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Sesquiterpene coumarins

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Abstract

Plants have a long history as therapeutic tools in the treatment of human diseases and have been used as a source of medicines for ages. In search of new biologically active natural products, many plants and herbs used in traditional medicine are screened for natural products with pharmacological activity. In this paper, we present a group of natural products, the sesquiterpene coumarins isolated from plants, and describe their wide range of biological activity. Sesquiterpene coumarins are found in some plants of the families Apiaceae (Umbelliferae), Asteraceae (Compositae) and Rutaceae. The coumarin moiety is often umbelliferone (7-hydroxycoumarin) but scopoletin (7-hydroxy-6-methoxycoumarin) and isofraxidin (7-hydroxy-6,8-dimethoxycoumarin) are also found. These coumarins are linked to a C15 terpene moiety through an ether linkage. Another group of sesquiterpene coumarins is the prenylated 4-hydroxycoumarins where the link between the coumarin and the C15 terpene moiety is a C–C-bond at carbon 3 of the coumarin moiety. Finally, the prenyl-furocoumarin-type sesquiterpenoids are a separate group of sesquiterpene coumarins based on the suggested biosynthetic pathway. Our relatively limited knowledge on the biosynthesis of sesquiterpene coumarins is reviewed.

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Abbreviations

AChE:

Acetylcholinesterase

BIS:

Bisphenyl synthase

CPE:

Cytopathic effect

F6′H1:

Fe(II)- and 2-oxoglutarate-dependent dioxygenase

FDP:

Farnesyl diphosphate

FDU7T:

Farnesyl diphosphate umbelliferone transferase

HRV:

Human rhinoviruses

INH:

Isonicotinic acid hydrazide

M4Beu:

Human metastatic pigmented malignant melanoma cells

MDR:

Multidrug resistance

MIC:

Minimum inhibitory concentration

NDP:

Nerolidyl diphosphate

SHC:

Squalene-hopene cyclase

SQE:

Squalene epoxidase

VEGF:

Vascular endothelial growth factor

UPE:

Umbelliprenin epoxidase

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Authors and Affiliations

  1. School of Natural Sciences, Linnaeus University, 39281, Kalmar, Sweden

    Anna Gliszczyńska & Peter E. Brodelius

  2. Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Wrocław, Poland

    Anna Gliszczyńska

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  1. Anna Gliszczyńska
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  2. Peter E. Brodelius
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Correspondence to Peter E. Brodelius.

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Gliszczyńska, A., Brodelius, P.E. Sesquiterpene coumarins. Phytochem Rev 11, 77–96 (2012). https://doi.org/10.1007/s11101-011-9220-6

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  • DOI: https://doi.org/10.1007/s11101-011-9220-6

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