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Volatile Leaf Oils of Some South-Western and Southern Australian Species of the Genus Eucalyptus

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Volatile Leaf Oils of Some South-Western and Southern Australian Species of the Genus Eucalyptus FLAVOUR AND FRAGRANCE JOURNAL, VOL. 11.107-112 (1996) Volatile Leaf Oils of some South-western and Southern Australian Species of the Genus Eucalyptus. Part XI. Subgenus Symphyomyrtus. A -Section Bisectaria. (a) Series Occidentales, (b) Unpublished Series Annulatae, (c) Series Micromembranae, (d) Series Obliquae, (e) Series Dundasianae, (f) Series Cooperianae, (g) Series Halophilae, (h) Series Salmonophloiae, and (i) Series Pubescentes. B -Section Dumaria. (a) Series Merrickianae C. M. Bignell and P. J. Dunlop Department of Chemistry, University of Adelaide, South Australia, 5005, Australia J. J. Brophy Department of Organic Chemisiry, University of New South Wales, Sydney. NSW. 2052. Australia J. F. Jackson Department of Viticulture, Oenology and Horiiculture, Waite Agricultural Research Institute, University of Adelaide, South Australia, 5005, Australia The volatile leaf oils of Eucalyptus occidentalis Endl. var. occidentalis, E. astringens (Maiden) Maiden, E. sargentii Maiden subsp. sargentii, E. stowardii Maiden, E. annulata Benth., E. macrandra F. Muell. ex. Benth., E. macrandra F. Muell. ex Benth. subsp. ‘olivacea’, E. aspratilis L.A.S. Johnson and K.D. Hill, E. grossa F. Muell. ex. Benth., E. dunhii Maiden, E. cooperiana F. Muell., E. halophila D.J. Carr & S.G.M. Carr, E. salmonophloia F. Muell., E. brockwayi C.A. Gardner, and E. merrickiae Maiden & Blakely isolated by vacuum distillation, were analysed by GC and by GC-MS. Most species contained a-pinene (5.1-47.2%), P-pinene (0.1- 16.4%), l,&ineole (2.7-48.6%), p-cymene (0.3-17.7%) and aromadendrene (1.2-20.0%) and bicyclogerma- crene (048.5%) as principal leaf oil components. KEY WORDS Eucalyptus occidentalis Endl. var. occidentalis; Eucalyptus astringens (Maiden) Maiden; Eucalyptus sargentii Maiden subsp. sargentii; Eucalyptus stowardii Maiden; Eucalyptus annulata Benth.; Eucalyptus macrandra F. Muell. ex. Benth.; Eucalyptus macrandra F. Muell. ex Benth. subsp. ‘olivacea’; Eucalyptus aspratilis L.A.S. Johnson and K.D. Hill; Eucalyptus grossa F. Muell. ex. Benth.; Eucalyptus dundasii Maiden; Eucalyptus cooperiana F. Muell .; Eucalyptus halophila D.J. Carr & S.G.M. Carr; Eucalyptus salmonophloia F. Muell.; Eucalyptus brockwayi C.A. Gardner; Eucalyptus merrickiae Maiden & Blakely; Myrtaceae; leaf essential oil composition; torquatone; mono- and sesquiterpenoids; GC-MS INTRODUCTION and one from Section Dumaria. The series classi- fications (see system M.I.H. Brooker and D.A. Continuing our investigation of indigenous Aus- Kleinig2 and Flora of Australia, Vol. 193) are tralian eucalypts’ we have examined the leaf oils given in Table 1 together with the locations of the of a further fifteen species belonging to Subgenus individual species which are all native to southern Symphyomyrtus, fourteen from Section Bisectaria Western Australia. To our knowledge the oils of ccc ~-5734/%/020107-06 Received 5 May 1995 @ 1996 by John Wiley & Sons, Ltd. Accepted 21 July 1995 108 C. M.BlGNELL ETAL. E. ~ccidentalis,~E. astringens,'-' E. dundasii,' E. column was calibrated by assuming times for salmonophloia'*'O and E. grossa" have been in- three markers, 1,&cineole, octadecane (OD vestigated previously. added to the ether) and torquatone. The raw retention times were first normalized to 525 s for OD, and times before and after OD adjusted by EXPERIMENTAL assuming linearity and using 99s for cineole and 997 s for torquatone. Torquatone was found to be For each species samples of clean, mature leaves present in almost all oil samples; when this was were picked from over ten positions on a single not the case a sufficient amount was added to the tree and, after drying and freezing with liquid oil solution to obtain that reference point. (A nitrogen, were reduced to a fine powder using a sample of pure torquatone was kindly supplied by stainless steel Waring blender (Model no. SSllO). Dr Emilio Ghisalberti, Chemistry Department, The dry powder was then vacuum distilled so that University of Western Australia.) The normal- the leaf oil condensed on to a gold-plated copper ized retention times of the column were identi- rod maintained at approximately -75°C. Com- fied with oil components analysed previously by plete details of the procedure have been pub- GC-MS for over 75 Eucalyptus species: some of lished previously. '* All the oils obtained were these results have been published. I colourless to pale yellow liquids which floated on All GC analyses were performed in duplicate water. Table 1 lists the oil yields (wt%, dry and the retention times and percentage compo- weight) for the fifteen species studied. sitions of each component averaged. Duplicate Analytical gas chromatography (GC) was car- times were discarded if they differed by more ried out on a Shimadzu GC6 AMP gas chromato- than one second. Components which contributed graph. A glass SCOT column of SPlOOO (85 m x less than 0.06% to the final analyses were not 0.5mm) which was programmed from 65°C to considered (an arbitrary but practical decision). 225°C at 3"C/min was used with helium carrier gas. The GC integrations of the peaks were per- formed on a SMAD electronic integrator. GC RESULTS AND DlSCUSSION analyses were also performed with a HP5890 Series I1 unit operated in conjunction with a Freshly isolated oils obtained by vacuum distil- HP3396 Series I1 integrator. The 'on-column' in- lation of powdered leaves from single trees were jection technique was used with a SGE BE0 analysed by GC and by GC-MS. The results for capillary column of (25m x 0.33mm i.d., and the fifteen species are listed in Table 2; only film thickness 0.5 pm). The carrier gas was hydro- those components with concentrations greater gen with an inlet pressure of 25 kPa: the flow rate than 0.05% are reported. The principal com- was 2.0cm3/min. The oven was programmed to ponents in the oils were the monoterpenes a- rise from 80°C to 220°C at 5"/min, and the inlet pinene (5.1-47.2%), P-pinene (0.1-16.4%), 1,8- temperature set to 83°C and increased at the same cineole (2.7-48.6%) and p-cymene (0.3- 17.7%). rate as the column. Using these conditions a There were smaller amounts of limonene (0.3- 1.0~1sample of 0.4% solution of oil in purified 3.0%) and y-terpinene (0-25.8%). Apart from dry ether essentially all the components were re- 1,&cineole, the main oxygenated monoterpenes corded by the integrator in 31 minutes. GC-MS detected with pinocarvone (0-4.0%) and trans- was performed on a VG Quattro mass spectro- pinocarveol (0.2-8 .O% ). meter operating at 70eV ionization energy. The The principal sesquiterpenes encountered in GC column in this case was a DB-Wax (60m x the species of these three series were the hydro- 0.32 mm). Compounds were identified by their carbons aromadendrene (1.2-20.0%), allo- GC retention indices to known compounds and aromadendrene (0.2-4.8%) and bicyclogerma- by comparison of their mass spectra either with crene (0-28.5%), and the related alcohols, globu- known compounds or published spectra. 13-15 lo1 (0.1-9.0%), viridiflorol (0.1-5.1%) and Only four of the species (E. occidentalis var. spathulenol (0.1-12.6%), as well as y-eudesmol occidentalis, E. astringens, E. salmonophloia and (0-1.2%), a-eudesmol(O-2.7%) and P-eudesmol E. halophila) were analysed with GC-MS. The (0-6.0%). The aromatic ketone torquatone oil components of the rest were identified using (2,4,6 - trimethoxy - 33- dimethyl - 1 - (3 - methyl- normalized retention times. For this purpose the butyroy1)-benzene) was detected in all but one VOLATILE LEAF OILS OF EUCALYPTUS SPECIES Table 1. Oil yields from the Eucalyptus species. A. Section Bisectaria. (a) Series Occidentalcs. (b) Serics Annulatae. (c) Series Micromembranae. (d) Series Obliquae. (e) Series Dundasianae. (9 Series Cooperianae, (g) Serics Halophi- lae. (h) Series Salmonophloiae and (i) Series Pubescentes. B. Section Dumaria. (a) Series Merrickianae." Oil yield Species and locality wt% (dry weight) Series Occidentales Blakely Eucalyptus occidentalis Endl. var. occidentalis 1.34 Waitc Arborctum. South Australia E. astringens (Maiden) Maidcn 2.89 Waite Arboretum. South Australia E. sargentii Maiden subsp. surgentii 1.55 Waite Arboretum, South Australia E. stowardii Maiden 1.40 Waite Arboretum, South Australia Series Annulatae Johnsonb E. annulota Benth. 1.47 Waite Arboretum. South Australia Swies Mkromembranw Maiden E. macrandra F. Muell. ex. Benth. 0.17 Waite Arboretum, South Australia E. macrandra F. Muell. ex. Benth. subsp. 'olivacea' tr Wake Arboretum, South Australia E. asprutilis L.A.S. Johnson and K.D. Hill 1.51 Currency Creek Arboretum, South Australia Series Oblique Blakely E. grossa F. Muell. ex. Benth. 2.53 Waite Arboretum, South Australia Series Dundnsianae Chippendale E. dundasii Maiden 0.53 Waite Arboretum, South Australia Series Cooperianae Brooked' E. cooperiana F. Muell. 2.38 Waite Arboretum, South Australia Series Halophihe Brooke#' E. halophila D.J. Cam & S.G.M. Carr 0.64 Waite Arboretum, South Australia Series SpLmOnophloiae Chippendale E. salmonophloia F. Muell. 2.73 Waite Arboretum, South Australia Series Pubescenten Brooked' E. brockwayi C.A. Gardner 0.17 Monarto Arboretum, South Australia Scries Mmldrianae Brooke# E. merrickiae Maiden & Blakely 1.a Waite Arboretum, South Australia 'The specimens for these species were authenticated by Mr M. I. H. Brooker, Australian National Herbarium, Canberra. or Dean Nicolle, Valley Orchids, South Australia. bunpublished Series. ~ E. occidentalis i Endl. var. occidenralis E. astringens (Maiden) Maiden E. sargentii Maiden subsp. sargentii E. slowardii Maiden E. annulata Bcnth. E. macrandra F. Muell. ex. Bcnth. E. macrandra F. Muell. cx. Bcnth. subsp. 'olivacea' E. aspratilis L.A.S. Johnson and K.D. Hill E. grossa F. Muell. ex. Benth. E. dundasii Maiden E. cooperiana F. Muell. E.
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