Boulebd Houssem
Chemistry Department, Faculty of Exact Science, University of Constantine 1, Constantine, 25000, Algeria.
Phytochemistry. 2023 Apr;208:113608. doi: 10.1016/j.phytochem.2023.113608. Epub 2023 Feb 2.
Phytocannabinoids are natural products primarily isolated from Cannabis sativa that exhibit the typical C21 terpenophenolic skeleton. This class of compounds has been shown to be effective in the treatment of various oxidation-related diseases, which has made their antioxidant properties the focus of increasing interest. In the present contribution, the primary antioxidant properties of eight representative phytocannabinoids have been systematically studied against a variety of biologically significant radical species using the density functional theory (DFT) method. The findings demonstrated that phytocannabinoids, in water at physiological pH, exhibit excellent radical scavenging capacity, mainly exerted by the single electron transfer (SET) process from the deprotonated state. In contrast, phytocannabinoids are moderate radical scavengers in non-polar environment via the formal hydrogen atom transfer (fHAT) process. Among the compounds examined, cannabichromene (CBC) and cannabifuran (CBF) had the greatest free radical scavenging capacity in water, surpassing even common antioxidants like BHT and Trolox. CBF is expected to have potent antiradical action toward peroxyl radicals, alkoxy radicals, and nitrogen dioxide in water at physiological pH. These results provide supporting evidence that phytocannabinoids may be useful in scavenging harmful free radicals in physiological environments.
植物大麻素是主要从大麻中分离出的天然产物，具有典型的C21萜酚骨架。这类化合物已被证明在治疗各种与氧化相关的疾病方面有效，这使得它们的抗氧化特性成为越来越受关注的焦点。在本论文中，使用密度泛函理论（DFT）方法，系统地研究了八种代表性植物大麻素对各种具有生物学意义的自由基的主要抗氧化特性。研究结果表明，在生理pH值的水中，植物大麻素表现出优异的自由基清除能力，主要通过去质子化状态的单电子转移（SET）过程发挥作用。相比之下，在非极性环境中，植物大麻素通过形式氢原子转移（fHAT）过程是中等强度的自由基清除剂。在所研究的化合物中，大麻色烯（CBC）和大麻二酚（CBF）在水中具有最大的自由基清除能力，甚至超过了常见的抗氧化剂如丁基羟基甲苯（BHT）和Trolox。预计CBF在生理pH值的水中对过氧自由基、烷氧自由基和二氧化氮具有强大的抗自由基作用。这些结果提供了支持性证据，表明植物大麻素可能有助于清除生理环境中的有害自由基。
