2-(O-β-D-glucopyranosyl)atractyligenin | 62022-40-6

• 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: 2-(O-β-D-glucopyranosyl)atractyligenin
• 英文别名: 2-Glucopyranosylatractyligenin；(1R,4R,5R,7R,9R,10S,13R,15S)-15-hydroxy-9-methyl-14-methylidene-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 62022-40-6
• 化学式: C₂₅H₃₈O₉
• 分子量: 482.571
• InChiKey: ZUDBDCBPZHGAEL-HGAXDMRMSA-N

物化性质

• 沸点：
  712.2±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(O-β-D-glucopyranosyl)atractyligenin 、 水 、 硫酸 生成 atractyligenin
  参考文献：
  名称：

  VARGAS, DAVID;DOMINGUEZ, XORGE A.;ACUNA-ASKAR, KARIM;GUTIERREZ, MARCOS;HO+, PHYTOCHEMISTRY, 27,(1988) N 5, 1532-1534

  摘要：

  DOI：
• 作为产物：
  描述：

  2-O-β-D-glucopyranosylcarboxyatractyligenin 以 neat (no solvent, solid phase) 为溶剂， 反应 0.17h， 生成 2-(O-β-D-glucopyranosyl)atractyligenin
  参考文献：
  名称：

  2-O-β-d-Glucopyranosyl-carboxyatractyligenin from Coffea L. inhibits adenine nucleotide translocase in isolated mitochondria but is quantitatively degraded during coffee roasting

  摘要：

  Atractyloside (1) and carboxyatractyloside (2) are well-known inhibitors of the adenine nucleotide translocase (ANT) in mitochondria, thus effectively blocking oxidative phosphorylation. Structurally related derivatives atractyligenin (3), 2-O-beta-D-glucopyranosyl-atractyligenin (4), 3'-O-beta-D-glucopyranosyl-2'-O-isovaleryl-2 beta-(2-desoxy-atractyligenin)-beta-D-glucopyranoside (5), and 2-O-beta-D-glucopyranosyl-carboxyatractyligenin (6) were isolated from raw beans of Coffea L and the impact of 1-6 on ANT activity was evaluated in isolated mitochondria. Among the coffee components, 6 significantly inhibited ANT activity leading to reduced respiration. Quantitative analysis in commercial coffees, experimental roastings of coffee, and model experiments using purified compound 6 consistently revealed a complete degradation during thermal treatment. In comparison, raw coffee extracts were found to contain high levels of 6, which are therefore expected to be present in food products enriched with raw coffee extracts. This implies the necessity of analytically controlling the levels of 6 in raw coffee extracts when used as additives for food products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.03.022

文献信息

• Acyl atractyligenin and carboxyatractyligenin glycosides from Antennaria rosea subsp. confinis
  作者：Yangyang Xiao、Ling Lv、Ping Gou、Haihui Xie

  DOI：10.1016/j.phytochem.2018.10.018

  日期：2019.1

  Eight previously undescribed acyl atractyligenin and carboxyatractyligenin glycosides were isolated from whole Antennaria rosea subsp. confinis (Greene) R. J. Bayer (Compositae) [syn. Leontopodium leontopodioides (Willd.) Beauv. (Asteraceae)] plants and their structures were determined by spectroscopic and chemical methods. The compounds were trivially named leontopodiosides F-M. Seven of the compounds

  从整个 Antennaria rosea subsp. 中分离出八种以前未描述的酰基苍术苷元和羧基苍术苷元。confinis (Greene) RJ Bayer (Compositae) [syn. Leontopodium leontopodioides (Willd.) Beauv。(菊科)]植物及其结构通过光谱和化学方法确定。这些化合物被简单地命名为leontopodiosides FM。其中七种化合物显示出对胰脂肪酶的有效体外抑制活性，IC50 值范围为 3.4 至 52.5 μM，表明它们参与了先前观察到的这种植物在减少大鼠甘油三酯吸收方面的作用。
• Lefranc, Journal de Pharmacie et de Chimie, 1873, vol. <4> 17, p. 187,188
  作者：Lefranc

  DOI：——

  日期：——
• VARGAS, DAVID;DOMINGUEZ, XORGE A.;ACUNA-ASKAR, KARIM;GUTIERREZ, MARCOS;HO+, PHYTOCHEMISTRY, 27,(1988) N 5, 1532-1534
  作者：VARGAS, DAVID、DOMINGUEZ, XORGE A.、ACUNA-ASKAR, KARIM、GUTIERREZ, MARCOS、HO+

  DOI：——

  日期：——
• 2-O-β-d-Glucopyranosyl-carboxyatractyligenin from Coffea L. inhibits adenine nucleotide translocase in isolated mitochondria but is quantitatively degraded during coffee roasting
  作者：Roman Lang、Tobias Fromme、Anja Beusch、Anika Wahl、Martin Klingenspor、Thomas Hofmann

  DOI：10.1016/j.phytochem.2013.03.022

  日期：2013.9

  Atractyloside (1) and carboxyatractyloside (2) are well-known inhibitors of the adenine nucleotide translocase (ANT) in mitochondria, thus effectively blocking oxidative phosphorylation. Structurally related derivatives atractyligenin (3), 2-O-beta-D-glucopyranosyl-atractyligenin (4), 3'-O-beta-D-glucopyranosyl-2'-O-isovaleryl-2 beta-(2-desoxy-atractyligenin)-beta-D-glucopyranoside (5), and 2-O-beta-D-glucopyranosyl-carboxyatractyligenin (6) were isolated from raw beans of Coffea L and the impact of 1-6 on ANT activity was evaluated in isolated mitochondria. Among the coffee components, 6 significantly inhibited ANT activity leading to reduced respiration. Quantitative analysis in commercial coffees, experimental roastings of coffee, and model experiments using purified compound 6 consistently revealed a complete degradation during thermal treatment. In comparison, raw coffee extracts were found to contain high levels of 6, which are therefore expected to be present in food products enriched with raw coffee extracts. This implies the necessity of analytically controlling the levels of 6 in raw coffee extracts when used as additives for food products. (C) 2013 Elsevier Ltd. All rights reserved.