3-O-[α-L-arabinopyranosyl-(1->2)-β-D-xylopyranosyl]-3β,6α,16β,23a,25-pentahydroxy-20(R),24(S)-epoxycycloartane

• 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: 3-O-[α-L-arabinopyranosyl-(1->2)-β-D-xylopyranosyl]-3β,6α,16β,23a,25-pentahydroxy-20(R),24(S)-epoxycycloartane
• 英文别名: (2S,3R,4S,5S)-2-[(2S,3S,4S,5R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,4S,5S)-4-hydroxy-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-4,5-dihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• 化学式: C₄₀H₆₆O₁₄
• 分子量: 770.956
• InChiKey: HVXPUJWFAWYJGU-ROVBKBNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  228
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-O-[α-L-arabinopyranosyl-(1->2)-β-D-xylopyranosyl]-3β,6α,16β,23a,25-pentahydroxy-20(R),24(S)-epoxycycloartane 在 盐酸 、 水 作用下， 反应 4.0h， 生成 D-木糖 、 L-阿拉伯糖
  参考文献：
  名称：

  Cycloartane glycosides from Astragalus campylosema Boiss. ssp. campylosema

  摘要：

  Four cycloartane glycosides, 3-O-[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-3 beta,6 alpha,16 beta,23 alpha, 25-pentahydroxy-20(R),24(S)-epoxycycloartane (1), 3-O-[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-16-O-hydroxyacetoxy-23-O-acetoxy-3 beta,6 alpha,25-trihydroxy-20(R),24(S)-epoxycycloartane (2), 3-O[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-3 beta,6 alpha,23 alpha,25-tetrahydroxy-20(R),24(R)-16 beta,24;20, 24-diepoxycycloartane (3), 3-O-[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-25-O-beta-D-glucopyranosyl-3 beta,6 alpha,16 beta,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), along with three known cycloartane glycosides were isolated from the MeOH extract of the roots of Astragalus campylosema ssp. campylosema. Their structures were established by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The occurrence of the hydroxyl function at position 23 (1-2) and of the ketalic function at C-24 (3) are very unusual findings in the cycloartane class. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.08.002

文献信息

• Cycloartane glycosides from Astragalus campylosema Boiss. ssp. campylosema
  作者：İhsan Çalış、Ali A. Dönmez、Angela Perrone、Cosimo Pizza、Sonia Piacente

  DOI：10.1016/j.phytochem.2008.08.002

  日期：2008.10

  Four cycloartane glycosides, 3-O-[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-3 beta,6 alpha,16 beta,23 alpha, 25-pentahydroxy-20(R),24(S)-epoxycycloartane (1), 3-O-[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-16-O-hydroxyacetoxy-23-O-acetoxy-3 beta,6 alpha,25-trihydroxy-20(R),24(S)-epoxycycloartane (2), 3-O[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-3 beta,6 alpha,23 alpha,25-tetrahydroxy-20(R),24(R)-16 beta,24;20, 24-diepoxycycloartane (3), 3-O-[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-25-O-beta-D-glucopyranosyl-3 beta,6 alpha,16 beta,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), along with three known cycloartane glycosides were isolated from the MeOH extract of the roots of Astragalus campylosema ssp. campylosema. Their structures were established by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The occurrence of the hydroxyl function at position 23 (1-2) and of the ketalic function at C-24 (3) are very unusual findings in the cycloartane class. (C) 2008 Elsevier Ltd. All rights reserved.