1-O-β-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 1-O-β-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol
• 化学式: C₄₆H₈₉NO₁₀
• 分子量: 816.213
• InChiKey: DHVCDRCUTFUDDR-LKYZGBKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  57.0
• 可旋转键数：
  39.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  189.17
• 氢给体数：
  8.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-O-β-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol 在 盐酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  Cytotoxic ceramides and glycerides from the roots of Livistona chinensis

  摘要：

  A 70% ethanol extract of the roots of Livistona chinensis has been investigated, led to the isolation of 13 compounds, including a new ceramide, (2S,35,4R,9Z)-2-[(2R)-2-hydroxytricosanoylamino]-9-octadecene-1,3,4-triol (2), a new glycosyl ceramide, 1-O-beta-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol (3), three new monoacylglycerols, 1-(34-hydroxytetratriacontanoyl)-sn-glycerol (9), 1-[nonadeca-(9Z,12Z)-dienoyl]-sn-glycerol (10), and 1-[12-hydroxypentatriaconta-(13E,15Z)-dienoyl]-sn-glycerol (11), a new diacylglycerol, 1-(heptadeca-6Z,9Z-dienoyl)-3-(octadeca-6Z,9Z,12Z-trienoyl)-sn-glycerol (12), as well as a new diacylglycerol aminoglycoside, 1-octadecanoyl-2-nonadecanoyl-3-O-(6-amino-6-deoxy)-beta-D-glucopyranosyl-sn-glycerol (13). The structures of new compounds were elucidated. based on spectroscopic, zymologic and chemical methods. Among the compounds tested, compounds 3, 4 and 13 showed significantly antiproliferative effects against the human tumor cell lines (K562, HL-60, HepG2, and CNE-1) with the IC50 of 10-65 mu M. To our knowledge, this is first report of the occurrence of ceramides and acylglycerols in the genus Livistona. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2012.01.008

文献信息

• Cytotoxic ceramides and glycerides from the roots of Livistona chinensis
  作者：Xiaobin Zeng、Limin Xiang、Chen-Yang Li、Yihai Wang、Guofu Qiu、Zhen-xue Zhang、Xiangjiu He

  DOI：10.1016/j.fitote.2012.01.008

  日期：2012.4

  A 70% ethanol extract of the roots of Livistona chinensis has been investigated, led to the isolation of 13 compounds, including a new ceramide, (2S,35,4R,9Z)-2-[(2R)-2-hydroxytricosanoylamino]-9-octadecene-1,3,4-triol (2), a new glycosyl ceramide, 1-O-beta-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol (3), three new monoacylglycerols, 1-(34-hydroxytetratriacontanoyl)-sn-glycerol (9), 1-[nonadeca-(9Z,12Z)-dienoyl]-sn-glycerol (10), and 1-[12-hydroxypentatriaconta-(13E,15Z)-dienoyl]-sn-glycerol (11), a new diacylglycerol, 1-(heptadeca-6Z,9Z-dienoyl)-3-(octadeca-6Z,9Z,12Z-trienoyl)-sn-glycerol (12), as well as a new diacylglycerol aminoglycoside, 1-octadecanoyl-2-nonadecanoyl-3-O-(6-amino-6-deoxy)-beta-D-glucopyranosyl-sn-glycerol (13). The structures of new compounds were elucidated. based on spectroscopic, zymologic and chemical methods. Among the compounds tested, compounds 3, 4 and 13 showed significantly antiproliferative effects against the human tumor cell lines (K562, HL-60, HepG2, and CNE-1) with the IC50 of 10-65 mu M. To our knowledge, this is first report of the occurrence of ceramides and acylglycerols in the genus Livistona. (C) 2012 Elsevier B.V. All rights reserved.