20(S)-protopanaxatriol (PPT) is a kind of tetracyclic triterpenoid, which is found in the roots of ginseng . It is well known as a potential herbal medicine or healthcare product. However, given its poor water solubility, its application has been limited. In this study, we successfully synthesized a novel mono-[6-( N,N -bis(3-aminopropyl)ethylenediamine)-6-deoxy]-β-cyclodextrin. We prepared inclusion complexes of PPT with three polyamine-modified β-cyclodextrins (CDs) ( H1, H2, and H3 ) of different lengths by the coprecipitation method, aiming at enhancing the aqueous solubility of PPT. The host–guest inclusion complexes of H1, H2, and H3 with PPT were characterized via 1 H NMR, XRD, FT-IR spectra, and SEM technology, and the inclusion modes were analyzed by 2D ROESY. The stability constant ( Ks ), inclusion ratios, and solubility of H1, H2, and H3 with PPT were determined via the phase solubility method. The stability constants ( K 1:1 ) were found to be 182.6, 94.2, and 524.4 M −1 for H1/ PPT , H2/ PPT, and H3/ PPT inclusion complexes, with A L -, A N -, and B S -type curves, respectively. That is, when the stoichiometric ratio was 1:1, H3 (with longest-length chain) displayed the strongest binding ability with PPT. The host–guest size/shape-fit relationship and hydrogen bond interaction play a role in improving the stability of H1/ PPT , H2/ PPT, and H3/ PPT inclusion complexes. Through complexation with H1, H2, and H3 , the apparent solubility of PPT was obviously increased from the initial value of 0.062 mg/L to 5.1, 3.0, and 7.5 g/L, respectively. Among the three CDs, the solubilization effect of PPT with H3 was the best. Furthermore, H1/ PPT , H2/ PPT, and H3/ PPT inclusion complexes exhibited some activity in inhibiting LPS-induced nitric oxide (NO) generation in macrophages. This satisfactory aqueous solubility and higher stability of H1/ PPT, H2/ PPT, and H3/ PPT inclusion complexes should be possibly useful for its utilization as a herbal medicine and healthcare product. Graphic Abstract

中文翻译：

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20(S)-原人参三醇和三种多胺修饰的β-环糊精之间的主客体相互作用：制备、表征、包合模式和增溶

20(S)-原人参三醇(PPT)是一种四环三萜，存在于人参的根中。众所周知，它是一种潜在的草药或保健产品。然而，由于其水溶性较差，其应用受到限制。在本研究中，我们成功合成了一种新型的单-[6-(N,N-双(3-氨基丙基)乙二胺)-6-脱氧]-β-环糊精。我们通过共沉淀法制备了PPT与三种不同长度的多胺改性β-环糊精（CDs）（H1、H2和H3）的包合物，旨在提高PPT的水溶性。通过 1 H NMR、XRD、FT-IR 光谱和 SEM 技术对 H1、H2 和 H3 的主客体包合物进行了表征，并通过 2D ROESY 分析了包合物模式。H1、H2、H2 的稳定性常数 (Ks)、夹杂率和溶解度 H3 和 PPT 是通过相溶度法测定的。发现 H1/ PPT、H2/ PPT 和 H3/ PPT 包合物的稳定性常数 (K 1:1) 为 182.6、94.2 和 524.4 M -1，具有 AL -、AN - 和 BS 型曲线， 分别。也就是说，当化学计量比为 1:1 时，H3（最长链）与 PPT 的结合能力最强。主客体尺寸/形状配合关系和氢键相互作用在提高 H1/ PPT、H2/ PPT 和 H3/ PPT 包合物的稳定性方面发挥作用。通过与H1、H2和H3的络合，PPT的表观溶解度从最初的0.062mg/L明显提高到5.1、3.0和7.5g/L。三张CD中，PPT加H3的增溶效果最好。此外，H1/ PPT、H2/ PPT、和 H3/PPT 包合物在抑制巨噬细胞中 LPS 诱导的一氧化氮 (NO) 生成方面表现出一定的活性。H1/PPT、H2/PPT 和 H3/PPT 包合物的这种令人满意的水溶性和更高的稳定性可能对其作为草药和保健产品有用。图形摘要