16-hydroxy-3β-O-[β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyloxyuronic acid]-5α,14β-poriferasta-7,16-diene-15,23-dione methyl ester | 1239011-29-0

• 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: 16-hydroxy-3β-O-[β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyloxyuronic acid]-5α,14β-poriferasta-7,16-diene-15,23-dione methyl ester
• 英文别名: pandaroside G methyl ester；Methyl Ester Pandaroside G；methyl (2S,3S,4S,5R,6R)-6-[[(3S,5S,9R,10S,13S,14R)-17-[(2R,5R)-5-ethyl-6-methyl-4-oxoheptan-2-yl]-16-hydroxy-10,13-dimethyl-15-oxo-1,2,3,4,5,6,9,11,12,14-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylate
• CAS: 1239011-29-0
• 化学式: C₄₁H₆₂O₁₄
• 分子量: 778.935
• InChiKey: GATYMFMUWLJDGJ-RKGAECKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  55
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  219
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  甲醇 、 16-hydroxy-3β-O-[β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyloxyuronic acid]-5α,14β-poriferasta-7,16-diene-15,23-dione 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 16-hydroxy-3β-O-[β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyloxyuronic acid]-5α,14β-poriferasta-7,16-diene-15,23-dione methyl ester
  参考文献：
  名称：

  Antiprotozoal Steroidal Saponins from the Marine Sponge Pandaros acanthifolium

  摘要：

  The chemical composition of the Caribbean sponge Pandaros acanthifolium was reinvestigated and led to the isolation of 12 new steroidal glycosides, namely, pandarosides E-J (1-6) and their methyl esters (7-12). Their structures were determined on the basis of extensive spectroscopic analyses, including two-dimensional NMR and HRESIMS data. Like the previously isolated pandarosides A-D (13-16), the new compounds 1-12 share an unusual oxidized D-ring and a cis C/D ring junction. The absolute configurations of the aglycones were assigned by interpretation of CD spectra, whereas the absolute configurations of the monosaccharide units were determined by chiral GC analyses of the acid methanolysates. The majority of the metabolites showed in vitro activity against three or four parasitic protozoa. Particularly active were the compounds 3 (pandaroside G) and its methyl ester (9), which potently inhibited the growth of Trypanosoma brucei rhodesiense (IC(50) values 0.78 and 0.038 mu M, respectively) and Leishmania donovani (IC(50)'s 1.3 and 0.051 mu M, respectively).

  DOI：

  10.1021/np100348x

文献信息

• Antiprotozoal Steroidal Saponins from the Marine Sponge <i>Pandaros acanthifolium</i>
  作者：Erik L. Regalado、Deniz Tasdemir、Marcel Kaiser、Nadja Cachet、Philippe Amade、Olivier P. Thomas

  DOI：10.1021/np100348x

  日期：2010.8.27

  The chemical composition of the Caribbean sponge Pandaros acanthifolium was reinvestigated and led to the isolation of 12 new steroidal glycosides, namely, pandarosides E-J (1-6) and their methyl esters (7-12). Their structures were determined on the basis of extensive spectroscopic analyses, including two-dimensional NMR and HRESIMS data. Like the previously isolated pandarosides A-D (13-16), the new compounds 1-12 share an unusual oxidized D-ring and a cis C/D ring junction. The absolute configurations of the aglycones were assigned by interpretation of CD spectra, whereas the absolute configurations of the monosaccharide units were determined by chiral GC analyses of the acid methanolysates. The majority of the metabolites showed in vitro activity against three or four parasitic protozoa. Particularly active were the compounds 3 (pandaroside G) and its methyl ester (9), which potently inhibited the growth of Trypanosoma brucei rhodesiense (IC(50) values 0.78 and 0.038 mu M, respectively) and Leishmania donovani (IC(50)'s 1.3 and 0.051 mu M, respectively).