Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from Cannabis sativa L.

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-09-25 DOI:10.1021/acs.jnatprod.5c00826

Luca Pozzi, Andrea Gotti, Marco Fumagalli, Andrea Citarella, Valerio Fasano, Giuseppe Paladino, Umberto Ciriello, Salvatore Princiotto, Francesca Annunziata, Giulia Martinelli, Enrico Sangiovanni, Andrea Pinto, Mario Dell'Agli, Daniele Passarella

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引用次数: 0

Abstract

We report the first isolation of a previously unknown cannabinoid, cannabizetol (CBGD, 7), from Cannabis sativa extracts, representing the third member of the rare class of methylene-bridged dimeric cannabinoids. The availability of a chemically synthesized standard was crucial for its unequivocal identification, thus confirming the natural occurrence of this new compound. In addition to this structural discovery, we demonstrate that cannabizetol exhibits remarkable antioxidant and skin anti-inflammatory activity, significantly higher than that observed for the known dimeric cannabinoid cannabitwinol (CBDD, 6). These results highlight cannabizetol as a promising bioactive metabolite with potential dermatological applications. To further enable its study, we developed a continuous flow approach to optimize the preparation of these dimers, achieving a substantial reduction in reaction times.

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新型大麻素大麻二酚的化学合成、抗炎活性及提取[j]。

我们报道了从大麻提取物中首次分离到一种以前未知的大麻素，大麻二酚（CBGD, 7），代表了罕见的亚甲基桥接二聚体大麻素类的第三个成员。化学合成标准的可用性对于其明确鉴定至关重要，从而确认这种新化合物的自然存在。除了这一结构发现，我们还证明大麻二酚具有显著的抗氧化和皮肤抗炎活性，显著高于已知的二聚大麻素大麻二酚（CBDD, 6）。这些结果突出了大麻酚作为一种具有潜在皮肤病学应用前景的生物活性代谢物。为了进一步进行研究，我们开发了一种连续流动方法来优化这些二聚体的制备，从而大大缩短了反应时间。

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来源期刊

Journal of Natural Products 生物-药学

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.