A New 1,5-Dihydroxy-4-methoxyisoquinoline from Scolopendra subspinipes mutilans

Chem Biodivers. 2017 Jun;14(6). doi: 10.1002/cbdv.201600478. Epub 2017 May 18.

Abstract

A new isoquinoline, 1,5-dihydroxy-4-methoxyisoquinoline (1), was obtained from Scolopendra subspinipes mutilans. Compound 1 showed moderate cytotoxicity on tumour cells with IC50 values ranging from 13 to 26 μm against five esophageal squamous cancer cells whereas low cytotoxicity against normal human esophageal epithelial cells. Isoquinoline ring oxidized at C(1), C(4), and C(5) can enhance its cytotoxicity. In addition, compound 1 showed potent inhibitory effect (inhibition rate > 50% at 13 μm) on cell migration in human umbilical vein endothelial cells. This article mainly studies the structure and activity of 1, and more modification of 1 as a potential anticancer agent.

Keywords: Scolopendra subspinipes mutilans; Cancer; Cytotoxic activities; Isoquinoline alkaloid; Migration.

MeSH terms

  • Animals
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Arthropods / chemistry*
  • Carcinoma, Squamous Cell / drug therapy*
  • Cell Line, Tumor
  • Cell Movement / drug effects
  • Esophageal Neoplasms / drug therapy*
  • Esophageal Squamous Cell Carcinoma
  • Humans
  • Inhibitory Concentration 50
  • Isoquinolines / isolation & purification
  • Isoquinolines / pharmacology*
  • Structure-Activity Relationship

Substances

  • 1,5-dihydroxy-4-methoxyisoquinoline
  • Antineoplastic Agents
  • Isoquinolines
  • 1,5-dihydroxyisoquinoline
  • isoquinoline