dimerumic acid | 26912-16-3

• 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: dimerumic acid
• 英文别名: Sds82xvn4Q；(E)-N,5-dihydroxy-N-[3-[(2S,5S)-5-[3-[hydroxy-[(E)-5-hydroxy-3-methylpent-2-enoyl]amino]propyl]-3,6-dioxopiperazin-2-yl]propyl]-3-methylpent-2-enamide
• CAS: 26912-16-3
• 化学式: C₂₂H₃₆N₄O₈
• 分子量: 484.55
• InChiKey: MKDKGLNKTMDNHY-URISWADMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimerumic acid 在 双氧水 、 myoglobin 作用下， 以 phosphate buffer 为溶剂， 生成
  参考文献：
  名称：

  Dimerumic acid as an antioxidant from the mold, Monascus anka: the inhibition mechanisms against lipid peroxidation and hemeprotein-mediated oxidation

  摘要：

  This study aimed to investigate the antioxidant mechanism of dimerumic acid isolated as the active component with a radical scavenging action from the mold Monascus anka, traditionally used for the fermentation of foods. Dimerumic acid inhibited NADPH- and iron(II)-dependent lipid peroxidation (LPO) of rat liver microsomes at 20 and 200 muM, respectively. When ferrylmyoglobin was incubated with dimerumic acid, the myoglobin was scavenged and an electron spin resonance (ESR) signal with nine peaks was observed. The spin adduct was identified as a nitroxide radical by analysis of hyperfine structure. Similar ESR signal was also detected by incubation of dimerumic acid with peroxyl radicals. Thus, it was clarified that the antioxidant action of dimerumic acid is due to one electron donation of the hydroxamic acid group in the dimerumic acid molecule toward oxidants resulting in formation of nitroxide radical. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0006-2952(01)00923-6

文献信息

• Metachelins, Mannosylated and N-Oxidized Coprogen-Type Siderophores from <i>Metarhizium robertsii</i>
  作者：Stuart B. Krasnoff、Ivan Keresztes、Bruno G. G. Donzelli、Donna M. Gibson

  DOI：10.1021/np500300s

  日期：2014.7.25

  Under iron-depleted culture conditions, the entomopathogenic fungus Metarhizium robertsii (Bischoff, Humber, and Rehner) (= M anisopliae) produces a complex of extracellular siderophores including novel O-glycosylated and N-oxidized coprogen-type compounds as well as the known fungal siderophores N-alpha-dimethylcoprogen (NADC) and dimenimic acid (DA). Metachelin A (1), the most abundant component in the M. robertsii siderophore mixture, was characterized as a 1094 Da analogue of NADC that is O-glycosylated by beta-mannose at both terminal hydroxyl groups and N-oxidized at the dimethylated alpha-nitrogen. The mixture also contained a 1078 Da analogue, metachelin B (2), which lacks the N-oxide modification. Also characterized were the aglycone of 1, i.e., the N-oxide of NADC (3), and the monomannoside of DA (6). N-Oxide and O-glycosyl substituents are unprecedented among microbial siderophores. At high ESIMS source energy and at room temperature in DMSO, 1 underwent Cope elimination, resulting in loss of the N-alpha-dimethyl group and dehydration of the alpha-beta bond. High-resolution ESIMS data confirmed that all tri- and dihydroxamate siderophores (1-6) complex with trivalent Fe, Al, and Ga. In a chrome azurol S assay, all of the M. robertsii siderophores showed iron-binding activity roughly equivalent to that of desferrioxamine B.
• Dimerumic acid as an antioxidant from the mold, Monascus anka: the inhibition mechanisms against lipid peroxidation and hemeprotein-mediated oxidation
  作者：Junsei Taira、Chika Miyagi、Yoko Aniya

  DOI：10.1016/s0006-2952(01)00923-6

  日期：2002.3

  This study aimed to investigate the antioxidant mechanism of dimerumic acid isolated as the active component with a radical scavenging action from the mold Monascus anka, traditionally used for the fermentation of foods. Dimerumic acid inhibited NADPH- and iron(II)-dependent lipid peroxidation (LPO) of rat liver microsomes at 20 and 200 muM, respectively. When ferrylmyoglobin was incubated with dimerumic acid, the myoglobin was scavenged and an electron spin resonance (ESR) signal with nine peaks was observed. The spin adduct was identified as a nitroxide radical by analysis of hyperfine structure. Similar ESR signal was also detected by incubation of dimerumic acid with peroxyl radicals. Thus, it was clarified that the antioxidant action of dimerumic acid is due to one electron donation of the hydroxamic acid group in the dimerumic acid molecule toward oxidants resulting in formation of nitroxide radical. (C) 2002 Elsevier Science Inc. All rights reserved.