Bioactive flavaglines and other constituents isolated from Aglaia perviridis

J Nat Prod. 2013 Mar 22;76(3):394-404. doi: 10.1021/np3007588. Epub 2013 Jan 9.

Abstract

Eight new compounds, including two cyclopenta[b]benzopyran derivatives (1, 2), two cyclopenta[b]benzofuran derivatives (3, 4), three cycloartane triterpenoids (5-7), and an apocarotenoid (8), together with 16 known compounds, were isolated from the chloroform-soluble partitions of separate methanol extracts of a combination of the fruits, leaves, and twigs and of the roots of Aglaia perviridis collected in Vietnam. Isolation work was monitored using human colon cancer cells (HT-29) and facilitated with an LC/MS dereplication procedure. The structures of the new compounds (1-8) were determined on the basis of spectroscopic data interpretation. The Mosher ester method was employed to determine the absolute configurations of 5-7, and the absolute configuration of the 9,10-diol unit of compound 8 was established by a dimolybdenum tetraacetate [Mo2(AcO)4] induced circular dichroism procedure. Seven known rocaglate derivatives (9-15) exhibited significant cytotoxicity against the HT-29 cell line, with rocaglaol (9) being the most potent (ED50 0.0007 μM). The new compounds 2-4 were also active against this cell line, with ED50 values ranging from 0.46 to 4.7 μM. The cytotoxic compounds were evaluated against a normal colon cell line, CCD-112CoN. In addition, the new compound perviridicin B (2), three known rocaglate derivatives (9, 11, 12), and a known sesquiterpene, 2-oxaisodauc-5-en-12-al (17), showed significant NF-κB (p65) inhibitory activity in an ELISA assay.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aglaia / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Benzofurans / chemistry
  • Benzofurans / pharmacology*
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors*
  • Nuclear Magnetic Resonance, Biomolecular
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology
  • Vietnam

Substances

  • Antineoplastic Agents, Phytogenic
  • Benzofurans
  • Benzopyrans
  • NF-kappa B
  • Triterpenes
  • rocaglaol