Monoterpene Indole Alkaloids from the Aerial Parts of Rhazya stricta Induce Cytotoxicity and Apoptosis in Human Adenocarcinoma Cells

Molecules. 2022 Feb 19;27(4):1422. doi: 10.3390/molecules27041422.

Abstract

Chromatographic investigation of the aerial parts of the Rhazya stricta (Apocynaceae) resulted in the isolation of two new monoterpene indole alkaloids, 6-nor-antirhine-N1-methyl (1) and razyamide (2), along with six known compounds, eburenine (3), epi-rhazyaminine (4), rhazizine (5), 20-epi-sitsirikine (6), antirhine (7), and 16-epi-stemmadenine-N-oxide (8). The chemical structures were established by various spectroscopic experiments. Compounds 1-8 exhibited cytotoxic effects against three cancer cells with IC50 values ranging between 5.1 ± 0.10 and 93.2 ± 9.73 µM against MCF-7; 5.1 ± 0.28 and 290.2 ± 7.50 µM against HepG2, and 3.1 ± 0.17 and 55.7 ± 4.29 µM against HeLa cells. Compound 2 showed the most potent cytotoxic effect against all cancer cell lines (MCF-7, HepG2 and HeLa with IC50 values = 5.1 ± 0.10, 5.1 ± 0.28, and 3.1 ± 0.17 µM, respectively). Furthermore, compound 2 revealed a significant increase in the apoptotic cell population of MCF-7, HepG2, and HeLa cells, with 31.4 ± 0.2%, 29.2 ± 0.5%, and 34.9 ± 0.6%, respectively. Compound 2 decreased the percentage of the phagocytic pathway on HepG2 cells by 15.0 ± 0.1%. These findings can explain the antiproliferative effect of compound 2.

Keywords: Apocynaceae; HeLa; HepG2; MCF-7; Saudi plants; alkaloids; cytotoxicity.

MeSH terms

  • Adenocarcinoma* / drug therapy
  • Adenocarcinoma* / metabolism
  • Antineoplastic Agents, Phytogenic* / chemistry
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Apocynaceae / chemistry*
  • Apoptosis / drug effects*
  • Cytotoxins* / chemistry
  • Cytotoxins* / pharmacology
  • Heel
  • Hep G2 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / pharmacology
  • MCF-7 Cells
  • Monoterpenes* / chemistry
  • Monoterpenes* / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Cytotoxins
  • Indole Alkaloids
  • Monoterpenes