glucomoringin | 316165-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: glucomoringin
• 英文别名: 4-(α-L-rhamnosyloxy)benzyl glucosinolate；glucomoringin potassium salt
• CAS: 316165-49-8
• 化学式: C₂₀H₂₈NO₁₄S₂*K
• 分子量: 609.671
• InChiKey: OVFNULRBAJGUQL-ZXXSMENNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -6.24
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  248.09
• 氢给体数：
  7.0
• 氢受体数：
  16.0

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  glucomoringin 在 myrosinase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.25h， 生成 4-（异硫氰酸甲酯）苯基6-脱氧-α-L-甘露聚糖苷
  参考文献：
  名称：

  Prospective role of mitochondrial apoptotic pathway in mediating GMG-ITC to reduce cytotoxicity in H2O2-induced oxidative stress in differentiated SH-SY5Y cells

  摘要：

  The antioxidant and neuroprotective activity of Glucomoringin isothiocyanate (GMG-ITC) have been reported in in vivo and in vitro models of neurodegenerative diseases. However, its neuroprotective role via mitochondrial-dependent pathway in a noxious environment remains unknown. The main objective of the present study was to unveil the mitochondrial apoptotic genes' profile and prospectively link with neuroprotective activity of GMG-ITC through its ROS scavenging. The results showed that pre-treatment of differentiated SH-SY5Y cells with 1.25 mu g/mL purified isolated GMG-ITC, significantly reduced reactive oxygen species (ROS) production level, compared to H2O2 control group, as evidenced by flow cytometry-based evaluation of ROS generation. Presence of GMG-ITC prior to development of oxidative stress condition, downregulated the expression of cyt-c, p5.3, Apaf-1, Bax, CASP3, CASP8 and CASP9 genes with concurrent upregulation of Bcl-2 gene in mitochondrial apoptotic signalling pathway. Protein Multiplex revealed significant decreased in cyt-c, p53, Apaf-1, Bax, CASP8 and CASP9 due to GMG-ITC pre-treatment in oxidative stress condition. The present findings speculated that pretreatment with GMG-ITC may alleviate oxidative stress condition in neuronal cells by reducing ROS production level and protect the cells against apoptosis via neurodegenerative disease potential pathways.

  DOI：

  10.1016/j.biopha.2019.109445

文献信息

• Antibacterial Activity of Glucomoringin Bioactivated with Myrosinase against Two Important Pathogens Affecting the Health of Long-Term Patients in Hospitals
  作者：Maria Galuppo、Gina Nicola、Renato Iori、Pia Dell'Utri、Placido Bramanti、Emanuela Mazzon

  DOI：10.3390/molecules181114340

  日期：——

  Glucosinolates (GLs) are natural compounds present in species of the order Brassicales and precursors of bioactive isothiocyanates (ITCs). In the recent years, they have been studied mainly for their chemopreventive as well as novel chemotherapeutics properties. Among them 4-(α-L-rhamnosyloxy)benzyl glucosinolate (glucomoringin; GMG), purified from seeds of Moringa oleifera Lam., a plant belonging to the Moringaceae family, represents an uncommon member of the GL family with peculiar characteristics. This short communication reports new evidences about the properties of GMG and presents a new innovative utilization of the molecule. The bioactivation of GMG by myrosinase enzyme just before treatment, permits to maximize the power of the final product of the reaction, which is the 4-(α-L-rhamnosyloxy)benzyl isothiocyanate (GMG-ITC). We tested the antibiotic activity of this latter compound on two strains of pathogens affecting the health of patients in hospital, namely Staphylococcus aureus and Enterococcus casseliflavus, and on the yeast Candida albicans. Results show that the sensibility of S. aureus BAA-977 strain and E. casseliflavus to GMG-ITC treatment reveals an important possible application of this molecule in the clinical care of patients, more and more often resistant to traditional therapies.

  芥子油苷 (GL) 是存在于芸苔目物种中的天然化合物，也是生物活性异硫氰酸酯 (ITC) 的前体。近年来，人们主要对其化学预防和新型化疗特性进行研究。其中4-(α-L-鼠李糖基氧基)苄基芥子油苷(glucomoringin；GMG)是从辣木科植物辣木的种子中纯化出来的，是GL家族中一个不常见的成员，具有独特的特性。这篇简短的通讯报告了有关 GMG 特性的新证据，并提出了该分子的新创新用途。在处理前，黑芥子酶对 GMG 进行生物活化，从而最大限度地提高反应最终产物的功效，即 4-(α-L-鼠李糖氧基)异硫氰酸苄酯 (GMG-ITC)。 我们测试了后一种化合物对影响医院患者健康的两种病原体菌株（即金黄色葡萄球菌和卡氏肠球菌）以及白色念珠菌的抗生素活性。结果表明，金黄色葡萄球菌 BAA-977 菌株和 E. cassseliflavus 对 GMG-ITC 治疗的敏感性揭示了该分子在越来越多地对传统疗法产生耐药性的患者临床护理中的重要可能应用。