":"Biochemistry"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"11665","DOI":"10.1021\/acs.jafc.1c01585","article-title":"Complexation between High-Amylose Starch and Binary Aroma Compounds of Decanal and Thymol: Cooperativity or Competition?","volume":"69","author":"Gao","year":"2021","journal-title":"J. Agric. Food Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.carres.2012.10.007","article-title":"Amylose folding under the influence of lipids","volume":"364","author":"Lopez","year":"2012","journal-title":"Carbohydr. Res."}],"container-title":["Antioxidants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2076-3921\/15\/6\/748\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T09:08:44Z","timestamp":1781687324000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2076-3921\/15\/6\/748"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6,13]]},"references-count":40,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2026,6]]}},"alternative-id":["antiox15060748"],"URL":"https:\/\/doi.org\/10.3390\/antiox15060748","relation":{},"ISSN":["2076-3921"],"issn-type":[{"value":"2076-3921","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,6,13]]}}}