2-O-[(2S,3R,4S)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)furan-2-yl]-1-O-[(3β)-3-(β-D-glucopyranosyloxy)-28-oxoolean-12-en-28-yl]-β-D-glucopyranose | 1207273-49-1

• 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-[(2S,3R,4S)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)furan-2-yl]-1-O-[(3β)-3-(β-D-glucopyranosyloxy)-28-oxoolean-12-en-28-yl]-β-D-glucopyranose
• 英文别名: 3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-[β-D-apiofuranosyl-(1->2)-β-D-glucopyranosyl] ester；[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1207273-49-1
• 化学式: C₄₇H₇₆O₁₇
• 分子量: 913.11
• InChiKey: OSBLHQXLZKRRBN-IXYBKOICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  64
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2-O-[(2S,3R,4S)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)furan-2-yl]-1-O-[(3β)-3-(β-D-glucopyranosyloxy)-28-oxoolean-12-en-28-yl]-β-D-glucopyranose 在 盐酸 、 水 作用下， 生成 洋芹糖 、 葡萄糖 、 齐墩果酸
  参考文献：
  名称：

  Saponins and Polyphenols from Fadogia ancylantha (Makoni Tea)

  摘要：

  Three new saponins (1-3) and a known saponin, together with four known polyphenolic compounds, have been isolated from the fermented and dried leaves of Fadogia ancylantha (Makoni tea). The structures of compounds 1-3 were established by analysis of their spectroscopic data. Both all ethanol-water extract of F. ancylantha and its phenolic constituents showed significant free-radical-scavenging and antimicrobial activities. No cytotoxicity, its evaluated by analysis of hypodiploid nuclei in HUVEC cells using propidium iodide staining, was observed for either the plant crude extract or its constituents.

  DOI：

  10.1021/np900466x
• 作为产物：
  描述：

  3,4,6-tri-O-benzoyl-2-O-{(2S,3R,4S)-3,4-bis(acetyloxy)-4-[(acetyloxy)methyl]tetrahydrofuran-2-yl}-1-O-{(3β)-28-oxo-3-[(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxy]olean-12-en-28-yl}-β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以91%的产率得到2-O-[(2S,3R,4S)-tetrahydro-3,4-dihydroxy-4-(hydroxymethyl)furan-2-yl]-1-O-[(3β)-3-(β-D-glucopyranosyloxy)-28-oxoolean-12-en-28-yl]-β-D-glucopyranose
  参考文献：
  名称：

  从Fadogia antlantha（Makoni茶）分离的三种天然三萜皂苷的合成与抗糖尿病作用

  摘要：

  所述bidesmosidic齐墩果酸皂甙的第一简明合成1 - 3从分离Fadogia ancylantha “ -锅顺序的糖基化一个”具有两个糖基1-（三氯乙酰亚胺酯）S作为糖供体的策略（马科尼茶）已通过来完成的。将合成的天然产物1 - 3然后评价它们对抑制活性α-葡糖苷酶，α-淀粉酶，和脂肪酶。间的测定化合物1 - 3，化合物1表现出较强的α-葡萄糖苷酶和α-淀粉酶抑制，IC 50的160和180μ值中号分别。更以上，化合物2和3显示出对强抑制α葡糖苷酶和脂肪酶，与respectivement IC 50个的170和190μ值中号，以及190和200μ中号。

  DOI：

  10.1002/hlca.201500061

文献信息

• Concise Synthesis and Antidiabetic Effect of Three Natural Triterpenoid Saponins Isolated from<i>Fadogia ancylantha</i>(Makoni tea)
  作者：Zi-Li Feng、Shao-Ping Wu、Wen-Hong Li、Tian-Tian Guo、Qing-Chao Liu

  DOI：10.1002/hlca.201500061

  日期：2015.9

  The first concise synthesis of the bidesmosidic oleanolic acid saponins 1–3 isolated from Fadogia ancylantha (Makoni tea) have been accomplished through a ‘one‐pot sequential glycosylation’ strategy with two glycosyl 1‐(trichloroacetimidate)s as glycosyl donors. The synthesized natural products 1–3 were then evaluated for their inhibitory activities against α‐glucosidase, α‐amylase, and lipase. Among

  所述bidesmosidic齐墩果酸皂甙的第一简明合成1 - 3从分离Fadogia ancylantha “ -锅顺序的糖基化一个”具有两个糖基1-（三氯乙酰亚胺酯）S作为糖供体的策略（马科尼茶）已通过来完成的。将合成的天然产物1 - 3然后评价它们对抑制活性α-葡糖苷酶，α-淀粉酶，和脂肪酶。间的测定化合物1 - 3，化合物1表现出较强的α-葡萄糖苷酶和α-淀粉酶抑制，IC 50的160和180μ值中号分别。更以上，化合物2和3显示出对强抑制α葡糖苷酶和脂肪酶，与respectivement IC 50个的170和190μ值中号，以及190和200μ中号。
• Saponins and Polyphenols from <i>Fadogia ancylantha</i> (Makoni Tea)
  作者：Teresa Mencherini、Patrizia Picerno、Pasquale Del Gaudio、Michela Festa、Anna Capasso、Rita Aquino

  DOI：10.1021/np900466x

  日期：2010.2.26

  Three new saponins (1-3) and a known saponin, together with four known polyphenolic compounds, have been isolated from the fermented and dried leaves of Fadogia ancylantha (Makoni tea). The structures of compounds 1-3 were established by analysis of their spectroscopic data. Both all ethanol-water extract of F. ancylantha and its phenolic constituents showed significant free-radical-scavenging and antimicrobial activities. No cytotoxicity, its evaluated by analysis of hypodiploid nuclei in HUVEC cells using propidium iodide staining, was observed for either the plant crude extract or its constituents.