Excelside B | 1149762-83-3

• 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: Excelside B
• 英文别名: (2S,4S,3E)-methyl 3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethyl]oxy-2-oxoethyl}-2-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-3, 4-dihydro-2H-pyran-5-carboxylate；(2S,3E,4S) 2H-pyran-4-acetic acid-3-ethylidene-2-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) oxy]-3,4-dihydro-5-(methoxycarbonyl) 2-(4-hydroxyphenyl)ethyl ester；methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4H-pyran-3-carboxylate
• CAS: 1149762-83-3
• 化学式: C₃₁H₄₂O₁₇
• 分子量: 686.664
• InChiKey: FVQYDVAAZIXQID-DTYPFZMBSA-N

物化性质

• 沸点：
  909.2±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  261
• 氢给体数：
  8
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  Excelside B 在 盐酸 、 水 作用下， 反应 3.0h， 生成 葡萄糖
  参考文献：
  名称：

  Iridoids from Fraxinus excelsior with Adipocyte Differentiation-Inhibitory and PPARα Activation Activity

  摘要：

  Two new secoiridoid glucosides, excelsides A (1) and B (2), were isolated from the seeds of Fraxinus excelsior. Their structures were elucidated as (2S,4S,3E)-methyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate and (2S,4S,3E)-methyl 3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethyl]oxy-2-oxoethyl}-2-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate, respectively, on the basis of NMR and MS data. Eight known compounds were identified as nuzhenide (3), GI3 (4), GI5 (5), ligstroside (6), oleoside 11-methyl ester (7), oleoside dimethyl ester (8), 1 '''-O-beta-D-glucosylformoside (9), and salidroside (10). Compounds 1-9 inhibited adipocyte differentiation in 3T3-L1 cells. Dilutions of the aqueous extract of F. excelsior (1: 10 000) as well as compounds 2, 3, 4, 5, and 8 activated the peroxisome proliferator-mediated receptor-alpha (PPAR alpha) reporter cell system in the range of 10(-4) M, compared to 10(-7)-10(-8) M for the synthetic PPARoL activiator. WY14,643. Both biological activity profiles support the hypothesis that inhibition of adipocyte differentiation and PPAR alpha-mediated mechanisms might be relevant pathways for the antidiabetic activity of F. excelsior extract.

  DOI：

  10.1021/np9003118

文献信息

• Iridoids from <i>Fraxinus excelsior</i> with Adipocyte Differentiation-Inhibitory and PPARα Activation Activity
  作者：Naisheng Bai、Kan He、Alvin Ibarra、Antoine Bily、Marc Roller、Xiaozhuo Chen、Ralph Rühl

  DOI：10.1021/np9003118

  日期：2010.1.22

  Two new secoiridoid glucosides, excelsides A (1) and B (2), were isolated from the seeds of Fraxinus excelsior. Their structures were elucidated as (2S,4S,3E)-methyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate and (2S,4S,3E)-methyl 3-ethylidene-4-2-[2-(4-hydroxyphenyl)ethyl]oxy-2-oxoethyl}-2-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate, respectively, on the basis of NMR and MS data. Eight known compounds were identified as nuzhenide (3), GI3 (4), GI5 (5), ligstroside (6), oleoside 11-methyl ester (7), oleoside dimethyl ester (8), 1 '''-O-beta-D-glucosylformoside (9), and salidroside (10). Compounds 1-9 inhibited adipocyte differentiation in 3T3-L1 cells. Dilutions of the aqueous extract of F. excelsior (1: 10 000) as well as compounds 2, 3, 4, 5, and 8 activated the peroxisome proliferator-mediated receptor-alpha (PPAR alpha) reporter cell system in the range of 10(-4) M, compared to 10(-7)-10(-8) M for the synthetic PPARoL activiator. WY14,643. Both biological activity profiles support the hypothesis that inhibition of adipocyte differentiation and PPAR alpha-mediated mechanisms might be relevant pathways for the antidiabetic activity of F. excelsior extract.