methyl 3β-(α-D-mannopyranosyloxy)-11-oxo-olean-12-en-30-oate | 1547223-30-2

• 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: methyl 3β-(α-D-mannopyranosyloxy)-11-oxo-olean-12-en-30-oate
• 英文别名: methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-10-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 1547223-30-2
• 化学式: C₃₇H₅₈O₉
• 分子量: 646.862
• InChiKey: QHCVXOFJCANAHD-ZBPSSOLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  、 (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以48%的产率得到methyl 3β-(α-D-mannopyranosyloxy)-11-oxo-olean-12-en-30-oate
  参考文献：
  名称：

  A “natural” approach: Synthesis and cytoxicity of monodesmosidic glycyrrhetinic acid glycosides

  摘要：

  Several pentacyclic triterpenoic acids have shown noteworthy antitumor activity, among them betulinic acid as well as oleanolic acid and derivatives thereof. Glycyrrhetinic acid (GA) exhibits some cytotoxic activity albeit this compound is not as active as betulinic acid, but GA came in the focus of scientific interest since it triggers apoptosis in tumor cells. In addition, it can be extracted from the roots of liquorice in high yields. Previous studies revealed that the introduction of an extra hydrophilic moiety increases the cytotoxicity of these compounds. Thus, a series of GA glycosides was prepared utilizing hexoses as well as pentoses (in D- and L-configuration) by using glycosyl trichloroacetimidates and TMSOTf as catalyst. The compounds were screened for cytotoxic activity against seven human cancer cell lines and the not malignant murine cell line NIH 3T3using a photometric SRB assay. The compounds trigger apoptosis as shown from extra trypan blue and acridine orange/ethidium bromide staining. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.024

文献信息

• A “natural” approach: Synthesis and cytoxicity of monodesmosidic glycyrrhetinic acid glycosides
  作者：Stefan Schwarz、Bianka Siewert、Nuno M. Xavier、Ana R. Jesus、Amélia P. Rauter、René Csuk

  DOI：10.1016/j.ejmech.2013.11.024

  日期：2014.1

  Several pentacyclic triterpenoic acids have shown noteworthy antitumor activity, among them betulinic acid as well as oleanolic acid and derivatives thereof. Glycyrrhetinic acid (GA) exhibits some cytotoxic activity albeit this compound is not as active as betulinic acid, but GA came in the focus of scientific interest since it triggers apoptosis in tumor cells. In addition, it can be extracted from the roots of liquorice in high yields. Previous studies revealed that the introduction of an extra hydrophilic moiety increases the cytotoxicity of these compounds. Thus, a series of GA glycosides was prepared utilizing hexoses as well as pentoses (in D- and L-configuration) by using glycosyl trichloroacetimidates and TMSOTf as catalyst. The compounds were screened for cytotoxic activity against seven human cancer cell lines and the not malignant murine cell line NIH 3T3using a photometric SRB assay. The compounds trigger apoptosis as shown from extra trypan blue and acridine orange/ethidium bromide staining. (C) 2013 Elsevier Masson SAS. All rights reserved.