SERCA-inhibiting activity of C-19 terpenolides from Thapsia garganica and their possible biogenesis

J Nat Prod. 2005 Aug;68(8):1213-7. doi: 10.1021/np050115m.

Abstract

An investigation of Thapsia garganica afforded a series of tetracyclic C-19 dilactones, whose production was dependent on the time and location of the collection. These unusual tetrahomosesquiterpenoids are presumably biosynthesized via a carbon dioxide-triggered electrophilic polyolefin cyclization. Despite the structural differences with thapsigargin, these compounds showed SERCA-inhibiting properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Apiaceae / chemistry*
  • Calcium-Transporting ATPases / antagonists & inhibitors*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Sarcoplasmic Reticulum Calcium-Transporting ATPases
  • Sea Urchins / enzymology*
  • Sea Urchins / metabolism
  • Stereoisomerism
  • Thapsigargin* / analogs & derivatives
  • Thapsigargin* / chemistry
  • Thapsigargin* / metabolism
  • Thapsigargin* / pharmacology

Substances

  • Enzyme Inhibitors
  • Thapsigargin
  • Sarcoplasmic Reticulum Calcium-Transporting ATPases
  • Calcium-Transporting ATPases