作为皮肤炎症抑制剂的小分子大麻素:化学合成与生物学评价。

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-07-26 Epub Date: 2024-06-18 DOI:10.1021/acs.jnatprod.4c00212
Alice Maiocchi, Marco Fumagalli, Manuel Vismara, Asja Blanco, Umberto Ciriello, Giuseppe Paladino, Stefano Piazza, Giulia Martinelli, Valerio Fasano, Mario Dell'Agli, Daniele Passarella
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引用次数: 0

摘要

尽管植物治疗用途已有数千年的历史,但对大麻的各种生物医学潜力的蓄意开发最近才引起人们的注意。生物活性研究主要集中在大麻二酚(CBD)和四氢大麻酚(THC)上,而关于更广泛的大麻素组的 "次要植物大麻素 "的信息却很有限。在这种情况下,我们的研究目标是合成含有 3 或 4 个碳原子侧链的次要大麻素,重点是大麻萜醇(CBG)和大麻色烯(CBC)类似物。利用已知和创新策略,我们合成了 11 种 C3 和 C4 类似物,其中 5 种是皮肤炎症抑制剂,CBG-C4 酯衍生物成为最有效的化合物。
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Minor Cannabinoids as Inhibitors of Skin Inflammation: Chemical Synthesis and Biological Evaluation.

Despite millennia of therapeutic plant use, deliberate exploitation of Cannabis's diverse biomedical potential has only recently gained attention. Bioactivity studies focus mainly on cannabidiol (CBD) and tetrahydrocannabinol (THC) with limited information about the broader cannabinome's "minor phytocannabinoids". In this context, our research targeted the synthesis of minor cannabinoids containing a lateral chain with 3 or 4 carbon atoms, focusing on cannabigerol (CBG) and cannabichromene (CBC) analogues. Using known and innovative strategies, we achieved the synthesis of 11 C3 and C4 analogues, five of which were inhibitors of skin inflammation, with the CBG-C4 ester derivative emerging as the most potent compound.

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来源期刊
CiteScore
9.10
自引率
5.90%
发文量
294
审稿时长
2.3 months
期刊介绍: The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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