Recent studies by our group have suggested that the vitamin D3 decomposition product VDP1 [(1R,3aR,7aR)-1-[(1R)-1,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-one] confers the potent bactericidal action to Helicobacter pylori by targeting the membranal dimyristoyl-phosphatidylethanolamine (di-14:0 PE). In this study we synthesized a new VDP1 derivative to advance further investigation as for the correlative relationship between VDP1 structure and anti-H. pylori activity or PE vesicle collapse induction activity. The derivative VD3-7 [(1R,7aR)-4-fluoro-7a-methyl-1-((R)-6-methylheptan-2-yl)octahydro-1H-indene] retained a fluorine atom in place of the oxygen atom of VDP1. The fluorination of the carbonyl portion of VDP1 forfeited the effective anti-H. pylori activity. We, therefore, prepared Coomassie brilliant blue (CBB)-containing unilamellar vesicles consisting of various PE molecular species, and examined the vesicle collapse induction activity of either VDP1 or VD3-7 by detecting the CBB eluted from the PE unilamellar vesicles. VDP1 strongly induced CBB elution from the unilamellar vesicles of rectus-PE retaining the same two fatty acid side-chains shorter than carbon numbers 14, indicating that VDP1 specifically disrupted the vesicular conformation of those PE unilamellar vesicles. Meanwhile, VD3-7 had no influence on the structural stability of any PE unilamellar vesicles. This study obtained additional evidence that VDP1 acts as a bactericidal agent on H. pylori by targeting the membranal di-14:0 PE.

中文翻译：

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茚对幽门螺杆菌的抗菌作用与其化合物与二肉豆蔻酰基磷脂酰乙醇胺之间的特异性相互作用有关。

我们小组最近的研究表明，维生素D3分解产物VDP1 [（1R，3aR，7aR）-1-[（1R）-1,5-二甲基己基]八氢-7a-甲基-4H-茚满-4-one]通过靶向膜二豆豆蔻酰磷脂酰乙醇胺（di-14：0 PE）赋予幽门螺杆菌有效的杀菌作用。在这项研究中，我们合成了一种新的VDP1衍生物，以进一步研究VDP1结构与抗H的相关关系。幽门螺杆菌活性或PE囊泡塌陷诱导活性。衍生物VD3-7 [（1R，7aR）-4-氟-7a-甲基-1-（（R）-6-甲基庚基-2-基）八氢-1H-茚]保留氟原子代替氧VDP1的原子。VDP1羰基部分的氟化作用丧失了有效的抗H原子。幽门螺杆菌活动。因此，我们 制备了由各种PE分子组成的含考马斯亮蓝（CBB）的单层囊泡，并通过检测从PE单层囊泡洗脱的CBB来检查VDP1或VD3-7的囊泡塌陷诱导活性。VDP1强烈诱导直肌-PE的单层囊泡洗脱CBB，保留相同的两个短于碳原子数14的脂肪酸侧链，表明VDP1特异性破坏了这些PE单层囊泡的囊泡构象。同时，VD3-7对任何PE单层囊泡的结构稳定性没有影响。这项研究获得了其他证据，表明VDP1通过靶向膜di-14：0 PE充当幽门螺杆菌的杀菌剂。并且通过检测从PE单层囊泡中洗脱的CBB来检查VDP1或VD3-7的囊泡塌陷诱导活性。VDP1强烈诱导直肌-PE的单层囊泡洗脱CBB，保留相同的两个短于碳原子数14的脂肪酸侧链，表明VDP1特异性破坏了这些PE单层囊泡的囊泡构象。同时，VD3-7对任何PE单层囊泡的结构稳定性没有影响。这项研究获得了其他证据，表明VDP1通过靶向膜di-14：0 PE充当幽门螺杆菌的杀菌剂。并且通过检测从PE单层囊泡中洗脱的CBB来检查VDP1或VD3-7的囊泡塌陷诱导活性。VDP1强烈诱导直肌-PE的单层囊泡洗脱CBB，保留相同的两个短于碳原子数14的脂肪酸侧链，表明VDP1特异性破坏了这些PE单层囊泡的囊泡构象。同时，VD3-7对任何PE单层囊泡的结构稳定性没有影响。这项研究获得了其他证据，表明VDP1通过靶向膜di-14：0 PE充当幽门螺杆菌的杀菌剂。这表明VDP1特异性破坏了这些PE单层囊泡的囊泡构象。同时，VD3-7对任何PE单层囊泡的结构稳定性没有影响。这项研究获得了其他证据，表明VDP1通过靶向膜di-14：0 PE充当幽门螺杆菌的杀菌剂。表明VDP1专门破坏那些PE单层囊泡的囊泡构象。同时，VD3-7对任何PE单层囊泡的结构稳定性没有影响。这项研究获得了其他证据，表明VDP1通过靶向膜di-14：0 PE充当幽门螺杆菌的杀菌剂。