Robert J. Goldsack

Analysis of the volatile components of Lavandula canariensis (L.) Mill., a Canary Islands endemic species, growing in Australia

Abstract The essential oil of a Canary Islands endemic species, Lavandula canariensis (L.) Mill., gathered from Australia, was extracted by hydrodistillation and solid phase micro-extraction (SPME). The oils have been studied by GC and GC–MS. A total of 38 compounds have been identified in the leaf oil extracted by hydrodistillation, the principal components being carvacrol (23.6%), β-bisabolene (20.8%), ( E,E )-α-farnesene (11.3%), β-caryophyllene (7.6%) and carvacrol methyl ether (7.3%), while the oil extracted by SPME showed carvacrol (42.6%) as the principal component with moderate amounts of ( E,E )-α-farnesene (9.1%), β-bisabolene (7.5%), cis -hex-3-en-1-ol (5.6%) and carvacrol methyl ether (4.6%). SPME extracts indicated that carvacrol, cis -hex-3-en-1-ol and linalool were in greater concentration in the head space vapours than in the oil. This is the first report describing the essential oil composition of this species.

Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.) S.T. Blake

Abstract An examination of the leaf oils of Melaleuca quinquenervia over its geographical range in Australia and Papua New Guinea has shown wide variation in chemical composition but only two major chemotypes. Chemotype 1 is comprised of E -nerolidol (74–95%) and linalool (14–30%) and is found from Sydney, north along the east coast of Australia to Selection Flat, New South Wales, with an isolated occurrence near Maryborough, Queensland. Two divisions occur in this chemotype which are based on the presence or absence of significant proportions of linalool (14–40%). Chemotype 2 contains 1,8-cineole (10–75%), viridiflorol (13–66%), α-terpineol (0.5–14%) and β-caryophyllene (0.5–28%) in varying proportions and order of dominance in the oils. It is found throughout the distribution of the species, from Sydney to Papua New Guinea and New Caledonia. Within chemotype 2 there appears to be a continuous spread of oil composition without formation of any further discrete divisions as in chemotype 1. Analyses have shown that M. quinquenervia trees that occur at latitudes south of 25°S have high oil yields (1–3% w/w%, fresh leaves) and comprise chemotypes 1 and 2. North of 25°S, however, chemotype 1 does not occur and oil yields amongst the Australian populations are uniformly low (0.1–0.2%).

The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae (Agathis and Araucaria).

The leaf essential oil of Wollemia nobilis (Wollemi Pine) has been investigated and compared with other members of the family Araucariaceae. All araucaroids examined yielded steam volatile oils in low yields. The oil from Wollemia nobilis was composed mainly of (+)-16-kaurene (60%), together with alpha-pinene (9%) and germacrene-D (8%). Oils from Agathis species endemic to Australia were high in monoterpenes, in contrast to those isolated from extra-Australian species. The major constituents of A. atropurpurea oil were phyllocladene (13%) and 16-kaurene (19%), followed by alpha-pinene (8%) and delta-cadinene (9%). A. microstachya yielded oil in which alpha-pinene (18%) was the major component; the only other components in excess of 5% were myrcene (7%), bicyclogermacrene (6%) and delta-cadinene (6%). A. robusta oil contained spathulenol (37%) and rimuene (6%). Approximately 40% of the oil was unidentified sesquiterpenes. A. australis oil contained 16-kaurene (37%), sclarene (5%) and an unidentified oxygenated diterpene K (12%) as major components; the only other compound in excess of 5% was germacrene-D (9%). 5,15-Rosadiene (60%), and 16-kaurene (7%) were the major constituents of A. macrophylla oil. A. moorei oil was rich in sesquiterpenes, but the only compounds in excess of 5% were allo-aromadendrene (6%), germacrene-D, delta-cadinene (10%), an unidentified sesquiterpene (12%) and 16-kaurene (6%). In A. ovata oil the most significant compounds were caryophyllene oxide (15%) and phyllocladene (39%). Araucaria angustifolia contained germacrene-D (9%) and the diterpenes hibaene (30%) and phyllocladene (20%) as major components of its essential oil. Oils of A. bidwillii, A. columnaris and A. cunninghamii were all low in mono- and sesquiterpenes and high in diterpenes. In the first, hibaene (76%) was the major constituent; the second contained hibaene (9%), sclarene (6%), luxuriadiene (13-epi-dolabradiene)(23%) and two unidentified diterpene hydrocarbons (B) (33%) and (E) (10%). In the last, 16-kaurene (53%) was the most significant component followed by hibaene (29%). A. heterophylla was unusual in that over half the oil was made up of the monoterpenoid alpha-pinene (52%), with phyllocladene (32%) being the only other compound of significance. alpha-Pinene (18%) was a significant component of A. hunsteinii oil; sclarene (11%) and germacrene-D (5%) were the only other compounds present in concentrations of more than 5%. A. luxurians oil was composed of 5,15-rosadiene (20%) and luxuriadiene (13-epi-dolabradiene) (66%), previously unreported from natural sources. The major components of A. montana were phyllocladene (61%) and 16-kaurene (23%). Sclarene (20%), luxuriadiene (19%) and the unidentified diterpene hydrocarbons (B) (25%) and (E) (10%) were the most important constituents of A. muelleri oil. A. scopulorum contained large amounts of 16-alpha-phyllocladanol (41%) as well as luxuridiene (10%) and delta-cadinene and alpha-copaene, both at 6%.

Essential Oil of Eryngium L. Species from New South Wales (Australia)

Abstract The essential oils from aerial parts of five Eryngium species of New South Wales have been examined by GC and GC/MS. The oil of Eryngium expansum F. Muell was characterized by a high amount of 7-epi-α-selinene (38.3%), cis-β-guaiene (10.8%), 2,3,6-trimethylbenzaldehyde (8.0%) and (E,E)-α-farnesene (7.3%). The leaf oil of E. pandanifolium Cham. et Schlecht contained bornyl acetate (20.8%), β-selinene (13.8%), α-selinene (11.3%) and α-muurolene (8.0%) as the main compounds, while the fruit oil was characterized by heptanol (11.5%) and β-selinene (9.2%). The principal compounds of E. rostratum Cav. were found to be spathulenol (20.0%) and β-bisabolol (8.6%) in the leaf oil while β-bisabolol (65.3%) was the main component in the fruit oil. β-Caryophyllene (20.3%), germacrene D (19.2%) and α-humulene (8.8%) were found to be the major compounds of E. vesiculosum Labill. Two populations of an undescribed species (E. sp.1, E. sp. 2) of this genus were also studied, the principal compounds being α-pinene (14.5–46.2%), bicyclogermacrene (7.1–16.4%), cubebol (0.6–9.0%) and spathulenol (0.8–8.7%). This is the first report on the essential oil composition of these Australian species.

Leaf Oils of the Genus Backhousia (Myrtaceae)

ABSTRACT The leaf oils of eight described and one undescribed species of Backhousia were examined by GC and GC/MS. The major components of the five suspected chemotypes of B. angustifolia F. Muell. were 1,8-cineole, (E)-β-ocimene, angustifolenone, angustifolionol, dehydroangustione and angustione. B. anisata Vickery was found to exist in two chemotypes in whch the major compound was either (E)-anethole or methyl chavicol. The oil from B. bancroftii F. M. Bailey & F. Muell., which varied quantitatively between trees, contained octyl acetate (0.3–61.7%), dodecyl acetate (0.2–21.0%), dodecanol (trace-22.9%), decyl acetate (0.5–39.0%), decanol (0.1–17.4%), 2,4,6-trimethoxy-3- methylacetophenone (trace-23.0%) and a novel compound, bancroftinone (6-hydroxy-2,4-dimethoxy-3-methylacetophenone) (trace-90.0%) as its major constituents. B. citriodora F. Muell. was found to exist as two chemotypes in which either citral or citronellal predominated. The major constituents of B. hughesii C. T. White were β-bisabolene (...

A comparative study of the seedling leaf oils of the spotted gums: species of the Corymbia (Myrtaceae), section Politaria

This study examines variation in seedling leaf oil composition and yield within and between populations of the spotted gum group of eucalypts, with the aim of better defining relationships between species in this taxonomic grouping of economically important forest trees. Eleven provenances from across the geographical distribution, consisting of three provenances of C. maculata (Hook.) K. D. Hill & L. A. S. Johnson (syn. Eucalyptus maculata), four provenances of C. variegata (F. Muell.) K. D. Hill & L. A. S. Johnson, one provenance of C. henryi (S. T. Blake) K. D. Hill & L. A. S. Johnson (syn. E. henryi) and three provenances of C. citriodora (Hook.) K. D. Hill & L. A. S. Johnson (syn. E. citriodora) were analysed. Chemometric analysis (PCA and LDA) of oil compositional data gave effective discrimination between all four species. The major findings were the clear separation of C. maculata populations from other members of the group based on chemical composition of their seedling leaf oils. Two chemotypes were identified in C. maculata, one with the cadinol–muurolol complex prominent and a second, less frequent type in which the eudesmols and elemol were prominent. Corymbia citriodora was also unambiguously separated from other group members through the presence of citronellal and citronellol in all amples tested, although abundance of these compounds in individual oils varied between regions of provenance (north cf. south). The oils from some trees in the southern most provenance comprised of low levels of these compounds, with an increase in α -pinene suggesting introgression with C. variegata. The seedling oils of C. variegata were mostly dominated by α -pinene and several sesquiterpene alcohols, while the oils of the single population of C. henryi studied were generally low in α-pinene and high in sesquiterpenes. Oil composition of C. henryi and the southernmost population of C. variegata showed affinities, suggesting intergradation of oil characteristics between these nearby stands. More intensive sampling of C. henryi and C. citriodora and populations in the zones of suspected intergradation between C. henryi–C. variegata–C. citriodora would be helpful in clarifying patterns of variation within and between these taxa.

Essential Oils from the Leaves of Some Queensland Annonaceae

Abstract The leaf oils of seven species from the family Annonaceae, growing in Queensland, Australia, have been examined. Artabotrys sp. (Claudie River B.Gray 3240) produced oil in poor yield in which unidentified oxygenated sesquiterpenes accounted for approximately 80% of the oil. Uvaria rufa gave an oil rich in sesquiterpenes, in which the principal component was a-humulene (50%), while in Uvaria concava the principal component was spathulenol (32%). Benzyl benzoate was also present (5%) in U. rufa. In Cyathostemma micranthum the principal components were caryophyllene oxide (26%), spathulenol (11%) and benzyl benzoate (4%). The oil of Mitrephora zippeliana existed in two forms in which either monoterpenes were more prominent with a-pinene (13%) and β-pinene (15%) being the major components together with the sesquiterpenes caryophyllene oxide (10%), spathulenol (10%) and β-caryophyllene (8%), or sesquiterpenes were prominent with β-caryophyllene (18%), α-humulene (7%), γ-curcumene (4%), bicyclogermacrene (4%), ar-curcumene (5%), caryophyllene oxide (3%) and spathulenol (5%) being the principal components. Goniothalamus australis presented a leaf oil that contained significant amounts of both mono-and sesquiterpenes; one sample contained pinocarvone (10%) and trans-pinocarveol (17%) as the principal monoterpenes, while a second collection contained α-pinene (10–11%) as the principal component. Cananga odorata gave a leaf oil in which the major components were β-caryophyllene (34–52%), sabinene (1–20%), α-humulene (6–11%) and a-pinene (1–17%).

Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 6. Leptospermum polygalifolium and allies.

The leaf essential oils of Leptospermum polygalifolium and related species were isolated and examined. L. morrisonlii produced an essential oil in which the principal component was the β-triketone grandiflorone, while in L. oreophilum the principal component was (E,E)-farnesol. L. variabile gave oils with a spread of composition, the majority of samples being rich in geranyl acetate, β-caryophyllene and humulene, while another sample was rich in 1,8-cineole and a further sample contained comparable amounts of α-pinene, β-caryophyllene and α-, β- and γ-eudesmol. Leptospermum sp. (Mt Maroon, A.R. Bean 6665) appeared to be a chemically variable species; one specimen showed β-caryophyllene and humulene as principal components, while a second gave an oil rich in sesquiterpenes with β-caryophyllene, δ-cadinene, calamenene and an unidentified sesquiterpene hydrocarbon being the major contributors. Of the seven subspecies of L. polygalifolium, ssp. polygalifolium, montanum and howense contained oils which were rich in α-, β, and γ-eudesmol. These were the only subspecies to contain these compounds in more than trace amounts. Of the remaining four subspecies, ssp. cismontanum, transmontanum, tropicum and ‘wallum’, all contained significant amounts of 1,8-cineole. They usually contained larger quantities of spathulenol. All seven subspecies contained α-pinene in significant amounts, while all but spp. howense also contained β-pinene, usually in comparable amounts. Leptospermum madidum spp. sativum gave an oil rich in monoterpenes, with α-pinene, β-pinene, and γ-terpinene being the major components. α-, β-, and γ-eudesmol also made significant contributions to the oil. Copyright

Essential oil composition of the seasonal heterophyllous leaves of Eryngium vesiculosum from Australia

Eryngium vesiculosum Labill. is seasonally heterophyllous. The essential oils of its aerial parts gathered during summer and winter from New South Wales (Australia) have been examined by analytical gas chromatography and gas chromatography/mass spectrometry. We have found quantitative but not qualitative differences between the two samples. The principal compounds of the winter leaves were identified as β-caryophyllene (20.3%), germacrene D (19.2%) and α-humulene (8.8%), while the summer leaves (SL) contained bicyclogermacrene (22.2%), β-caryophyllene (15.6%), germacrene D (15.8%) and α-humulene (8.1%) as major constituents. The amount of bicyclogermacrene changes by a factor of ten, ranging from 2.4% in winter leaves to being the principal compound (22.2%) in summer leaves. The oil of the flowers and fruits contained almost the same composition as the summer leaves. This is the first comparative study on the chemistry of both kinds of leaves of E. vesiculosum.

The Essential Oil of Ocimum tenuiflorum L. (Lamiaceae) Growing in Northern Australia

ABSTRACT The essential oil of Ocimum tenuiflorum L. growing in northern Australia was isolated in 4.1% w/w yield on dry weight of leaves. It contained methyl chavicol (87%) and much lesser amounts of camphor (4%) and β-caryophyllene (5%). Terpenes, both mono- and sesqui-, accounted for the remainder of the oil.