Abstract
The leaf oils of the Australian members of the genera Geijera and Coatesia have been examined by GC and GC/MS. Coatesia paniculata gave a consistent oil in which the principal components were α-pinene (27-57%) and β-caryophyllene (4-12%). Geijera linearifolia gave a leaf oil dominated by spathulenol (10-17%), geranyl acetate (4-9%), bicyclogermacrene (3-6%) and (E,E)-farnesol (23-30%). Four chemotypes of Geijera parviflora were detected: (1) in which geijerene/pregeijerene and linalool predominated, (2) in which linalool and α-and β-eudesmol predominated, (3) in which α-pinene and camphene predominated and (4) in which phloroacetophenone dimethyl ether predominated. Geijera salicifolia also existed in several chemotypes, one of which contained large amounts of phloroacetophenone dimethyl ether (> 65%). Also present in this particular chemorype was the geijerene/pregeijerene and attendant C^sub 12^H^sub 18^ complex, totaling approximately 5%. In a second sample of this chemotype, this complex was absent. A second chemotype of this species contained α-pinene (38.6%), camphene (22.4%) and limonene (7.5%) as principal components.
Key Word Index
Coatesia paniculata, Geijera linearifolia, Geijera parviflora, Geijera salicifolia, Rutaceae, essential oil composition, α-pinene, camphene, linalool, geijerene, pregeijerene, β-caryophyllene, spathulenol, α-eudesmol, β-eudesmol, (E,E)-farnesol, dimethylphloracetophenone.
Introduction
The genus Geijera Schott is considered to comprise about five species (1), although erroneous figures of eight species have sometimes been mentioned (2). Three species are native to Australia, with one species (G. salicifolia Schott) also found in New Guinea (3) and New Caledonia (1). Two other species (G. balansae Schintz et Guillaumin and G. cauliflora Baill.) are endemic to New Caledonia (T.G.Hartley, pers. comm. 2002). Until recently, the species known as G. paniculata (F.Muell.) Druce (syn. G. helmsiae F.M.Bailey) was also referred to as Geijera, however, Hartley (1) has recently resurrected the monotypic genus Coatesia F.Muell. for this species.
All the species of Coatesia and Geijera are large shrubs or small trees. Hartley (1) defined Coatesia as having unarmed foliage, alternate simple leaves, bisexual flowers, the fruit dehiscent and with an endocarp that is elastically discharged with the seed, the testa thin, brittle and lustrous, and endosperm lacking. By comparison he defined Geijera as having unarmed foliage, alternate simple leaves, bisexual flowers, the fruit dehiscent and with an endocarp that (together with the seed) is not discharged, the seeds with a thick testa, shiny pellicle, and a copious endosperm. In his synoptical key to Rutaceous genera, he placed Coatesia and Geijera adjacent to Zanthoxylum, but species of that genus have usually aculeate (spiny) foliage, leaves that are iinparipinnate, paripinnate orthree-foliolate and flowers that are unisexual. All three of these genera are currently classified in the subfamily Rutoideae, tribe Zanthoxyleae, and are probably allied to other genera occurring in Australia such as Bosistoa F.Muell. ex Benth., Bronibya F.Muell., Bouchardatia Baill., Dinospenna T.G.Hartley, Euodia J.R.Forst. et G.Forst., Halfordia F.Muell., Lunasia Blanco, Medicosma Hook.f., Melicope J.R.Forst. et G.Forst., Pentaceras Hook.f. and Pitaviaster T.G. Hartley. In this current paper we examine the leaf essential oils of the Australian species of Geijera and the Australian endemic Coatesia paniculata.
Coatesia paniculata (axebreaker, capivi, scrub wilga) is endemic to subcoastal eastern Australia where it occurs from near Townsville in the north to Wardell in north-eastern New South Wales in the south. This species forms a shrub or small tree between 2-8 m in height and grows in dry rainforest (araucarian microphyll vineforest, semi-evergreen vinethicket) on a variety of substrates (often talus) derived from andesite, basalt, chert, sandstone and serpentinite.
Geijera linearifolia (DC.) J.Black (oilbush or sheepbush) is endemic to subcoastal south Australia (2) and adjacent parts of Western Australia (4). It is a shrub or small tree up to 4 m tall and grows on the edges of salt lakes or on limestone substrates.
Geijera parviflora Lind. (wilga, tree wilga, lavender bush) is endemic to eastern mainland Australia and widespread in Queensland (northern limit north-east of Mt Coolon, 21° 18'S) and New South Wales, with a southern limit near Nenley in north-western Victoria (5). It is usually found in woodland of brigalow (Acacia harjwphylla), or mixed woodland of eucalypts (e.g. Eucalyptus populnea), mulga (Acacia aneura), cypress pine (Callitris glaucophylla) or belah (Casuarina cristata). Geijera parviflora invariably forms a shrub or small tree up to 7 m high, always with a distinct weeping foliage. The crushed foliage generally has a very distinctive scent ('wilga smell') although can be more prevalent at different times of the year. The foliage is often eaten by domestic stock during drought conditions. According to Everist (6), two distinct forms exist of G. parviflora in terms of edibility to domestic stock (e.g. sheep). One of these (tree wilga) occurs in drier areas (with less than 500 mm per annum) and is readily browsed. The other (lavender bush) occurs in wetter areas (with more than 500 mm per annum) and is not browsed. Wilga is also considered of value as a source of pollen and nectar in honey production (7).
Geijera salicifolia (syn. G. latifolia Lindl., G. muelleri Benth.) (greenheart, green satinheart, scrub wilga) is widespread in eastern Australia from the Mcllwraith Range in the far north of Queensland to Jerry's Plains (32° 35'S) in New South Wales in the south. This species is also found in the northern parts of Western Australia and the Northern Territory, parts of eastern New Guinea (Morobe and Central provinces of Papua New Guinea) and New Caledonia. In Australia it is an extremely variable species, particularly in terms of leaf morphology, but with no apparent discontinuities between the different forms. Plants may grow in dry rainforest (littoral microphyll vineforest, semi-evergreen vinethicket, semideciduous notophyll vineforest) or open eucalypt dominated woodland, on a wide range of substrates derived from basalt, granite, limestone, pegmatite or serpentinite. It fonns a shrub or small tree up to 16 m in height. Hartley (1) considered that this was the most primitive species of Geijera, presumably based on its relict distribution. As with G. parviflora, the foliage may be eaten by domestic stock during droughts (6). The timber is suitable for use as fishing rods, interiors or cabinet work (8).
It is now over 70 years since the first chemical investigations into the chemistry of Geijera (and Coatsea) were first undertaken by Penfold (9), who examined the essential oils of three species viz.: G. parviflora, Coatesia paniculata (as G. paniculata) and G. salicifolia.
Essential oils isolated from the leaves of NSW and Queensland collections showed remarkable differences in their chemical and physical properties. The NSW oils were bright yellow, mobile and pleasant smelling and were of fairly uniform composition, with the major constituents being d-α-pinene and camphene. In contrast, the Queensland oils were viscous, sickly smelling and a dark green to deep blue in color. The latter was attributed to the presence of an azulene. The major components were linalool and a new hydrocarbon, geijerene (9,10). Later, geijerene was shown to be 3-isopropenyl-4-methyl-4-vinylcyclohex-1-ene by Sutherland (11,12). Further work by Jones and Sutherland (13) showed that geijerene was formed from an isomeric precursor, pregeijerene (1,5-dimethylcyclodeca-1,5,7-triene), during steam distillation. The presence of a third isomer, cogeijerene (6,10-dimethyl-3,5-didehydrodecalin), has been found to occur in G. parviflora oil (14). It would seem that the composition of the leaf oil of this species can be quite variable. Some trees contained no pregeijerene or geijerene while others contained substantial quantities of these hydrocarbons.
An oil obtained from G. parviflora collected at Rockhampton, Queensland contained phloracetophenone dimethyl ether, whereas material from Eidsvold, Queensland contained none of this compound (9).
The coumarins, dehydrogeijerin and geiparvarin have been isolated from Queensland collections of G. parviflora (BRI 039139 and 0339140) (15). Seeds from Californian-grown material also contained coumarins (16).
The leaves of the sheep-preferred variety of G. parviflora contained geiparvarin but no dehydrogeijerin. Nobleetal. (17) found that that the leaf oil increases the hepatic microsomal oxidative metabolism in mice.
The major components of G. paniculata oil were found to be d-α-pinene, d-camphene and cadinene (9).
Continued from page 1.
Geijera salicifolia (var. not given) leaves yielded large amounts of phloracetophenone dimethyl ether when steam distilled. Other components in the oil were not identified, presumably due to the lack of material. Geijerin, a coumarin, has been isolated from the bark of this species, but not alkaloids (18). However, alkaloids have been found in leaves of this species collected (TGH 10881A) in New Guinea (19). From the same collection Ritchie et al. (20) were able to isolate umbelliferone, β-sitosterol, geiparvarin, geijerin and dehydrogeijerin.
Alkaloids have been found in the wood, leaves and bark of the New Caledonian G. balansae Schintz & Guillaumin (21,22).
Here we present the results of our analyses of all the Australian species of Geijera and Coatesia paniculata.
Experimental
Leaves were obtained from the following species, usually from two individual plants and a bulk of a further three plants. Coatesia paniculata: PIF13152: Mt Biggenden, Qld, 25° 32'S, 151°58'E; PIF15079: Stony Creek, 4 km E of Didcot, Qld, 25° 28'S, 151° 54'E. Geijera linearifolia: RG832: ocean facing cliff top opposite Pioneers Memorial Park, Kangaroo Island, South Australia, 35° 39'S, 137° 38'E. Geijera parviflora: PIF13161: Back Derra road, 6 km S of Boyne River Crossing, Qld, 25° 43'S, 151° 13'E; PIF13168: 4 km NNE of Monogorilby, Qld, 26° 01'S, 151° 01'E; PIF13198: Lukritz's road, 1.5 km NW of Mt Stradbroke, Qld, 27° 30'S, 152° 34'E; PIF14221: Dingo Hole Dam, S.F.267 Pilliga West, NSW, 30° 43'S, 148° 52'E; PIF15924: Gundy to Scone road, NSW, 32° 02'S, 150° 56'E; PIF17757: Mapala Homestead, Qld, 25° 05'S, 149° 07'E. Geijera salicifolia: PIF13156: Binjour Plateau, 4km S of Binjour, Qld, 26° 27'S, 151° 26'E; PIF13162: Back Derra road, 6 km S of Boyne River crossing, Qld, 25° 43'S, 151° 13'E; PIF13196: Lutzow's road, S of Lowood, Qld, 27° 29'S, 152° 33'E; PIF13409: Mt Blackjack, "Weetalaba," Qld, 21° GO'S, 147° 55'E.
All P.I. Forster (PIF) and R. Goldsack (RG) vouchers are deposited at the Queensland Herbarium (BRI).
Isolation of oils: The leaf oils were isolated by hydrodistillation with cohabitation as previously outlined (23). Analyses of the oils were carried out by gas chromatography and combined gas chromatography/mass spectrometry. The oil yields quoted below are w/w, based on fresh material.
Identification of components: Analytical gas chromatography (GC) was carried out on a Shimadzu GC17 gas chromatograph. A WCOT DB-Wax (60 m x 0.5 mm, film thickness 1 µm) was used, programmed from 50°0-225°C at 3°C/min with helium at 3.5 mL/min as carrier gas. GC integrations were performed on a SMAD electronic integrator without the use of correction factors. GC/MS was performed on both a VG Quattro mass spectrometer operating at 70 eV ionization energy; the column used was DB-Wax (60 m x 0.32 mm, film thickness 0.25 µm) programmed from 35°0-220°C at 3°C/min, with helium at 35 cm/sec as carrier gas and a Shimadzu QP5000 instrument equipped with a DB-5 column (30 in x 0.25 mm, film thickness 0.25 µm). The column was programmed from 35°0-250°C at 5°C/min, helium carrier gas flow rate was 30 cm/sec. Compounds were identified by their identical GC retention times to known compounds and by comparison of their mass spectra with either known compounds or published spectra (24-28).
Results and Discussion
Coatesia paniculata gave a consistent oil in which the principal component was α-pinene (27-57%). This was accompanied by lesser amounts of the monoterpenes camphene (1-9%), myrcene (1-3%), limonene (1-3%), β-phellandrene (0.9-2%), linalool (0.1-3%), terpinen-4-ol (0.7-4%) and α-terpineol (0.1-2%). The major sesquiterpenes encountered in the oil were β-caryophyllene (3-12%), α-humulene (1-4%), germacrene D (0.2-3%), bicyclogennacrene (0.6-10%), δ-cadinene (1-4%), globulol (0.4-3%) and spathulenol (1-4%). There was no sign of the geijerene/pregeijerene complex of compounds in the oils of this species.
Geijera linearifolia gave a leaf oil unlike the oils of its east coast relatives. The leaf oil of this species was dominated by spathulenol (10-17%), geranyl acetate (4-9%), bicyclogermacrene (3-6%) and (E,E)-farnesol (23-30%). There were lesser quantities of (E,E)-farnesal (1-2%), α-, β- and γ-eudesmol (2-3%, 3-5%, 2-4%, respectively), globulol (2-3%), nerol (0.8-5%) and caryophyllene oxide (0.4-13%). Monoterpene hydrocarbons were not important, with (E)-β-ocimene (0.2-2%) being the only member above 0.1%. Sesquiterpene hydrocarbons, also, were not plentiful, with most members also being less than 1%. Overall, the oil from the samples examined was uniform and did not exhibit the many chemotypes shown in the east coast species. The geijerene/pregeijerene complex of compounds was not detected in this species.
Four chemotypes of G. parviflora were detected: (1) in which geijerene/pregeijerene and linalool predominated, (2) in which linalool and α-and β-eudesmol predominated, (3) in which α-pinene and camphene predominated and (4) in which phloroacetophenone dimethyl ether predominated. Chemotype (1) contained geijerene (26.2%), pregeijerene (14.0%) and linalool (19.3%) as principal components, with lesser amounts of α-pinene (4.5%), 1,8-cineole (2.2%), β-caryophyllene (3.1%) and elemol (2.1%). There were several isomers of C^sub 12^H^sub 18^, totaling approximately 5% as well as several compounds of formula C^sub 12^H^sub 20^O, which appeared to be hydrated geijerene/pregeijerene, the largest of these accounted for 6.7% of the oil.
Chemotype (2) contained linalool (29%), β-caryophyllene (9.1%) and α-, β- and γ-eudesmol (12.1%, 10.2% and 3.4%, respectively) as principal components. Monoterpene hydrocarbons, in total, contributed less than 2% to the oil and 1,8-cineole (2.4%) was the only monoterpene of any note. Other sesquiterpenes were not conspicuous, with bicyclogermacrene (1.1%) and spathulenol (2.2%) being the only significant components.
Chemotype (3) was decidedly monoterpene in character, with α-pinene (34.2%), camphene (31.9%), sabinene (3.5%), myrcene (4.2%), limonene (5.8%) and linalool (3.3%) being the principal components. Apart from a-bergamotene (1.1%), γ-elemene (1.9%), bicyclogermacrene (3.2%) and spathulenol (1.1%), no other component reached 1% or more.
Our sample of chemotype (4) contained phloroacetophenone dimethyl ether (55%), spathulenol (20%), globulol (6.4%) and viridiflorol (2.2%) as the major components in the oil. There were no other components present at greater than 1% and no monoterpenes present at a level greater than 0.1%. This sample was, however, some years old when we analyzed it and it is not possible to say if monoterpenes had evaporated or if the spathulenol we observed had originally been bicyclogermacrene.
Geijera salicifolia also existed in several chemotypes, one of which contained large amounts of phloroacetophenone dimethyl ether (> 65%). Also present in this oil were lesser amounts of α-pinene (5.4%), β-caryophyllene (5.1%), caryophyllene oxide (1%), elemol (1.4%) and α-, β- and γ-eudesmol (total 5.8%). Also present in this particular chemotype was the geijerene/pregeijerene and attendant C^sub 12^H^sub 18^ complex, totaling approximately 5%. In a second sample of this chemotype, this complex was absent.
A second chemotype of this species contained α-pinene (38.6%), camphene (22.4%) and limonene (7.5%) as principal components. These were accompanied by lesser amounts of β-pinene (1.1%), sabinene (3.0%), myrcene (2.8%), 1,8-cineole (1.2%), p-cymene (2.1%), linalool (1.6%), terpinen-4-ol (3.0%) and spathulenol (1.8%) as the only compounds in amounts greater than 1%.
Our studies on the genus Geijera in Australia confirm the variable nature of the oil in the two eastern Australian species G. parviflora and G. salicifolia. Both of these species existed in a form containing large amounts of phloroacetophenone dimethyl ether, and a form containing significant amounts of α-pinene and camphene. Geijera parviflora also existed in a form containing significant amounts of linalool and α-, β- and γ-eudesmol. Both the linalool and phloroacetophenone dimethyl ether forms of G. parviflora also contained significant amounts of geijerene/pregeijerene. In contrast to these two variable species, G. linearifolia exhibited only one chemical form, rich in sesquiterpenes, while Coatesia paniculata also exhibited only one chemical form, rich in α-pinene and camphene, and similar to this chemotype of G. parviflora. Where these species have been studied previously, our results are in agreement with earlier work (9,10).
Continued from page 2.
Geijerene and pregeijerene have been found in few plant families, including Rutaceae. Major amounts of these compounds have so far been found from the Rutaceae in Geijera parviflora, Melicope polyhotria (29), Flindersia maculosa (J. Brophy unpublished), Ruta graveolens L. (30,31), Ainyris diatrypa Sprengel (32), Vepris heterophylla R.Let. (33), Boenninghausenia albiflora Reichb. et Meissner (34), Lamiaceae (Wiedermannia orientalis Fisch. et Mey. (35), Nepeta govaniana Benth. (36), Lalleinantia peltata (L.) Fisch. et Mey. (37), Apiaceae (Pimpinella ssp. (38)), Asteraceae (Chromolaena odorata (L.) R. King et H. Robinson (39) and Rosaceae (Rubus rosifolius Sm.) (40).
Acknowledgements
We wish to thank E. Dimitriadis and E.V. Lassak for samples of G. parviflora and its oil, respectively. PIF wishes to thanks L.H. Bird, P. Machin and M. Tucker for assistance with the collection of some of the material. Permits to collect in State Forests in NSW were issued by the NSW Forestry Commission.
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Joseph J. Brophy* and Robert J. Goldsack
School of Chemical Sciences, University of New South Wales, UNSW Sydney 2052, Australia
Paul I. Forster
Queensland Herbarium, Environmental Protection Agency, Brisbane Botanic Gardens, Mt Coot-tha Road, Toowong QM 4066, Australia
* Address for correspondence
Received: July 2003
Revised: November 2003
Accepted: December 2003
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