Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation-State Research Institute, Czartoryskich 8, 24-100 Puławy, Poland.
Institute of Pharmacy/Pharmacognosy, Center for Molecular Biosciences Innsbruck, University of Innsbruck, Innrain 80/82, Innsbruck 6020, Austria.
Molecules. 2019 Nov 16;24(22):4162. doi: 10.3390/molecules24224162.
The ethyl acetate fraction of the methanolic extract of Roezl ex Ortgies bark exhibited moderate acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity (IC 47.44 and 47.40 µg mL, respectively). Gel filtration on Sephadex LH-20 and further RP-C preparative HPLC of EtOAc fraction afforded 15 known and 3 new compounds, stereoisomers of larixinol. The structures of the isolated spirobiflavonoids , , and were elucidated using 1D and 2D NMR and MS spectroscopic techniques. The relative configuration of isolated compounds was assigned based on coupling constants and ROESY (rotating-frame Overhauser spectroscopy) correlations along with applying the DP4+ probability method in case of ambiguous chiral centers. Determination of absolute configuration was performed by comparing calculated electronic circular dichroism (ECD) spectra with experimental ones. Compounds and , obtained in sufficient amounts, were evaluated for activities against AChE and BChE, and they showed a weak inhibition only towards AChE (IC 294.18 µM for , and 655.18 µM for ). Furthermore, molecular docking simulations were performed to investigate the possible binding modes of and with AChE.
罗泽尔树皮的甲醇提取物的乙酸乙酯部分表现出中等乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）抑制活性（IC 47.44 和 47.40 µg mL，分别）。Sephadex LH-20 上的凝胶过滤和进一步的 EtOAc 部分的 RP-C 制备 HPLC 提供了 15 种已知和 3 种新化合物，是 larixinol 的立体异构体。使用 1D 和 2D NMR 和 MS 光谱技术阐明了分离出的螺二黄酮类化合物 、 和 的结构。根据偶合常数和 ROESY（旋转框架 Overhauser 光谱）相关以及在存在歧义手性中心的情况下应用 DP4+概率方法，分配了分离化合物的相对构型。通过将计算的电子圆二色性（ECD）光谱与实验光谱进行比较来确定绝对构型。获得了足够量的化合物 和 ，并对它们的 AChE 和 BChE 活性进行了评估，它们仅对 AChE 表现出较弱的抑制作用（IC 294.18 µM 用于 ，而 655.18 µM 用于 ）。此外，还进行了分子对接模拟，以研究 和 与 AChE 可能的结合模式。
