UPLC-ESI-QTOF-MS2 characterisation of Cola nitida resin fractions with inhibitory effects on NO and TNF-α released by LPS-activated J774 macrophage and on Trypanosoma cruzi and Leishmania amazonensis

Phytochem Anal. 2018 Nov;29(6):577-589. doi: 10.1002/pca.2771. Epub 2018 May 29.

Abstract

Introduction: The resin of Cola nitida is used in western Cameroon as incense for spiritual protection and during ritual ceremonies. This plant secretion has never been investigated although previous chemical and biological studies on other resins have drawn many attentions.

Objective: The resin fractions which revealed inhibitory effect on nitric oxide (NO) and tumour necrosis factor alpha (TNF-α) released by lipopolysaccharide (LPS)-activated J774 macrophage as well as on intracellular forms of Leishmania amazonensis and Trypanosoma cruzi amastigote were chemically characterised. Moreover, their antiparasitic activities were compared to those of semi-synthetic triterpenes.

Methodology: The anti-inflammatory activity was evaluated by measuring the nitrite production and the TNF-α concentration in the supernatants of LPS-activated macrophages by antigen capture enzyme-linked immunosorbent assay. Moreover, the antiparasitic assay was performed by infecting the host cells (THP-1) in a ratio parasite/cell 10:1 (L. amazonensis) and 2:1 (T. cruzi) and then exposed to the samples. The resin was separated in vacuo by liquid chromatography because of its sticky behaviour and the chemical profiles of the obtained fractions (F1-F4) were established by dereplication based on UPLC-ESI-MS2 data while semi-synthetic triterpenes were prepared from α-amyrin by oxidation reactions.

Results: Fractions F1-F4 inhibited NO and TNF-α almost similarly. However, only F1, F3 and F4 showed promising antiparasitic activities while F2 was moderately active against both parasites. Hence, F1-F4 were exclusively composed of pentacyclic triterpenes bearing oleanane and ursane skeletons. Semi-synthetic compounds revealed no to moderate antiparasitic activity compared to the fractions.

Conclusion: Although it will be difficult to prove the interaction resin-spirit, interesting bioactivities were found in the resin fractions.

Keywords: Cola nitida resin; NO and TNF-α inhibition; UPLC-ESI-QTOF-MS2; antiprotozoal activity; pentacyclic triterpenes.

MeSH terms

  • Animals
  • Cell Line
  • Chromatography, Liquid / methods*
  • Cola / chemistry*
  • Gene Expression Regulation / drug effects
  • Interleukin-1beta / genetics
  • Interleukin-1beta / metabolism
  • Interleukin-6 / genetics
  • Interleukin-6 / metabolism
  • Leishmania / drug effects*
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects*
  • Mass Spectrometry / methods*
  • Mice
  • Nitric Oxide / metabolism
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Resins, Plant / chemistry
  • Trypanosoma cruzi / drug effects*
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Interleukin-1beta
  • Interleukin-6
  • Lipopolysaccharides
  • Plant Extracts
  • Resins, Plant
  • Tumor Necrosis Factor-alpha
  • Nitric Oxide