Chemical constituents of Aloe barbadensis Miller and their inhibitory effects on phosphodiesterase-4D

Fitoterapia. 2013 Dec:91:159-165. doi: 10.1016/j.fitote.2013.08.027. Epub 2013 Sep 9.

Abstract

Aloe barbadensis Mill has been used as food and medicine for a long time. In order to investigate the chemical constituents of A. barbadensis and their inhibitory activities towards phosphodiesterase-4D (PDE4D), 70% methanol extract of the dried A. barbadensis powder was employed. Phytochemical investigation has led to the isolation of three new chromones, 5-(hydroxymethyl)-7-methoxy-2-methylchromone (4), 5-((4E)-2'-oxo-pentenyl)-2-hydroxymethylchromone (6), and 7-hydroxy-5-(hydroxymethyl)-2-methylchromone (7), together with eighteen known compounds. Their chemical structures were determined based on spectroscopic methods including UV, IR, 1D and 2D NMR, and HRMS spectrometry. In addition, their inhibition against PDE4D was evaluated using tritium-labeled adenosine 3',5'-cyclic monophosphate ((3)H-cAMP) as the substrate. Inhibition was calculated by the variation of radioactivity after the reaction, and compounds 1-4, 10, and 21 exhibited certain inhibitory activities towards PDE4D, which can provide an explanation why A. barbadensis can serve as anti-inflammatory agents.

Keywords: 10-Hydroxyaloin B (PubChem CID: 14889737); 7-Hydroxy-2,5-dimethylchromone (PubChem CID: 5316891); Aloe barbadensis Mill; Aloe-emodin (PubChem CID: 10207); Aloenin aglycone (PubChem CID: 5242842); Aloesin (PubChem CID: 160190); Aloin A (PubChem CID: 313325); Aloin B (PubChem CID: 5458894); Anthraquinones; Chromones; Chrysophanol (PubChem CID: 10208); PDE4D inhibition; Pyrones; Saikochromone A (PubChem CID: 10013795); and Aloenin B (PubChem CID: 6442939).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aloe / chemistry*
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Chromones / pharmacology*
  • Cyclic Nucleotide Phosphodiesterases, Type 4 / metabolism*
  • Molecular Structure
  • Phosphodiesterase Inhibitors / chemistry
  • Phosphodiesterase Inhibitors / isolation & purification
  • Phosphodiesterase Inhibitors / pharmacology*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*

Substances

  • Chromones
  • Phosphodiesterase Inhibitors
  • Plant Extracts
  • Cyclic Nucleotide Phosphodiesterases, Type 4