(25S)-5β-spirostan-3β-ol 3-O-α-L-arabinopyranosyl-(1->6)-[α-L-arabinopyranosyl-(1->4)]-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranoside

• 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
• 英文名称: (25S)-5β-spirostan-3β-ol 3-O-α-L-arabinopyranosyl-(1->6)-[α-L-arabinopyranosyl-(1->4)]-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranoside
• 英文别名: asparacoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-4-hydroxy-2-[(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-3-yl]oxyoxane-3,4,5-triol
• 化学式: C₄₉H₈₀O₂₁
• 分子量: 1005.16
• InChiKey: GLLQBFOUGGRCKY-YDJQLIBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  70
• 可旋转键数：
  10
• 环数：
  10.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  315
• 氢给体数：
  11
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (25S)-5β-spirostan-3β-ol 3-O-α-L-arabinopyranosyl-(1->6)-[α-L-arabinopyranosyl-(1->4)]-[β-D-glucopyranosyl-(1->2)]-β-D-glucopyranoside 在 吡啶 作用下， 反应 36.0h， 以14.21 mg的产率得到[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4-acetyloxy-2-[(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-5-[(2R,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxy-6-[[(2R,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxymethyl]oxan-3-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Bioactive Constituents from Asparagus cochinchinensis

  摘要：

  Bioassay-directed fractionation of the dried roots of Asparagus cochinchinensis led to the isolation of a new spirostanol saponin, asparacoside (1), two new C-27 spirosteroids, asparacosins A (2) and B (3), a new acetylenic derivative, 3"-methoxyasparenydiol (4), and a new polyphenol, 3'-hydroxy-4'-methoxy-4'dehydroxynyasol (6), as well as five known phenolic compounds, asparenydiol (5), nyasol (7), 3"-methoxynyasol (8), 1,3-bis-di-p-hydroxyphenyl-4-penten-1-one (9), and trans-coniferyl alcohol (10). Compounds 1, 6, and 8 demonstrated moderate cytotoxicities in a panel comprised of KB, Col-2, LNCaP, Lu-1, and HUVEC cells, with IC50 values ranging from 4 to 12 mug/mL. The structures were determined by spectroscopic and chemical methods.

  DOI：

  10.1021/np030370b

文献信息

• Bioactive Constituents from <i>Asparagus cochinchinensis</i>
  作者：Hong-Jie Zhang、Kongmany Sydara、Ghee Teng Tan、Cuiying Ma、Bounhoong Southavong、D. Doel Soejarto、John M. Pezzuto、Harry H. S. Fong

  DOI：10.1021/np030370b

  日期：2004.2.1

  Bioassay-directed fractionation of the dried roots of Asparagus cochinchinensis led to the isolation of a new spirostanol saponin, asparacoside (1), two new C-27 spirosteroids, asparacosins A (2) and B (3), a new acetylenic derivative, 3"-methoxyasparenydiol (4), and a new polyphenol, 3'-hydroxy-4'-methoxy-4'dehydroxynyasol (6), as well as five known phenolic compounds, asparenydiol (5), nyasol (7), 3"-methoxynyasol (8), 1,3-bis-di-p-hydroxyphenyl-4-penten-1-one (9), and trans-coniferyl alcohol (10). Compounds 1, 6, and 8 demonstrated moderate cytotoxicities in a panel comprised of KB, Col-2, LNCaP, Lu-1, and HUVEC cells, with IC50 values ranging from 4 to 12 mug/mL. The structures were determined by spectroscopic and chemical methods.