Hostname: page-component-cd9895bd7-hc48f Total loading time: 0 Render date: 2024-12-26T06:33:08.458Z Has data issue: false hasContentIssue false
  • English
  • Français

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 ,
Andrew W. Douglas ,
Erdal Bedir ,
Franck E. Dayan ,
Nese Kirimer ,
K. Husnu Can Baser ,
Zeki Aytac ,
Ikhlas A. Khan  and
Brian E Scheffler
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
Get access Rights & Permissions [Opens in a new window]

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.

Keywords

Apiaceaeessential oilsinternal transcribed spacermolecular phylogenynorsesquiterpenesphenylpropanoidsPimpinellaPsbA-trnH spacer
Type
Research Article
Information
Plant Genetic Resources , Volume 3 , Issue 2 , August 2005 , pp. 149 - 169
Copyright
Copyright © NIAB 2005

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Alman, AH, Jawad, ALM, Al-Bana, AS and Ali, KF (1988) Antiviral activity of some Iraqi indigenous plants. International Journal of Crude Drug Research 26: 107–111.CrossRefGoogle Scholar
Baser, KHC (1997) Tibbi ve aromatik bitkilerin ilac ve alkollu icki sanayinde kullanimi. Istanbul: Istanbul Ticaret Odasi yayinlari, 33–35.Google Scholar
Baser, KHC, Ozek, T, Duman, H and Guner, A (1996) Essential oil of Pimpinella aromatica Bieb. from Turkey. Journal of Essential Oil Research 8: 463–464.CrossRefGoogle Scholar
Bisset, NG (1994) Herbal Drugs and Phytopharmaceuticals. London: CRS Press, 375–377.Google Scholar
Bohn, I, Kubeczka, KH and Schultze, W (1989) The essential root oil of Pimpinella major. Planta Medica 55: 489–490.CrossRefGoogle Scholar
Branther, A and Grein, E (1994) Antibacterial activity of plant extracts used externally in traditional medicine. Journal of Ethnopharmacology 44: 35–40.CrossRefGoogle Scholar
Constance, L (1971) History of the classification on Umbelliferae (Apiaceae). In: Heywood, VH (ed.) The Biology and Chemistry of the Umbelliferae. New York: Academic Press, 109–155.Google Scholar
Crellin, JK and Philpott, J (1990) Herbal Medicine Past and Present. Durham, NC: Duke University Press, 58–59.Google Scholar
Downie, SR, Ramanath, S, Katz-Downie, DS and Llanas, E (1998) Molecular systematics of Apiaceae subfamily Apioideae: phylogenetic analysis of nuclear ribosomal DNA internal transcribed spacer and plastid rpoC1 intron sequences. American Journal of Botany 85: 563–591.CrossRefGoogle Scholar
Downie, SR, Katz-Downie, DS and Spalik, K (2000 a) A phylogeny of Apiaceae tribe Scandiceae: evidence from nuclear ribosomal DNA internal transcribed spacer sequences. American Journal of Botany 87: 76–95.CrossRefGoogle ScholarPubMed
Downie, SR, Katz-Downie, DS and Watson, MF (2000 b) A phylogeny of the flowering Apiaceae based on chloroplast DNA rpl16 and rpoC1 intron sequences: towards a suprageneric classification of subfamily Apioideae. American Journal of Botany 87: 273–292.CrossRefGoogle ScholarPubMed
Downie, SR, Watson, MF, Spalik, K and Katz-Downie, DS (2000 c) Molecular systematic of old world Apioideae (Apiaceae): relationship among some members of tribe Peucedaneae Sensu Lato, the placement of several island-endemic species and resolution within the Apioid Superclade. Canadian Journal of Botany 78: 506–528.CrossRefGoogle Scholar
Downie, SR, Plunkett, GM, Watson, MF, Spalik, K, Katz-Downie, DS, Valiejo-Roman, CM, Terentieva, EI, Troitsky, AV, Lee, BY, Lahham, J and El-Oqlah, A (2001) Tribes and clades within Apiceae subfamily Apioidea: the contribution of molecular data. Edinburgh Journal of Botany 58: 301–330.CrossRefGoogle Scholar
Drude, O (1897–98) Umbelliferae Die naturlichen pflanzenfamilien. In: Engler, A and Prantl, K Vol. 3. Leipzig: Wilhelm Engelmann, 63–250.Google Scholar
Duke, JA (1985) Handbook of Medicinal Herbs. London: CRC Press, 374–375.Google Scholar
Grieve, M (1970 a) The Medicinal, Culinary, Cosmetic and Economic Properties, Cultivation and Folk-lore of Herbs, Grasses, Fungi, Shrubs and Trees, Vol. 1. New York: Hafner Publishing Co, 41–43.Google Scholar
Grieve, M (1970 b) The Medicinal, Culinary, Cosmetic and Economic Properties, Cultivation and Folk-lore of Herbs, Grasses, Fungi, Shrubs and Trees, New York: Hafner Publishing Co, 146–147.Google Scholar
Haranath, PS, Akther, MH and Sharif, SI (1985) Acetylcholine and choline in common spices. Phytotherapy Research 1: 91–92.CrossRefGoogle Scholar
Hasegawa, M, Kishino, H and Yano, T (1985) Dating of the human-ape splitting by a molecular clock of mitochondrial DNA. Journal of Molecular Evolution 22: 160–174.CrossRefGoogle ScholarPubMed
Kiuchi, F (1995) Studies on the nematodical constituents of natural medicines. Natural Medicines 49: 364–372.Google Scholar
Kollmannsberger, H, Fricke, G, Paulus, H and Nitz, S (2000) The flavor composition of umbelliferous fruits. Part 1. Anise (Pimpinella anisum) Advances in Food Sciences 22(1/2): 47–61.Google Scholar
Kleiman, R and Spencer, GF (1982) Search for new industrial oils. Journal of the American Oil Chemists' Society 59: 29–32.CrossRefGoogle Scholar
Kleiman, R, Plattner, DR and Weisleder, D (1988) Antigermination of phenylpropanoids from the genus Pimpinella. Journal of Natural Products 52: 249–256.CrossRefGoogle Scholar
Kubeczka, KH (1997) The essential oil composition of Pimpinella species. In: Baser, KHC and Kirimer, N (eds) The 28th International Symposium on Essential Oils, Proceedings, 1–3 September, Eskisehir Turkey, Eskisehi Anadolu University, 35–56.Google Scholar
Kubeczka, KH and Ullmann, I (1980) Occurrence of 1,5-dimethylcyclodeca-1,5,7-triene (pregeijerene) in Pimpinella species and chemosystematic implications. Biochemical Systematics and Ecology 8: 39–41.CrossRefGoogle Scholar
Kubeczka, KH, Bohn, I and Wuerzburg, F (1985) Thin layer and gas chromatography, structure revision of the principal components of the essential oils. Deutsche Apoteker Zeitung 125: 399–402.Google Scholar
Kubeczka, KH, Bohn, I and Schultze, W (1989) The compositions of the essential roots oils from Pimpinella saxifraga L. and chemotaxonomic implications. Zeitschrift für Naturforschung 44: 177–182.CrossRefGoogle Scholar
Lokar, LC and Poldini, L (1988) Herbal remedies in the traditional medicine of the Venezia Giulia. Journal of Ethnopharmacology 22: 231–278.CrossRefGoogle ScholarPubMed
Maddison, DR and Maddison, WP (2003) MacClade 4.06—Analysis of Phylogeny and Character Evolution. Sunderland: MA Sinauer PressGoogle Scholar
Marcus, C and Lichtenstein, EP (1979) Biologically active components of anise: toxicity and interactions with insecticides in insects. Journal of Agricultural and Food Chemistry 27: 1217–1223.CrossRefGoogle Scholar
Martin, R and Reichling, J (1992) NIH-shift during biosynthesis of epoxypseudoisoeugenol-2-methylbutyrate in tissue cultures of Pimpinella anisum. Zeitschrift für Naturforschung 43: 42–46.Google Scholar
Matthew, VA (1972) Pimpinella In: Davis, PH (ed.) Flora of Turkey and East Aegean Islands, Vol. 4. Edinburgh: Edinburgh University Press, 352–364.Google Scholar
Miller, LG and Murray, WJ (1998) Herbal Medicines. New York: The Haworth PressGoogle Scholar
Pimenov, MG and Leonov, MV (2004) The Asian Umbelliferae Biodiversity Database (ASIUM) with particular reference to SW Asian taxa. Turkish Journal of Botany 28: 139–145.Google Scholar
Reichling, J and Martin, R (1990) Further studies on the biosynthesis of pseudoisoeugenols in tissue cultures of Pimpinella anisum. Zeitschrift für Naturforschung 45: 942–948.CrossRefGoogle Scholar
Reichling, J and Martin, R (1991) Pseudoisoeugenol-eine gruppe seltener phenylpropanoide im genus Pimpinella: Biosynthese und biologische wirkung. Pharmazeutische Zeitung- Wissenschaft 45: 225–231.Google Scholar
Reichling, J and Merkel, B (1991) Studies on the biological activities of rare phenylpropanoids of the genus Pimpinella. Journal of Natural Products 54: 1416–1418.CrossRefGoogle ScholarPubMed
Reichling, J, Martin, R and Kemmeter, B (1995) Biosynthesis of pseudoisoeugenol-derivatives in liquid tissue cultures of Pimpinella anisum. Plant Cell, Tissue & Organ Culture 43: 131–136.CrossRefGoogle Scholar
Ross, SA, El-Keltawi, NE and Megalla, SE (1980) Antimicrobial activity of some Egyptian aromatic plants. Fitoterapia 51: 201–205.Google Scholar
Shashikanth, KN and Hosono, A (1986) In vitro mutagenity of tropical species to Streptomycin dependent strains of Salmonella typhimurium TA 98. Agricultural and Biological Chemistry 50: 2947–2948.Google Scholar
Swofford, DL (2001) PAUP*: Phylogenetic Analysis Using Parsimony (*and Other Methods), Version 4.0b10. Sunderland, MA Sinauer AssociatesGoogle Scholar
Tabanca, N, Bedir, E, Kirimer, N, Baser, KHC, Khan, SI, Jacob, MR and Khan, IA (2003) Antimicrobial compounds from Pimpinella species growing in Turkey. Planta Medica 69: 933–938.Google ScholarPubMed
Tabanca, N, Khan, SI, Bedir, E, Annavarapu, S, Willett, K, Khan, IA, Kirimer, N and Baser, KHC (2004) Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen. Planta Medica 70: 728–735.CrossRefGoogle ScholarPubMed
Tabanca, N, Bedir, E, Ferraaira, D, Slade, D, Wedge, DE, Jacob, MR, Khan, SI, Kirimer, N, Baser, KHC and Khan, IA (2005) Bioactive constituents from Turkish Pimpinella species. Chemistry & Biodiversity 2: 221–232.CrossRefGoogle ScholarPubMed
Twaij, HA, Elisha, EE, Khalid, RM and Paul, NJ (1987) Analgesic studies on some Iraqi medicinal plants. International Journal of Crude Drug Research 25: 251–254.CrossRefGoogle Scholar
Xue, KF, Wang, JZ and Wen, YS (1992) A new flavone glucoside from Pimpinella thellungiana. Chung Ts'Ao Yao 29: 452–455.Google Scholar