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FLAVOUR AND FRAGRANCE JOURNAL, VOL. 11.95-100 (1996) C. M. BigneU and P. J. Dunlop Department of Chemistry. University of Adelaide, South Australia. 5005, Australia J. J. Brophy Department of Organic Chemistry, University of New South Wales, Sydney, NSW, 2052, Australia J. F. Jackson Department of Viticulture, Oenology and Horticulture, Wai!e Agricultural Research Institute, University of Adelaide, South Australia. 5005, Australia The volatile leaf oils of Eucalyptus cylindriflora Maiden and Blakely, E. erythronema Turcz var. erythronema, E. erythronema Turcz var. marginata (Benth.) Domin, E. dielsii C.A. Gardner, E. stricklandii Maiden, E. carnei C.A. Gardner, E. kruseana F. Muell., E. brachyphylla C.A. Gardner, E. ewartiana Maiden, E. orbijolia F. Muell., E. websteriana Maiden, E. crucis Maiden subsp. cruck, E. caesia Benth. subsp. caesia and E. caesia, Benth. subsp. magna Brooker and Hopper, isolated by vacuum distillation, were analysed by GC-MS and by GC. All species contained a-pinene (5.1-49.6%), l$-cineole (4.2-75.1%), p-cymene (0.2-23.5%) and aromadendrene/terpinen-4-ol (0-26.8%) as principal leaf oil components. KEY WORDS Eucalyptus cylindriflora Maiden and Blakely ; Eucalyptus erythronema, Turcz var. erythronema; Eucalyptus erythronema Turcz var. marginata, (Benth.) Domin; Eucalyptus dielsii C.A. Gardner; Eucalyptus stricklandii Maiden; Eucalyptus carnei C.A. Gardner; Eucalyptus kruseana, F. Muell. ; Eucalyptus brachyphylla C. A. Gardner; Eucalyptus ewartiana Maiden; Eucalyptus orbifolia F. Muell; Eucalyptus websteriana Maiden; Eucalyptus crucis Maiden subsp. crucis; Eucalyptus caesia Benth. subsp. caesia; Eucalyptus caesia Benth. subsp. magna, Brooker and Hopper; Myrtaceae; leaf essential oil composition; torquatone; mono- and sesquiterpenoids; GC-MS INTRODUCTION All of these species are native to southern West- em Australia. A more detailed description of the Continuing our investigation of indigenous Aus- occurrence of these eucalypts have been given tralian eucalypts’ we have examined the leaf oils elsewhere.* To our knowled e the oils of E. of fourteen species belonging to Subgenus Sym- erythr~nema,~E. srricklandii! E. caesia,6 and phyomyrtus, Section Bisectaria: four from Series E. orbifolia’ have been investigated previously. Elongatae, two from Series Stricklandiae, two from Series Kruseanae and six from Series Orbi- foliae (see system M. I. H. Brooker and D. A. EXPERIMENTAL Kleinig2 and Flora of Australia, Vol. 193.) Lo- cations of individual species are listed in Table 1. Samples of clean, mature leaves were picked from CCC 0882-5734/%/020095-06 Received 15 March 1995 0 1996 by John Wiley & Sons, Ltd. Accepted 20 June 1995 % C. M. BIGNELL ET AL. Table 1. Oil yields from the Eucalyprw species. Series Elongatae, Series Strick- landiae, Series Kruseanae and Series Orbifoliae" Oil yield Species and locality wt% (dry weight) Series Elongatae Blnkely E. cylindripora Maiden & Blakelyb 1.46 North of Esperence. Western Australia (S33"08'49"/E1229xi'290) E. eryrhronema Turcz. var. erythronema 2.36 Waite Arboretum, South Australia E. eryrhronema Turcz. var. mrginara (Benth.) Domin 1.70 Waite Arboretum, South Australia E. dielsii C. A. Gardner 4.11 Waite Arboretum. South Australia Series Stricklandiae Bmokef E. srricklandii Maiden 2.81 Waite Arboretum, South Australia E. carnei C. A. Gardner 1.70 Waite Arboretum. South Australia Series Kruseanae Chippendale E. kruseana F. Muell. 0.94 Waite Arboretum, South Australia E. brachyphylla C. A. Gardner 1.69 Waite Arboretum, South Australia Series Orbifolie Brooker and Hopper Eucalyprus ewarriana Maiden 1.48 Valley Orchids Arboretum, South Australia E. orbifolio F. Muell. tr Waite Arboretum, South Australia E. websreriana Maiden 1.38 Waite Arboretum, South Australia E. crucis Maiden subsp. crucis 2.17 Waite Arboretum, South Australia E. caesia Benth. subsp. caesia 0.79 Waite Arboretum, South Australia E. caesia Benth. subsp. magna Brooker & Hopper 0.48 Valley Orchids Arboretum, South Australia "The specimens for these species were authenticated by Mr M. I. H. Brooker, Australian National Herbarium, or Dean Nicolle. Valley Orchids, South Aus- tralia. bA botanical voucher specimen (DN1103) has been deposited at the South Australian Herbarium in Adelaide by Dean Nicolle. 'An unpublished Series. over ten sites on single trees and, after drying and ried out on a Shimadzu GC6 AMP gas chromato- freezing with liquid nitrogen, were reduced to a graph. A glass SCOT column of SPlOOO (85 m x fine powder using a stainless steel Waxing blender 0.5 mm) which was programmed from 65°C to (model no. SS110). The dry powder was then 225°C at 3"C/min was used with helium carrier vacuum-distilled so that the leaf oil condensed on gas. The GC integrations of the peaks were to a gold-plated copper rod maintained at ap- performed on a SMAD electronic integrator. GC proximately -75°C. Complete details of this analyses were also performed with a HP5890 procedure have been published previously. All Series I1 unit operated in conjunction with a oils obtained were colourless to pale yellow liquids HP3396 Series I1 integrator. The 'on-column' which floated on water. Table 1 lists the oil yields injection technique was used with a SGE BP20 (wt% ,dry weight) for the fourteen species studied. capillary column of (25m x 0.33mm i.d., and Analytical gas chromatography (GC)was car- film thickness 0.5 pm). The carrier gas was hydro- VOLATILE LEAF OILS OF EUCALYPTUS SPECIES 97 gen with an inlet pressure of 25 kPa: the flow rate Component B, m/z (%), 280 (M+,4) 224 (13), 223 was 2.0cm3/min. The oven was programmed to (loo), 208 (4), 193 (5), 165 (lo), 135 (4), 107 (6), rise from 80°C to 220°C at 5"/min, and the inlet 91 (lo), 77 (8), 57 (20). temperature set to 83°C and increased at the same rate as the column. Using these conditions a 2.0 Torquatone, m/z (%), 280 (M+,7), 224 (12), 223 pI sample of 0.2% solution of oil in purified dry (loo), 208 (4), 193 (5), 165 (12), 139 (ll), 125 ether essentially all the components were re- (18), 97 (23), 79 (%), 77 (33), 43 (82). corded by the integrator in 31 minutes. GC-MS was performed on a VG Quattro mass spectro- meter operating at 70eV ionization energy. The RESULTS AND DISCUSSION GC column in this case was a DB-Wax (60m x 0.32 mm). Compounds were identified by their Freshly isolated oils obtained by vacuum-distil- GC retention indices to known compounds and lation of powdered leaves from single trees were by comparison of their mass spectra either with analysed by GC-MS and by GC. The results for known compounds or published spectra.Y-" four species of series Elongatae, two species of Only three of the species (E. erythronema var. series Stricklandiae, two species of series Kru- marginata, E. caesia subsp. caesia and E. caesia seanae and six species of series Orbifoliae are subsp. magna) were analysed with GC-MS. The listed in Table 2; only those components with oil components of the rest were identified using concentrations greater than 0.05% are reported. normalized retention times. For this purpose the The principal components in the oils were the column was calibrated by assuming times for monoterpenes a-pinene (5.1-49.6%), limonene three markers, 1,&cineole, octadecane (OD (0.3-2.8%), l,&cineole (4.2-75.1%) and p- added to the ether) and torquatone.6 The raw cymene (0.2-23.5%). Apart from 1,8-cineole, the retention times were first normalized to 525 s for main oxygenated monoterpenes detected were OD, and times before and after OD adjusted by trans-pinocarveol (0.1-12.2%), a-terpineol (0.1- assuming linearity and using 99s for cineole and 4.5%) and pinocarvone (0-4.5%). 997 s for torquatone. Torquatone was found to be present in almost all oil samples; when this was not the case a sufficient amount was added to the Me oil solution to obtain that reference point.* The normalized retention times of the column were identified with oil components analysed previously by GC-MS for over 75 Eucalyptus species: some of these results have been published. ' All GC analyses were performed in duplicate and the retention times and percentage compo- sitions of each component averaged. Duplicate Me0 0 times were discarded if they differed by more than one second. Components which contri- buted less than 0.06% to the final analyses were Component A not considered (an arbitrary but practical de- cision). Me The principal ions in the mass spectra of I the unknown components A and B and of tor- quatone are: MeO*oMe Component A, m/z (%), 266 (M+,5), 224 (2), 223 (lOO), 208 (4). 193 (7), 165 (14), 135 (5), 107 Mewc4 (6),91 (14), 77 (13), 43 (50). Me0 0 *A sample of pure torquatone was kindly supplied by Dr Emilio Ghisalberti. Chemistrv*. Deoartment. Universitv of Western Australia. Comnonent~~ B Table 2. Compounds identified and their percentage Occurrence (>0.05%) in the leaf oils of the Eucalyptus species" Series: Elongatae Stricklandiae Kruseanae Orbifoliae 1 a-Pinene 20.37 10.31 8.04 49.57 20.14 33.24 22.37 17.87 5.14 6.49 15.85 16.31 13.92 6.59 2 Camphene 0.06 - - - - 0.06 - - - - - - - - 3 4-Methylpent-2-yl acetate - - - - 0.37 - - 0.72 - - - - - - 4 p-Pinene 0.41 0.30 0.36 0.79- 0.48 0.20 0.61 0.35 0.50 0.68 0.29 0.62- 0.44- 0.11 5 Sabinene - - 1.35 - - - - - 0.08 - - 6 Myrcene 0.07 - 1.06 0.40 - 0.32 0.22 - 0.27 0.24 0.07 7 a-Phellandrene 0.32 0.09 0.68 0.44 - 0.11 0.23 - - 1.31 - - - - 8 Limonene 0.49 0.21 0.83 2.57 1.07 3.57 1.81 1.55 2.44 2.80 1.64 1.41 0.37 0.29 9 1.8-Cineole 33.91 56.57 13.02 33.56 13.95 45.38 50.95 57.95 75.10 65.91 33.83 62.33 4.24 5.42 10 a-cis-Ocimene
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    Taxonomy Genus (common name, if any) Subgenus (common name, if any) Section (common name, if any) Series (common name, if any) Subseries (common name, if any) Species (common name, if any) Subspecies (common name, if any) ? = Dubious or poorly-understood taxon requiring further investigation [ ] = Hybrid or intergrade taxon (only recently-described and well-known hybrid names are listed) ms = Unpublished manuscript name Natural distribution (states listed in order from most to least common) WA Western Australia NT Northern Territory SA South Australia Qld Queensland NSW New South Wales Vic Victoria Tas Tasmania PNG Papua New Guinea (including New Britain) Indo Indonesia TL Timor-Leste Phil Philippines ? = Dubious or unverified records Research O Observed in the wild by D.Nicolle. C Herbarium specimens Collected in wild by D.Nicolle. G(#) Growing at Currency Creek Arboretum (number of different populations grown). G(#)m Reproductively mature at Currency Creek Arboretum. – (#) Has been grown at CCA, but the taxon is no longer alive. – (#)m At least one population has been grown to maturity at CCA, but the taxon is no longer alive. Synonyms (commonly-known and recently-named synonyms only) Taxon name ? = Indicates possible synonym/dubious taxon D.Nicolle, Classification of the eucalypts (Angophora, Corymbia and Eucalyptus) | 2 Angophora (apples) E. subg. Angophora ser. ‘Costatitae’ ms (smooth-barked apples) A. subser. Costatitae, E. ser. Costatitae Angophora costata subsp. euryphylla (Wollemi apple) NSW O C G(2)m A. euryphylla, E. euryphylla subsp. costata (smooth-barked apple, rusty gum) NSW,Qld O C G(2)m E. apocynifolia Angophora leiocarpa (smooth-barked apple) Qld,NSW O C G(1) A.
  • Rangelands, Western Australia

    Rangelands, Western Australia

    Biodiversity Summary for NRM Regions Species List What is the summary for and where does it come from? This list has been produced by the Department of Sustainability, Environment, Water, Population and Communities (SEWPC) for the Natural Resource Management Spatial Information System. The list was produced using the AustralianAustralian Natural Natural Heritage Heritage Assessment Assessment Tool Tool (ANHAT), which analyses data from a range of plant and animal surveys and collections from across Australia to automatically generate a report for each NRM region. Data sources (Appendix 2) include national and state herbaria, museums, state governments, CSIRO, Birds Australia and a range of surveys conducted by or for DEWHA. For each family of plant and animal covered by ANHAT (Appendix 1), this document gives the number of species in the country and how many of them are found in the region. It also identifies species listed as Vulnerable, Critically Endangered, Endangered or Conservation Dependent under the EPBC Act. A biodiversity summary for this region is also available. For more information please see: www.environment.gov.au/heritage/anhat/index.html Limitations • ANHAT currently contains information on the distribution of over 30,000 Australian taxa. This includes all mammals, birds, reptiles, frogs and fish, 137 families of vascular plants (over 15,000 species) and a range of invertebrate groups. Groups notnot yet yet covered covered in inANHAT ANHAT are notnot included included in in the the list. list. • The data used come from authoritative sources, but they are not perfect. All species names have been confirmed as valid species names, but it is not possible to confirm all species locations.