1-O-isopropyl-6-O-(5'',9''-dimethyl-2'',8''-decadienoyl)-β-D-glucopyranoside | 1255789-51-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1-O-isopropyl-6-O-(5'',9''-dimethyl-2'',8''-decadienoyl)-β-D-glucopyranoside
• 英文别名: citrusoside A；[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-propan-2-yloxyoxan-2-yl]methyl (2E,5R)-5,9-dimethyldeca-2,8-dienoate
• CAS: 1255789-51-5
• 化学式: C₂₁H₃₆O₇
• 分子量: 400.513
• InChiKey: MHJOAVXYKHQVFT-NWECRORVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-isopropyl-6-O-(5'',9''-dimethyl-2'',8''-decadienoyl)-β-D-glucopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成
  参考文献：
  名称：

  Citrusosides A−D and Furanocoumarins with Cholinesterase Inhibitory Activity from the Fruit Peels of Citrus hystrix

  摘要：

  Four new compounds, citrusosides A-D (1-4), and 15 known compounds were isolated from the hexanes and CH2Cl2 extracts of the peels of Citrus hystrix fruits. Compound 1 is a 1-O-isopropyl-6-O-beta-D-glucopyranosyl ester of 5 '',9 ''-dimethyl-2 '',8 ''-decadienoic acid. Compounds 2-4 possess a 1-O-isopropyl-beta-D-glucopyranosyl and a dihydroxyprenylfuranocoumarin moiety conjugated to the 3-hydroxy-3-methylglutaric acid as diesters. Several furanocoumarins were evaluated for their cholinesterase inhibitory activity. (R)-(+)-6'-Hydroxy-7'-methoxybergamottin, (R)-(+)-6',7'-dihydroxybergamottin, and (+)-isoimparatorin showed IC50 values of 11.2 +/- 0.1, 15.4 +/- 0.3, and 23 +/- 0.2 mu M. respectively. Bioassay results indicated that the presence of a dioxygenated geranyl chain in the test compounds is crucial for the inhibitory activity.

  DOI：

  10.1021/np100531x