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Patterns of essential oil relationships in Pimpinella (Umbelliferae) based on phylogenetic relationships using nuclear and chloroplast sequences

Published online by Cambridge University Press:  12 February 2007

Nurhayat Tabanca
Affiliation:
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, MS 38677, USA
Andrew W. Douglas
Affiliation:
Harding Lab, New York Botanical Garden, 200th St. and Kazimiroff Blvd., Bronx, NY 10458, USA
Erdal Bedir
Affiliation:
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, MS 38677, USA Department of Bioengineering, Faculty of Engineering, Ege University, Bornova, Izmir, 35100, Turkey
Franck E. Dayan
Affiliation:
USDA-ARS-NPURU, University, MS 38677, USA
Nese Kirimer
Affiliation:
Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskisehir, Turkey
K. Husnu Can Baser
Affiliation:
Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskisehir, Turkey
Zeki Aytac
Affiliation:
Department of Biology, Faculty of Science and Letters, Gazi University, 06500, Ankara, Turkey
Ikhlas A. Khan
Affiliation:
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, University of Mississippi, MS 38677, USA Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS 38677, USA
Brian E Scheffler*
Affiliation:
USDA-ARS-NPURU, University, MS 38677, USA
*
*Corresponding author: USDA-ARS MSA Genomics Laboratory, Stoneville, MS 38776, USA. E-mail: bscheffler@ars.usda.gov

Abstract

Hydro-distilled essential oils from fruits, aerial parts (without fruits) and roots of Pimpinellaspecies native to Turkey and their phylogenetic relationships to one another were examined. Phytochemical investigation of the essential oils of 19 species resulted in isolation of 16 phenylpropanoids, four sesquiterpenes and two azulene-type norsesquiterpenes. The structures of the isolated compounds were determined primarily from 1D- and 2D-NMR experiments as well as liquid chromatography–mass spectrometry and gas chromatography–mass spectrometry. Phylogenetic relationships among 26 species were evaluated using ITS 1, ITS 4 nuclear rDNA and psbA-trnH cpDNA sequences. In this study, significance and occurrence of phenylpropanoids, azulenes and geijerenes are discussed from a phylogenetic, chemical and biosynthetic perspective. The distribution of different classes of compounds and their putative associations with one another as per current knowledge of their biosynthetic pathways indicates that this information, in conjunction with the phylogeny, could provide valuable information regarding the presence and perhaps evolution of the different classes of compounds. Analysis of the phenylpropanoid components indicates that (E)-anethole is an obligatory intermediate of this pathway. The various Pimpinellaspecies differ primarily in their ability to acylate anethole, suggesting that while the pathway leading to anethole is common to this genus, species differ in their enzymatic machinery leading to acylate. The relationship between azulenes and geijerenes is not as intuitive, but all Pimpinellaspecies analysed in this study have the biochemical machinery required to synthesize these chemical classes.

Type
Research Article
Copyright
Copyright © NIAB 2005

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Patterns of essential oil relationships in Pimpinella (Umbelliferae) based on phylogenetic relationships using nuclear and chloroplast sequences
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