6-(oxymethyl)-2-hydroxyphenyl-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside | 1435477-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(oxymethyl)-2-hydroxyphenyl-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-6-(hydroxymethyl)phenoxy]oxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 1435477-31-8
• 化学式: C₁₉H₂₈O₁₃
• 分子量: 464.424
• InChiKey: ZPQOXWLHAKLROW-XXQLXNJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-(oxymethyl)-2-hydroxyphenyl-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  Anti-adipogenic activity of compounds isolated from Idesia polycarpa on 3T3-L1 cells

  摘要：

  Recently, obesity is a complex multifactorial chronic disease increasing the risk for type 2 diabetes, coronary heart disease and hypertension, and has become a major worldwide health problem. In the course of screening natural products employing 3T3-L1 cells as an in vitro system, the methanol extract of Idesia polycarpa Maxim. Fruits (Flacourtiaceae) significantly inhibited adipocyte differentiation by measuring lipid contents using oil red O staining. One new compound, 6-(oxymethyl)-2-hydroxyphenyl-O- beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (8), was isolated along with nine known compounds (1-7 and 9-10) from CHCl3 and n-BuOH fractions of the methanol extract of I. polycarpa fruits. Among them, idescarpin (1) with 1-hydroxy-6-oxo-2-cyclohexenecarboxylate moiety showed the most potent inhibitory activity on adipocyte differentiation with IC50 values of 23.2 mu M. Idescarpin (1) dramatically suppressed the induction of C/EBP alpha expression, whereas it significantly increased the induction of PPAR gamma expression, supported by quantitative real time PCR and Western blot analysis. The down-regulation in mRNA levels of SREBP1c, SCD-1, and FAS by idescarpin (1) during adipocyte differentiation revealed that the inhibition of adipocyte differentiation was mediated by the regulation of lipogenesis. Taken together, we suggest that idescarpin (1) shows a great potential against obesity and diabetes though the anti-adipogenic activity and the up-regulation of PPAR gamma. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.011

文献信息

• Anti-adipogenic activity of compounds isolated from Idesia polycarpa on 3T3-L1 cells
  作者：Mina Lee、Hyang Hwa Lee、Jin-Ku Lee、Sang-Kyu Ye、Seung Hyun Kim、Sang Hyun Sung

  DOI：10.1016/j.bmcl.2013.04.011

  日期：2013.6

  Recently, obesity is a complex multifactorial chronic disease increasing the risk for type 2 diabetes, coronary heart disease and hypertension, and has become a major worldwide health problem. In the course of screening natural products employing 3T3-L1 cells as an in vitro system, the methanol extract of Idesia polycarpa Maxim. Fruits (Flacourtiaceae) significantly inhibited adipocyte differentiation by measuring lipid contents using oil red O staining. One new compound, 6-(oxymethyl)-2-hydroxyphenyl-O- beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (8), was isolated along with nine known compounds (1-7 and 9-10) from CHCl3 and n-BuOH fractions of the methanol extract of I. polycarpa fruits. Among them, idescarpin (1) with 1-hydroxy-6-oxo-2-cyclohexenecarboxylate moiety showed the most potent inhibitory activity on adipocyte differentiation with IC50 values of 23.2 mu M. Idescarpin (1) dramatically suppressed the induction of C/EBP alpha expression, whereas it significantly increased the induction of PPAR gamma expression, supported by quantitative real time PCR and Western blot analysis. The down-regulation in mRNA levels of SREBP1c, SCD-1, and FAS by idescarpin (1) during adipocyte differentiation revealed that the inhibition of adipocyte differentiation was mediated by the regulation of lipogenesis. Taken together, we suggest that idescarpin (1) shows a great potential against obesity and diabetes though the anti-adipogenic activity and the up-regulation of PPAR gamma. (C) 2013 Elsevier Ltd. All rights reserved.