A new DNA-intercalative cytotoxic allylic xanthone from Swertia corymbosa

Chem Biodivers. 2015 Mar;12(3):358-70. doi: 10.1002/cbdv.201400055.

Abstract

Phytochemical investigation of the CHCl3 fraction of Swertia corymbosa resulted in the isolation of a new 3-allyl-2,8-dihydroxy-1,6-dimethoxy-9H-xanthen-9-one (1), along with four known xanthones, gentiacaulein (3), norswertianin (4), 1,3,6,8-tetrahydroxyxanthone (5), and 1,3-dihydroxyxanthone (6). Structure of compound 1 was elucidated with the aid of IR, UV, NMR, and MS data, and chemical transformation via new allyloxy xanthone derivative (2). Compounds 1-6 exhibited various levels of antioxidant and anti-α-glucosidase activities. Absorption and fluorescence spectroscopic studies on 1-6 indicated that these compounds could interact with calf thymus DNA (CT-DNA) through intercalation and with bovine serum albumin (BSA) in a static quenching process. Compound 1 was found to be significantly cytotoxic against human cancer cell lines HeLa, HCT116, and AGS, and weakly active against normal NIH 3T3 cell line.

Keywords: Anti-α-glucosidase activity; Antioxidant activity; Cytotoxic activity; DNA; Protein binding; Swertia corymbosa; Xanthones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antioxidants / chemistry*
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology
  • Cattle
  • Cell Line, Tumor
  • DNA / metabolism
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / isolation & purification
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Humans
  • Intercalating Agents / chemistry*
  • Intercalating Agents / isolation & purification
  • Intercalating Agents / pharmacology
  • Mice
  • NIH 3T3 Cells
  • Neoplasms / drug therapy
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Swertia / chemistry*
  • Xanthones / chemistry*
  • Xanthones / isolation & purification
  • Xanthones / pharmacology
  • alpha-Glucosidases / metabolism

Substances

  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Glycoside Hydrolase Inhibitors
  • Intercalating Agents
  • Plant Extracts
  • Xanthones
  • DNA
  • calf thymus DNA
  • xanthone
  • alpha-Glucosidases