A new benzophenone, and the antiplasmodial activities of the constituents of Securidaca longipedunculata fresen (Polygalaceae)

Nat Prod Res. 2022 Jun;36(11):2758-2766. doi: 10.1080/14786419.2021.1925272. Epub 2021 May 18.

Abstract

Extracts from Securidaca longipedunculata showed antiplasmodial activities against reference clones and clinical isolates using SYBR Green I method. A new benzophenone, 2,3,4,5-tetramethoxybenzophenone (1) was isolated and characterized along with seven known compounds: 4-hydroxy-2,3-dimethoxybenzophenone (2); 3-hydroxy-5-methoxybiphenyl (3), methyl-2-hydroxy-6-methoxybenzoate (4), benzyl-2-hydroxy-6-methoxybenzoate (5), 2-hydroxy-6-methoxybenzoic acid (6), 2,4,5-trimethoxybenzophenone (7) and 2-methoxy-3,4-methylenedioxybenzophenone (8). Compounds 1 and 2 showed ex vivo antiplasmodial activities (IC50 28.8 μM and 18.6 μM, respectively); while 5 and 8 showed in vivo activities (IC50 19.7 μM and 14.5 μM, respectively) against D6 strain. In a cytotoxicity assay, all the extracts (with an exception of the MeOH extract of the leaves) and pure compounds were not toxic to the normal LO2 and BEAS cell-lines, while the methanol roots extract (IC50 66.4 µg/mL against A549, and 77.4 µg/mL against HepG2), compounds 6 (IC50 22.2 µM against A549) and 7 (IC50 45.2 µM against HepG2) were weakly active against cancerous cell-lines.

Keywords: 2,3,4,5-tetramthoxybenzophenone; Antiplasmodial; Securidaca longipedunculata; benzophenone; cytotoxicity; ex vivo.

MeSH terms

  • Antimalarials* / pharmacology
  • Benzophenones / pharmacology
  • Hydroxybenzoate Ethers
  • Plant Extracts / pharmacology
  • Plasmodium falciparum
  • Polygalaceae*
  • Securidaca*

Substances

  • Antimalarials
  • Benzophenones
  • Hydroxybenzoate Ethers
  • Plant Extracts