Anti-biofilm and anti-inflammatory active diterpene isolated from the fruit of Xylopia benthamii R.E.Fr

Nat Prod Res. 2024 Mar;38(6):956-967. doi: 10.1080/14786419.2023.2208357. Epub 2023 May 8.

Abstract

Xylopia benthamii (Annonaceae) is a plant with limited phytochemical and pharmacological evidence. Thus, using LC-MS/MS, we performed exploratory analyses of the fruit extract of X. benthamii, resulting in the tentative identification of alkaloids (1-7) and diterpenes (8-13). Through the application of chromatography techniques with the extract of X. benthamii, two kaurane diterpenes were isolated, xylopinic acid (9) and ent-15-oxo-kaur-16-en-19-oic acid (11). Their structures were established using spectroscopy (NMR 1D/2D) and mass spectrometry. The isolated compounds were submitted to anti-biofilm analysis against Acinetobacter baumannii, anti-neuroinflammatory and cytotoxic activity in BV-2 cells. Compound 11 (201.75 µM) inhibited 35% of bacterial biofilm formation and high anti-inflammatory activity in BV-2 (IC50 = 0.78 µM). In conclusion, the results demonstrated that compound 11 was characterized for the first time with pharmacological potential in the development of new alternatives for studies with neuroinflammatory diseases.

Keywords: Diterpenes; anti-biofilm; anti-neuroinflammatory; cytotoxic activity; mass spectrometry; spectroscopy.

MeSH terms

  • Chromatography, Liquid
  • Diterpenes* / chemistry
  • Fruit
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Tandem Mass Spectrometry
  • Xylopia* / chemistry

Substances

  • Diterpenes
  • Plant Extracts