(1S,4aS,5R,7S,7aS)-7-Hydroxy-5-(4-hydroxy-3,5-dimethoxy-benzoyloxy)-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester | 100414-76-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (1S,4aS,5R,7S,7aS)-7-Hydroxy-5-(4-hydroxy-3,5-dimethoxy-benzoyloxy)-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
• CAS: 100414-76-4
• 化学式: C₂₆H₃₄O₁₅
• 分子量: 586.547
• InChiKey: SQPWKBVQYGYOMC-XSWJAZFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.45
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  220.13
• 氢给体数：
  6.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  6-O-syringyl-8-O-acetylshanzhiside methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (1S,4aS,5R,7S,7aS)-7-Hydroxy-5-(4-hydroxy-3,5-dimethoxy-benzoyloxy)-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Sweet and bitter glycosides of the Chinese plant drug, Bai-Yun-Shen (roots of Salvia digitaloides).

  摘要：

  从中国植物药白云参（洋地黄鼠尾草的根）中分离出一种新的甜味苷，命名为白云苷（1）。通过 MS 和 NMR 光谱，特别是通过与 β-onocerin (3) 的 13C 化学位移进行比较，阐明了 1 的酸不稳定糖苷配基 baiyunol (2) 的结构。通过MS和NMR光谱确定1的结构为2的β-D-吡喃木糖基(1→2)-β-D-吡喃葡萄糖苷。除了这种甜味成分 (1) 之外，还从这种植物中分离出了几种苦味环烯醚萜苷。其中两种糖苷分别被鉴定为山栀苷甲酯 (13) 及其 8-O-乙酸酯 (=乙酰基巴勒林, 10)。通过与13的关联，将新的葡萄糖苷(9)定为6-O-紫丁香基-8-O-乙酰山枝苷甲酯。

  DOI：

  10.1248/cpb.31.780

文献信息

• Sweet and bitter principles of the Chinese plant drug, Bai-Yun-Shen: Revision of the assignment of the source plant and isolation of two new diterpene glycosides.
  作者：TAKASHI TANAKA、OSAMU TANAKA、ZHONGWEN LIN、JUN ZHOU

  DOI：10.1248/cpb.33.4275

  日期：——

  The assignment of the source plant of the Chinese plant drug "Bai-Yun-Shen" as Salvia digitaloides DIELS (Labiatae), was revised to Phlomis betonicoides DIELS of the same family. From roots of this plant, a sweet glycoside named phlomisoside-I (5) and a bitter glycoside named phlomisoside-II (6) were isolated. The aglycone of both compounds was proved to be baiyunol (7, furano-labdane-type diterpene), the aglycone of baiyunoside (1), which has already been isolated as the sweet principle from this plant drug. The structures of 5 and 6 were elucidated as the 3-O-α-rhamnopyranosyl-(1→2)-β-glucopyranoside and the 3-O-sophoroside of 7, respectively.

  将中国植物药 "白云参 "的来源植物定为唇形科植物丹参（Salvia digitaloides DIELS），并修正为同科植物白云参（Phlomis betonicoides DIELS）。从该植物的根中分离出了一种名为 phlomisoside-I (5) 的甜苷和一种名为 phlomisoside-II (6) 的苦苷。经证实，这两种化合物的苷元都是白云醇（7，呋喃-唇丹型二萜），即白云苷（1）的苷元。5 和 6 的结构已被阐明，分别为 3-O-α-rhamnopyranosyl-(1→2)-β-glucopyranoside 和 7 的 3-O-sophoroside 。