Patterns of essential oil relationships in Pimpinella (Umbelliferae) based on phylogenetic relationships using nuclear and chloroplast sequences | Plant Genetic Resources | Cambridge Core

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.

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