A new conjugated amide-dimer from the aerial parts of Piper submultinerve

Nat Prod Res. 2012;26(19):1824-30. doi: 10.1080/14786419.2011.639071. Epub 2011 Nov 25.

Abstract

Bioassay-guided fractionation and purification of the aerial parts of Piper submultinerve led to the isolation of a new conjugated amide-dimer, submultinamide A (1), along with 11 known compounds. The structures were determined on the basis of spectroscopic methods. Among the tested compounds, pellitorine (2), guineensine (4), N-benzylcinnamide (6) and aristolactam BII (8) showed significant activities in the anti-syncytium assay using (ΔTat/Rev)MC99 virus and 1A2 cell line system, whereas 2 was most active (EC₅₀ 35.1 µM and selectivity index 4.7). In the HIV-1 reverse transcriptase assay, only 4 was active with IC₅₀ 50.8 µM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Alkenes / pharmacology
  • Amides / chemistry
  • Amides / isolation & purification
  • Amides / pharmacology
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology*
  • Cell Line / virology
  • Dimerization
  • Drug Evaluation, Preclinical / methods
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / pharmacology
  • HIV Reverse Transcriptase / metabolism
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Heterocyclic Compounds, 2-Ring / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Lactams / chemistry
  • Lactams / pharmacology
  • Molecular Structure
  • Piper / chemistry*
  • Plant Components, Aerial / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Polyunsaturated Alkamides / chemistry
  • Polyunsaturated Alkamides / pharmacology

Substances

  • Alkenes
  • Amides
  • Anti-HIV Agents
  • Fatty Acids, Unsaturated
  • Heterocyclic Compounds, 2-Ring
  • Lactams
  • Plant Extracts
  • Polyunsaturated Alkamides
  • aristolactam BII
  • guineensine
  • submultinamide A
  • pellitorine
  • reverse transcriptase, Human immunodeficiency virus 1
  • HIV Reverse Transcriptase