epijasminoside A | 189148-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: epijasminoside A
• 英文别名: (4S)-4-[(I(2)-D-Glucopyranosyloxy)methyl]-3,5,5-trimethyl-2-cyclohexen-1-one；(4S)-3,5,5-trimethyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]cyclohex-2-en-1-one
• CAS: 189148-81-0
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: FOONTNRMWNJWCL-PLJUSGQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 epijasminoside A 在 吡啶 作用下， 生成 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((S)-2,6,6-trimethyl-4-oxo-cyclohex-2-enylmethoxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Novel Glycosidic Constituents from Saffron

  摘要：

  The methanolic extract of saffron was prefractionated with the aid of multilayer coil countercurrent chromatography (MLCCC). After subsequent purification of certain fractions by high-performance liquid chromatography, the following glycoconjugates were isolated and identified on the basis of their spectral (UV, MS, NMR) data: the beta-n-glucosides of (4R)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone (5), (4S)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone (6), and (4S)-4-(hydroxymethyl)-3,5,5-trimethylcyclohex-2-enone (7), as well. as the beta-D-gentiobiosyl ester of 2-methyl-6-oxohepta-2,4-dienoic acid (4). In addition to these new natural products, known saffron constituents, i.e., the di-beta-D-gentiobiosyl and beta-D-gentiobiosyl-beta-D-glucopyranosyl esters of crocetin, have also been isolated and separated using MECCC.

  DOI：

  10.1021/jf960861k
• 作为产物：
  描述：

  jasminoside H 在 alpha-L-rhamnosidase 作用下， 反应 3.0h， 以5 mg的产率得到(-)-crocusatin C
  参考文献：
  名称：

  Pyronane Monoterpenoids from the Fruit of Gardenia jasminoides

  摘要：

  Five new pyronane-type monocyclic monoterpenoids, jasminodiol (1), jasminoside H (6), 6'-O-sinapoyljasminoside A (7), 6'-O-sinapoyljasminoside C (8), and jasminoside 1 (9), together with four known analogues, were isolated from the fruit of Gardenia jasminoides. The structures of the new metabolites were characterized using spectroscopic data, and the absolute configurations of 1, 6, and 7 were established using circular dichroism (CD) analysis. Compound 1 showed tyrosinase inhibitory activity (IC(50) 2.2 mM).

  DOI：

  10.1021/np800002z