N¹,N⁴,N⁸-tris(dihydrocaffeoyl)spermidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N¹,N⁴,N⁸-tris(dihydrocaffeoyl)spermidine
• 英文别名: N1,N5,N10-tris(dihydrocaffeoyl)spermidine；N1,N4,N8-tris(dihydrocaffeoyl)spermidine；Tris(dihydrocaffeoyl)spermidine；3-(3,4-dihydroxyphenyl)-N-[4-[3-(3,4-dihydroxyphenyl)propanoyl-[3-[3-(3,4-dihydroxyphenyl)propanoylamino]propyl]amino]butyl]propanamide
• 化学式: C₃₄H₄₃N₃O₉
• 分子量: 637.73
• InChiKey: GDPWISSAARFOCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  200
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-[3,4-(亚甲二氧基)苯基]丙酸 在 三氯化硼 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 N¹,N⁴,N⁸-tris(dihydrocaffeoyl)spermidine
  参考文献：
  名称：

  Spermidine Derivatives in Lulo (Solanum quitoense Lam.) Fruit: Sensory (Taste) versus Biofunctional (ACE-Inhibition) Properties

  摘要：

  The bitterness in lulo (Solanum quitoense Lam.) fruit is increased during processing (juicing or drying). To identify the bitter-active compounds, the ethanolic fruit pulp extract was subjected to RP-18 solid-phase extraction, and then sensory-guided fractionated by HPLC. Two spermidine derivatives, N-1,N-4,N-8-tris(dihydrocaffeoyl)spermidine and N-1,N-8-bis(dihydrocaffeoyl)spermidine, were isolated and their structures confirmed by analysis of their HPLC-ESI/MS and H-1 and C-13 NMR data. The N-1,N-4,N-8-tris(dihydrocaffeoyl)spermidine was synthesized and used as an authentic sample to unequivocally confirm the structure of this compound and to quantitate it in both fresh and dried fruit. In silico analyses demonstrated that spermidine derivatives identified in lulo pulp exhibited a strong ACE-I (angiotensin I-converting enzyme) inhibitory activity. Subsequently, these results were confirmed by in vitro analyses and showed the potential use of lulo fruit pulp as an ingredient of functional foods related to the prevention of blood hypertension.

  DOI：

  10.1021/acs.jafc.6b01631

文献信息

• Spermidine Derivatives in Lulo (<i>Solanum quitoense</i> Lam.) Fruit: Sensory (Taste) versus Biofunctional (ACE-Inhibition) Properties
  作者：Diana Paola Forero、Chieko Masatani、Yoshinori Fujimoto、Ericsson Coy-Barrera、Devin G. Peterson、Coralia Osorio

  DOI：10.1021/acs.jafc.6b01631

  日期：2016.7.6

  The bitterness in lulo (Solanum quitoense Lam.) fruit is increased during processing (juicing or drying). To identify the bitter-active compounds, the ethanolic fruit pulp extract was subjected to RP-18 solid-phase extraction, and then sensory-guided fractionated by HPLC. Two spermidine derivatives, N-1,N-4,N-8-tris(dihydrocaffeoyl)spermidine and N-1,N-8-bis(dihydrocaffeoyl)spermidine, were isolated and their structures confirmed by analysis of their HPLC-ESI/MS and H-1 and C-13 NMR data. The N-1,N-4,N-8-tris(dihydrocaffeoyl)spermidine was synthesized and used as an authentic sample to unequivocally confirm the structure of this compound and to quantitate it in both fresh and dried fruit. In silico analyses demonstrated that spermidine derivatives identified in lulo pulp exhibited a strong ACE-I (angiotensin I-converting enzyme) inhibitory activity. Subsequently, these results were confirmed by in vitro analyses and showed the potential use of lulo fruit pulp as an ingredient of functional foods related to the prevention of blood hypertension.