Sillanpää Mimosa, Tähtinen Petri, Karonen Maarit
Department of Chemistry, University of Turku, FI-20014 Turku, Finland.
ACS Omega. 2025 Jul 15;10(29):32174-32188. doi: 10.1021/acsomega.5c03937. eCollection 2025 Jul 29.
The interactions between plant polyphenols and commercial anthelmintics remain largely unexplored, despite the benefits of understanding these interactions for mitigating anthelmintic resistance. This study investigated the interactions of flavan-3-ols, dimeric proanthocyanidins, and selected hydrolyzable tannins with two anthelmintics, ivermectin (IVM) and thiabendazole (TBZ), at various polyphenol to anthelmintic molar ratios using nuclear magnetic resonance (NMR) spectroscopy. Chemical shift changes (Δs), indicating interaction, were observed for specific regions of the compounds and at all polyphenol to anthelmintic molar ratios. For IVM interactions with polyphenols, downfield Δs were observed and were primarily associated with hydroxyl groups within the structures of the anthelmintic and polyphenols, suggesting that the interactions involved hydrogen bond formation. For TBZ interactions with polyphenols, however, both upfield and downfield Δs were observed, suggesting that both hydrogen bonding and hydrophobic interactions were involved. All of the studied polyphenols interacted more strongly with TBZ than with IVM.
尽管了解植物多酚与商用驱虫剂之间的相互作用对于缓解驱虫抗药性有益，但这些相互作用在很大程度上仍未得到探索。本研究使用核磁共振（NMR）光谱法，研究了黄烷 - 3 - 醇、二聚原花青素和选定的可水解单宁与两种驱虫剂伊维菌素（IVM）和噻苯达唑（TBZ）在不同多酚与驱虫剂摩尔比下的相互作用。在所有多酚与驱虫剂摩尔比下，均观察到化合物特定区域的化学位移变化（Δs），表明存在相互作用。对于IVM与多酚的相互作用，观察到向低场的Δs，主要与驱虫剂和多酚结构内的羟基有关，这表明相互作用涉及氢键形成。然而，对于TBZ与多酚的相互作用，观察到既有向高场的Δs，也有向低场的Δs，这表明同时涉及氢键和疏水相互作用。所有研究的多酚与TBZ的相互作用都比与IVM的相互作用更强。
