Polyanthumin, a novel cyclobutane chalcone trimmer from Memecylon polyanthum

J Asian Nat Prod Res. 2015;17(2):170-7. doi: 10.1080/10286020.2014.945439. Epub 2014 Dec 1.

Abstract

A novel unusual trimmer chalcone, polyanthumin (1), together with five known compounds myricetin 3-O-(3″-O-galloyl)-α-l-rhamnopyranoside (2), sulfuretin (3), fustin (4), gallic acid (5), and ethyl gallate (6), was isolated from the dry stems of Memecylon polyanthum H.L. Li. Among them, compound 1 is a new chalcone trimmer with a novel cyclobutane skeleton in nature. Compounds 3 and 4 are flavonoids carrying a single 7-OH in A ring, which provided the first example of these class flavonoids from the family Melastomataceae. In addition, the antitumor activities for 2-4 were reported for the first time in this study. The antitumor effects of the isolated compounds 1-6 in vitro were assayed by the SRB method using human cancer K562 cells, with the inhibition rates ranging from 39.4% to 54.5% at 100 μg/ml. The IC50 values of compounds 1 and 3 for the inhibition of K562 cell proliferation were determined to be 45.4 and 30.5 μg/ml, respectively. To the best of our knowledge, compound 1 was the second sample as chalcone trimer. In addition, the antitumor activities for 2-4 were reported for the first time in this study.

Keywords: Melastomataceae; Memecylon polyanthum; antitumor activity; cyclobutane chalcone trimmer; structure determination.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Benzofurans / isolation & purification
  • Chalcone / chemistry
  • Chalcone / isolation & purification*
  • Chalcone / pharmacology
  • Chalcones
  • Cyclobutanes / chemistry
  • Cyclobutanes / isolation & purification*
  • Cyclobutanes / pharmacology
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Electron Spin Resonance Spectroscopy
  • Flavonoids / isolation & purification
  • Gallic Acid / analogs & derivatives
  • Gallic Acid / isolation & purification
  • Humans
  • K562 Cells
  • Melastomataceae / chemistry*
  • Molecular Structure
  • Plant Stems / chemistry
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Benzofurans
  • Chalcones
  • Cyclobutanes
  • Drugs, Chinese Herbal
  • Flavonoids
  • polyanthumin
  • ethyl gallate
  • fustin
  • Chalcone
  • Gallic Acid
  • myricetin
  • sulfuretin