2-(3,4-dihydroxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1→6)-O-[O-β-apiofuranosyl-(1→4)-α-D-rhamnopyranosyl-(1→3)]-4-O-(E)-caffeoyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,4-dihydroxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1→6)-O-[O-β-apiofuranosyl-(1→4)-α-D-rhamnopyranosyl-(1→3)]-4-O-(E)-caffeoyl-β-D-glucopyranoside
• 英文别名: stewartiiside
• 化学式: C₄₀H₅₄O₂₃
• 分子量: 902.855
• InChiKey: VHBAQLWUQDXPHG-UIKNMKQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  63.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  363.13
• 氢给体数：
  13.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  2-(3,4-dihydroxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1→6)-O-[O-β-apiofuranosyl-(1→4)-α-D-rhamnopyranosyl-(1→3)]-4-O-(E)-caffeoyl-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 3.0h， 生成 D-apiose 、 L-鼠李糖 、 葡萄糖 、 羟基酪醇 、 咖啡酸
  参考文献：
  名称：

  Isolation of natural compounds from Phlomis stewartii showing α-glucosidase inhibitory activity

  摘要：

  Stewartiiside (1), a phenylethanoid glycoside and three 28-nortriterpenoids: stewertiisins A-C [(17R)-19(18 -> 17)-abeo-3 alpha,18 beta,23,24-tetrahydroxy-28-norolean-12-ene, 2; (17R)-19(18 -> 17)-abeo-2 alpha,16 beta, 18 beta,23,24-pentahydroxy-28-norolean-12-en-3-one, 3; (17R)-19(18 -> 17)-abeo-2 alpha,3 alpha,23,24-tetrahydroxy-28-noroleane-11,13-diene, 4] together with eight known compounds: lunariifolioside (5), notohamosin A (6), phlomispentanol (7), isorhamnetin 3-(6-p-coumaroyl)-beta-D-glucopyranoside (8), tiliroside (9), caffeic acid (10), p-hydrxybenzoic acid (11) and oleanolic acid (12) were isolated from the ethyl acetate soluble fraction of the methanolic extract of whole plant of Phlomis stewartii. The structures of these isolates (1-12) were elucidated by the combination of 1D (H-1 and C-13 NMR), 2D (HMQC, HMBC COSY, NOESY) NMR spectroscopy and mass spectrometry (EIMS, HREIMS, FABMS, HRFABMS) and in comparison with literature data of related compounds. All the isolates (1-12) showed alpha-glucosidase inhibitory activity with IC50 values ranging between 14.5 and 355.4 mu M, whereas, compounds 1, 5, 9 and 10 showed promising alpha-glucosidase inhibitory activity with IC50 values below 30 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.09.015