21,22-di-O-tigloyl barrigenol 3-O-β-D-glucopyranosyl(1->2)[α-L-rhamnopyranosyl(1->2)-β-D-galactopyranosyl(1->3)]-β-D-glucopyranosiduronic acid | 1160430-51-2

• 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: 21,22-di-O-tigloyl barrigenol 3-O-β-D-glucopyranosyl(1->2)[α-L-rhamnopyranosyl(1->2)-β-D-galactopyranosyl(1->3)]-β-D-glucopyranosiduronic acid
• 英文别名: yuchasaponin A；(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9,10-bis[[(E)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 1160430-51-2
• 化学式: C₆₄H₁₀₀O₂₈
• 分子量: 1317.48
• InChiKey: MWOHZWYDIQDYSO-CAMGZPBRSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  92
• 可旋转键数：
  18
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  447
• 氢给体数：
  15
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  21,22-di-O-tigloyl barrigenol 3-O-β-D-glucopyranosyl(1->2)[α-L-rhamnopyranosyl(1->2)-β-D-galactopyranosyl(1->3)]-β-D-glucopyranosiduronic acid 在 氢氧化钾 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以8.0 mg的产率得到desacyl yuchasaponin A
  参考文献：
  名称：

  Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of <i>Camellia oleifera</i>&mdash;Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects&mdash;

  摘要：

  山茶花（Camellia oleifera ABEL）花蕾的甲醇提取物及其丁醇可溶部分对大鼠乙醇和吲哚美辛诱导的胃黏膜损伤显示出抑制作用。乙酸乙酯和丁醇可溶部分还表现出对大鼠晶状体醛糖还原酶的抑制作用以及对1,1-二苯基-2-苦基肼自由基和超氧自由基的清除效果。从丁醇可溶部分中分离出四种新的酰化齐墩果烷型三萜寡糖苷，命名为玉茶皂苷A、B、C和D，其结构根据化学和物理化学证据得以阐明。另一方面，从乙酸乙酯和丁醇可溶部分中分离出槲皮素3-O-α-L-鼠李糖苷和山柰酚3-O-α-L-鼠李糖苷作为主要成分，并对其胃保护作用进行了研究。

  DOI：

  10.1248/cpb.57.269

文献信息

• Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of &lt;i&gt;Camellia oleifera&lt;/i&gt;&amp;mdash;Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects&amp;mdash;
  作者：Sachiko Sugimoto、Guihua Chi、Yasuyo Kato、Seikou Nakamura、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.57.269

  日期：——

  The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia oleifera ABEL were found to exhibit inhibitory effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. The ethyl acetate- and 1-butanol-soluble fractions also showed inhibitory effects on rat lens aldose reductase and scavenging effects on 1,1-diphenylpicryl-2-hydrazyl radical and superoxide. From the 1-butanol-soluble fraction, four new acylated oleanane-type triterpene oligoglycosides, yuchasaponins A, B, C, and D, were isolated and their structures were elucidated on the basis of chemical and physicochemical evidence. On the other hand, quercetin 3-O-α-L-rhamnopyranoside and kaempferol 3-O-α-L-rhamnopyranoside were isolated from the ethyl acetate- and 1-butanol-soluble fractions as the principal constituents, and their gastroprotective effects were examined.

  山茶花（Camellia oleifera ABEL）花蕾的甲醇提取物及其丁醇可溶部分对大鼠乙醇和吲哚美辛诱导的胃黏膜损伤显示出抑制作用。乙酸乙酯和丁醇可溶部分还表现出对大鼠晶状体醛糖还原酶的抑制作用以及对1,1-二苯基-2-苦基肼自由基和超氧自由基的清除效果。从丁醇可溶部分中分离出四种新的酰化齐墩果烷型三萜寡糖苷，命名为玉茶皂苷A、B、C和D，其结构根据化学和物理化学证据得以阐明。另一方面，从乙酸乙酯和丁醇可溶部分中分离出槲皮素3-O-α-L-鼠李糖苷和山柰酚3-O-α-L-鼠李糖苷作为主要成分，并对其胃保护作用进行了研究。