Meng Jikun, Sagawa Moeri, Toshima Kazunobu, Takahashi Daisuke
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Chembiochem. 2025 Jun 3;26(11):e202401059. doi: 10.1002/cbic.202401059. Epub 2025 Apr 28.
α-Galacto-oligosaccharides (α-GOSs) are natural oligomeric saccharides found in plants that have garnered significant interest due to their indigestible nature and various biological activities. However, they often exist as inseparable mixtures, particularly long-chain substances. This study successfully achieves the total synthesis of α-GOSs 1-6, featuring different lengths of galactose chains, using the boron-mediated aglycon delivery method developed in our laboratory. Additionally, this study investigates the immune-enhancing activity and structure-activity relationships of the chemically synthesized α-GOSs. It reveals that the length of the galactose chain in the α-GOSs significantly influences their immune-enhancing properties. Specifically, α-GOS 2, which contains two galactose units, is found to markedly promote macrophage phagocytosis and increase the production of cytokines such as IL-6, TNF-α, and IL-1β. These results suggest that α-GOS 2 could serve as a natural immunomodulatory agent in functional foods.
α-半乳糖寡糖（α-GOSs）是存在于植物中的天然低聚糖，因其不可消化的特性和多种生物活性而备受关注。然而，它们通常以不可分离的混合物形式存在，尤其是长链物质。本研究利用我们实验室开发的硼介导苷元传递方法，成功实现了具有不同半乳糖链长度的α-GOSs 1-6的全合成。此外，本研究还考察了化学合成的α-GOSs的免疫增强活性及构效关系。结果表明，α-GOSs中半乳糖链的长度对其免疫增强特性有显著影响。具体而言，含有两个半乳糖单元的α-GOS 2被发现能显著促进巨噬细胞吞噬作用，并增加细胞因子如IL-6、TNF-α和IL-1β的产生。这些结果表明，α-GOS 2可作为功能性食品中的天然免疫调节剂。
