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Volatile Leaf Oils of Some South-Western and Southern Australian Species of the Genus Eucalyptus (Series I)

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Volatile Leaf Oils of Some South-Western and Southern Australian Species of the Genus Eucalyptus (Series I) FLAVOUR AND FRAGRANCE JOURNAL, VOL. 12, 177±183 (1997) Volatile Leaf Oils of some South-western and Southern Australian Species of the Genus Eucalyptus (Series I). Part XIV. Subgenus Monocalyptus C. M. Bignell1, P. J. Dunlop1, J. J. Brophy2 and C. J. R. Fookes3 1Department of Chemistry, University of Adelaide, South Australia 5005, Australia 2Department of Organic Chemistry, University of New South Wales, Sydney, New South Wales 2052, Australia 3CSIRO, Division of Coal and Energy Technology, PMB 7, Bangor, New South Wales 2234, Australia The volatile leaf oils of Eucalyptus jacksonii Maiden, E. patens Benth., E. diversifolia Bonpl., E. pachyloma Benth., E. suberea Brooker & Hopper, E. insularis Brooker, E. buprestium F. Muell., E. erectifolia Brooker & Hopper, E. lateritica Brooker & Hopper, E. todtiana F. Muell., E. johnsoniana Brooker & Blaxell, E. exilis Brooker, E. pendens Brooker, E. sepulcralis F. Muell., E. ligulata Brooker, E. aquilina Brooker, E. coronata Gardner, E. preissiana Schauer, E. acies Brooker, E. marginata Donn ex. Smith subsp. marginata, E. marginata Donn ex. Smith subsp. thalassica Brooker & Hopper, E. staeri (Maiden) Kessell & Gardner, E. baxteri (Benth.) Maiden & Blakely ex. J. Black, E. obliqua L'He r. and E. remota Blakely, isolated by vacuum distillation, were analysed by GC and by GC±MS. Many species contained a-pinene (0±20.0%), limonene (0±22.2%), 1,8-cineole (0±62.3%), p-cymene (0±12.6%), aroma- dendrene (0±6.4%), allo-aromadendrene (0±3.7%), bicyclogermacrene (0±21.8%), globulol (0±4.3%), viridi¯orol (0±2.5%), spathulenol (0.1±14.2%), g-eudesmol (0±5.5%), a-eudesmol (0±14.8%), b-eudesmol (0±32.0%) and torquatone (0.1±7.5%) as principal leaf oil components. In several species the b-triketones agglomerone, tasmanone and lateriticone, together with the terpenoid ketone jacksonone, were detected at concentrations much greater than 10%. # 1997 by John Wiley & Sons, Ltd. Flavour Fragr. J., 12, 177±183 (1997) (No. of Figures: 1 No. of Tables: 3 No. of Refs: 15) KEY WORDS: Eucalyptus jacksonii Maiden; Eucalyptus patens Benth.; Eucalyptus diversifolia Bonpl.; Eucalyptus pachyloma Benth.; Eucalyptus suberea Brooker & Hopper; Eucalyptus insularis Brooker; Euca- lyptus buprestium F. Muell.; Eucalyptus erectifolia Brooker & Hopper; Eucalyptus lateritica Brooker & Hopper; Eucalyptus todtiana F. Muell.; Eucalyptus johnsoniana Brooker & Blaxell; Eucalyptus exilis Brooker; Eucalyptus pendens Brooker; Eucalyptus sepulcralis F. Muell.; Eucalyptus ligulata Brooker; Eucalyptus aquilina Brooker; Eucalyptus coronata C. Gardner; Eucalyptus preissiana Schauer; Eucalyptus acies Brooker; Eucalyptus marginata Donn ex. Smith subsp. marginata; Eucalyptus marginata Donn ex. Smith subsp. thalassica Brooker & Hopper; Eucalyptus staeri (Maiden) Kessell & C. Gardner; Eucalyptus baxteri (Benth.) Maiden & Blakely ex. J. Black; Eucalyptus obliqua L'He r.; Eucalyptus remota Blakely; Myrtaceae; jacksonone; 8-acetoxy- p-menth-1-en-6-one; lateriticone; 1-isovaleroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione; tasmanone; 1-isobutyroyl-4-methyoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione; agglomerone; 1-iso- butyroyl-4-methoxy-5,5-dimethylcyclohex-3-en-2,6-dione; torquatone; insect repellent; leaf essen- tial oil composition; mono- and sesquiterpenoids; GC±MS INTRODUCTION this study we have followed the system of M. I. H. Brooker and D. A. Kleinig2 and the botanic Continuing our investigation of indigenous nomenclature of the Flora of Australia.3 Locations Australian eucalypts1 we have examined the leaf of all species, which are native to south-western oils of 25 species of subgenus Monocalyptus. In and southern Australia, are listed in Table 1. A more detailed description of the occurrence of Correspondence to: P. J. Dunlop. these eucalypts has been given elsewhere.2 Contract grant sponsor: Australian Council for International To our knowledge, analyses of the oils of 4 4 Agricultural Research. E. marginata subsp. marginata, E. diversifolia, CCC 0882±5734/97/030177±07$17.50 Received 27 April 1996 # 1997 by John Wiley & Sons, Ltd. Accepted 1 July 1996 178 C. M. BIGNELL ET AL. Table 1. Oil yields from the Eucalyptus species, subgenus E. baxteri,5 E. obliqua,4;6 and E. remota5 have Monocalyptusa been published previously. Species and locality Oil yield wt% (dry weight) Eucalyptus jacksonii Maidenb 1.03 EXPERIMENTAL (S35858'48@/E116853'12@) E. patens Benth. tr. Samples of clean, mature leaves were picked from Toodyay, western Australia single trees and, after freezing with liquid nitrogen, E. diversifolia Bonpl. 0.57 Waite Arboretum, South Australia were reduced to a ®ne powder using a stainless steel E. pachyloma Benth.b 0.67 Waring Blender (Model No. SS110). This proce- (S34819'31@/E118805'40@) dure was necessary to rupture the oil glands. The E. suberea Brooker & Hopper 1.35 dry powder was then vacuum-distilled so that the Badgingarra, Western Australia E. insularis Brookerb tr. leaf oil condensed on to a gold-plated copper rod (S33858'24@/E122807'53@) maintained at approximately 758C. Complete E. buprestium F. Muell.b 0.18 details of this procedure have been published (S34819'31@/E118805'40@) previously.7 All oils obtained were colourless to E. erectifolia Brooker & Hopperb 0.33 Stirling National Park, Western Australia pale yellow and lighter than water. Table 1 lists the (S34821'32@/E118804'29@) oil yields (wt%, leaves dried in an oven at 388C) E. lateritica Brooker & Hopper 0.87 for the 25 species studied. Mount Lesueur, Western Australia The GC analyses were performed with a HP5890 E. todtiana F. Muell. tr. Moora, Western Australia Series II unit operated in conjunction with a E. johnsoniana Brooker & Blaxell 0.80 HP3396 Series II integrator. The `on-column' Badgingarra, Western Australia injection technique was used with a SGE BP20 E. exilis Brooker 0.07 capillary column (25 m  0:33 mm i.d., ®lm thick- Badgingarra, Western Australia E. pendens Brooker tr. ness 0:5 mm). The carrier gas was hydrogen, with Badgingarra, Western Australia an inlet pressure of 25 kPa: the ¯ow rate was E. sepulcralis F. Muell.b 0.42 2:0 cm3=min. The oven was programmed to rise Fitzgerald River National Park, Western Australia from 808C to 2208C at 58C/min, and the inlet (S33854'18@/E119856'59@) E. ligulata Brooker 0.11 temperature set to 838C and increased at the same Currency Creek Arboretum, South Australia rate as the column. Using these conditions with a E. aquilina Brooker 1.44 1:0 ml sample of 0.4% solution in oil in puri®ed dry Currency Creek Arboretum, South Australia diethyl ether, essentially all the components were E. coronata C. Gardnerb 0.80 Mt. Barren, Western Australia recorded by the integrator in 31 minutes. GC±MS (S33855'34@/E120801'32@) was performed on a VG Quattro mass spectro- E. preissiana Schauer 0.57 meter operating at 70 eV ionization energy. The Waite Arboretum, South Australia E. acies Brookerb 0.23 GC column in this case was a DB-Wax (S34853'04@/E118824'22@) (60 m  0:32 mm). Compounds were identi®ed by E. marginata Donn ex. Smith subsp. marginata 0.45 the GC retention indices to known compounds and Perth, Western Australia by comparison of their mass spectra with either E. marginata Donn ex. Smith subsp. thalassica tr. 8 ±10 Brooker & Hopper known compounds or published spectra. Toodyay, Western Australia Only four of the species (E. jacksonii, E. suberea, E. staeri (Maiden) Kessell & C. Gardner tr. E. lateritica and E. insularis) were analysed with Albany, Western Australia GC±MS. The oil components of the rest were E. baxteri (Benth.) Maiden & Blakely ex. J. Black 0.33 Currency Creek Arboretum, South Australia identi®ed using normalized retention times. For this E. obliqua L'He r. tr. purpose the column was calibrated by assuming Waite Arboretum, South Australia times for three markers, 1,8-cineole, octadecane E. remota Blakely tr. (OD added to the ether) and torquatone. The raw Kangaroo Island, South Australia retention times were ®rst normalized to 525 s for a The specimens for these species were authenticated by OD, and times before and after OD adjusted by Mr M. I. H. Brooker, Australian National Herbarium, or assuming linearity and using 99 s for cineole and Dean Nicolle, Currency Creek Arboretum, South Australia. 997 s for torquatone. Torquatone was found to be b Botanical voucher specimens have been deposited at the South Australian Herbarium by Dean Nicolle, who collected the present in all oil samples. The normalized retention leaves for these species. times of the column were identi®ed with oil # 1997 by John Wiley & Sons, Ltd. Flavour and Fragrance Journal, Vol. 12, 177±183 (1997) # Table 2. Compounds identi®ed and their percentage occurrence (> 0:05%) in the leaf oils of the Eucalyptus species 1997 ck by ta ica Bla John ina J. x. e thalass marg W dner . ile ely Gar y r & subsp subsp xell Blak C. pper Sons, & & Bla pper Ho & Hoppe Smith Smith Ho & ssell Ltd. aiden er & ll. x. x. & e e . l. er uell. ll. M Ke er er V uer er en ook er ) er er er M Mue OLA k k r. ook .  . Gardner Br ely er ook er Mue ook Bonp F Benth ook F nth.) oo ook Donn Donn Br oo Scha . Br Maid C. Br F Hopp Br TILE Br Br ook lia Br ta ta i L'He ook Blak a (Be Benth. is alis s ta tium (Maiden & Br Br ea ta oniana ina ina ua ina es tifolia teri er ona ersifo chyloma tens LEAF eissiana ec teritic cksoni cies xilis emota taeri suber pa div insular er pa la obliq r bupr ja todtiana johns e penden sepulcr ligula s aquil marg cor pr a marg bax KI a ook E. E. E. E. E. E. E. E. E. E. E. E.
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