(1R,2R,4S)-p-menthane-1,2,8-triol 1-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,4S)-p-menthane-1,2,8-triol 1-O-β-D-glucopyranoside
• 英文别名: distyloside A；NSC# 742190；(2R,3S,4R,5R,6S)-2-[(1R,2R,4S)-2-hydroxy-4-(2-hydroxypropan-2-yl)-1-methylcyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₆H₃₀O₈
• 分子量: 350.409
• InChiKey: HWSOHMCMQHZNFN-NDRUJCHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S)-p-menthane-1,2,8-triol 1-O-β-D-glucopyranoside 在 盐酸 、 水 、 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.08h， 生成 可得然胶
  参考文献：
  名称：

  New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H

  摘要：

  Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6 ''-O-galloylsalidroside (6) showed potent inhibitory effects with an IC(50) value of 3.5 mu M on HIV-2, and 1.7 mu M on human RNase H, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.091

文献信息

• New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H
  作者：Jeong Ah Kim、Seo Young Yang、Anthony Wamiru、James B. McMahon、Stuart F.J. Le Grice、John A. Beutler、Young Ho Kim

  DOI：10.1016/j.bmcl.2011.03.091

  日期：2011.5

  Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6 ''-O-galloylsalidroside (6) showed potent inhibitory effects with an IC(50) value of 3.5 mu M on HIV-2, and 1.7 mu M on human RNase H, respectively. (C) 2011 Elsevier Ltd. All rights reserved.