Synthesis and biological evaluation of mirror isomers of β-(1 → 3)-glucans as immune modulators

IF 10.7 1区 化学 Q1 CHEMISTRY, APPLIED Carbohydrate Polymers Pub Date : 2025-03-08 DOI:10.1016/j.carbpol.2025.123477
Ao Sun , Zipeng Li , Wenjian Zhao , Jiayi Zheng , Yuhan Zhang , Mingju Yao , Wang Yao , Xiao Zhang , Xiangbao Meng , Zhongtang Li , Zhongjun Li
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Abstract

β-(1 → 3)-glucan is widely distributed in the cell walls of bacteria, fungi, yeasts and algae. A variety of pharmacological effects of β-(1 → 3)-glucan have been demonstrated, including immune modulation. The enzyme recognition pocket can recognize the chirality of the ligand and often give rise to disparate biological activities. The bioactivity of the mirror-image isomers of natural oligosaccharides is scarcely studied due to the difficulty of acquiring them. In this study, we have successfully completed the total synthesis of the naturally occurring β-ᴅ-(1 → 3)-glucans and their mirror image β-ʟ-(1 → 3)-glucans containing three, four, eight, and twelve monosaccharides for the first time. Subsequently, the immunomodulatory activities of ᴅ- and ʟ-type β-glucans were evaluated to explore their bioactivity and preliminary mechanism of action. The results indicated that mirror-image β-(1 → 3)-glucans exerted bidirectional regulatory effects on M0/M1-type macrophages. The ᴅ-type β-(1 → 3)-glucans have the potential to regulate macrophage polarization through the GPCR and CR3 signalling pathways. In contrast, the ʟ-type β-(1 → 3)-glucans achieved bidirectional regulation of macrophage polarization by influencing cellular metabolism. The findings presented herein provide new evidence for the further investigation of the biological activities of oligosaccharides and their mirror image isomers.

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来源期刊
Carbohydrate Polymers
Carbohydrate Polymers 化学-高分子科学
CiteScore
22.40
自引率
8.00%
发文量
1286
审稿时长
47 days
期刊介绍: Carbohydrate Polymers stands as a prominent journal in the glycoscience field, dedicated to exploring and harnessing the potential of polysaccharides with applications spanning bioenergy, bioplastics, biomaterials, biorefining, chemistry, drug delivery, food, health, nanotechnology, packaging, paper, pharmaceuticals, medicine, oil recovery, textiles, tissue engineering, wood, and various aspects of glycoscience. The journal emphasizes the central role of well-characterized carbohydrate polymers, highlighting their significance as the primary focus rather than a peripheral topic. Each paper must prominently feature at least one named carbohydrate polymer, evident in both citation and title, with a commitment to innovative research that advances scientific knowledge.
期刊最新文献
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