Essential Oil of Conyza sumatrensis (Retz) Walk

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Essential Oil of Conyza sumatrensis (Retz) Walk a

a

Samisia M.F. Machado , Júlio S.L.T. Militão , Valdir a

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A. Facundo , Adauto Ribeiro , Selene Maia de b

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Morais , Jose W. de Alencar & Raimundo Braz Filho

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Departamento de Ciências Exatas da , Universidade Federal de Rondônia , Av. Pres. Dutra 2965, 78.900-000, Porto Velho, Rondônia, Brazil b

Departamento de Quimica Orgânica e Inorgânica da Universidade Federal do Ceará Laboratorio de Produtos Naturais , Cx. Postal 12.200, 60.021-970, Fortaleza, Ceará, Brazil c

Departamento de Quimica da , Universidade Federal Rural do Rio de Janeiro , Cx. Postal 74.541, 23851-970, Seropédica, Itaguai, Rio de Janeiro, Brazil Published online: 28 Nov 2011.

To cite this article: Samisia M.F. Machado , Júlio S.L.T. Militão , Valdir A. Facundo , Adauto Ribeiro , Selene Maia de Morais , Jose W. de Alencar & Raimundo Braz Filho (1995) Essential Oil of Conyza sumatrensis (Retz) Walk, Journal of Essential Oil Research, 7:1, 83-84, DOI: 10.1080/10412905.1995.9698470 To link to this article: http://dx.doi.org/10.1080/10412905.1995.9698470

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J. Essent. Oil Res., 7,83-84 (JadFeb 1995)

RESEARCH NOTE

Essential Oil of Conyxa surnatrensis (Retz) Walk

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Samisia M.F. Machado, Jlilio S.L.T. Militgo, Valdir A. Facundo and Adauto Ribeiro Departamento de Ci&nciasExatas da Universidade Federal de Ronddnia Av. Pres. Dutra 2965, 78.900-000 Port0 Velho, Rondhia, Brazil Selene Maia de Morais" and Jose W. de Alencar Departamento de Quimica Orgdnica e Znorgdnica da Universidade Federal do Cearti Laboratbrio de Produtos Naturais, Cx. Postal 12.200,60.021-970 Fortahza, Cearti, Brazil Raimundo Braz Filho Departamento de Quimica da Universidade Federal Rural do Rio de Janeiro Cx.Postal 74,541,23851-970 Seropkdica, Itaguai, Rio de Janeiro, Brazil Received:June 1994 ABSTRACT: The essential oil of Conyza sumatrensis (Retz)Walk, an endemic species of Amazon forest, obtained by steam distillation of the leaves, has been analyzed by GC/MS, Kovats indices and 'H- and 13C-NMRspectroscopy. Lachnophyllum ester, an acetylenic compound was found to be the major component of the oil.

KEY WORD INDEX: Conym sumatrensis (Retz) Walk, Compositae, essential oil composition, lachnophyllum ester, limonene. PLANT NAME: Conyza sumatrensis, (syn. Baccharis viaefolia L. Erigon globosa L., Laennecia gnophalioides Kunt. Cass, Dimorphantes gonari L. Cass). SOURCE:Wild plants from RondGndia state situated in the southern part of Amazon forest. PLANT PART: Aerial parts of the plant were steam distilled to produce oil (code number F1867) in 0.34% yield. Voucher specimens are deposited in the Universidade Federal de RondGnia herbarium (Number 016). PREVIOUS WORK: Acetylenic compounds are common in species of Compositae family (1).Investigationson the constituents of the volatile oil of this plant have not been reported previously. PRESENTWORK: The oil of aerial parts of C. sumatrensis was analyzed using a Hewlett Packard GC/MS apparatus model 5971A, equippedwith a25 m methyl silicone fused silica capillary column, using helium (1mumin) as carrier gas. Temperature program was 50"~~

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'Address for correspondence 1041-2905/95/0001-0083$04.00/0-~1995 Allured Publishing Corp.

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JOURNAL OF ESSENTIAL OIL RESEARCH Table 1. Percentage composition of the oil of Conyza sumafrensis

Component a-thujene sabinene P-pinene myrcene limonene E-P-ocimene

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Major MS peaks*

KI

77,91,93,105,121,136 3.35 5.34 41,77,93,105,121,136 4.81 41,69,77,93,121,136 41,53,69,93,121,136 1.36 41,68,79,93,121,136 22.90 4.98 79,91,93,105,121,136 3.42 41,69,93,105,121,136 41,69,93,120,133,204 5.25 41,77,91,105,161,204 1.13 41,67,93,105,121,204 1.57 75103,133,145,147,176 43.70 77,87,103,115,159,174 2.14 100.00

924 963 967 976 1021 1036 1419 1442 1474 1488 1504 1509

isocaryophyllene (E)-P-farnesene y-muurolene y-elemene lachnophyllum ester matricaria ester Total

re1 %

'MS ions in bold indicate base peaks

rH3

079

/7

_ _ _ ___--.J' 8

7

6

S

4

I

2

3

Figure 1. Structure of IachnophyIluin ester

180°C at 4'C/min, and then 18O"-25O0Cat 10"Chnin. The identification of the constituents was carried out by computer library search, Kovats indices and 'H- and W-NMR spectroscopy (2-5).The results of the analysiscan be seen in Table I. The main constituents were limonene (22.9%)and lachnophyllum ester (43.7%).The structure oflachnophyllum ester is presented in Figure 1.The configuration cis of double bond was confirmed by comparison with other similar compounds (1). Spectral data of lachnophyllum ester: 'H-NMR (200MHz):d(ppm) 3.6(s,OCH,), 6.1(s, H-2 and H-3), 2.2(t, J=7.0 Hz, H-8), 1.6-1.4(m, H-9), 0.9(t, J=7.0 Hz, H-lo), %-NMR (50 MHz): d(ppm) 51.3(OCH3), 164.5(C-1), 122.3(C-2) 130.4(C-3), 86.3(C-4), 70.6(C-5), 64.9(C-6),89.7(C-7),21.3 or 21.4(C-8, C-9) and 13.2(C-10).

ACKNOWLEDGMENTS:The authors thank the Brazilian governmentagencies CNPQ, CAPES and SUDAM for financial support. REFERENCES 1. F. Bohlmann, T. Burkhardt and C. Zdero, Natural Occrm-ing Acetylenes. Academic Press, London (1973). 2. A. A. Craveiro, F.J.A. Matos and J. W. Alencar, Kovats indices as a presele~fionroutine in inass spectra library search of volntiles. J. Nat. Prod., 47, 890-892 (1984). 3. E. Stennhagen, S. Abrahamson and F. W. Mc Lafferty, Registry 1fMns.s Spectral Data. John Wiley & Sons, New York (1974). 4. R. P. Adams, Identification ofEssentia1 Oils by lon Trap Mass Spectroscopy. Academic Press, London (1989). 5. V. Forinacek and K. H. Kubeczka, Essential Oils Analysis by Capillanj Gas Chronuztograplay and Carbon-13 N M R Spectroscopy. Wiley Heyden Ltd., New York (1985).