Total synthesis and antihypertensive activity of (+/-)7,8-dihydroxy-3-methyl-isochromanone-4

Bioorg Med Chem Lett. 2009 Mar 15;19(6):1822-4. doi: 10.1016/j.bmcl.2008.12.102. Epub 2008 Dec 31.

Abstract

This letter describes the total synthesis, preliminary biological evaluation and mechanism studies of a novel and structurally unique isochromanone, (+/-)7,8-dihydroxy-3-methyl-isochromanone-4 (1), a nature product contained in banana (Musa sapientum L.) peel. The bioassay showed that compound 1 displays potent antihypertensive activity in renal hypertensive rats and further mechanism studies revealed that it is an ACE inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiotensin-Converting Enzyme Inhibitors / chemistry*
  • Angiotensin-Converting Enzyme Inhibitors / pharmacology
  • Animals
  • Antihypertensive Agents / chemistry*
  • Antihypertensive Agents / pharmacology
  • Chemistry, Pharmaceutical / methods*
  • Chromones / chemistry*
  • Chromones / pharmacology
  • Drug Design
  • Hypertension, Renal / drug therapy*
  • Hypertension, Renal / metabolism
  • Liver / drug effects
  • Models, Chemical
  • Molecular Structure
  • Musa / metabolism
  • Plant Extracts / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • 7,8-dihydroxy-3-methyl-isochromanone-4
  • Angiotensin-Converting Enzyme Inhibitors
  • Antihypertensive Agents
  • Chromones
  • Plant Extracts