Sitoindoside I; (6'-O-棕榈酰基)-3beta-D-吡喃葡萄糖基谷甾醇 | 18749-71-8

• 物质功能分类: 天然产物 - 甾体化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: Sitoindoside I; (6'-O-棕榈酰基)-3beta-D-吡喃葡萄糖基谷甾醇
• 中文别名: (6'-O-棕榈酰基)-3BETA-D-吡喃葡萄糖基谷甾醇；SitoindosideI;(6'-O-棕榈酰基)-3beta-D-吡喃葡萄糖基谷甾醇
• 英文名称: sitoindoside I
• 英文别名: β-sitosteryl-3-O-β-D-glucopyranoside-6′-O-palmitate；6'-(β-sitosteroyl-3-O-β-glucopyranosidyl) hexadecanoate；6'-(β-sitosteryl-3-O-β-D-glucopyranosidyl)hexadecanoate；6'-(β-sitosteryl-3-O-β-glucopyranosidyl) hexadecanoate；3-O-(6'-O-palmitoyl)-β-D-glucopyranosyl-β-sitosterol；3-O-[(6′-O-palmitoyl)-β-D-glucopyranosyl]sitosterol；[(2R,3S,4S,5R,6R)-6-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl hexadecanoate
• CAS: 18749-71-8
• 化学式: C₅₁H₉₀O₇
• 分子量: 815.271
• InChiKey: JCLYMCVRBRHEHI-TWDDPRSNSA-N

物化性质

• 熔点：
  163-165 °C
• 沸点：
  811.2±65.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.1
• 重原子数：
  58
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Sitoindoside I; (6'-O-棕榈酰基)-3beta-D-吡喃葡萄糖基谷甾醇 在 sodium acetate-acetic acid buffer 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 豆甾醇
  参考文献：
  名称：

  Ghosal, Shibnath; Saini, Kulwant S., Journal of Chemical Research, Miniprint, 1984, # 4, p. 965 - 975

  摘要：

  DOI：
• 作为产物：
  描述：

  豆甾醇 在 吡啶 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 乙醚 、 苯 为溶剂， 反应 72.0h， 生成 Sitoindoside I; (6'-O-棕榈酰基)-3beta-D-吡喃葡萄糖基谷甾醇
  参考文献：
  名称：

  Suppressors of Cancer Cell Proliferation from Fig (Ficus carica) Resin:  Isolation and Structure Elucidation

  摘要：

  A mixture of 6-O-acyl-beta -D-glucosyl-beta -sitosterols, the acyl moeity being primarily palmitoyl and linoleyl with minor amounts of stearyl and oleyl, has been isolated as a potent cytotoxic agent from fig (Ficus carica) latex and soybeans. Identity was established by spectroscopic methods (NMR, MS) and confirmed by chemical synthesis. Both the natural and the synthetic compounds showed in vitro inhibitory effects on proliferation of various cancer cell lines.

  DOI：

  10.1021/np000592z

文献信息

• Studies on the Constituents from the Bark of<i>Bauhinia Purpurea</i>
  作者：Yueh-Hsiung Kuo、Pei-Hung Chu

  DOI：10.1002/jccs.200200042

  日期：2002.4

  previous paper, were ported a new stigmasteroyl glucoside derivative together with four known compounds. In addition to the above compounds, the isolation and identification of twenty-four compounds from the same source are described here. Their structures were deter mined on the basis of spectral evidence as well as comparison with authentic samples. Those compounds included four waxes, four triterpenes

  在之前的一篇论文中，移植了一种新的豆甾酰葡糖苷衍生物以及四种已知化合物。除上述化合物外，本文还介绍了来自同一来源的 24 种化合物的分离和鉴定。它们的结构是根据光谱证据以及与真实样品的比较确定的。这些化合物包括四种蜡、四种三萜类、八种类固醇、两种甘油酯、三种类黄酮和三种苯丙烷。在三个 ω-羟基链烷酸烷基酯、甘油酯和苯丙烷的混合物中发现了一些新化合物。
• Constituents of the Bark of<i>Ficus microcarpa</i>Lf.
  作者：Yueh-Hsiung Kuo、Yen-Cheng Li

  DOI：10.1002/jccs.199700048

  日期：1997.6

  AbstractThe isolation and identification of twenty‐eight crystalline components from the bark of Ficus microcarpa L.f. are described. Their structures were determined on the basis of spectral data and values taken from the literature. These compounds include fourteen triterpenoids, one fatty alcohol, eight steroids, one coumarin, one flavane, two 4‐hydroxybenzoates, and one carotenoid‐like compound.
• ULUBELEN, A.;OKSUZ, S.;MERICLI, A. H., PHYTOCHEMISTRY, 27,(1988) N 12, C. 3964-3965
  作者：ULUBELEN, A.、OKSUZ, S.、MERICLI, A. H.

  DOI：——

  日期：——