(-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside | 124673-17-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 124673-17-2
• 化学式: C₃₆H₅₄O₁₈
• 分子量: 774.814
• InChiKey: QRSQZPLEDUJJCM-URSPHTFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 6.0h， 生成 (1R,3R,4S)-p-menthane-3-yl O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic menthyl α/β-(1→6)-diglucopyranosides-induced cell death in human leukemia cells is dependent on caspases

  摘要：

  A series of alkyl alpha/beta-(1 -> 6)-diglucopyranosides 1-12 were synthesized and assessed for cytotoxicity against HL-60, U937, Molt-3 and MCF-7 cancer cell lines. The menthyl derivatives displayed strong cytotoxic properties showing IC50 values between 6 and 16 mu M. Furthermore, we demonstrated that the selected synthetic (+)-menthyl beta-(1 -> 6)-diglucopyranoside 5 induces apoptotic cell death in human leukemia cells through a mechanism that involves activation of multiple caspases. Cell death was completely prevented by the non-specific caspase inhibitor z-VAD-fmk and found to be associated with the release of cytochrome c, an increase in the expression of Bax levels and a decrease in the generation of reactive oxygen species. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.035
• 作为产物：
  描述：

  gentiobiose hepta-acetate 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic menthyl α/β-(1→6)-diglucopyranosides-induced cell death in human leukemia cells is dependent on caspases

  摘要：

  A series of alkyl alpha/beta-(1 -> 6)-diglucopyranosides 1-12 were synthesized and assessed for cytotoxicity against HL-60, U937, Molt-3 and MCF-7 cancer cell lines. The menthyl derivatives displayed strong cytotoxic properties showing IC50 values between 6 and 16 mu M. Furthermore, we demonstrated that the selected synthetic (+)-menthyl beta-(1 -> 6)-diglucopyranoside 5 induces apoptotic cell death in human leukemia cells through a mechanism that involves activation of multiple caspases. Cell death was completely prevented by the non-specific caspase inhibitor z-VAD-fmk and found to be associated with the release of cytochrome c, an increase in the expression of Bax levels and a decrease in the generation of reactive oxygen species. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.035

文献信息

• FURUYA, TSUTOMU;ORIHARA, YUTAKA;MIYATAKE, HIROMITSU, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N0, C. 1711-1719
  作者：FURUYA, TSUTOMU、ORIHARA, YUTAKA、MIYATAKE, HIROMITSU

  DOI：——

  日期：——