Composition of the Leaf Oils of Rutaceae: Zanthoxylum hyemale A. St. Hill, Z. rhoifolium Lam. and Z. rugosum A. St. Hill et. Tul.

Journal of Essential Oil Research: JEOR, Nov/Dec 2006 by de Moura, Neusa F, Strapazzon, Juliana O, Loro, Felipe, Morel, Ademir F, Flach, Adriana

Abstract

The volatile oil composition obtained from the leaves of Zanthoxylum hyemale, Z. rhoifolium and Z. rugosum have been investigated by GC and GC/MS. Twenty-five compounds were identified representing ca. 93.8%, 93.1% and 90.1% of the oils, respectively. The main constituents of the oil of Z. hijemale were found to be (E)-nerolidol (49.8%) and germacrene D (13.5%). The oils of Z. rhoifolium and Z. rugosum were found to contain germacrene D (11.7% and 28.8%, respectively) and bicyclogermacrene (35.4% and 26.8%).

Key Word Index

Zanthoxylum hyemale, Zanthoxylum rhoifolium, Zanthoxylum rugosum, essential oil composition, (E)-nerolidol, germacrene D, bicyclogermacrene.

Introduction

The species Zanthoxylum hyemale A. St. Hill, Z. rhoifolium Lam and Z. rugosum A. St. Hill et. Tul., locally called "coentrilho" and "mamica-de-cadela" are originally from South America (Southern Brazil, Uruguay, Paraguay and Argentina) (1,2). They have been used in Brazilian folk medicine as a potent antithermic, tonic agent, anti-inflamatory and antimicrobial effects (3-5). Previous studies on the crude extract of Z. hyemale and Z. rhoifolium reported the antispasmodic activity (6,7). As a continuation on our chemical studies on plants of the Rutaceae family (8,9), the present work describes the chemical composition of the volatile compounds obtained through hydrodistillation of the leaves of these plants.

Experimental

The leaves of Z. hyemale, Z. rhoifolium and Z. rugosum were collected in the town of Jaguari, state of Rio Grande do Sul, Brazil in August 1998, and were identified by Renato Zachia. A voucher specimen (SMDB 5687,6691 and 6690) has been deposited in the Herbarium of the Federal University of Santa Maria.

The fresh leaves were submitted to water distillation for 4 h, using a modified Clevenger-type apparatus to yield near 0.8% (Z. hyemale and Z. rhoifnlium) and 0.6% (Z. rugosum) of yellowish oils. The oil after preparation was submitted to GC analysis in a Varian 3800 gas chromatograph equipped with a capillary fused silica column (25 m x 0.25 mm, 0.25 µm film thickness) coated with SE-54. The GC analysis conditions utilized were as follow: carrier gas He (1 mL/min); column injector temperature 200°C; FID temperature 280°C; column temperature 5000 -250°Cat4°C/min.GC/MS analyses were performed on an HP 5973-6890 GC-MSD system operating in the EI mode at 70 eV, equipped with a HP-5 cross-linked capillary column (30 m x 0.25 mm, 0.25 µm film thickness). The column and injector temperature were the same as those for GC. The identification of the compounds was based on comparison of the retention times and retention indices calculated using a homologous series of n-alkanes and mass spectra with those of the NBS Library ( 10) and with those described by Adams (11). Quantitative data were calculated from the integration of GC peak areas without the use of correction factors.

Results and Discussion

The results of the analysis are given in Table I. Inspection of Table I clearly shows that all oils consisted of sesquiterpenes (84%-Z. hyemale; 81.1%-Z. rhoifolium; 83.8%-Z. rugosum) with lower amounts of monoterpenes. The main constituents of the Z. hyemale, Z. rhoifolium and Z. rugosum oil were (E)-nerolidol (49.8%), biclyclogermacrene (35.4%) andgermacrene D (28.8%), respectively. The 2-undecanone, epi-oc-bisabolol and spathulenol were also reported these species (12-14).

The samples of oils from these species showed some component variation: α-phellandrene, β-phellandrene, globulol and α-cadinol from Z. rugosum; α-fenchene and α-muurolene from Z. hyemale and sabinene, linalool, cubebol and α-muurolol from Z. rhoifolium. These preliminary results offer a way to establish the differentiation of Z. hyemale, Z. rhoifolium and Z. rugosum, which are morphologically similar that is assuming infraspecific chemical differences are not found.

Acknowledgments

The author would like to thank CNPq (Conselho National de Desenvolvimento Científico e Tecnólogico) for its financial support.

References

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3. G.L. Cruz, Dicionário de Plantas Útels do Brasil. Editera Clvilização Braslleira S. A., Rio de Janeiro, Brazil (1985).

4. N.F de Moura, S.R. Giacomelli, E.C.S. Machado, A.F. Morel, S.F.S. Silveira and C.F. Bittencourt, Antibacterial activity of Zanthoxylum rhoifolium. Fitoterapia, 69, 271-272 (1998).

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6. N.F. de Moura, A.F. Morel, E.G. Dessoy, N.Zanatta, M.M Burger, N. Ahlert, G. Porto and B. Baldisserotto, Alkaloids, amides andantispasmodlcactivity of Zanthoxylum hyemale. Planta Med., 68,534-538 (2002).