brachystemin F | 1312415-65-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: brachystemin F
• 英文别名: cyclo(Pro(1)-Val(2)-Gly(3)-Leu(4)-Thr(5)-Pro(6)-Thr(7)-Phe(8))；(3S,6S,9S,15S,18S,24S,27S)-3-benzyl-6,15-bis[(1R)-1-hydroxyethyl]-18-(2-methylpropyl)-24-propan-2-yl-1,4,7,13,16,19,22,25-octazatricyclo[25.3.0.09,13]triacontane-2,5,8,14,17,20,23,26-octone
• CAS: 1312415-65-8
• 化学式: C₄₀H₆₀N₈O₁₀
• 分子量: 812.964
• InChiKey: QCYGONJLNWMGTQ-AMDHWJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  58
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  256
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  brachystemin F 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 19.0h， 生成 Gly-L-FDAA 、 L-FDAA-L-Thr 、 L-DAA-L-Leu 、 L-FDAA-L-Pro 、 L-Phe-L-FDAA 、 (S)-2-(5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenylamino)-3-methylbutanoic acid
  参考文献：
  名称：

  Bioactive Compounds from the Aerial Parts of Brachystemma calycinum and Structural Revision of an Octacyclopeptide

  摘要：

  Four new cyclic peptides, brachystemins F-I (1-4), and 11 known compounds were isolated from the aerial parts of Brachystemma calycinim. The absolute configurations of compounds 1-4 were assigned using Marfey's method. The structure of compound 5 was revised from cyclo-(Pro(1)-Phe(2)-Leu(3)-Ala(4)-Thr(5)-Pro(6)-Ala(7)-Gly(8)) to cyclo-(Pro(1)-Pro(2)-Ala(3)-Gly(4)-Leu(5)-Ala(6)-Thr(7)-Phe(8)) with QTOF/MS and X-ray diffraction analysis. The N-containing compounds were assessed for their inhibitory effects on the secretion of monocyte chemokine ligand 2 (CCL-2), interleukin 6 (IL-6), and collagen IV against high-glucose-stimulated mesangial cells. Compound 5 was evaluated for its effects on collagen I, reactive oxygen species (ROS), superoxide anion (O(2)(center dot-)) production, and cell viability in mesangial cells, and on nitric oxide (NO) production in macrophage cells.

  DOI：

  10.1021/np200048u

文献信息

• Bioactive Compounds from the Aerial Parts of <i>Brachystemma calycinum</i> and Structural Revision of an Octacyclopeptide
  作者：Jun Zhao、Li-Li Zhou、Xi Li、Hong-Bin Xiao、Fan-Fan Hou、Yong-Xian Cheng

  DOI：10.1021/np200048u

  日期：2011.6.24

  Four new cyclic peptides, brachystemins F-I (1-4), and 11 known compounds were isolated from the aerial parts of Brachystemma calycinim. The absolute configurations of compounds 1-4 were assigned using Marfey's method. The structure of compound 5 was revised from cyclo-(Pro(1)-Phe(2)-Leu(3)-Ala(4)-Thr(5)-Pro(6)-Ala(7)-Gly(8)) to cyclo-(Pro(1)-Pro(2)-Ala(3)-Gly(4)-Leu(5)-Ala(6)-Thr(7)-Phe(8)) with QTOF/MS and X-ray diffraction analysis. The N-containing compounds were assessed for their inhibitory effects on the secretion of monocyte chemokine ligand 2 (CCL-2), interleukin 6 (IL-6), and collagen IV against high-glucose-stimulated mesangial cells. Compound 5 was evaluated for its effects on collagen I, reactive oxygen species (ROS), superoxide anion (O(2)(center dot-)) production, and cell viability in mesangial cells, and on nitric oxide (NO) production in macrophage cells.