26-O-β-D-glucopyranoside-3β,26-dihydroxy-(25R)-5α-furostan-20(22)-en-6-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 26-O-β-D-glucopyranoside-3β,26-dihydroxy-(25R)-5α-furostan-20(22)-en-6-one
• 英文别名: 26-O-β-D-glucopyranosyl 3β,26-dihydroxy-25(R)-5α-furostan-20(22)-en-6-one
• 化学式: C₃₃H₅₂O₉
• 分子量: 592.77
• InChiKey: PFDGFBVNDFOPOT-PGZPVGLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  145.91
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  26-O-β-D-glucopyranoside-3β,26-dihydroxy-(25R)-5α-furostan-20(22)-en-6-one 在 盐酸 作用下， 以 水 为溶剂， 生成 葡萄糖
  参考文献：
  名称：

  Furostanol saponins from Chinese onion induce G2/M cell-cycle arrest and apoptosis through mitochondria-mediate pathway in HepG2 cells

  摘要：

  Phytochemical investigations on the bulbs of Chinese onion led to the isolation of three new furostanol saponins (1, 2, 5) together with seven known furostanol saponins (3, 4, 6-10). Their chemical structures were elucidated on the basis of spectroscopic and chemical methods, including IR, MS, NMR, and GC analyses. The anti-proliferative and anti-inflammatory activities of the isolates were evaluated. Compounds 7-10 showed potential anti-proliferative activities against human cancer cell lines (HepG2, A549, SPC-A-1, MGC80-3, MDA-MB-231, SW620 and CNE-1) with IC50 values below 30 mu M. Compounds 4 and 7 could induce G2/M cell-cycle arrest and apoptosis through mitochondria-mediate pathway in HepG2 cells. Compounds 7 and 10 showed strong inhibitory effects against LPS induced NO production in RAW264.7 cells with IC50 values of 2.01 +/- 1.40 mu M and 2.49 +/- 1.54 mu M, respectively.

  DOI：

  10.1016/j.steroids.2019.04.003

文献信息

• Four New Furostanol Saponins from the Rhizomes and Roots of Smilax scobinicaulis and Their Cytotoxicity
  作者：Jing Xu、Shixiu Feng、Qi Wang、Yingli Cao、Miao Sun、Cunli Zhang

  DOI：10.3390/molecules191220975

  日期：——

  Four new furostanol saponins 1–4, along with two known furostanol saponins 5 and 6 and one known spirostanol saponin 7 were isolated from the rhizomes and roots of Smilax scobinicaulis. The structures of the new saponins were elucidated as 26-O-β-D-glucopyranoside-3β,26-dihydroxy-(25R)-5α-furostan-22-methoxyl-6-one-3-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (1), 26-O-β-D-glucopyranoside-3β,26-dihydroxy-(25R)-5α-furostan-22-methoxyl-6-one (2), 26-O-β-D-glucopyranoside-3β,26-dihydroxy-(25R)-5α-furostan-20(22)-en-6-one (3), 26-O-β-D-glucopyranoside-3β,23,26-trihydroxy-(23R, 25R)-5α-furostan-20(22)-en-6-one (4) on the basis of spectroscopic analysis. The isolated saponins were evaluated for cytotoxic activity against two human cancer cell lines including Hela (cervical carcinoma) and SMMC-7221 (hepatocellular carcinoma). Compounds 1 and 7 demonstrated cytotoxicity against the tested cell lines.

  从菝葜（Smilax scobinicaulis）的根茎和根中分离出了四种新的呋喃甾醇皂苷 1-4，以及两种已知的呋喃甾醇皂苷 5 和 6 和一种已知的螺甾醇皂苷 7。26-dihydroxy-(25R)-5α-furostan-22-methoxyl-6-one (2), 26-O-β-D-glucopyranoside-3β,26-dihydroxy-(25R)-5α-furostan-20(22)-en-6-one (3),根据光谱分析，还发现了 26-O-β-D-吡喃葡萄糖苷-3β,23,26-三羟基-(23R, 25R)-5α-呋喃甾-20(22)-烯-6-酮 (4)。评估了分离出的皂苷对两种人类癌细胞系（包括 Hela（宫颈癌）和 SMMC-7221（肝细胞癌））的细胞毒性活性。化合物 1 和 7 对测试的细胞株具有细胞毒性。