operculinic acid B | 126572-20-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: operculinic 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,5S,6S)-3-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexadecanoic acid
• CAS: 126572-20-1
• 化学式: C₄₆H₈₂O₂₅
• 分子量: 1035.14
• InChiKey: LJJIBKCHKKEYAS-LZAQUJCFSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  1142.4±65.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  71
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  393
• 氢给体数：
  14
• 氢受体数：
  25

反应信息

• 作为产物：
  描述：

  operculinic acid B methyl ester 在 氢氧化钾 作用下， 反应 1.0h， 以35 mg的产率得到operculinic acid B
  参考文献：
  名称：

  Resin glycosides. V. Identification and characterization of the component organic and glycosidic acids of the ether-soluble crude resin glycosides ("jalapin") from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata).

  摘要：

  对厣苕（旋花科）根部的醚溶性树脂苷（"jalapin"）部分进行碱性水解，得到了五种苷酸，即厣苕酸 A (1)、B (2)、C (3)、D 和 E，以及正癸酸和正十二烷酸。operculinic acids A、B 和 C 的特征为 11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhmnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside 、11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-葡萄糖苷和 11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopy6ranoside、根据化学和光谱数据，分别命名为本研究发现的正癸酸和正十二烷酸是迄今为止研究的树脂苷中的第一种有机酸成分。

  DOI：

  10.1248/cpb.37.3209

文献信息

• Resin glycosides from Ipomoea wolcottiana as modulators of the multidrug resistance phenotype in vitro
  作者：Berenice Corona-Castañeda、Daniel Rosas-Ramírez、Jhon Castañeda-Gómez、Manuel Alejandro Aparicio-Cuevas、Mabel Fragoso-Serrano、Gabriela Figueroa-González、Rogelio Pereda-Miranda

  DOI：10.1016/j.phytochem.2016.01.004

  日期：2016.3

  Recycling liquid chromatography was used for the isolation and purification of resin glycosides from the CHCl3-soluble extracts prepared using flowers of Ipomoea wolcottiana Rose var. wolcottiana. Bioassay guided fractionation, using modulation of both antibiotic activity against multidrug-resistant strains of Gram-negative bacteria and vinblastine susceptibility in breast carcinoma cells, was used to isolate the active glycolipids as modulators of the multidrug resistance phenotype. An ester-type dimer, wolcottine I, one tetra- and three pentasaccharides, wolcottinosides I-IV, in addition to the known intrapilosin VII, were characterized by NMR spectroscopy and mass spectrometry. In vitro assays established that none of these metabolites displayed antibacterial activity (MIC > 512 mu g/mL) against multidrug-resistant strains of Escherichia coli, and two nosocomial pathogens: Salmonella enterica serovar Typhi and Shigella flexneri; however, when tested (25 mu g/mL) in combination with tetracycline, kanamycin or chloramphenicol, they exerted a potentiation effect of the antibiotic susceptibility up to eightfold (64 mu g/mL from 512 mu g/mL). It was also determined that these non-cytotoxic (CI50 > 8.68 mu M) agents modulated vinblastine susceptibility at 25 mu g/mL in MFC-7/Vin(+) cells with a reversal factor (RFMcF-7/Vin+) of 2-130 fold. (C) 2016 Elsevier Ltd. All rights reserved.
• Resin glycosides. V. Identification and characterization of the component organic and glycosidic acids of the ether-soluble crude resin glycosides ("jalapin") from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata).
  作者：Masateru ONO、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.37.3209

  日期：——

  Alkaline hydrolysis of the ether-soluble resin glycoside ("jalapin") fraction of the roots of Ipomoea operculata (Convolvulaceae) gave five glycosidic acids, operculinic acids A (1), B (2), C (3), D and E, along with n-decanoic and n-dodecanoic acids. Operculinic acids A, B and C were characterized to be 11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhmnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside, 11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside and 11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopy6ranoside, respectively, on the basis of chemical and spectroscopic data.n-Decanoic and n-dodecasnoic acids found in this study are the first component organic acids of the resin glycosides so far studied.

  对厣苕（旋花科）根部的醚溶性树脂苷（"jalapin"）部分进行碱性水解，得到了五种苷酸，即厣苕酸 A (1)、B (2)、C (3)、D 和 E，以及正癸酸和正十二烷酸。operculinic acids A、B 和 C 的特征为 11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhmnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside 、11S-jalapinolic acid 11-O-β-D-glucopyranosyl-(1→3)-O-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-葡萄糖苷和 11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopy6ranoside、根据化学和光谱数据，分别命名为本研究发现的正癸酸和正十二烷酸是迄今为止研究的树脂苷中的第一种有机酸成分。