Chiral separation, configurational identification and antihypertensive evaluation of (±)-7,8-dihydroxy-3-methyl-isochromanone-4

Bioorg Med Chem Lett. 2012 Oct 15;22(20):6490-3. doi: 10.1016/j.bmcl.2012.08.040. Epub 2012 Aug 16.

Abstract

(±)-7,8-Dihydroxy-3-methyl-isochromanone-4 [(±)-XJP] is a natural antihypertensive product contained in banana (Musa sapientum L.) peel. (-)-XJP and (+)-XJP were first obtained by chiral resolution, meanwhile circular dichroism (CD) calculations and chiral synthesis were employed to investigate the absolute configuration. The results indicated that the absolute configuration of (+)-XJP is S-configured and the absolute configuration of (-)-XJP is R-configured. Furthermore, the evaluation of antihypertensive effects in vivo proved that R-(-)-XJP was more potent than S-(+)-XJP and [(±)-XJP].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antihypertensive Agents / chemistry*
  • Antihypertensive Agents / therapeutic use*
  • Chromones / chemistry*
  • Chromones / therapeutic use*
  • Circular Dichroism
  • Hypertension / drug therapy*
  • Musa / chemistry*
  • Rats
  • Rats, Inbred SHR
  • Stereoisomerism

Substances

  • 7,8-dihydroxy-3-methyl-isochromanone-4
  • Antihypertensive Agents
  • Chromones