5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-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: 5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-[[(1S,2R,5R,6R,9R,10R,13S,15R)-5-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadecan-13-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₃₄H₅₆O₈
• 分子量: 592.814
• InChiKey: VOCXDRSORWGXMU-AGBBTXFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 4 Angstroem MS 、 三氟化硼乙醚 、 Eosin Y 、 氧气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-D-glucopyranoside
  参考文献：
  名称：

  Antitumor sterols from the mycelia of Cordyceps sinensis

  摘要：

  Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-glucopyranoside and 22-dihydroergosteryl-3-O-beta-D-glucopyranoside were also isolated. The structures of hitherto unknown sterols were established by 1D and 2D NMR spectroscopic techniques with the former synthesized in order to confirm the identity of the sugar moiety by chemical correlation. The glycosylated form of ergosterol peroxide was found to be a greater inhibitor to the proliferation of K562, Jurkat, WM-1341, HL-60 and RPMI-8226 tumor cell lines by 10 to 40% at 10 mu g/ml than its previously identified aglycone, 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-ol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00128-4

文献信息

• Antitumor sterols from the mycelia of Cordyceps sinensis
  作者：Jin Woo Bok、Leonard Lermer、Jeff Chilton、Hans G Klingeman、G.H.Neil Towers

  DOI：10.1016/s0031-9422(99)00128-4

  日期：1999.8

  Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-glucopyranoside and 22-dihydroergosteryl-3-O-beta-D-glucopyranoside were also isolated. The structures of hitherto unknown sterols were established by 1D and 2D NMR spectroscopic techniques with the former synthesized in order to confirm the identity of the sugar moiety by chemical correlation. The glycosylated form of ergosterol peroxide was found to be a greater inhibitor to the proliferation of K562, Jurkat, WM-1341, HL-60 and RPMI-8226 tumor cell lines by 10 to 40% at 10 mu g/ml than its previously identified aglycone, 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-ol. (C) 1999 Elsevier Science Ltd. All rights reserved.