Toralactone 9-O-beta-D-gentiobioside | 119170-52-4

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: Toralactone 9-O-beta-D-gentiobioside
• 英文别名: toralactone 9-O-yl β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside；toralactone-9-O-β-D-gentiobioside；toralactone-9-O-gentiobioside；cassiaside C；10-hydroxy-7-methoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one
• CAS: 119170-52-4
• 化学式: C₂₇H₃₂O₁₅
• 分子量: 596.542
• InChiKey: GBGJNKYTLIUCMX-YUMVGKRXSA-N

物化性质

• 熔点：
  235-237 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  932.2±65.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  15

制备方法与用途

生物活性

Cassiaside C（Toralactone 9-O-β-D-gentiobioside）是从决明子种子中分离出的一种萘酚类化合物，能够抑制晚期糖基化终产物 (AGE) 的形成。

靶点

IC50: 抑制 AGE 形成

反应信息

• 作为反应物：
  描述：

  Toralactone 9-O-beta-D-gentiobioside 在 β-glucosidase 作用下， 以 水 为溶剂， 反应 20.0h， 生成 决明内酯
  参考文献：
  名称：

  Kitanaka, Susumu; Takido, Michio, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 10, p. 3980 - 3984

  摘要：

  DOI：
• 作为产物：
  描述：

  决明内酯 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 69.0h， 生成 Toralactone 9-O-beta-D-gentiobioside
  参考文献：
  名称：

  Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds

  摘要：

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.

  DOI：

  10.1021/jo034223u

文献信息

• KITANAKA, SUSUMU;TAKIDO, MICHIO, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 3980-3984
  作者：KITANAKA, SUSUMU、TAKIDO, MICHIO

  DOI：——

  日期：——
• Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds
  作者：Zhaojun Zhang、Biao Yu

  DOI：10.1021/jo034223u

  日期：2003.8.1

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.
• Kitanaka, Susumu; Takido, Michio, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 10, p. 3980 - 3984
  作者：Kitanaka, Susumu、Takido, Michio

  DOI：——

  日期：——