operculinic acid methyl ester | 120552-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: operculinic acid methyl ester
• 英文别名: (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 methyl ester；operculinic acid A methyl ester；methyl (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]oxyhexadecanoate
• CAS: 120552-47-8
• 化学式: C₄₇H₈₄O₂₄
• 分子量: 1033.17
• InChiKey: VLFAALNRPIUJNL-YFGRCRJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  361
• 氢给体数：
  12
• 氢受体数：
  24

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  mammoside H1 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 operculinic acid methyl ester
  参考文献：
  名称：

  Kitagawa, Isao; Baek, Nam In; Ohashi, Kazuyoshi, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 4, p. 1131 - 1133

  摘要：

  DOI：

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. VIII. Four new glycosidic acids, operculinic acids D,E,F, and G, of the ether-soluble crude resin glycosides ("Jalapin") from Rhizoma Jalapae Braziliensis(roots of Ipomoea operculata).
  作者：Masateru ONO、Tomoji FUKUNAGA、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.38.2650

  日期：——

  Four glycosidic acids, operculinic acids D, E, F and G, were isolated from the glycosidic acid fraction afforded by alkaline hydrolysis of the ether-soluble crude resin glycoside ("jalapin") from Rhizoma Jalapae Braziliensis (roots of Ipomoea operculata).They were respectively characterized as 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-xylopyranoside, 11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside, 11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside and 11S-jalapinolic acid 11-O-(2-O-methyl-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, on the bases of chemical and spectroscopic data.

  根据化学和光谱数据，从巴西叶下珠（Ipomoea operculata）根茎的醚溶性粗树脂苷（“jalapin”）的碱性水解产物中分离出四种糖苷酸，即D、E、F和G型operculin酸。它们分别被鉴定为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-xylopyranoside、11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside、11S-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→4)-O-α-
• 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.
• Ono, Masateru; Kubo, Kenji; Miyahara, Kazumoto, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 1, p. 241 - 244
  作者：Ono, Masateru、Kubo, Kenji、Miyahara, Kazumoto、Kawasaki, Toshio

  DOI：——

  日期：——