Department of Quantum Chemistry, Faculty of Chemistry, Adam Mickiewicz University of Poznań, ul. Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.
Molecules. 2024 Jul 21;29(14):3414. doi: 10.3390/molecules29143414.
Utilizing Density Functional Theory (DFT) calculations at the B3LYP/QZVP level and incorporating the Conductor-like Polarizable Continuum Model (C-PCM) for solvation, the thermodynamic and chemical activity properties of 21-(hydroxymethoxy)henicosadecaenal, identified in cultured freshwater pearls from the mollusk , have been elucidated. The study demonstrates that this compound releases formaldehyde, a potent antimicrobial agent, through dehydrogenation and deprotonation processes in both hydrophilic and lipophilic environments. Moreover, this polyenal exhibits strong anti-reductant properties, effectively scavenging free radicals. These critical properties classify the pearl-derived ingredient as a natural multi-functional compound, serving as a coloring, antiradical, and antimicrobial agent. The 2-(hydroxymethoxy)vinyl (HMV) moiety responsible for the formaldehyde release can be transferred to other compounds, thereby enhancing their biological activity. For instance, tyrosol (4-(2-hydroxyethyl)phenol) can be modified by substituting the less active 2-hydroxyethyl group with the active HMV one, and hinokitiol (4-isopropylotropolone) can be functionalized by attaching this moiety to the tropolone ring. A new type of meso-carrier, structurally modeled on pearls, with active substances loaded both in the layers and the mineral part, has been proposed.
利用密度泛函理论（DFT）计算在 B3LYP/QZVP 水平，并纳入溶剂化的导体类似极化连续模型（C-PCM），已经阐明了在淡水珍珠贝养殖珍珠中鉴定出的 21-（羟甲氧基）二十一碳烯醛的热力学和化学活性性质。该研究表明，这种化合物通过在亲水和亲脂环境中的脱氢和去质子化过程释放甲醛，一种有效的抗菌剂。此外，这种多烯醛表现出很强的抗还原剂性质，有效地清除自由基。这些关键性质将珍珠衍生的成分归类为天然多功能化合物，用作着色剂、抗氧化剂和抗菌剂。负责释放甲醛的 2-（羟甲氧基）乙烯基（HMV）部分可以转移到其他化合物上，从而提高它们的生物活性。例如，酪氨酸（4-（2-羟乙基）苯酚）可以通过用活性 HMV 部分取代不活跃的 2-羟乙基基团来修饰，而扁柏醇（4-异丙基托罗酮）可以通过将该部分连接到三唑酮环上来官能化。提出了一种新型介孔载体，其结构基于珍珠，活性物质同时加载在层和矿物部分中。
