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Isomeric effect of coumaric acid on the structure, digestion, and gut microbiota regulation of starch-based V-type
Yongxing Li1, Shuang Yang1, Haiyu Ji1
1Center for Mitochondria and Healthy Aging, School of Life Sciences, Yantai University, Yantai, 264005, PR China.
Abstract:
This study investigated the interaction between three coumaric acid isomers (para-, meta-, and ortho-CA) and corn starch under high-pressure processing. Isomer position critically influenced the multi-scale structure, digestibility, and gut microbiota-modulating function of the resulting complexes. All isomers formed V-type inclusion complexes within the starch helices, with para-CA conferring stronger binding affinity and more compact structures. This structural recombination significantly increased the content of resistant starch (up to 68.43 ± 0.16% with 20% p-CA), while reducing rapidly digestible starch (9.76 ± 0.19%), resulting in the estimated glycemic index decreasing in the order of para < ortho < meta-coumaric acid. During in vitro fecal fermentation, these complexes exhibited slow release of encapsulated polyphenols over 24 h, significantly boosting short-chain fatty acid (especially acetic acid) production, lowering pH value, and selectively regulating gut microbiota (a reduced Firmicutes/Bacteroidetes ratio and an increased abundance of beneficial genera such as Bifidobacterium). These findings provide a theoretical basis for designing targeted starch-based functional foods for precise glycemic control and gut health promotion.
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Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...