3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside | 145075-83-8

• 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: 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside
• 英文别名: 3β,17α-dihydroxy-16β-[(O-β-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one；(S)-2-((3S,8R,9S,10R,13S,14S,16S,17S)-16-(((2S,3R,4S,5S)-3,5-Dihydroxy-4-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,17-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptan-3-one；(2S)-2-[(3S,8R,9S,10R,13S,14S,16S,17S)-16-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-one
• CAS: 145075-83-8
• 化学式: C₃₇H₆₀O₁₂
• 分子量: 696.876
• InChiKey: NBDNCFSGTFOYKR-GDHSCZBXSA-N

物化性质

• 沸点：
  847.6±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以12.1 mg的产率得到(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-17-[(2R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-3,5-dihydroxyoxan-4-yl]oxyoxane-3,4,5-triol
  参考文献：
  名称：

  Cytotoxic Cholestane Glycosides from the Bulbs of Ornithogalum saundersiae

  摘要：

  Further phytochemical analysis of the bulbs of Ornithogalum saundersiae has yielded two new cytotoxic cholestane triglycosides (1 and 2). The structures of these compounds were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and the results of hydrolytic cleavage. Compounds 1 and 2 and several analogues were evaluated for their cytotoxicity against HL-60 cells.

  DOI：

  10.1021/np0003084
• 作为产物：
  描述：

  3β,17α-dihydroxy-16β-[[O-(2-O-(4-hydroxybenzoyl)-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl]oxy]-cholest-5-en-22-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-β-D-xylopyranosyl-(1->3)-α-L-arabinopyranoside
  参考文献：
  名称：

  虎眼万年青的胆甾醇苷和OSW-1通过线粒体独立信号通路诱导HL-60细胞凋亡。

  摘要：

  一种用于从细胞毒性胆甾苷搜索虎眼万年青灯泡造成的三个新的OSW-1类似物（隔离1 - 3），一个新的胆甾bisdesmoside（4），一个5β-胆甾烷二糖苷（5），和四个新的24（23 →22） -的abeo- -cholestane苷（6 - 9）中，用11节已知的胆甾苷（一起10 - 20），包括OSW-1（11）。1 – 9的结构是根据常规光谱分析和化学证据确定的。不出所料，根据之前的数据，1– 3对HL-60人早幼粒细胞白血病细胞和A549人肺腺癌细胞具有有效的细胞毒活性。此外，检查了OSW-1诱导HL-60细胞凋亡的能力。在用OSW-1处理的HL-60细胞中评估了核染色质的聚集，亚G1细胞的积累，DNA片段化和caspase-3活化，为OSW-1诱导的HL-60细胞凋亡提供了证据。在OSW-1处理的凋亡HL-60细胞中未观察到线粒体膜电位或细胞色素c释放到细胞质中，表明线粒体非依赖性信号通路参与凋亡细胞的死亡。

  DOI：

  10.1007/s11418-018-1252-4

文献信息

• Development of Chemical Probes for Functional Analysis of Anticancer Saponin OSW‐1
  作者：Rina Komatsu、Kaori Sakurai

  DOI：10.1002/tcr.201900042

  日期：2019.12

  reviews recent progress in the development of OSW‐1 derived probes for exploring the mechanism of its action. The key to the probe development is a judicious choice of functionalization sites and a selective functionalization strategy. The types of probes include fluorescent probes for cellular imaging analysis and affinity probes for target identification analysis.

  近年来，在天然产物的目标识别研究中，基于化学探针的方法已被证明是有效的。OSW-1是一种天然的皂素类产品，对各种癌细胞具有高度有效的选择性细胞毒性。了解其作用机理对于开发具有潜在新型靶途径的抗癌药物很重要。此帐户回顾了OSW-1衍生探针在探索其作用机理方面的最新进展。探针开发的关键是明智选择功能化位点和选择性功能化策略。探针的类型包括用于细胞成像分析的荧光探针和用于靶标鉴定分析的亲和探针。
• Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae
  作者：Satoshi Kubo、Yoshihiro Mimaki、Miki Terao、Yutaka Sashida、Tamotsu Nikaido、Taichi Ohmoto

  DOI：10.1016/s0031-9422(00)97565-4

  日期：1992.1

  Phytochemical examination of the bulbs of Ornithogalum saundersiae led to the isolation of three new acylated cholestane glycosides. Their structures were elucidated, on the basis of the spectroscopic data and chemical evidences, and by comparing them with those of known compounds, as 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one 16-O-beta-D-xylopyranosyl-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside), 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-Xylopyranosyl)-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside) and 3beta,16beta,17alpha-trihydroxy-cholest-5-en-22-one 16-O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside). Inhibitory activity on cyclic AMP phosphodiesterase of the cholestane glycosides was evaluated.
• Cytotoxic Cholestane Glycosides from the Bulbs of <i>Ornithogalum </i><i>s</i><i>aundersiae</i>
  作者：Minpei Kuroda、Yoshihiro Mimaki、Akihito Yokosuka、Yutaka Sashida、John A. Beutler

  DOI：10.1021/np0003084

  日期：2001.1.1

  Further phytochemical analysis of the bulbs of Ornithogalum saundersiae has yielded two new cytotoxic cholestane triglycosides (1 and 2). The structures of these compounds were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and the results of hydrolytic cleavage. Compounds 1 and 2 and several analogues were evaluated for their cytotoxicity against HL-60 cells.
• Cholestane glycosides from Ornithogalum saundersiae bulbs and the induction of apoptosis in HL-60 cells by OSW-1 through a mitochondrial-independent signaling pathway
  作者：Tomoki Iguchi、Minpei Kuroda、Rei Naito、Tomoyuki Watanabe、Yukiko Matsuo、Akihito Yokosuka、Yoshihiro Mimaki

  DOI：10.1007/s11418-018-1252-4

  日期：2019.1

  A search for cytotoxic cholestane glycosides from Ornithogalum saundersiae bulbs resulted in the isolation of three new OSW-1 analogues (1–3), a new cholestane bisdesmoside (4), a 5β-cholestane diglycoside (5), and four new 24(23 → 22)-abeo-cholestane glycosides (6–9), together with 11 known cholestane glycosides (10–20), including OSW-1 (11). The structures of 1–9 were determined based on conventional

  一种用于从细胞毒性胆甾苷搜索虎眼万年青灯泡造成的三个新的OSW-1类似物（隔离1 - 3），一个新的胆甾bisdesmoside（4），一个5β-胆甾烷二糖苷（5），和四个新的24（23 →22） -的abeo- -cholestane苷（6 - 9）中，用11节已知的胆甾苷（一起10 - 20），包括OSW-1（11）。1 – 9的结构是根据常规光谱分析和化学证据确定的。不出所料，根据之前的数据，1– 3对HL-60人早幼粒细胞白血病细胞和A549人肺腺癌细胞具有有效的细胞毒活性。此外，检查了OSW-1诱导HL-60细胞凋亡的能力。在用OSW-1处理的HL-60细胞中评估了核染色质的聚集，亚G1细胞的积累，DNA片段化和caspase-3活化，为OSW-1诱导的HL-60细胞凋亡提供了证据。在OSW-1处理的凋亡HL-60细胞中未观察到线粒体膜电位或细胞色素c释放到细胞质中，表明线粒体非依赖性信号通路参与凋亡细胞的死亡。