Aplyronine A, a potent antitumour macrolide of marine origin, and the congeners aplyronines B-H: chemistry and biology

Nat Prod Rep. 2009 Jan;26(1):27-43. doi: 10.1039/b800263k.

Abstract

Aplyronines A-H are cytotoxic macrolides isolated from the sea hare Aplysia kurodai. Aplyronine A is the major constituent among the aplyronines, and this review concentrates on the results of chemical and biological research into this natural product. The isolation, determination of stereostructure and enantioselective total synthesis of the aplyronines are covered, together with discussion of their antitumour activity and structure-activity relationships, and the three-dimensional X-ray structure of the actin-aplyronine A complex.

Publication types

  • Review

MeSH terms

  • Animals
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / isolation & purification
  • Antineoplastic Agents* / pharmacology
  • Aplysia / chemistry*
  • Crystallography, X-Ray
  • Lactones* / chemistry
  • Lactones* / isolation & purification
  • Lactones* / pharmacology
  • Macrolides* / chemical synthesis
  • Macrolides* / chemistry
  • Macrolides* / pharmacology
  • Marine Biology
  • Marine Toxins / chemistry
  • Marine Toxins / metabolism
  • Molecular Conformation
  • Molecular Structure
  • Serine / analogs & derivatives*
  • Serine / chemistry
  • Serine / isolation & purification
  • Serine / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Lactones
  • Macrolides
  • Marine Toxins
  • aplyronine A
  • Serine