Intraspecific variation in essential oil composition of the medicinal plant Lippia integrifolia (Verbenaceae). Evidence for five chemotypes

Phytochemistry

Volumn 122, Issue , 2016, Pages 203-212

  Marcial, Guillermo ^a   De Lampasona, Marina P ^a   Vega, Marta I ^a   Lizarraga, Emilio ^a   Viturro, Carmen I ^b   Slanis, Alberto ^c   Juárez, Miguel A ^d   Elechosa, Miguel A ^d   Catalán, César A N ^a  

^a UNIVERSIDAD NACIONAL DE TUCUMÁN   (Argentina)

^b UNIVERSIDAD NACIONAL DE JUJUY   (Argentina)

^c FUNDACIÓN MIGUEL LILLO   (Argentina)

^d INSTITUTO NACIONAL DE TECNOLOGÍA AGROPECUARIA INTA   (Argentina)

Author keywords

Absolute configuration; Biogenesis; Chemotypes; Essential oil; Incayuyo; Lippia integrifolia; Monoterpene; Sesquiterpene; trans Davanone; Verbenaceae

Indexed keywords

DAVANONE; ESSENTIAL OIL; SESQUITERPENE; TERPENE; VEGETABLE OIL;

ARGENTINA; CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; ISOLATION AND PURIFICATION; LIPPIA; MASS FRAGMENTOGRAPHY; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE; PLANT STRUCTURES; POLYMERASE CHAIN REACTION; STEREOISOMERISM;

ARGENTINA; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LIPPIA; MOLECULAR STRUCTURE; MONOTERPENES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OILS, VOLATILE; PLANT COMPONENTS, AERIAL; PLANT OILS; PLANTS, MEDICINAL; POLYMERASE CHAIN REACTION; SESQUITERPENES; STEREOISOMERISM; TERPENES;

EID: 84955740698     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2015.11.004     Document Type: Article

References (40)

1. R.P. Adams Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectrometry fourth ed. 2007 Allured Publishing Corporation Carol Stream, Illinois, USA
2. J. Alonso, and C. Desmarchelier Plantas Medicinales Autóctonas de la Argentina 2006 Ediciones Fitociencia Buenos Aires, Argentina pp. 267-270
3. G. Appendino, P. Garibold, G.M. Nano, and P. Tetenyi Tetrahydrofuran-type terpenoids from Tanacetum vulgare Phytochemistry 23 1984 2545 2551
4. N. Barbieri, M. Costamagna, M. Gilabert, M. Perotti, C. Schuff, M. Isla, and A. Benavente Antioxidant activity and chemical composition of essential oils of three aromatic plants from La Rioja province Pharm. Biol. 2015 10.3109/13880209.2015.1028077
5. G.B. Bassols, and A.A. Gurni Especies del género Lippia utilizadas en medicina popular latinoamericana Dominguezia 13 1996 7 25
6. C.A.N. Catalán, and M.E.P. de Lampasona The chemistry of the genus Lippia (Verbenaceae) S.E. Kintzios, Oregano. The genera Origanum and Lippia 2002 Taylor & Francis Inc. New York 127 149
7. C.A.N. Catalán, I.J.S. de Fenik, G.H. Dartayet, and E.G. Gros Integrifolian-1,5-dione and a revised structure for 'africanone', biogenetically related sesquiterpene ketones from Lippia integrifolia Phytochemistry 30 1991 1323 1326
8. C.A.N. Catalán, I.J.S. de Fenik, P.J. Arriazu, and W.C.M.C. Kokke 4,5-Seco-african-dione from Lippia integrifolia Phytochemistry 31 1992 4025 4026
9. C.A.N. Catalán, M.E.P. de Lampasona, I.J.S. de Fenik, C.M. Cerda-García-Rojas, and P. Joseph-Nathan Structure and conformation of a humulendione from Lippia integrifolia J. Nat. Prod. 56 1993 381 385
10. C.A.N. Catalán, I.J.S. de Fenik, C.M. Cerda-García-Rojas, Y. Mora-Pérez, and P. Joseph-Nathan Total assignment of the 13C NMR spectra of integrifolian-1,5-dione and derivatives by 2D spectroscopy Spectroscopy 11 1993 1 8
11. C.A.N. Catalán, M.E.P. de Lampasona, I.J.S. de Fenik, C.M. Cerda-García-Rojas, Y. Mora-Pérez, and P. Joseph-Nathan Minor constituents of Lippia integrifolia J. Nat. Prod. 57 1994 206 210
12. C.A.N. Catalán, M.E.P. de Lampasona, C.M. Cerda-García-Rojas, and P. Joseph-Nathan Trace constituents of Lippia integrifolia J. Nat. Prod. 58 1995 1713 1717
13. C.M. Cerda-Garcia-Rojas, A.C. Coronel, M.E. de Lampasona, C.A.N. Catalán, and P. Joseph-Nathan Absolute configuration of Lippifoliane and africanane derivatives J. Nat. Prod. 68 2005 659 665
14. C. Cerda-García-Rojas, C.A.N. Catalán, C. Muro, and P. Joseph-Nathan Vibrational circular dichroism of africanane and lippiafoliane sesquiterpenes from Lippia integrifolia J. Nat. Prod. 71 2008 967 971
15. A.C. Coronel, M.E. de Lampasona, and C.A.N. Catalán Variability of essential oils of Lippia fissycalix and Lippia turbinata from Argentina Rev. Latinoamer. Quim. 33 2005 40 48
16. A.C. Coronel, C.M. Cerda-García-Rojas, P. Joseph-Nathan, and C.A.N. Catalán Chemical composition, seasonal variation and a new sesquiterpene alcohol from the essential oil of Lippia integrifolia Flavour Frag. J. 21 2006 839 847
17. M.E.P. De Lampasona, I.S. de Fenik, C.A.N. Catalán, G.H. Dartayet, E.G. Gros, C.M. Cerda-García-Rojas, Y. Mora-Pérez, and P. Joseph-Nathan Constituents of the essential oil of Lippia integrifolia (Griseb.) Hieron. (Verbenaceae) Acta Hort. 500 1999 81 88
18. S. Denham, M.E. Múlgura de Romero, A. Slanis, and E. Bulacio Lippia integrifolia versus L. boliviana (Verbenaceae) Darwiniana 44 2006 363 364
19. C. Duschatzky, P. Bailac, N. Firpo, and M. Ponzi Composición de los Aceites Esenciales de Lippia juneilliana, L. integrifolia y L. turbinata de la provincia de San Luis (Argentina) Rev. Colomb. Quím. 27 1998 9 16
20. C. Fricke, I.H. Hardt, W. König, D. Joulian, J.A. Zygadlo, and C.A. Guzmán Sesquiterpenes from Lippia integrifolia essential oil J. Nat. Prod. 62 1999 694 696
21. R.M. Gleiser, M.A. Bonino, and J.A. Zygadlo Repellence of essential oils of aromatic plants growing in Argentina against Aedes aegypti (Diptera: Culicidae) Parasitol. Res. 108 2011 69 78
22. S. Gorzalczany, V. Sülsen, F. Redko, C. Vescina, L. Muschietti, V. Martino, and C. Acevedo Choleretic and antispasmodic effects of Lippia integrifolia aqueous extract Braz. J. Pharmacog. 18 2008 16 20
23. M.J. Jansen-Jacobs Verbenaceae A.R.A. Rijn, Flora of the Guianas. Series A: Phanerogams, Fascicle 4 vol. 148 1988 Görts-Van Hoetz Scientific Books Koenigstein 116
24. H.R. Juliani, A. Koroch, J.E. Simon, F.N. Biurrum, V. Castellano, and J.A. Zygadlo Essential oils from Argentinean aromatic plants Acta Hort. 629 2004 491 498
25. B. Laribi, K. Kouki, T. Bettaieb, A. Mougou, and B. Marzouk Essential oils and fatty acids composition of Tunisian, German and Egyptian caraway (Carum carvi L.) seed ecotypes: a comparative study Ind. Crop Prod. 41 2013 312 318
26. B. Lima, S. López, L. Luna, M.B. Agüero, L. Aragon, A. Tapia, S. Zacchino, M.L. Lopez, J. Zygadlo, and G.E. Feresin The essential oils of medicinal plants of the Central Andes of Argentina; chemical composition, antifungal, antibacterial and insect repellent activities Chem. Biodivers. 8 2011 924 936
27. G. Marcial, J. Sendker, S. Brandt, M.P. de Lampasona, C.A.N. Catalán, G.F. de Valdez, and A. Hensel Gastroprotection as an example: antiadhesion against Helicobacter pylori, anti-inflammatory and antioxidant activities of aqueous extracts from the aerial parts of Lippia integrifolia Hieron J. Ethnopharmacol. 155 2014 1125 1133
28. A.L. Medina-Holguín, S. Micheletto, F.O. Holguín, J. Rodriguez, M.A. O'Conell, and C. Martin Environmental influences on essential oils in roots of Anemopsis californica HortScience 42 2007 1578 1583
29. R. Nurzyńska-Wierdak, A. Bogucka-Kocka, I. Sowa, and G. Szymczak The composition of essential oil from three ecotypes of Origanum vulgare L. ssp. vulgare cultivated in Poland Farmacia 60 2012 571-57
30. M.E. Pascual, K. Slowing, E. Carretero, D. Sánchez Mata, and A. Villar Lippia: traditional uses, chemistry and pharmacology: a review J. Ethnopharmacol. 76 2001 201 214
31. H. Sadeghi, Z. Robati, and M.J. Saharkhiz Variability in Zataria multiflora Bioss. essential oil of twelve populations from Fars province Iran. Ind. Crop Prod. 67 2015 221 226
32. F.A. Souto-Bachiller, M. de Jesus-Echevarria, and O. Cárdenas-Gonzalez Hernandulcin is the major constituent of Lippia dulcis Trev. (Verbenaceae) Nat. Prod. Lett. 8 1996 151 158
33. F.C. Terblanché, and G. Kornelius Essential oil constituents of the genus Lippia (Verbenaceae) - a literature review J. Essent. Oil Res. 8 1996 471 485
34. A.F. Thomas, and R. Dubini Terpenoids derived from linalyl oxide, Part 4. The oxidation of davanone. Isolation and synthesis of the davana ethers, sesquiterpenes of Artemisia pallens Helv. Chim. Acta 57 1974 2076 2081
35. A.F. Thomas, W. Thommen, B. Willhalm, E.W. Hagaman, and E. Wenkert Terpenoids derived from linalyl oxide, part 1. The stereochemistry of the davanones Helv. Chim. Acta 57 1974 2055 2061
36. V. Vajs, S. Trifunović, P. Janaćković, M. Soković, S. Milosavljević, and V. Tešević Antifungal activity of davanone-type sesquiterpenes from Artemisia lobelii var. conescens J. Serb. Chem. Soc. 69 2004 969 972
37. J.A. Velasco-Negueruela, M.J. Perez-Alonso, C.A. Guzmán, J.A. Zygadlo, L. Ariza Espinar, J. Sanz, and M.C. García Vallejo Volatile constituents of four Lippia species from Córdoba Argentina. J. Essent. Oil Res. 5 1993 513 524
38. P. Weyerstahl, H. Marschall, M. Schröder, H.-C. Wahlburg, and V.K. Vkaul The sesquiterpene fraction of the essential oil of Artemisia laciniata Willd Flavour Fragrance J. 12 1997 315 325
39. Zuluaga, F.O., Morrone, O. (Eds), 1999. Catálogo de las Plantas Vasculares de la República Argentina II. Fabaceae-Zygophyllaceae (Dicotyledoneae). Monographs in Systematic Botany from the Missouri Botanical Garden, vol. 74, St. Louis, Missouri, pp. 1153-1158.
40. J.A. Zygadlo, A.L. Lamarque, C.A. Guzmán, and N.R. Grosso Composition of the flowers oils of some Lippia and Aloysia species from Argentina J. Essent. Oil Res. 7 1995 593 595