cis-verbascoside | 97747-56-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cis-verbascoside
• 英文别名: cis-acteoside；verbascoside；[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 97747-56-3
• 化学式: C₂₉H₃₆O₁₅
• 分子量: 624.596
• InChiKey: FBSKJMQYURKNSU-FSIAKBNXSA-N

物化性质

• 沸点：
  908.8±65.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  cis-verbascoside 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.42h， 生成 (Z)-3-(3,4-Dihydroxy-phenyl)-acrylic acid (2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxy-phenyl)-ethoxy]-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Potential antitumor agents from Lantana camara : Structures of flavonoid -, and phenylpropanoid glycosides

  摘要：

  Besides the known glycosides, verbascoside and a flavone glycoside, a novel flanonol glycoside named camaraside and a new phenylpropanoid glycoside, lantanaside have been isolated from the leaves of Lantana camara and defined as 3,5-dihydroxy-4',6-dimethoxyflavonol-7-O-glucopyranoside and 3,4-dihydroxy-beta-phenylethyl-O-alpha-L-rhamnopyranosyl (1-->3)-4-O-cis-caffeoyl-beta-D-glucopyranoside respectively by spectroscopic methods and chemical transformations.

  DOI：

  10.1016/s0040-4020(01)85518-6
• 作为产物：
  描述：

  毛蕊花糖苷 以 氘代甲醇 为溶剂， 生成 cis-verbascoside
  参考文献：
  名称：

  Terpenoids, flavonoids and caffeic acid derivatives from Salvia viridis L. cvar. Blue Jeans

  摘要：

  Three diterpenoids, 1-oxomicrostegiol (1), viroxocin (2), viridoquinone (3), were isolated from the roots of Salvia viridis L. cvar. Blue Jeans. Five known diterpenoids, microstegiol (4), 7 alpha-acetoxy-14-hydroxy-8,13-abietadiene-11,12-dione (5; 7-O-acetylhorminone tautomer), 7 alpha,14-dihydroni-8,13-abietadiene-11,12-dione (6; horminone tautomer), ferruginol and salvinolonyl 12-methyl ether (7) were also found in the roots together with 1-docosyl ferulate (8), and a mixture of 2-(4'-alkoxyphenyl) ethyl alkanoates (9). Two lupane triterpenoids, 2 alpha-acetoxy-lup-20(29)-en-3 beta-ol (10), and 3 beta-acetoxy-lup-20(29)-en-2 alpha-ol (11) were found in the aerial parts together with known compounds, lup-20(29)-ene-2 alpha,3 beta-diol (12), ursolic acid, oleanolic acid, beta-sitosterol and beta-sitosterol glucoside. A known phenylpropanoid, trans-verbascoside (or acteoside; 13), was the main constituent in the polar fraction of the aerial part, and it is now reported in the genus Salvia for the first time. Other polyphenolic compounds were cis-verbascoside (14), leucosceptoside A (15), martynoside (16), caffeic acid, 6-O-caffeoyl-glucose (18), rosmarinic acid, salidroside, luteolin-7-O-alpha-rhamnopyranosyl-(1 -> 6)-beta-galactopyranoside, luteolin-7-O-beta-galactopyranoside, luteolin-7-O-alpha-rhamnopyranosyl-(1 -> 6)-beta-glucopyranoside, luteolin-7-O-beta-glucopyranoside, and apigenin-7-O-alpha-glucopyranoside. The structures were determined by 1D-, 2D-NMR and HR-ESI-MS techniques. Compounds 6, 10, ferruginol, ursolic acid and oleanolic acid exhibited antibacterial activity against Entero coccus faecalis (ATCC 775) with MIC 50 mu M, 25 mu M, 50 mu M, 12.5 mu M, 12.5 mu M respectively. Ferruginol, ursolic acid and oleanolic acid were also active against Staphylococcus aureus (ATCC 6571), and Bacillus cereus (ATCC 2599) with MIC 12.5-50 mu M. 4 was also active against S. aureus (ATCC 6571) with MIC 50 mu M. These values are consistent with previous studies on the antimicrobial activity of Salvia diterpenoids. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.08.029

文献信息

• Potential antitumor agents from Lantana camara : Structures of flavonoid -, and phenylpropanoid glycosides
  作者：Shashi B. Mahato、Niranjan P. Sahu、Subodh K. Roy、Om P. Sharma

  DOI：10.1016/s0040-4020(01)85518-6

  日期：——

  Besides the known glycosides, verbascoside and a flavone glycoside, a novel flanonol glycoside named camaraside and a new phenylpropanoid glycoside, lantanaside have been isolated from the leaves of Lantana camara and defined as 3,5-dihydroxy-4',6-dimethoxyflavonol-7-O-glucopyranoside and 3,4-dihydroxy-beta-phenylethyl-O-alpha-L-rhamnopyranosyl (1-->3)-4-O-cis-caffeoyl-beta-D-glucopyranoside respectively by spectroscopic methods and chemical transformations.
• Terpenoids, flavonoids and caffeic acid derivatives from Salvia viridis L. cvar. Blue Jeans
  作者：Supattra Rungsimakan、Michael G. Rowan

  DOI：10.1016/j.phytochem.2014.08.029

  日期：2014.12

  Three diterpenoids, 1-oxomicrostegiol (1), viroxocin (2), viridoquinone (3), were isolated from the roots of Salvia viridis L. cvar. Blue Jeans. Five known diterpenoids, microstegiol (4), 7 alpha-acetoxy-14-hydroxy-8,13-abietadiene-11,12-dione (5; 7-O-acetylhorminone tautomer), 7 alpha,14-dihydroni-8,13-abietadiene-11,12-dione (6; horminone tautomer), ferruginol and salvinolonyl 12-methyl ether (7) were also found in the roots together with 1-docosyl ferulate (8), and a mixture of 2-(4'-alkoxyphenyl) ethyl alkanoates (9). Two lupane triterpenoids, 2 alpha-acetoxy-lup-20(29)-en-3 beta-ol (10), and 3 beta-acetoxy-lup-20(29)-en-2 alpha-ol (11) were found in the aerial parts together with known compounds, lup-20(29)-ene-2 alpha,3 beta-diol (12), ursolic acid, oleanolic acid, beta-sitosterol and beta-sitosterol glucoside. A known phenylpropanoid, trans-verbascoside (or acteoside; 13), was the main constituent in the polar fraction of the aerial part, and it is now reported in the genus Salvia for the first time. Other polyphenolic compounds were cis-verbascoside (14), leucosceptoside A (15), martynoside (16), caffeic acid, 6-O-caffeoyl-glucose (18), rosmarinic acid, salidroside, luteolin-7-O-alpha-rhamnopyranosyl-(1 -> 6)-beta-galactopyranoside, luteolin-7-O-beta-galactopyranoside, luteolin-7-O-alpha-rhamnopyranosyl-(1 -> 6)-beta-glucopyranoside, luteolin-7-O-beta-glucopyranoside, and apigenin-7-O-alpha-glucopyranoside. The structures were determined by 1D-, 2D-NMR and HR-ESI-MS techniques. Compounds 6, 10, ferruginol, ursolic acid and oleanolic acid exhibited antibacterial activity against Entero coccus faecalis (ATCC 775) with MIC 50 mu M, 25 mu M, 50 mu M, 12.5 mu M, 12.5 mu M respectively. Ferruginol, ursolic acid and oleanolic acid were also active against Staphylococcus aureus (ATCC 6571), and Bacillus cereus (ATCC 2599) with MIC 12.5-50 mu M. 4 was also active against S. aureus (ATCC 6571) with MIC 50 mu M. These values are consistent with previous studies on the antimicrobial activity of Salvia diterpenoids. (c) 2014 Elsevier Ltd. All rights reserved.