Antiviral Activity of Cannabidiolic Acid and Its Methyl Ester against SARS-CoV-2

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-07-04 DOI:10.1021/acs.jnatprod.3c00111

Martina Tamburello, Stefano Salamone, Lisa Anceschi, Paolo Governa, Virginia Brighenti, Alice Morellini, Giada Rossini, Fabrizio Manetti, Giorgio Gallinella, Federica Pollastro* and Federica Pellati*,

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引用次数: 1

Abstract

In the present study, the antiviral activity of cannabinoids isolated from Cannabis sativa L. was assessed in vitro against a panel of SARS-CoV-2 variants, indicating cannabidiolic acid (CBDA) was the most active. To overcome the instability issue of CBDA, its methyl ester was synthesized and tested for the first time for its antiviral activity. CBDA methyl ester showed a neutralizing effect on all the SARS-CoV-2 variants tested with greater activity than the parent compound. Its stability in vitro was confirmed by ultra-high-performance liquid chromatography (UHPLC) analysis coupled with high-resolution mass spectrometry (HRMS). In addition, the capacity of both CBDA and its derivative to interact with the virus spike protein was assessed in silico. These results showed that CBDA methyl ester can be considered as a lead compound to be further developed as a new effective drug against COVID-19 infection.

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大麻二酚酸及其甲酯对SARS-CoV-2的抗病毒活性

在本研究中，从大麻中分离的大麻素对一组SARS-CoV-2变体的抗病毒活性进行了体外评估，结果表明大麻二酚酸(CBDA)最具活性。为了克服CBDA的不稳定性问题，首次合成了其甲酯，并对其抗病毒活性进行了测试。CBDA甲酯对所有测试的SARS-CoV-2变体都有中和作用，活性高于母体化合物。通过超高效液相色谱(UHPLC) -高分辨率质谱(HRMS)分析证实了其体外稳定性。此外，在计算机上评估了CBDA及其衍生物与病毒刺突蛋白相互作用的能力。这些结果表明，CBDA甲酯可以作为一种新的抗COVID-19感染有效药物进一步开发的先导化合物。

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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.