Phytochemistry Reviews

, Volume 8, Issue 3, pp 581–599

Guaianolides in apiaceae: perspectives on pharmacology and biosynthesis

  • Damian Paul Drew
  • Nadja Krichau
  • Kirsten Reichwald
  • Henrik Toft Simonsen
Article

DOI: 10.1007/s11101-009-9130-z

Cite this article as:
Drew, D.P., Krichau, N., Reichwald, K. et al. Phytochem Rev (2009) 8: 581. doi:10.1007/s11101-009-9130-z

Abstract

The guaianolide group of sesquiterpene lactones contains a large number of compounds with biological activity. One of these guaianolides, thapsigargin from the genus Thapsia (Apiaceae), has been a subject of particular interest in recent years because of its ability to induce apoptosis, as the active part of a pro-drug, has produced promising results for the targeted treatment of prostate cancer. In this review, recent advances in understanding the biosynthetic pathway of sesquiterpenes in plants is described with a special emphasis on guaianolides, and a hypothetical pathway for the biosynthesis of thapsigargin is presented. Eighty-seven guaianolides from Apiaceae are presented. These compounds provide clues to possible enzymatic mechanisms generating the guaianolides in Apiaceae. Some of these 87 compounds have proven or might prove interesting with regards to their biological activity.

Keywords

Sesquiterpene lactones Thapsigargin SERCA inhibition 

Abbreviations

DMAPP

Dimethylallyl diphosphate

DXP

1-Deoxy-d-xylulose-5-phosphate

FPP

Farnesyl diphosphate

GGPP

Geranylgeranyl diphosphate

GPP

Geranyl diphosphate

HMG-CoA

(S)-3-Hydroxy-3-methylglutaryl-CoA

HPMA

N-(2-hydroxypropyl) methacrylamide

IPP

Isopentenyl diphosphate

MEP

2-C-methyl-d-erythritol-4-phosphate

MVA

Mevalonate

PSA

Prostate specific antigen

SERCA

Sarco/endoplasmatic reticulum calcium ATPase

Copyright information

© Springer Science+Business Media B.V. 2009

Authors and Affiliations

  • Damian Paul Drew
    • 1
  • Nadja Krichau
    • 1
  • Kirsten Reichwald
    • 1
  • Henrik Toft Simonsen
    • 1
  1. 1.VKR Research Centre Pro-Active Plants, Plant Biochemistry Laboratory, Department of Plant Biology, Faculty of Life SciencesUniversity of CopenhagenFrederiksberg CDenmark