albinosinic acid B | 1400878-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: albinosinic acid B
• 英文别名: (11S)-11-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-methyl-3,4-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxytetradecanoic acid
• CAS: 1400878-62-7
• 化学式: C₄₄H₇₈O₂₃
• 分子量: 975.09
• InChiKey: RKBPEBQIAZDHDR-HGVDCYHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  67
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  352
• 氢给体数：
  12
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 albinosinic acid B 、 乙酸酐 在 吡啶 作用下， 以9 mg的产率得到peracetylalbinosinic acid B Methyl ester
  参考文献：
  名称：

  Mammalian Multidrug Resistance Lipopentasaccharide Inhibitors fromIpomoea albaSeeds

  摘要：

  As part of an ongoing project to identify inhibitors of multidrug efflux pumps, three new resin glycosides, albinosides I-III (1-3), were isolated from a CHCl3-soluble extract from the seeds of moon vine (Ipomoea alba). Their structures were established through NMR spectroscopy and mass spectrometry as partially acylated branched pentasaccharides derived from three new glycosidic acids, named albinosinic acids A-C (4-6). The same oligosaccharide core formed by two D-quinovose, one D-glucose, and two L-rhamnose units was linked to either convolvulinolic or jalapinolic acid for 1 and 3, respectively. They were partially esterified with (2R,3R)-3-hydroxy-2-methylbutanoic, acetic, or 2-methyl-2-butenoic acid. Compound 2 has two D-quinovose and three L-rhamnose units, linked to convolvulinolic acid, and its esterifying residues were characterized as two units of 2-methyl-2-butenoic acid. The aglycone lactonization site was located at C-2 of the terminal rhamnose unit (Rha) for 1, at C-3 of the terminal rhamnose unit (Rha') for 2, and at C-3 of the second saccharide unit (Glc) for 3. Reversal of multidrug resistance by this class of plant metabolites was also evaluated in vinblastine-resistant human breast carcinoma cells (MCF-7/Vin). The noncytotoxic compound 3 exerted the strongest potentiation effect of vinblastine susceptibility to over 2140-fold, while a moderate activity was observed for 1 (3.1-fold) and 2 (2.6-fold) at a concentration of 25 mu g/mL.

  DOI：

  10.1021/np300414d
• 作为产物：
  描述：

  albinoside II 在 水 、 potassium hydroxide 作用下， 反应 3.0h， 以8.5 mg的产率得到albinosinic acid B
  参考文献：
  名称：

  Mammalian Multidrug Resistance Lipopentasaccharide Inhibitors fromIpomoea albaSeeds

  摘要：

  As part of an ongoing project to identify inhibitors of multidrug efflux pumps, three new resin glycosides, albinosides I-III (1-3), were isolated from a CHCl3-soluble extract from the seeds of moon vine (Ipomoea alba). Their structures were established through NMR spectroscopy and mass spectrometry as partially acylated branched pentasaccharides derived from three new glycosidic acids, named albinosinic acids A-C (4-6). The same oligosaccharide core formed by two D-quinovose, one D-glucose, and two L-rhamnose units was linked to either convolvulinolic or jalapinolic acid for 1 and 3, respectively. They were partially esterified with (2R,3R)-3-hydroxy-2-methylbutanoic, acetic, or 2-methyl-2-butenoic acid. Compound 2 has two D-quinovose and three L-rhamnose units, linked to convolvulinolic acid, and its esterifying residues were characterized as two units of 2-methyl-2-butenoic acid. The aglycone lactonization site was located at C-2 of the terminal rhamnose unit (Rha) for 1, at C-3 of the terminal rhamnose unit (Rha') for 2, and at C-3 of the second saccharide unit (Glc) for 3. Reversal of multidrug resistance by this class of plant metabolites was also evaluated in vinblastine-resistant human breast carcinoma cells (MCF-7/Vin). The noncytotoxic compound 3 exerted the strongest potentiation effect of vinblastine susceptibility to over 2140-fold, while a moderate activity was observed for 1 (3.1-fold) and 2 (2.6-fold) at a concentration of 25 mu g/mL.

  DOI：

  10.1021/np300414d

文献信息

• Resin Glycosides from <i>Ipomoea alba</i> Seeds as Potential Chemosensitizers in Breast Carcinoma Cells
  作者：Sara Cruz-Morales、Jhon Castañeda-Gómez、Daniel Rosas-Ramírez、Mabel Fragoso-Serrano、Gabriela Figueroa-González、Argelia Lorence、Rogelio Pereda-Miranda

  DOI：10.1021/acs.jnatprod.6b00782

  日期：2016.12.23

  coadministered with antineoplastic agents, is an alternative approach for increasing the success rate of therapy regimes with different drug combinations. This report describes the isolation and structure elucidation of six new resin glycosides from moon vine seeds (Ipomoea alba) as potential mammalian multidrug-resistance-modifying agents. Albinosides IV–IX (1–6), along with the known albinosides I–III (7–9)

  多药耐药性是一种或多种外排泵的表达，例如P-糖蛋白，是癌症治疗的主要障碍。与抗肿瘤药共同使用的新型有效且无细胞毒性的外排泵调节剂是增加采用不同药物组合治疗方案成功率的替代方法。该报告描述了从月藤种子（Ipomoea alba）中分离出的六种新的树脂糖苷，并对其结构进行了阐明，这些糖苷是潜在的哺乳动物多药耐药性改良剂。Albinosides IV-IX（1 - 6），与已知的albinosides I-III（沿7 - 9），从该纯化氯仿3可溶提取物。降解化学反应结合NMR光谱和质谱用于阐明其结构。四个新的糖苷酸，albinosinic酸d-G（10 - 13），是由天然产物的皂化释放3 - 6。它们表征为convolvulinolic的四糖（11 š -hydroxytetradecanoic）或jalapinolic（11 š -hydroxyhexadecanoic）酸。长春碱的易感性
• Mammalian Multidrug Resistance Lipopentasaccharide Inhibitors from<i>Ipomoea alba</i>Seeds
  作者：Sara Cruz-Morales、Jhon Castañeda-Gómez、Gabriela Figueroa-González、Alma Delia Mendoza-García、Argelia Lorence、Rogelio Pereda-Miranda

  DOI：10.1021/np300414d

  日期：2012.9.28

  As part of an ongoing project to identify inhibitors of multidrug efflux pumps, three new resin glycosides, albinosides I-III (1-3), were isolated from a CHCl3-soluble extract from the seeds of moon vine (Ipomoea alba). Their structures were established through NMR spectroscopy and mass spectrometry as partially acylated branched pentasaccharides derived from three new glycosidic acids, named albinosinic acids A-C (4-6). The same oligosaccharide core formed by two D-quinovose, one D-glucose, and two L-rhamnose units was linked to either convolvulinolic or jalapinolic acid for 1 and 3, respectively. They were partially esterified with (2R,3R)-3-hydroxy-2-methylbutanoic, acetic, or 2-methyl-2-butenoic acid. Compound 2 has two D-quinovose and three L-rhamnose units, linked to convolvulinolic acid, and its esterifying residues were characterized as two units of 2-methyl-2-butenoic acid. The aglycone lactonization site was located at C-2 of the terminal rhamnose unit (Rha) for 1, at C-3 of the terminal rhamnose unit (Rha') for 2, and at C-3 of the second saccharide unit (Glc) for 3. Reversal of multidrug resistance by this class of plant metabolites was also evaluated in vinblastine-resistant human breast carcinoma cells (MCF-7/Vin). The noncytotoxic compound 3 exerted the strongest potentiation effect of vinblastine susceptibility to over 2140-fold, while a moderate activity was observed for 1 (3.1-fold) and 2 (2.6-fold) at a concentration of 25 mu g/mL.