3β-O-[α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl]-17-O-[β-D-glucuronopyranosyl]-ent-kaur-15-ene | 1283735-73-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-O-[α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl]-17-O-[β-D-glucuronopyranosyl]-ent-kaur-15-ene
• 英文别名: amoxanthoside A
• CAS: 1283735-73-8
• 化学式: C₃₈H₆₀O₁₇
• 分子量: 788.884
• InChiKey: ZUOOXYNFSVFVNY-XBXOKBKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.49
• 重原子数：
  55.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  274.75
• 氢给体数：
  10.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  3β-O-[α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl]-17-O-[β-D-glucuronopyranosyl]-ent-kaur-15-ene 在 hesperidinase 作用下， 以 水 为溶剂， 反应 72.0h， 以1.5 mg的产率得到ent-kaur-15-en-3β,17-diol
  参考文献：
  名称：

  Terpene Glycosides and Cytotoxic Constituents from the Seeds ofAmomum xanthioides

  摘要：

  通过柱色谱分离 Amomum xanthioides 种子的 MeOH 提取物，得到了一种新的二萜糖苷 amoxanthoside A (1)，两种新的单萜糖苷 (1S,4S,5S)-5-exo-hydroxycamphor 5-O-β-D-glucopyranoside (2) 和 (1R,4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)、4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)，以及四种已知化合物：hedychiol A (4)、pygmol (5)、(1S,4R,6R)-(+)-6-endo-hydroxycamphor (6) 和 dihydroyashabushiketol (7)。新化合物的结构是通过光谱分析（包括大量二维核磁共振数据）确定的。利用磺胺 B 生物测定法测试了分离出的化合物对四种人类癌细胞系的体外细胞毒性。

  DOI：

  10.1055/s-0029-1186194
• 作为产物：
  描述：

  2-benzyl-4-pentenoic acid 在 polystyrene-supported selenium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3β-O-[α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranosyl]-17-O-[β-D-glucuronopyranosyl]-ent-kaur-15-ene
  参考文献：
  名称：

  Solid-Phase Organic Synthesis of 5-Iodomethyl-dihydrofuran-2-ones with Recyclable Polymer-Supported Selenium Bromide

  摘要：

  Reaction of polystyrene-supported selenium bromide with gamma,delta-unsaturated acids and subsequent cleavage from the polymer by treatment with methyl iodide efficiently afforded 5-iodomethyl-dihydrofuran-2-ones in excellent yields. The polymeric reagent can be regenerated and reused as an environmentally friendly reagent.

  DOI：

  10.1080/00397911.2010.524064

文献信息

• Terpene Glycosides and Cytotoxic Constituents from the Seeds of<i>Amomum xanthioides</i>
  作者：Ki Kim、Jung Choi、Sang Choi、Kang Lee

  DOI：10.1055/s-0029-1186194

  日期：2010.3

  Column chromatographic isolation of the MeOH extract of the seeds of Amomum xanthioides afforded a new diterpene glycoside, amoxanthoside A (1), two new monoterpene glycosides, (1S,4S,5S)-5-exo-hydroxycamphor 5-O-β-D-glucopyranoside (2) and (1R,4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3), together with four known compounds, hedychiol A (4), pygmol (5), (1S,4R,6R)-(+)-6-endo-hydroxycamphor (6), and dihydroyashabushiketol (7). The structures of the new compounds were determined through spectral analysis, including extensive 2D NMR data. The isolated compounds were tested for their cytotoxicity against four human cancer cell lines in vitro using a sulforhodamine B bioassay.

  通过柱色谱分离 Amomum xanthioides 种子的 MeOH 提取物，得到了一种新的二萜糖苷 amoxanthoside A (1)，两种新的单萜糖苷 (1S,4S,5S)-5-exo-hydroxycamphor 5-O-β-D-glucopyranoside (2) 和 (1R,4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)、4R,5S)-5-endo-hydroxycamphor 5-O-β-D-glucopyranoside (3)，以及四种已知化合物：hedychiol A (4)、pygmol (5)、(1S,4R,6R)-(+)-6-endo-hydroxycamphor (6) 和 dihydroyashabushiketol (7)。新化合物的结构是通过光谱分析（包括大量二维核磁共振数据）确定的。利用磺胺 B 生物测定法测试了分离出的化合物对四种人类癌细胞系的体外细胞毒性。
• Solid-Phase Organic Synthesis of 5-Iodomethyl-dihydrofuran-2-ones with Recyclable Polymer-Supported Selenium Bromide
  作者：Chao-Li Wang、Shou-Ri Sheng、Xin Cheng、Ming-Zhong Cai

  DOI：10.1080/00397911.2010.524064

  日期：2012.2.1

  Reaction of polystyrene-supported selenium bromide with gamma,delta-unsaturated acids and subsequent cleavage from the polymer by treatment with methyl iodide efficiently afforded 5-iodomethyl-dihydrofuran-2-ones in excellent yields. The polymeric reagent can be regenerated and reused as an environmentally friendly reagent.