Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra

Molecules. 2019 Mar 15;24(6):1026. doi: 10.3390/molecules24061026.

Abstract

A phytochemical study of leaves and twigs of Psychotria nuda resulted in 19 compounds, including five indole alkaloids, N,N,N-trimethyltryptamine, lyaloside, strictosamide, strictosidine, and 5α-carboxystrictosidine; two flavonolignans, cinchonain Ia and cinchonain Ib; an iridoid, roseoside; a sugar, lawsofructose; a coumarin, scopoletin; a diterpene, phytol; three triterpenes, pomolic acid, spinosic acid, and rotungenic acid; and five steroids, sitosterol, stigmasterol, campesterol, β-sitosterol-3-O-β-d-glucoside, and β-stigmasterol-3-O-β-d-glucoside. Some compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis and their ability to inhibit NO production by macrophages stimulated by lipopolysaccharide (LPS). The compounds pomolic acid, spinosic acid, strictosidine, and 5α-carboxystrictosidine displayed antimycobacterial activity with minimum inhibitory concentrations ranging from 7.1 to 19.2 µg/mL. These compounds showed promising inhibitory activity against NO production (IC50 3.22 to 25.5 μg/mL). 5α-carboxystrictosidine did not show cytotoxicity against macrophages RAW264.7 up to a concentration of 100 µg/mL. With the exception of strictosamide, this is the first report of the occurrence of these substances in P. nuda.

Keywords: Mycobacterium; Psychotria nuda; Rubiaceae; alkaloids; inflammation; nitric oxide.

MeSH terms

  • Alkaloids / analysis*
  • Alkaloids / pharmacology
  • Animals
  • Anti-Bacterial Agents / analysis*
  • Anti-Bacterial Agents / pharmacology
  • Antioxidants / analysis*
  • Antioxidants / pharmacology
  • Lipopolysaccharides / adverse effects
  • Macrophages / cytology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • Nitric Oxide / metabolism
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry
  • Psychotria / chemistry*
  • RAW 264.7 Cells
  • Triterpenes / analysis*
  • Triterpenes / pharmacology

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Antioxidants
  • Lipopolysaccharides
  • Plant Extracts
  • Triterpenes
  • Nitric Oxide