Antitumor agents, 154. Cytotoxic and antimitotic flavonols from Polanisia dodecandra

J Nat Prod. 1995 Apr;58(4):475-82. doi: 10.1021/np50118a001.


Three flavonols, 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone [1], 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone [2], and quercetin 3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside [3], were isolated from Polanisia dodecandra. Compound 1 showed remarkable cytotoxicity in vitro against panels of central nervous system cancer (SF-268, SF-539, SNB-75, U-251), non-small cell lung cancer (HOP-62, NCI-H266, NCI-H460, NCI-H522), small cell lung cancer (DMS-114), ovarian cancer (OVCAR-3, SK-OV-3), colon cancer (HCT-116), renal cancer (UO-31), a melanoma cell line (SK-MEL-5), and two leukemia cell lines (HL-60 [TB], SR), with GI50 values in the low micromolar to nanomolar concentration range. This substance also inhibited rubulin polymerization (IC50 = 0.83 +/- 0.2 microM) and the binding of radiolabeled colchicine to tubulin with 59% inhibition when present in equimolar concentrations with colchicine. Compound 2 also showed cytotoxicity against medulloblastoma (TE-671) tumor cells with an ED50 value of 0.98 microgram/ml. Compound 1 appears to be the first example of a flavonol to exhibit potent inhibition of tubulin polymerization and, therefore, warrants further investigation as an antimitotic agent.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Chemical Phenomena
  • Chemistry, Physical
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Humans
  • KB Cells
  • Magnetic Resonance Spectroscopy
  • Tubulin / metabolism
  • Tumor Cells, Cultured


  • 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Flavonoids
  • Tubulin
  • 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone