6-O-syringyl-8-O-acetylshanzhiside methyl ester | 86450-76-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 6-O-syringyl-8-O-acetylshanzhiside methyl ester
• 英文别名: methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-(4-hydroxy-3,5-dimethoxybenzoyl)oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• CAS: 86450-76-2
• 化学式: C₂₈H₃₆O₁₆
• 分子量: 628.584
• InChiKey: UYVOQGVJJDNTHV-IOOZZJQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  226
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  6-O-syringyl-8-O-acetylshanzhiside methyl ester 在 吡啶 、 sodium hydroxide 作用下， 生成 hexaacetylshanzhiside methyl ester
  参考文献：
  名称：

  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.

  摘要：

  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 。

  DOI：

  10.1248/cpb.33.4275

文献信息

• Sweet and bitter glycosides of the Chinese plant drug, Bai-Yun-Shen (roots of Salvia digitaloides).
  作者：Takashi Tanaka、Osamu Tanaka、ZhongWen Lin、Jun Zhou、Hiroyuki Ageta

  DOI：10.1248/cpb.31.780

  日期：——

  From a Chinese plant drug, Bai-Yun-Shen (roots of Salvia digitaloides), a new sweet glycoside named baiyunoside (1) was isolated. The structure of the acid-unstable aglycone of 1 named baiyunol (2) was elucidated by MS and NMR spectroscopy especially by comparison with the 13C chemical shifts of β-onocerin (3). The structure of 1 was determined to be β-D-xylopyranosyl (1→2)-β-D-glucopyranoside of 2 by MS and NMR spectroscopy. Besides this sweet principle (1), several bitter iridoid glucosides were also isolated from this plant. Two of these glucosides were identified as shanzhiside methyl ester (13) and its 8-O-acetate (=acetylbarlerin, 10), respectively. A new glucoside (9) was formulated as 6-O-syringyl-8-O-acetyl shanzhiside methyl ester by the correlation with 13.

  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。
• 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 。