Secondary metabolites with antiproliferative effects from Albizia glaberrima var glabrescens Oliv. (Mimosoideae)

Nat Prod Res. 2017 Sep;31(17):1981-1987. doi: 10.1080/14786419.2016.1269097. Epub 2017 Jan 20.

Abstract

A new 5-dehydroxyflavan, namely Albiziaflavan B or (+)-(2R, 3S, 4R)-3',4', 7-trihydroxy-4-methoxy-2,3-trans-flavan-3,4-trans-diol (1) was isolated from the root bark of Albizia glaberrima, together with six known compounds including three flavans: (+)-mollisacacidin (2), (+)-fustin (3) and butin (4); two steroids: chondrillasterol (5) and chondrillasterone (6), and a triterpenoid: lupeol (7). The structure of 1 was established by detailed analysis of its spectroscopic data, especially 1D and 2D NMR spectra, HRESIMS and CD data. Compounds 1-6 were assayed for their antiproliferative effects on two human cancer cells, HeLa at 50 μM (n = 2) and HL60 at 20 μM (n = 2). Compound 3 and 4 were the most active on HL60 with IC50 of 8.1 and 8.3 μM, respectively. Compound 6 was the most active with an IC50 of 4.6 μM on HeLa.

Keywords: Albizia glaberrima var glabrescens Oliv.; Albiziaflavan B; antiproliferative effects; butin; chondrillasterone; fustin.

MeSH terms

  • Albizzia / chemistry
  • Albizzia / metabolism*
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification
  • Benzopyrans / pharmacology
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor / methods
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology*
  • HL-60 Cells
  • HeLa Cells
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Secondary Metabolism
  • Steroids / chemistry*
  • Steroids / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Benzopyrans
  • Flavonoids
  • Steroids
  • albiziaflavan B
  • chondrillasterol
  • butin
  • fustin