(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-fucopyranoside | 120583-62-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (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-fucopyranoside
• 英文别名: (11S)-hydroxyhexadecanoic acid 11-O-β-D-glucopyranosyl-[α-L-rhamnopyranosyl-(1→4)]-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-fucopyranoside；operculinic acid A；operculinic acid；mammoside J；(11S)-11-[(2R,3R,4S,5R,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-methyloxan-2-yl]oxyhexadecanoic acid
• CAS: 120583-62-2
• 化学式: C₄₆H₈₂O₂₄
• 分子量: 1019.14
• InChiKey: RMSDLBJXDTYRAX-SRWHAWSISA-N

物化性质

• 沸点：
  1112.1±65.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  70
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  372
• 氢给体数：
  13
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (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-fucopyranoside 生成 operculinic acid methyl ester
  参考文献：
  名称：

  Ono, Masateru; Kubo, Kenji; Miyahara, Kazumoto, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 1, p. 241 - 244

  摘要：

  DOI：
• 作为产物：
  描述：

  operculinic acid methyl ester 在 氢氧化钾 作用下， 反应 1.0h， 生成 (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-fucopyranoside
  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

• Indonesian Medicinal Plants. XIX. Chemical Structures of Four Additional Resin-Glycosides, Mammosides A, B, H1, and H2, from the Tuber of Merremia mammosa (Convolvulaceae).
  作者：Isao KITAGAWA、Kazuyoshi OHASHI、Nam In BAEK、Masahiro SAKAGAMI、Masayuki YOSHIKAWA、Hirotaka SHIBUYA

  DOI：10.1248/cpb.45.786

  日期：——

  Four new resin-glycosides, named mammosides A (10), B (11), H1 (12), and H2 (13), were isolated from the tuber of Merremia mammosa (Convolvulaceae), a Jamu raw material. Their chemical structures have been elucidated on the bases of chemical and physicochemical evidence, including synthesis of a glycosidic acid designated as mammoside I.

  从一种佳木原料 Merremia mammosa（旋花科）的块茎中分离出了四种新的树脂苷，分别命名为猛犸苷 A (10)、B (11)、H1 (12) 和 H2 (13)。根据化学和物理化学证据阐明了它们的化学结构，包括合成了一种糖苷酸，命名为猛犸苷 I。
• Resin Glycosides from the Herbal Drug Jalap (<i>Ipomoea purga</i>)
  作者：Jhon Castañeda-Gómez、Rogelio Pereda-Miranda

  DOI：10.1021/np200080k

  日期：2011.5.27

  Three new resin glycosides, purginosides I and II (1 and 2) and purgin I (3), were isolated from the aerial parts of Ipomoea purga and purified by preparative-scale recycling HPLC from a chloroform-soluble extract. Their structures were established through NMR spectroscopy and mass spectrometry. Purginosides I and II (1 and 2) are partially acylated branched pentasaccharides derived from operculinic

  从番薯叶的地上部分分离出三种新的树脂糖苷，紫gin苷I和II（1和2）和紫gin I（3），并通过制备规模的回收HPLC从可溶于氯仿的提取物中进行纯化。它们的结构通过NMR光谱法和质谱法建立。嘌呤苷I和II（1和2）是衍生自草酸A的部分酰化的支链五糖，其由一个d-岩藻糖，一个d-葡萄糖和三个l-鼠李糖单元组成。糖苷配基大内酯化的位点在第二种糖（鼠李糖）的C-2处。在这两种化合物中1和2，三个不同的酯化残基位于第二鼠李糖单元的C-2和第三鼠李糖部分的C-2（或C-3）和C-4。酰化残基的特征为反式肉桂酸，正癸酸和（+）-（2S）-2-甲基丁酸或正己酸。发现嘌呤I（3）是酸A的酯型二聚体，在相同的寡糖核心位置被正十二烷酸，（+）-（2 S）-2-甲基丁酸和反式肉桂酸酰化在化合物1和2中。单元A中的糖苷配基的内酯化位点位于第二糖的C-2处。大环单元A上的单体单元B的酯键的位置被确定为末端葡萄糖的
• Novel acylated lipo-oligosaccharides from the tubers of Ipomoea batatas
  作者：Yong-Qin Yin、Jun-Song Wang、Jian-Guang Luo、Ling-Yi Kong

  DOI：10.1016/j.carres.2008.12.022

  日期：2009.3

  Nine new lipo-oligosaccharides, batatosides H-P, were isolated from the tubers of Ipomoea batatas (Convolvulaceae). Spectral and chemical methods allowed to characterize them as tetra- or penta-saccharides that form a macrolactone with the aglycone, (11S)-hydroxyhexadecanoic acid (jalapinolic acid), the absolute configuration of which was established by Mosher's method. Batatosides L and O showed a weak inhibitory effect on the growth of Hep-2 cells, while the others proved to be inactive. (C) 2009 Elsevier Ltd. All rights reserved.
• Kitagawa, Isao; Baek, Nam In; Ohashi, Kazuyoshi, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 4, p. 1131 - 1133
  作者：Kitagawa, Isao、Baek, Nam In、Ohashi, Kazuyoshi、Sakagami, Masahiro、Yoshikawa, Masayuki、et al.

  DOI：——

  日期：——
• 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.