3-O-[α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl]augustic acid 28-O-β-D-glucopyranosyl ester | 139742-09-9

• 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: 3-O-[α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl]augustic acid 28-O-β-D-glucopyranosyl ester
• 英文别名: beta-D-Glucopyranosiduronic acid, (2beta,3beta)-28-(beta-D-glucopyranosyloxy)-2-hydroxy-28-oxoolean-12-en-3-yl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-；(2S,3S,4S,5R,6R)-6-[[(2S,3R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 139742-09-9
• 化学式: C₄₈H₇₆O₁₉
• 分子量: 957.12
• InChiKey: ITPLQPXCONKMAX-VLKNSCRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  67
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  312
• 氢给体数：
  11
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  3-O-[α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl]augustic acid 28-O-β-D-glucopyranosyl ester 在 2,6-二甲基吡啶 、 lithium iodide 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以12 mg的产率得到3-O-[α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl]augustic acid
  参考文献：
  名称：

  Saponins from Amaranthus hypochondriacus.

  摘要：

  Four triterpenoid saponins were isolated from Amaranthus hypochondriacus which are grain crops in the Nepal, Mexico and South America. Their structures were elucidated based on spectral evidence to be : (1) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester. (2) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxyolean-12-en-23-al-28-oic acid 28-O-β-D-glucopyranosyl ester; (3) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxy-30-norolean-12, 20(29)-dien-28-oic acid 28-O-β-D-glucopyranosyl ester. (4) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxy-30-norolean-12, 20(29)-dien-23-al-28-oic acid 28-O-β-D-glucopyranosyl ester.

  DOI：

  10.1248/cpb.39.2609

文献信息

• Saponins from Amaranthus hypochondriacus.
  作者：Hiroshi KOHDA、Seiji TANAKA、Yasutoshi YAMAOKA、Yoshie OHHARA

  DOI：10.1248/cpb.39.2609

  日期：——

  Four triterpenoid saponins were isolated from Amaranthus hypochondriacus which are grain crops in the Nepal, Mexico and South America. Their structures were elucidated based on spectral evidence to be : (1) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester. (2) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxyolean-12-en-23-al-28-oic acid 28-O-β-D-glucopyranosyl ester; (3) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxy-30-norolean-12, 20(29)-dien-28-oic acid 28-O-β-D-glucopyranosyl ester. (4) 3-O-α-L-rhamnopyranosyl(1→3)-β-D-glucuronopyranosyl-2β, 3β-dihydroxy-30-norolean-12, 20(29)-dien-23-al-28-oic acid 28-O-β-D-glucopyranosyl ester.