Marinković Aleksandar, Nakarada Đura, Marinković Miloš, Waisi Hadi, Živanić Vladislav, Vazquez Arcadio, Mojović Miloš
Institute of General and Physical Chemistry, Studentski trg 12/V, 11158 Belgrade, Serbia.
Center for Physical Chemistry of Biological Systems, BioScope Labs, Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11158 Belgrade, Serbia.
Molecules. 2025 Aug 20;30(16):3433. doi: 10.3390/molecules30163433.
This study explores the antioxidant potential and delivery performance of five structurally distinct cannabinoids, with a particular focus on cannabinol (CBN). Comprehensive structural characterization using mass spectrometry (MS) and nuclear magnetic resonance (NMR) revealed key molecular features relevant to antioxidant function. Among the tested compounds, CBN exhibited the most potent and balanced radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl, and superoxide radicals. Based on these findings, CBN was selected for formulation into soy lecithin liposomes. The resulting CBN-loaded liposomes displayed favorable colloidal properties, with an average size of approximately 122.9 ± 0.4 nm. Results indicating increased membrane order upon CBN incorporation suggest enhanced stability of the liposomal bilayer. Antioxidant activity assays showed that CBN-loaded liposomes retain significant radical scavenging capacity, though with a moderate reduction compared to free CBN. EPR imaging further demonstrated superior diffusion of liposomal CBN through a gelatin-based semi-solid model compared to the control solution. While the current model does not replicate skin architecture, it provides a cost-effective and reproducible platform for early-stage screening of formulation mobility. These results position CBN-loaded liposomes as a promising candidate for dermal antioxidant applications, combining favorable physicochemical properties with enhanced diffusion behavior.
本研究探索了五种结构不同的大麻素的抗氧化潜力和递送性能，尤其关注大麻酚（CBN）。使用质谱（MS）和核磁共振（NMR）进行的全面结构表征揭示了与抗氧化功能相关的关键分子特征。在测试的化合物中，CBN对2,2-二苯基-1-苦基肼（DPPH）、羟基和超氧阴离子自由基表现出最强且最平衡的自由基清除活性。基于这些发现，选择CBN制备大豆卵磷脂脂质体。所得的载CBN脂质体表现出良好的胶体性质，平均尺寸约为122.9±0.4 nm。结果表明，掺入CBN后膜有序性增加，表明脂质体双层的稳定性增强。抗氧化活性测定表明，载CBN脂质体保留了显著的自由基清除能力，尽管与游离CBN相比有适度降低。电子顺磁共振成像进一步证明，与对照溶液相比，脂质体CBN在基于明胶的半固体模型中的扩散性更佳。虽然当前模型无法复制皮肤结构，但它为制剂流动性的早期筛选提供了一个经济高效且可重复的平台。这些结果表明，载CBN脂质体结合了良好的物理化学性质和增强的扩散行为，是皮肤抗氧化应用的一个有前景的候选物。
