(4R)-p-menth-1-ene-7,8-diol 7-O-[β-D-xylopyranosyl-(1->6)-β-D-glucopyranosyl] ester

• 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: (4R)-p-menth-1-ene-7,8-diol 7-O-[β-D-xylopyranosyl-(1->6)-β-D-glucopyranosyl] ester
• 英文别名: distyloside B；NSC# 742191；(2S,3S,4R,5R,6S)-2-[[(4R)-4-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-6-[[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• 化学式: C₂₁H₃₆O₁₁
• 分子量: 464.51
• InChiKey: MQXZFEFINCOMLT-SVOIQLESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (4R)-p-menth-1-ene-7,8-diol 7-O-[β-D-xylopyranosyl-(1->6)-β-D-glucopyranosyl] ester 在 β-glucosidase 作用下， 以 水 为溶剂， 反应 168.0h， 以1 mg的产率得到(4R)-p-menth-1-ene-7,8-diol
  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.