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Guaianolides in apiaceae: perspectives on pharmacology and biosynthesis

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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.

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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

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Authors and Affiliations

  1. VKR Research Centre Pro-Active Plants, Plant Biochemistry Laboratory, Department of Plant Biology, Faculty of Life Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg C, Denmark

    Damian Paul Drew, Nadja Krichau, Kirsten Reichwald & Henrik Toft Simonsen

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  1. Damian Paul Drew
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  2. Nadja Krichau
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  3. Kirsten Reichwald
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  4. Henrik Toft Simonsen
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Correspondence to Henrik Toft Simonsen.

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Drew, D.P., Krichau, N., Reichwald, K. et al. Guaianolides in apiaceae: perspectives on pharmacology and biosynthesis. Phytochem Rev 8, 581–599 (2009). https://doi.org/10.1007/s11101-009-9130-z

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  • DOI: https://doi.org/10.1007/s11101-009-9130-z

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