Inhibition of dihydrofolate reductase and cell growth activity by the phenanthroindolizidine alkaloids pergularinine and tylophorinidine: the in vitro cytotoxicity of these plant alkaloids and their potential as antimicrobial and anticancer agents

Toxicol In Vitro. 2000 Feb;14(1):53-9. doi: 10.1016/s0887-2333(99)00092-2.

Abstract

The phenanthroindolizidine plant alkaloids pergularinine (PGL) and tylophorinidine (TPD) isolated from the Indian medicinal herb Pergularia pallida have been evaluated for their biological activity and assessed for the first time employing dihydrofolate reductase (DHFR) (5,6,7,8-THF: NADP(+) oxidoreductase, EC 1.5.1.3) as the probe in the present investigations. The enzyme is a key target in cancer chemotherapy and has been purified from Lactobacillus leichmannii. Cytotoxicity studies showed that both PGL and TPD are potently toxic and inhibited the growth of L. leichmannii cells (IC(50)=45 and 40 microM, respectively). Both the alkaloids significantly inhibited DHFR activity (IC(50)=40 and 32 microM for PGL and TPD, respectively). Alkaloid concentrations greater than 75-95 microM resulted in a complete loss of DHFR activity. Our results are suggestive of the alkaloids as potential antimicrobial and antitumour compounds. Alkaloid binding to DHFR is slow and reversible. Inhibition kinetics revealed K(i) values of 9x10(-6) M and 7x10(-6) M for PGL and TPD, respectively for the enzyme and inhibition in both the cases was a simple linear 'non-competitive' type.

MeSH terms

  • Alkaloids*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Division / drug effects
  • Folic Acid Antagonists / pharmacology*
  • India
  • Isoquinolines / isolation & purification
  • Isoquinolines / pharmacology*
  • Lactobacillus / drug effects
  • Plants, Medicinal / chemistry
  • Tetrahydrofolate Dehydrogenase / metabolism*

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Antineoplastic Agents, Phytogenic
  • Folic Acid Antagonists
  • Isoquinolines
  • tylophorinidine
  • pergularinine
  • Tetrahydrofolate Dehydrogenase