(4-[(3′-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate) | 1251949-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-[(3′-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate)
• 英文别名: [4-(3'-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate；4-(3'-O-acetyl-alpha-l-rhamnosyloxy) benzyl isothiocyanate；[(2S,3R,4R,5S,6S)-3,5-dihydroxy-2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxan-4-yl] acetate
• CAS: 1251949-76-4
• 化学式: C₁₆H₁₉NO₆S
• 分子量: 353.396
• InChiKey: XPDXZQFSZGBCCC-FSDJSFAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 葡糖硫苷酶(-20℃) 作用下， 生成 (4-[(3′-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate)
  参考文献：
  名称：

  Stable, water extractable isothiocyanates from Moringa oleifera leaves attenuate inflammation in vitro

  摘要：

  Moringa (Moringa oleifera Lam.) is an edible plant used as both a food and medicine throughout the tropics. A moringa concentrate (MC), made by extracting fresh leaves with water, utilized naturally occurring myrosinase to convert four moringa glucosinolates into moringa isothiocyanates. Optimum conditions maximizing MC yield, 4-[(α-L-rhamnosyloxy)benzyl]isothiocyanate, and 4-[(4'-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate content were established (1:5 fresh leaf weight to water ratio at room temperature). The optimized MC contained 1.66% isothiocyanates and 3.82% total polyphenols. 4-[(4'-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate exhibited 80% stability at 37°C for 30 days. MC, and both of the isothiocyanates described above significantly decreased gene expression and production of inflammatory markers in RAW macrophages. Specifically, both attenuated expression of iNOS and IL-1β and production of nitric oxide and TNFα at 1 and 5 μM. These results suggest a potential for stable and concentrated moringa isothiocyanates, delivered in MC as a food-grade product, to alleviate low-grade inflammation associated with chronic diseases.

  DOI：

  10.1016/j.phytochem.2014.03.028