FLAVOUR AND FRAGRANCE JOURNAL, VOL. 5,91-95 (1990) Chemical Composition of Eucalyptus Essential Oils Grown in Uruguay Eduardo Dellacassa, Pilar Menkndez and Patrick Moyna Catedra de Farmacognosia y Productos Naturales, Facultad de Quimica, General Flores 2124, Montevideo, Uruguay Eduardo Soler Dexin Ltda, Las Heras 1790, Montevideo, Uruguay The chemical composition of essential oils from 22 Eucalyptus species growing in Uruguay are described. It was found that 1, 8-cineole, citronellal, p-cymene and benzaldehyde are the main constituents. KEY WORDS Essential oil analysis Genus Eucalyptus INTRODUCTION 1, 8-Cineole Uruguay. The leaves and twigs collected were placed in plastic bags and kept at - 4" C for two to three days prior to extraction. Herbarium samples are kept in the Botanical Department of the Agronomy Faculty, Universidad de la Republica, Montevideo. Owing to their adaptability and fast growth, more than 70% of the trees planted in Uruguay are represented by species of the genus Eucalyptus.' Their wood finds use as firewood, as industrial fuel and in the national paper industry. Several Eucalyptus essential oils have been used Essential Oils in traditional medicine. Their antimicrobial activity The leaves and twigs were steam-distilled in an has been reported and their ability to inhibit the all-glass apparatus for two hours. The condensed growth of other organisms has resulted in the use of leaves in grain storage and their proposed use as Table 1. Yield of Eucalyptus essential oils grown in Uruguay potential natural Yield (wt of oil/wt of fresh Only the essential oil from E. globulus growing in Eucalyptus leaves (%)) Uruguay has been described,6 so the chemical 0.44 composition of other species introduced into Uru- E . viminalis Labill. paniculata Sm. 0.23 guay is still unknown. This article is an approach to E. E. melliodora Cunn. 0.20 the correlation of the Eucalyptus introduced into E. botryoides Sm. 0.03 0.06 Uruguay with those described in the literature. This E . grandis Sm. 0.17 could be of interest because of the very large E. sideroxylon C u m . E. rnaculata Hook. 0.18 intraspecific variations in this genus. E. pellita F.v.Muell. 0.10 The essential oils of Eucalyptus could be consid- E. longijolia Link & Otto 0.10 ered as valuable by-products, should their compo- E. amplgolia Naud. 0.36 0.14 sition be of interest. In this paper we describe the E. diversicolor F.v.Meul1. 0.13 chemical composition of the essential oils from 22 E . ujjinis Deane & Maiden E. globulus Labill. 0.80 of the most common Eucalyptus species growing in E. lehmanii Preiss. 0.20 Uruguay. E. polyanthemos Schau. 0.02 EXPERIMENTAL Plant Material The foliage samples obtained were of representative trees from the most common species growing in 0882-5734/90/02009 1-05%05.00 0 1990 by John Wiley & Sons, Ltd. E. tereticornis Sm. E. cladocalyx F.v.Meul1. E. citriodora Hook E. camaldulensis Dehn. E. obliqua L'Herit. E. punctata DC. E. gornphocephala DC. 0.17 0.07 1.30 0.30 0.07 0.13 0.02 Received 2 May I989 Accepted I November 1989 x CT W N B ow d 2 2 2 m v! r! d 0 d c?9 4 - v! rn W 0 9 A - 4 2 z 3°C N O 0 u, 0 - W 9 0 '"v! 0 - 4 m d *v 0 W - L? 4 M x v) P3 d 2 - 2 p! d "WN 2 0 - b ?"?9 91- P- % O m 3 d v) 0 '9'"" 0 0 0 L? 0 '9 0 E. DELLACASSA ET AL. 94 water was separated from the supernatant oil Analysis and extracted three times with diethyl ether. The ethereal extract was added to the oil layer, dried The identification was done by means of the over anhydrous Na2S0, and Et,O was carefully retention times of the different components in relaremoved by distillation under atmospheric pres- tion to standards using two GC columns (PEG 20M and OV-17) and by GC-MS. sure. Capillary GC was carried out using a Shimadzu The yields of the oils obtained are given in Table 1. GC6-AM with PEG 20M and OV-17 bonded Table 3. Composition of Eucalyptus essential oils with low l,8-cineole content. Concentration in percentage (wtjwt) as determined by peak area percentages in GC. E. ~ tereticornis Sm. a-Pinene 8-Pinene Sabinene Myrcene a-Terpinene Limonene 8-Phellandrene 1, 8-Cineole y-Terpinene p-Cy mene 4-Isopropenyltoluene (*) Ci tronellal Benzaldehyde Linalol Isopulegol trans-p-menth-2-en-1-01 (*) B-Car yophyllene Terpinen-4-01 cis-p-Menth-2-en-1-01(*) do-Arornadendrene (*) Cryptone Pin-3-ene-2-01(*) Citronellyl acetate Piperitol (*) a-Terpineol p-Menth-3-en-7-01(*) p-Menth-3-en-3,8-dioI (*) Unknown 6-Cadinene (*) cis-piperitol (*) Pulegol (*) Ci tronellol Terpinyl acetate Cuminaldehyde (*) Carveol (*) p-Cymen-8-01 (*) j3-Epoxycaryophyllene(*) p- Mentha- 1,3-dien-7-ol (*) Cedryl formate (*) Globulol (*) Methyleugenol (*) Viridiflorol (*) Cumin alcohol (*) Cuminaldehyde (*) Spathulenol (*) C-15 alcohol M'222 (*\ C- I 5 alcohol M 220 (*j Thymol Citronellic acid (*) a-Cadinol (*) CarvacroI pj 8-Eudesmol (*) 0.5 E. ciadocalyx F.v.Muell. E. citriodora Hook. E. obliqua L'Herit 0.9 0.8 0.7 1.2 0.8 E. punctata DC. E. gomphocephala DC 4.1 1.5 6.1 0.7 1.5 0.9 E. camaldulensis Dehn 0.9 1.5 1.6 0.8 16.6 6.5 0.6 28.8 1.o 11.1 8.9 5.0 14.1 1.5 1.2 30.8 14.6 0.6 0.8 0.6 2.6 4.1 9.2 12.5 4.9 2.1 5.8 3.6 2.0 2.0 0.7 2.2 24.4 59.2 34.2 0.7 22.9 1.0 2.7 4.6 4.2 19.5 3.1 5.5 1.9 3.2 7.4 0.5 0.8 2.3 1.3 1.1 1.4 2.9 7.5 1.4 0.9 6.1 17.7 0.6 2.0 2.0 5.6 6.2 1.1 2.0 1.5 0.5 3.0 1.2 0.7 0.8 1.1 1.1 0.6 1.o 0.9 0.5 1.1 0.6 0.5 0.9 15.3 2.0 20.1 0.5 0.6 1.6 2.4 15.5 3.8 2.1 0.7 1.6 2.5 23.4 22.9 4.6 + 0.7 0.8 0.7 0.5 1.1 2.5 0.6 Identification key: (*) indicates identification by GC-MS. 0.9 8.8 EZICALYPTUIS ESSENTIAL OILS phase capillary columns (50 m x 0.25 mm i.d.), N, at 0.8ml/min, split ratio 1/32, and temperature programmed from 50°C to 210°C at 50"C/min. GC-MS was measured on a Hitachi M-808 GC-MS with an ionization potential of 20 eV, with PEG 20M bonded phase capillary column (50 m x 0.25 mm i.d.), He at 1 ml/min, and temperature programmed from 70°C to 215°C at 4"C/min. 95 are to E. viminalis7 and E. yarraensis." E. gomphocephala has methyleugenol as major component. Acknowledgements-The authors wish to thank the International Foundation for Sciences (Stockholm) for grant F741, the Japanese Embassy at Montevideo for an important equipment grant to the Facultad de Quimica, and the PEDECIBA project UNDP-URU/84/002 for support that made the work possible. They also acknowledge the collaboration of Professor C. Brussa (Facultad de Agronomia, Montevideo) for the identification of plant samples, Mr T. Iwai (Takasago PC, Japan) for GC-MS data, and Mr D. Lorenzo for typing. RESULTS AND DISCUSSION Although more than 150 compounds were identified in the different essential oils, they could be simply classified as 'high cineole' or 'low cineole' types. Table 2 shows the essential oil composition for the 15 species of Eucalyptus where 1,8-cineole is the main constituent. E. globulus has the highest 1, 8cineole content, although E . pellita and E . longifolia have similar percentages. The results for E. melliodora, E . longifolia,' E . maculata,8 E. lehmanii and E. polyanthemos' agree with those described in the literature. Those for E. paniculata, E . botryoides, E . diversicolor, E . afinis,' E. amplifolia,' E . sideroxylon,". and E . viminalis12 differ. In four of the seven 'low cineole' species (Table 3) the main components are from the phellandrene series. p-Cymene is present in E . tereticornis with p menth-3-en-7-01, cryptone and cuminaldehyde, as previously reported;8*l 3 in E. obliqua with cis- and trans-p-menth-2-en-1-01, small amounts of cryptone and an unidentified compound; in E. camaldulensis with cryptone as previously r e p ~ r t e d ; ' ~l 5. and in E . punctata with 8-phellandrene. In E . camaldulensis and E. punctata important amounts of spathulenol were also detected. The E. citriodora sample in Table 2 corresponds to the so-called 'type I',I6 with a composition of 60% of citronella1 and 23% of isop~legol.'~E . cladocalyx, with benzaldehyde as the main constituent, is also included here. The only references found on benzaldehyde in Eucalyptus essential oils REFERENCES 1. C. Brussa, Estudio Sistematico de Especies Importantes de Eucalyptus, Tesis Doctoral, Montevideo, Facultad de Agronomia (1980). 2. R. T. Yousef and G. Tawil, Phurmuzie, 35,698 (1980). 3. A. M. Janssen, N. L. J. Chin, J. J. C. Scheffer and A. B. Svendsen, Pharm. Weekbfad Sci. 8,289 (1986). 4. A. Kumar, V. D. Sharma, A. K. Singh and K. Singh, Fitoterapia, 59, 141 (1988). 5. E. Dellacassa, P. Menkndez, P. Cerdeiras and P. Moyna, Fitoterapia, in press. 6. M. Castiglioni and P. Moyna, X Congreso Panamericano de Farmacia y Bioquimica, Punta del Este, Uruguay (1975). 7. E. Guenther, 7he Essential Oils, Vol. IV, Van Nostrand, New York (1953). 8. H. H. G. McKern, M. C. Spies and J. L. Willis, J . Proc. Roy. SOC.N.S.Ct: 88, 15 (1954). 9. R. 0.Hellyer and H. H. G. McKern, Australian J. Chem., 19, 1541 (1966). 10. C. Garcia-Vallejo and D. Garcia-Martin, 6th Int. Congr. Essent. Oils, Allured Publishing Corp., Oak Park, IL (1974). 11. C. Garcia-Vallejo and D. Garcia-Martin, 7th Int. Congr. Essent. Oils, Tokyo, Japan 1977, (1979). 12. V. K. L. Handa, L. D. Kapoor and 0.N. Channa, Indian J . Agr. Sci., 25, 73 (1955). 13. E. C. De Riscala, H. R. Julian, M. J. Fumarola and J. A. Retamar, Essenze Deriu. Agrum., 46,176 (1976). 14. D. I. Acosta, M. E. Lalli de Viana and J. A. Retamar, Rio. Ital. Essenze, Profumi, Pianti Off, Aromi, Saponi, Cosmet., Aerosol, 59, 538 (1977). 15. A. Martelli, G. M. Nan0 and A. Fundar, Annal. Chim., 60, 697 (1978). 16. A. R. Penfold, H. H. G. McKern and J. L. Willis, Researches on Essential Oils of the Australian Flora, 3, IS (1953). 17. C. Garcia-Vallejo and D. Garcia-Martin, 6th Int. Congr. Essent. Oils, Allured Publishing Corp., Oak Park, IL (1974). 18. E. V. Lassak and I. A. Southwell, Internat. Flauour and Food Additives, 8, 126 (1977).
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