Antibacterial, antifungal and cytotoxic isoquinoline alkaloids from Litsea cubeba

Molecules. 2012 Nov 1;17(11):12950-60. doi: 10.3390/molecules171112950.

Abstract

Five novel isoquinoline alkaloids (+)-N-(methoxylcarbonyl)-N-nordicentrin (1), (+)-N-(methoxylcarbonyl)-N-norpredicentrine (2), (+)-N-(methoxylcarbonyl)-N-norbulbodione (3), and (+)-N-(methoxylcarbonyl)-N-norisocorydione (4), and (+)-8-methoxyisolaurenine-N- oxide (5) were isolated, together with one known compound, (+)-N-(methoxylcarbonyl)- N-norglaucine (6), from a 70% EtOH extract of the barks of Litsea cubeba. Structural elucidation of all the compounds were performed by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. Alkaloids 1, 2 and 6 showed antimicrobial activity against the bacterium S. aureus and two fungi (A. alternata and C. nicotianae). Compounds 3,4 exhibited significant cytotoxicity against all of six tested tumor cell lines.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology
  • Alternaria / drug effects
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Disk Diffusion Antimicrobial Tests
  • Humans
  • Isoquinolines / chemistry*
  • Isoquinolines / isolation & purification
  • Isoquinolines / pharmacology
  • Litsea / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Spectrometry, Mass, Electrospray Ionization
  • Staphylococcus aureus / drug effects

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Isoquinolines
  • Plant Extracts