Morphological, chemical and genetic differentiation of two subspecies of Cistus creticus L. (C. creticus subsp. eriocephalus and C. creticus subsp. corsicus)

Phytochemistry

Volumn 70, Issue 9, 2009, Pages 1146-1160

  Paolini, Julien ^a   Falchi, Alessandra ^b   Quilichini, Yann ^a   Desjobert, Jean Marie ^a   Cian, Marie Cecile De ^a   Varesi, Laurent ^a   Costa, Jean ^a  

^a UNIVERSITÉ DE CORSE   (France)

^b INSERM   (France)

Author keywords

Cistus creticus; GC MS; HS SPME; ISSR; Labdane diterpene; SEM; Statistical analysis

Indexed keywords

DITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CISTUS; GENETIC POLYMORPHISM; GENETICS; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE; NUCLEOTIDE SEQUENCE; PLANT LEAF;

BASE SEQUENCE; CISTUS; DITERPENES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT LEAVES; POLYMORPHISM, GENETIC;

CISTUS; CISTUS CRETICUS; ERIOCEPHALUS;

EID: 68349146219     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.06.013     Document Type: Article

References (53)

1. Adams R.P. Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectroscopy (2001), Allured Publishing, Carol Stream
2. Anastasaki T., Demetzos C., Perdetzoglou D., Gazouli M., Loukis A., and Harvala C. Analysis of labdane-type diterpenes from Cistus creticus (subsp. Creticus and subsp. eriocephalus), by GC and GC-MS. Planta Med. 65 (1999) 735-739
3. Angelopoulou D., Demetzos C., Dimas C., Perdetzoglou D., and Loukis A. Essential oils and hexane extracts from leaves and fruits of Cistus monspeliensis. Cytotoxic activity of ent-13-epi-manoyl oxide and its isomers. Planta Med. 67 (2001) 168-171
4. Batista F., Bañares A., Caujapé-Castells J., Carque E., Marrero-Gómez M., and Sosa P.A. Allozyme diversity in three endemic species of Cistus (Cistaceae) from the Canary Islands: intraspecific comparisons and implications for genetic conservation. Am. J. Bot. 88 (2001) 1582-1592
5. Bazina E., Makris A., Vender C., and Skoula M. Genetic and chemical relations among selected clones of Salvia officinalis. J. Herbs Spices Med. Plants 9 (2002) 269-273
6. Belliardo F., Bicchi C., Cordero C., Liberto E., Rubiolo P., and Sgorbini B. Headspace-solid-phase microextraction in the analysis of the volatile fraction of aromatic and medicinal plants. J. Chromatogr. Sci. 44 (2006) 416-429
7. Brereton R.G. Chemometrics: Data Analysis for the Laboratory and Chemical Plant (2003), Wiley, New York
8. Chinou I., Demetzos C., Harvala C., Roussakis C., and Verbist J.F. Cytotoxic and antibacterial labdane-type diterpenes from the aerial parts of Cistus incanus subsp. Creticus. Planta Med. 60 (1994) 34-36
9. Coste H. Flore Descriptive et Illustrée de la France, de la Corse et des Contrées Limitrophes (1937), Albert Blanchard, Paris
10. Council of Europe. European Pharmacopoeia. third ed. (1997), Council of Europe, Strasbourg p. 121
11. Dellagreca M., Fiorentino A., Isidori M., Monaco P., and Zarrelli A. Antialgal ent-labdane diterpenes from Ruppia maritima. Phytochemistry 55 (2000) 909-913
12. Demetzos C., and Loukis A. Composition and antimicrobial activity of the essential oil of Cistus creticus L. J. Essent. Oil Res. 7 (1995) 407-410
13. Demetzos C., and Perdetzoglou D.K. Chemotaxonomic survey of wild and cultivated Cistus L. Species. Plant Biosyst. 133 (1999) 251-253
14. Demetzos C., Harvala C., Philianos S.M., and Skaltsounis A.L. A labdane-type diterpene and other compounds from the leaves of Cistus incanus subsp. Creticus. J. Nat. Prod. 53 (1990) 1365-1368
15. Demetzos C., Mitaku S., Loukis A., and Harvala C. A drimane sesquiterpene, isomers of manoyle oxide and other volatile constituents from the resin "ladano" of Cistus incanus subsp. Creticus (L.) Heywood. J. Essent. Oil Res. 6 (1994) 37-41
16. Demetzos C., Mitaku S., Couladis M., Harvala C., and Kokkinopoulos D. Natural metabolites of ent-13-epi-manoyl oxide and other cytotoxic diterpenes from the resin ladano of Cistus creticus. Planta Med. 60 (1994) 590-591
17. Demetzos C., Mitaku S., Skaltsounis A.L., Couladis M., Harvala C., and Libot F. Diterpene esters of malonic acid from the resin ladano of Cistus creticus. Phytochemistry 35 (1994) 979-981
18. Demetzos C., Katerinopoulos H.E., Kouvalaris A., Stratigakis N., Loukis A., Ekonomakis C., Spiliotis V., and Tsaknis J. Composition and antimicrobial activity of the essential oil of Cistus creticus subsp. Eriocephalus. Planta Med. 63 (1997) 477-479
19. Demetzos C., Stahl B., Anastasaki T., Gazouli M., Tzouvelekis L.S., and Rallis M. Chemical analysis and antimicrobial activity of the resin ladano, of its essential oil and of the isolated compounds. Planta Med. 65 (1999) 76-78
20. Demetzos C., Dimas K., Hatziantoniou S., Anastasaki T., and Angelopoulou D. Cytotoxic and anti-inflammatory activity of labdane and cis-clerodane type diterpenes. Planta Med. 67 (2001) 614-618
21. Demetzos C., Anastasaki T., and Perdetzoglou D. A chemometric interpopulation study of the essential oils of Cistus creticus L. Growing in Crete (Greece). Z. Naturforsch., C 57 (2002) 89-94
22. Demirci B., Demirci F., and Baser K.H.C. Headspace-SPME and hydrodistillation of two fragrant Artemisia sp. Flavour Fragr. J. 20 (2005) 395-398
23. Dimas K., Demetzos C., Marsellos M., Sotiriadou R., Malamas M., and Kokkinopoulos D. Cytotoxic activity of labdane type diterpenes against human leukemic cell lines in vitro. Planta Med. 64 (1998) 208-211
24. Dimas K., Demetzos C., Mitaku S., Vaos B., Marselos M., Tzavaras M., and Kokkinopoulos D. Cytotoxic activity and antiproliferative effects of a semi-synthetic derivative of ent-3β-hydroxy-13-epi-manoyl oxide on human leukemic cell lines. Anticancer Res. 19 (1999) 4065-4072
25. Dimas K., Demetzos C., Vaos V., Ioannidis P., and Trangas T. Labdane type diterpenes down-regulate the expression of c-Myc protein, but not of Bcl-2, in human leukemia T-cells undergoing apoptosis. Leuk. Res. 25 (2001) 449-454
26. Dolmazon R., Albrand M., Bessiere J.M., Mahmout Y., Wernerowska D., and Kolodziejczyk K. Diterpenoids from Killinga erecta. Phytochemistry 38 (1995) 917-919
27. Echeverrigaray S., Agostini G., Atti-Serfini L., Paroul N., Pauletti G.F., and Dos Santos A.C. Correlation between the chemical and genetic relationships among commercial thyme cultivars. J. Agric. Food Chem. 49 (2001) 4220-4223
28. Ellul P., Boscaiu M., Vicente O., Moreno V., and Rosello J.A. Intra- and interspecific variation in DNA content in Cistus (Cistaceae). Ann. Bot. 90 (2002) 345-351
29. Fanciullino A.L., Tomi F., Luro F., Desjobert J.M., and Casanova J. Chemical variability of peel and leaf oils of mandarins. Flavour Fragr. J. 21 (2006) 359-367
30. Farley R.A., and McNeilly T. Diversity and divergence in Cistus salvifolius (L.) populations from contrasting habitats. Hereditas 132 (2000) 183-192
31. Flamini G., Cioni P.L., and Morelli I. Use of solid-phase micro-extraction as a sampling technique in the determination of volatiles emitted by flowers, isolated flower parts and pollen. J. Chromatogr. A 998 (2003) 229-233
32. Formácek V., and Kubeczka K.H. Essential Oil Analysis by Capillary Gas Chromatography and Carbon-13 NMR Spectroscopy (1982), Wiley, Chichester, UK
33. Godwin I.D., Aitken E.A., and Smith L.W. Application of inter simple sequence repeat (ISSR) markers to plant genetics. Electrophoresis 18 (1997) 1524-1528
34. Gray C.A., Davies-Coleman M.T., and Rivett D.E.A. An improved synthesis of rhinocerotinoic acid. Tetrahedron 59 (2002) 165-173
35. Greuter W., Burdet H.M., and Long G. Med Checklist. A Critical Inventory of Vascular Plants of the Circum-Mediterranean Contries (1984), Conservatoire et Jardin Botanique de la Ville de Genève, Genève
36. Grosser W. Cistaceae. In: Engler A. (Ed). Das Pflanzenreich (1903), Wilhelm Engelmann, Berlin 1-161
37. Gulz P.G., Herrmann T., and Hangst K. Leaf trichomes in the genus Cistus. Flora 191 (1996) 85-104
38. Guzmán B., and Vargas P. Systematics, character evolution, and biogeography of Cistus L. (Cistaceae) based on ITS, trnL-trnF, and matK sequences. Mol. Phylogenet. Evol. 37 (2005) 644-660
39. Hamilton J.G., Zangerl A.R., Delucia E.H., and Berenbaum M.R. The carbon-nutrient balance hypothesis: its rise and fall. Ecol. Lett. 4 (2001) 86-95
40. Hatzellis K., Pagona G., Spyros A., Demetzos C., and Katerinopoulos H.E. Correction of the structure of a sesquiterpene from Cistus creticus ssp. Creticus. J. Nat. Prod. 67 (2004) 1996-2001
41. Jeanmonod D., and Gamisans J. Flora Corsica (2007), Edisud, Aix-en-Provence pp. 581-583
42. Jennings W., and Shibamoto T. In: Jovanovitch H.B. (Ed). Qualitative Analysis of Flavour and Fragrance Volatiles by Glass-Capillary Gas Chromatography (1980), New York, Academic Press
43. Joulain D., and König W.A. The Atlas of Spectral Data of Sesquiterpene Hydrocarbons (1998), EB-Verlag, Hamburg
44. König W.A., Hochmuth D.H., and Joulain D. Terpenoids and Related Constituents of Essential Oils, Library of MassFinder 2.1 (2001), University of Hamburg, Institute of Organic Chemistry, Hamburg, Germany
45. Kosman E., and Leonard K.J. Similarity coefficients for molecular markers in studies of genetic relationships between individuals for haploid, diploid, and polyploid species. Mol. Ecol. 14 (2005) 415-424
46. Lu T., Vargas D., Franzblau S.G., and Fischer N.H. Diterpenes from Solidago rugosa. Phytochemistry 38 (1994) 451-456
47. Massart D.L. Chemometrics: A Textbook (1998), Elsevier Sciences Ltd., New York
48. Matsingou C., Dimas K., and Demetzos C. Design and development of liposomes incorporating a bioactive labdane-type diterpene. In vitro growth inhibiting and cytotoxic activity against human cancer cell lines. Biomed. Pharmacother. 60 (2006) 191-199
49. McLafferty F.W., and Stauffer D.B. The Wiley/NBS Registry of Mass Spectral Data. fourth ed. (1988), Wiley-Interscience, New York
50. Mc Lafferty, F.W., Stauffer, D.B., 1994. Wiley Registry of Mass Spectral Data, sixth ed. Mass Spectrometry Library Search System Bench-Top/PBM Version 3.10d. Palisade, Newfield.
51. Muñoz-Bertomeu J., Arrillaga I., and Segura J. Essential oil variation within and among natural population of Lavandula latifolia and its relation to their ecological areas. Biochem. Syst. Ecol. 35 (2007) 479-488
52. Nei M. Analysis of gene diversity in subdivided populations. Proc. Natl. Acad. Sci. USA 70 (1973) 3321-3323
53. National Institute of Standards and Technology, 1999. NIST/EPA/NIH Mass Spectra Library. PC Version 1.7. Perkin-Elmer Corp., Norwalk, CT, USA.