4'-Demethyl-deoxypodophyllotoxin glucoside isolated from Podophyllum hexandrum exhibits potential anticancer activities by altering Chk-2 signaling pathway in MCF-7 breast cancer cells

Chem Biol Interact. 2014 Dec 5:224:100-7. doi: 10.1016/j.cbi.2014.09.022. Epub 2014 Oct 18.

Abstract

We investigated the root of Podophyllum hexandrum as a potential source of lead bioactive metabolites with anticancer activity. The present study led to the isolation of six known aryltetralin-type lignans designated as 4'-demethyl-deoxypodophyllotoxin (1), podophyllotoxin (2), 4'-demethyl-podophyllotoxin (3), podophyllotoxin-4-O-β-d-glucopyranoside (4), 4'-demethyl-deoxypodophyllotoxin-4-O-β-d-glucopyranoside (5), 4'-demethyl-podophyllotoxin-4-O-β-d-glucopyranoside (6), along with three known flavones Kaempferol (7), Quercetin (8), Astragalin (9) from the root of P. hexandrum. Compounds (1-9) exhibited the remarkable cytotoxic potential in diverse cancer cell lines. 5 therapeutic potential was extensively studied first time which exhibiting antiproliferative and ROS generating activity than its non-glycoside analogue 1. Furthermore, 5 augmented the apoptotic cascades in MCF-7 breast cancer cells, viz. nuclear condensation, membrane blebbing, probably by destabilizing the micro-tubular protein tubulin. Strikingly, our docking study and in vitro assays demonstrate that 5 binds to and modulate checkpoint kinase-2, a key cell cycle regulatory protein in normal and cancer cells.

Keywords: Breast cancer; Chk2; Cytotoxicity; G2/M arrest; Podophyllum hexandrum.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Checkpoint Kinase 2 / metabolism*
  • G2 Phase Cell Cycle Checkpoints / drug effects
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glucosides / pharmacology*
  • Humans
  • Molecular Docking Simulation
  • Phosphorylation
  • Podophyllotoxin / analogs & derivatives*
  • Podophyllotoxin / chemistry
  • Podophyllotoxin / isolation & purification
  • Podophyllotoxin / pharmacology
  • Podophyllum / chemistry*
  • Proto-Oncogene Proteins c-akt / metabolism
  • Reactive Oxygen Species / metabolism
  • Signal Transduction
  • Tubulin Modulators / chemistry
  • Tubulin Modulators / isolation & purification
  • Tubulin Modulators / pharmacology

Substances

  • 4'-demethyldeoxypodophyllotoxin-4-O-glucopyranoside
  • Antineoplastic Agents, Phytogenic
  • Glucosides
  • Reactive Oxygen Species
  • Tubulin Modulators
  • Checkpoint Kinase 2
  • CHEK2 protein, human
  • Proto-Oncogene Proteins c-akt
  • Podophyllotoxin