Essential Oil Composition of Three Species of Senecio from Argentina

Jeobp 11 (6) 2008 pp 623 - 627

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ISSN 0972-060X

Essential Oil Composition of Three Species of Senecio from Argentina J.S. Dambolena 1*, M.P. Zunino 1, E. Banchio 2, E.I. Lucini 1, F.N. Biurrun 3, A. Rotman 4, O. Ahumada 4 and J.A. Zygadlo 1 1

Cátedra de Química Orgánica y Productos Naturales (IMBIV-CONICET), Facultad de Ciencias Exactas Físicas y Naturales, Universidad Nacional de Córdoba, Av. Vélez Sarsfield 1611, Córdoba, Argentina 2 Universidad Nacional de Río Cuarto, CONICET 3 Laboratorio de Diversidad Vegetal y Fitosociología, INTA EEA La Rioja, Instituto de Investigaciones para el Desarrollo Socioeconómico de los Llanos de La Rioja, Universidad Nacional de La Rioja-Sede Chamical, La Rioja, Argentina 4 Cátedra de Botánica General-Herbario JUA. Facultad de Ciencias Agrarias, Universidad Nacional de Jujuy, Argentina Received 08 April 2008; accepted in revised form 19 July 2008

Abstract: The essential oils from the aerial parts of three species of Senecio (Senecio subulatus var. salsus, S. subulatus var. erectus, Senecio viridis and Senecio argophylloides.) were collected in different phytogeographic areas of Northern Argentina. The oils were obtained by hydrodistillation and characterized by GC and GC-MS analyses. Monoterpene hydrocarbons dominated the chemical profile of the oils with β-pinene (17-31 %), p-cymene (18-33 %) and γterpinene (16-54 %) as the main constituents of S. subulatus and α-thujene (13-32 %), camphene (539 %), sabinene (12-7 %) and β-phellandrene (11-16 %) for S. argophylloides and S. viridis, respectively. Key words. Senecio subulatus, Senecio viridis, Senecio argophylloides, essential oils composition, monoterpene hydrocarbons. Introduction: The phytogeographic area of Puneña, Prepuneña, of the Yungas and Chaqueña provinces are known to be the natural habitat of the genus Senecio (Asteraceae). Its smell is characteristic and in popular medicine, it is reputed to counteract mountain sickness, and also as an emenagogue, digestive and cough suppressant. In the region, where it grows spontaneously and in the rest of Argentina, it is commercialized to those ends 1,2. There are previous studies on essential oils composition of S. graveolens 2, S. nutans 3,4, *Corresponding author (J.S. Dambolena) E- mail: < [email protected] >

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S. farfarifolius 5, S. aegyptius 6, S. chrysanthemoides 7, S. ambavilla 8, S. squalidus 9, S. filaginoides 10, S. vulgaris, S. jacobaea, S. congestus and S. fuchsi 11, 12. Monoterpene and sesquiterpenes hydrocarbons predominated in oils of species of Senecio, however others main constituents, 1,10-epoxyfuranoeremophilane were observed in S. aegyptius. As a part of our ongoing work on aromatic plants from Argentina and since information about secondary metabolites in the genus is scarce, we initiated this study to characterize the essential oil content and composition of these Senecio species. Experimental Plant material: The essential oils from the aerial parts of S. subulatus var. salsus, S. subulatus var. erectus, S. viridis and S. argophylloides, collected in two different phytogeographic areas of Argentina: Prepuneña province (the first sp.) and Puneña province (the others sp.)13 were studied. Voucher specimens were deposited at Jujuy Herbarium (Index herbarium code, JUA) and INTA EEA La Rioja Herbarium (CHAM) (Table 1). Essential oil isolation: Dried leaves of these species were hydrodistilled in Clevenger-like apparatus for 2 h. The yield of oil for each species was recorded and the oils dried over anhydrous sulphate and stored in a refrigerator until analysis. Gas Chromatography analyses: Analyses were performed in a Shimadzu GCR1A gas-chromatograph (GC) coupled to a flame ionization detector (FID), fitted with a 30 m x 0.25 mm (0.25 μm film thickness) fused silica capillary column coated with a phase 5 % phenyl 95 % dimethylpolysiloxane, non polar DB-5 column. The GC operating conditions were as follows: oven temperature programmed from 40-230°C at 20C/min, injector and detector temperatures 2400C. The carrier gas was nitrogen at a constant flow of 0.9 ml/ min. The constituents of the essential oils were identified on the basis of their GC retention index (RI) with reference to a homologous series of n-alkanes (C12 - C25), by comparison of their retention times with those of pure authentic samples from Sigma, Fluka and Palma Companies, peak enrichment on co-injection with authentic standards wherever possible, by GC-Mass Spectrometry (MS) library search (Adams and Nist) and using visual inspection of the mass spectra from literature, for confirmation. GC-MS analyses were performed with a Perkin Elmer Q-700 equipped with a SE-30 (DB5 equivalent) capillary column (30 m x 0.25 mm; coating thickness 0.25 μm film) following the same conditions as those of the GC-FID. Co-elution GC with reference components (α and β pinene) was used for additional confirmation of compound identity. Results and discussion: The oils were yellow with a strong odour, Senecio viridis showed a higher yield of oil (0.2 %), while the others yielded lower amounts (0.1 %). Chemical analysis of the components of the oil from species of Senecio, resulted in the identification of 20 components (Table 2). Comparison of the oil composition from the two varieties of S. subulatus showed, the amounts of p-cymene and β-pinene were higher in the oil of variety “salsus” (33.3 % and 31.2 %, respectively compared with 18.3 % and 17.3 % of “erectus” variety). Another difference is the amount of γ-terpinene, which was


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53.6 % in “erectus” variety and 15.6 % in “salsus” variety. Three compounds, (E)caryophyllene, germacrene D and germacrene B were not found in the oil of “erectus” variety. However, both oils were very similar in the minor components. S. argophylloides and S. viridis showed high levels of camphene (52.7 %) and α-thujene (31.7 %), respectively. Other terpenes with percentages higher than 10 % were β-phellandrene and sabinene (Table 2). The chemical profile of the volatile components from the aerial parts of these Senecio species from Argentina, were found to be very similar to those species cited in the literature 2-12 . Our results showed that monoterpene hydrocarbons dominated the oil chemical profile of these Senecio species (Table 2). Acknowledgements: J.A.Z., E.B, A.R. and M.P.Z. are researchers from CONICET. J.S.D. is also thankful to CONICET for a research fellowship. We are grateful to SECyT-UNC and Proyunga Foundation for partially funding this study.

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References Giberti, G.C. (1983). Herbal folk medicine in northwestern Argentina: Compositae. J. Ethnopharmacol. 7(3): 321-341. Perez, C., Agnese, A.M. and Cabrera, J.L. (1999). The essential oil of Senecio graveolens (Compositae): Chemical composition and antimicrobial activity tests. J. Ethnopharmacol. 66(1): 91-96. De Feo, V., Soria, E.U., Soria, R.U. and Senatore, F. (2003). Chemical composition of essential oils of Senecio nutans Sch.-Bip. (Asteraceae). Flav. Fragr. J. 18(3): 234-236. Belaunde, A.J., Sandoval, J.G., De Martino, L., Senatore, F. and De Feo, V. (2007). Chemical composition and antibacterial activity of Senecio nutans essential oil. J. Essent. oil Bearing Plants. 10(4): 332-338. Baser, K.H.C. and Demirci, B. (2004). The essential oil of Senecio farfarifolius Boiss. et Kotschy growing in Turkey. J. Essent. Oil Res. 16(6): 558-559. El-Shazly, A., Doral, G. and Wink, M. (2002). Chemical composition and biological activity of the essential oils of Senecio aegyptius var. discoideus Boiss. Zeitschrift fur Naturforschung - Section C Journal of Biosciences. 57(5-6): 434-439. Mengi, N., Garg, S.N., Agarwal, S.K. and Mathela, C.S. (1995). Occurrence of β-thujone and a new p-menthane derivative in Senecio chrysanthemoides leaf oil. J. Essent. Oil Res. 7(5): 511-514. Vera, R.R., Laurent, S.J. and Fraisse, D.J. (1994). Chemical composition of the essential oil of Senecio ambavilla (Bory) Pers. from Reunion Island. J. Essent.Oil Res. 6(1): 21-25. Chalchat, J.C., Maksimovic, Z.A., Petrovic, S.D. and Gorunovic, M.S. (2004). Essential oil of Senecio squalidus L., Asteraceae. J. Essent. Oil Res. 16(3): 227228. Balzaretti, V.T., Arancibia, A., Marchiaro, A. and Arce, M.E.(2000). Variation in the composition of the essential oil of Senecio filaginoides Dc. Molecules 5(3): 459-461.

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van Dooren, B., Bos, R. and Tattje, D.H. (1981). Composition of essential oils of some Senecio species. Planta Med. 42(8): 385-389. Bordoloi, M., Shukla, V.S. and Nath, S.C., Sharma, R.P. (1989). Naturally occurring cadinenes. Phytochemistry 28(8): 2007-2037. Cabrera, A.L. (1976). Regiones fitogeográficas argentinas. Enc. Arg. Agr. y Ganadería. 2nd Ed., 2(1):1-85. Bs. As. Argentina.

Table 1. Collection sites and voucher specimens of Senecio sp used in this study Species

Collection site

Senecio subulatus D. Don Jujuy. Dpto. Humahuaca, ex Hook. & Arn. var. salsus Chucalezna, (Griseb.) Cabrera Phytogeographic area: Prepuneña province Senecio subulatus Don ex Catamarca. Dpto. Belén, Hook. & Arn. var. erectus Laguna Blanca, Hook. & Arn. Phytogeographic area: Puneña province Senecio viridis Phil. Catamarca. Dpto. Belén, Laguna Blanca, Phytogeographic area: Puneña province Senecio argophylloides Catamarca. Dpto. Belén, Griseb. Laguna Blanca, Phytogeographic area: Puneña province

Voucher number (Index Herbarium Code) 1384 Rotman (JUA)

8289 Biurrun (CHAM)

8308 Biurrun (CHAM)

8324 Biurrun (CHAM)


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Table 2. Percentage composition of essential oils of Senecio subulatus var. salsus, Senecio subulatus var. erectus, Senecio viridis and Senecio argophylloides. RI 1

Components

927 931 940 955 972 980 1026 1029 1031 1037 1059 1089 1178 1254 1291 1300 1419 1442 1485 1563

Tricycline α-Thujene α-Pinene 2 Camphene Sabinene β-Pinene 2 p-Cymene Limonene β-Phellandrene β-(Z)-Ocimene γ-Terpinene Terpinolene Terpinen-4-ol Piperitone Thymol Carvacrol (E)-Caryophyllene Aromadendrene Germacrene D Germacrene B Total analyzed

1

S. subulatus S. subulatus S. argophylloides S. viridis var. salsus var. erectus 0.1 5.0 1.7 0.5 0.9 31.2 33.3 0.2 0.2 0.2 15.6 0.4 2.2 2.1 0.3 0.4 1.1 0.1 t t 95.5

0.2 5.2 0.7 0.8 t 17.3 18.3 0.2 0.3 0.5 53.6 0.1 0.2 0.1 t t -3 t 97.5

0.9 12.9 1.1 52.7 12.3 1.1 0.5 3.2 10.7 t 0.3 0.3 2.9 0.9 t t 99.8

0.5 31.7 9.0 8.9 7.0 0.9 8.0 5.3 15.7 3.0 2.8 0.9 0.6 0.5 t 94.8

RI: retention index, Compounds listed in elution order from a DB-5 capillary column Co-elution t = trace, GC Compositional values less than 0.1 % are denoted as traces

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