本文报道了从沼王根(Olax subscorpioidea Oliv., 橄榄科)中分离得到的细胞毒性三萜皂苷。
Cytotoxic triterpenoid saponins from the root of Olax subscorpioidea Oliv. (Olacaceae).
发表日期:2023 Sep 07
作者:
Yemi A Adekunle, Babatunde B Samuel, Lutfun Nahar, Amos A Fatokun, Satyajit D Sarker
来源:
PHYTOCHEMISTRY
摘要:
对Olax subscorpioidea根部的甲醇提取物进行生物活性引导的植物化学分离得到了六种三萜类化合物。其中三种化合物是尚未报道的三萜类皂苷化合物:绿原酸3-O-[α-L-鼠李糖苷-(1→3)-β-D-葡萄糖苷-(1 → 2)-6-O-甲基-β-D-葡萄糖醛酸酯]-28-O-β-D-葡萄糖苷酯 (2)、绿原酸3-O-[β-D-葡萄糖苷-(1 → 4)-β-D-葡萄糖苷-(1 → 3)-β-D-葡萄糖苷] (3) 和绿原酸3-O-[β-D-葡萄糖苷-(1 → 4)-6-O-甲基-β-D-葡萄糖醛酸酯] (5)。其他报道的已知化合物包括两种三萜类糖苷:绿原酸3-O-[β-D-葡萄糖苷-(1 → 4)-6-O-甲基-β-D-葡萄糖醛酸酯]-28-O-β-D-葡萄糖苷酯 (1) 和绿原酸3-O-[β-D-葡萄糖苷-(1 → 4)-β-D-葡萄糖醛酸酯] (4);以及一个三萜酸,绿原酸 (6)。利用光谱手段阐明了这些化合物的结构。采用体外3-[4,5-二甲基噻唑-2-基] 3,5-二苯基四唑溴化物 (MTT) 测定法,以长春新碱作为阳性对照,测试了所分离的化合物对人子宫颈癌(HeLa)、结肠癌(Caco-2)和乳腺癌(MCF-7)细胞株的细胞毒性。细胞毒性实验显示化合物3和5对HeLa细胞株表现出明显的抑制作用,IC50值分别为7.42 ± 0.34 μM和10.27 ± 1.26 μM;对MCF-7(IC50值,36.67 ± 1.23 μM和43.83 ± 0.65 μM)和Caco-2(IC50值,35.83 ± 0.55 μM和39.03 ± 4.38 μM)细胞株表现出中等的抑制作用。与长春新碱相比,它们对癌细胞株的细胞毒性更具选择性,而与正常肺细胞株MRC5的细胞毒性相比较低。版权所有 © 2023,由Elsevier Ltd.发布。
Bioactivity-guided phytochemical fractionation of the methanol extract of Olax subscorpioidea root has led to the isolation of six triterpenes. Three of these compounds are previously undescribed triterpenoid saponins: oleanolic acid 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1 → 2)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl ester (2), oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside] (3), and oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside] ester (5). Other reported known compounds include two triterpene glycosides: oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl ester (1) and oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranoside] (4); and a triterpene acid, oleanolic acid (6). The structures of these compounds were elucidated by spectroscopic means. The isolated compounds were tested against human cervical cancer (HeLa), colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines using the in vitro 3-[4,5-dimethylthiazole-2-yl] 3,5-diphenyltetrazolium bromide (MTT) assay, with vincristine as positive control. The cytotoxicity assay showed that compounds 3 and 5 exhibited significant inhibitory effects on the HeLa cell line, with IC50 values of 7.42 ± 0.34 μM and 10.27 ± 1.26 μM; and moderate effects on MCF-7 (IC50 values, 36.67 ± 1.23 μM and 43.83 ± 0.65 μM) and Caco-2 (IC50 values, 35.83 ± 0.55 μM and 39.03 ± 4.38 μM, respectively) cell lines. They were also more selectively cytotoxic than vincristine against the cancer cell lines, when compared with cytotoxicity against the normal lung cell line MRC5.Copyright © 2023. Published by Elsevier Ltd.