High-Resolution Mass Spectrometry Identification and Characterization of Flavonoids from Fridericia chica Leaves Extract with Anti-Arbovirus Activity

Molecules. 2022 Sep 16;27(18):6043. doi: 10.3390/molecules27186043.

Abstract

Plant extracts are complex mixtures that are difficult to characterize, and mass spectrometry is one of the main techniques currently used in dereplication processes. Fridericia chica is a species with medicinal uses in Latin American countries, used in the treatment of inflammatory and infectious diseases. Extracts of this plant species are characterized by the presence of anthocyanidins. In this study, using high-resolution mass spectrometry coupled with liquid chromatography, it was possible to determine the molecular formula of thirty-nine flavonoids. Fragmentation analysis, ultraviolet spectrum and nuclear magnetic resonance data allowed the partial characterization of the structures of these compounds. The spectral dataset allowed the identification of a series of flavones in addition to the desoxyanthocyanidins common in extracts of the species. The occurrence of some of the proposed structures is uncommon in extracts of species of the Bignoniaceae family, and they are reported for the first time in the extract of this species. Quantitative analyses of total flavonoids confirmed the high content of these constituents in the species, with 4.09 ± 0.34 mg/g of dry plant material. The extract under study showed low in vitro cytotoxicity with CC50 ≥ 296.7 ± 1.4 µg/mL for Vero, LLC-MK2 and MRC-5 cell lines. In antiviral activity assays, inhibition of the cytopathic effects of Dengue, Zika and Mayaro viruses was observed, with EC50 values ranging between 30.1 and 40.9 µg/mL. The best result was observed against the Mayaro virus, with an EC50 of 30.1 µg/mL.

Keywords: Arrabidaea chica; Bignoniaceae; anti-dengue activity; flavonoids.

MeSH terms

  • Anthocyanins / analysis
  • Antiviral Agents / analysis
  • Antiviral Agents / pharmacology
  • Bignoniaceae* / chemistry
  • Flavones* / analysis
  • Flavones* / pharmacology
  • Flavonoids / analysis
  • Flavonoids / pharmacology
  • Mass Spectrometry
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry
  • Zika Virus Infection*
  • Zika Virus*

Substances

  • Anthocyanins
  • Antiviral Agents
  • Flavones
  • Flavonoids
  • Plant Extracts

Grants and funding

This work was supported by the FAPEMIG (Fundação de Amparo à Pesquisa do Estado de Minas Gerais, Brazil), process number: CDS—APQ-00970-21 providing research resources for acquisition of materials and equipment.; PROPPI-UFOP (Pró-Reitoria de Pesquisa, Pós-Graduação e Inovação da UFOP), process numbers N.: 18/2022 providing fund for the APC fee; CAPES (Coordenação de Aperfeiçoamento de Pessoal de Ensino Superior, Brazil) and CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico, Brazil) providing scholarships.