2. Academic Validation
  3. Isolation of Anti-SARS-CoV-2 Natural Products Extracted from Mentha canadensis and the Semi-synthesis of Antiviral Derivatives

Isolation of Anti-SARS-CoV-2 Natural Products Extracted from Mentha canadensis and the Semi-synthesis of Antiviral Derivatives

  • J Nat Prod. 2023 Jun 23;86(6):1428-1436. doi: 10.1021/acs.jnatprod.3c00104.
Osbert Chou 1,  Yu-Pu Juang 1,  Tai-Ling Chao 2,  Sheng-Fa Tsai 1,  Pei-Fang Chiu 1,  Chun-Tang Chiou 3,  Keng-Chang Tsai 3,  Sui-Yuan Chang 2,  Pi-Hui Liang 1 4,  Chi-Huey Wong 4 5
Affiliations

Affiliations

  • 1 School of Pharmacy, College of Medicine, National Taiwan University, Taipei 100, Taiwan.
  • 2 Department of Clinical Laboratory Sciences and Medical Biotechnology, College of Medicine, National Taiwan University, Taipei 100, Taiwan.
  • 3 Ministry of Health and Welfare, National Research Institute of Chinese Medicine, Taipei 112, Taiwan.
  • 4 The Genomics Research Center, Academia Sinica, Taipei 128, Taiwan.
  • 5 Scripps Research Institute, La Jolla, California 92037, United States.
PMID: 37267066 DOI: 10.1021/acs.jnatprod.3c00104
Abstract

Traditional herbal medicine offers opportunities to discover novel therapeutics against SARS-CoV-2 mutation. The dried aerial part of mint (Mentha canadensis L.) was chosen for bioactivity-guided extraction. Seven constituents were isolated and characterized by nuclear magnetic resonance (NMR) and mass spectrometry (MS). Syringic acid and methyl rosmarinate were evaluated in drug combination treatment. Ten amide derivatives of methyl rosmarinate were synthesized, and the dodecyl (13) and 3-ethylphenyl (19) derivatives demonstrated significant improvement in the anti-SARS-CoV-2 plaque reduction assay, achieving IC50 of 0.77 and 2.70 μM, respectively, against Omicron BA.1 as compared to methyl rosmarinate's IC50 of 57.0 μM. Spike protein binding and 3CLpro inhibition assays were performed to explore the viral inhibition mechanism. Molecular docking of compounds 13 and 19 to 3CLpro was performed to reveal potential interaction. In summary, Natural Products with anti-Omicron BA.1 activity were isolated from Mentha canadensis and derivatives of methyl rosmarinate were synthesized, showing 21- to 74-fold improvement in Antiviral activity against Omicron BA.1.

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