Department of Pharmacognosy, University of Ibadan, Ibadan, Nigeria; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, TU Dortmund, Dortmund, Germany.
Department of Pharmacognosy, University of Ibadan, Ibadan, Nigeria.
Fitoterapia. 2022 Jul;160:105206. doi: 10.1016/j.fitote.2022.105206. Epub 2022 May 8.
Tetrapleura tetraptera is a medicinal plant used in East and West Africa to treat inflammation and related diseases. From the stem bark of the plant, three previously undescribed flavan-3-ol derivatives named (2R,3S)-3,3',5',7-tetrahydroxy-4'-methoxyflavane (1), (2R,3S)-3',5',7-trihydroxy-4'-methoxyflavane-3-O-β-D-glucopyranoside (2), and (2R,3S,4S)-3,3',4,5',7-pentahydroxy-4'-methoxyflavane (3) were isolated with three known analogues. The structural elucidation of the compounds was performed based on NMR spectroscopy and HRMS data analyses. The absolute configurations around the stereogenic carbons were determined using Circular Dichroism (ECD) and density functional theory (DFT) calculations. The cytotoxicity of the isolated compounds was tested using resazurin reduction assay. Compound 1 was moderately active against both recalcitrant leukemia cell lines with IC values of 21.90 μM towards CCRF-CEM and 50.80 towards CEM/ADR5000. Similar level of activity was observed for compound 3 against CCRF-CEM cell line, IC = 35.50 μM. All the tested compounds were not cytotoxic compared with the standard drug, doxorubicin, with IC values of 0.0075 against CCRF-CEM and 24.30 μM against CEM/ADR5000.
四棱豆是一种在东非和西非被用于治疗炎症及相关疾病的药用植物。从该植物的茎皮中分离得到了三种先前未被描述的黄烷-3-醇衍生物，分别命名为(2R,3S)-3,3',5',7-四羟基-4'-甲氧基黄烷（1）、(2R,3S)-3',5',7-三羟基-4'-甲氧基黄烷-3-O-β-D-吡喃葡萄糖苷（2）和(2R,3S,4S)-3,3',4,5',7-五羟基-4'-甲氧基黄烷（3），同时还分离得到了三种已知的类似物。通过 NMR 光谱和 HRMS 数据分析对化合物的结构进行了阐明。利用圆二色性（ECD）和密度泛函理论（DFT）计算确定了手性碳原子的绝对构型。通过 Resazurin 还原测定法测试了分离化合物的细胞毒性。化合物 1 对耐药性白血病细胞系 CCRF-CEM 和 CEM/ADR5000 的 IC 值分别为 21.90 μM 和 50.80 μM，表现出中等的活性。化合物 3 对 CCRF-CEM 细胞系也表现出相似的活性，IC = 35.50 μM。与标准药物阿霉素相比，所有测试的化合物均无细胞毒性，其对 CCRF-CEM 的 IC 值为 0.0075 μM，对 CEM/ADR5000 的 IC 值为 24.30 μM。
