Joseph J. Brophy

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%).

Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series 1). Part XIX

The volatile leaf oils of Eucalyptus miniata Cunn. ex Schauer, E. canaliculata Maiden, E. pumila Cambage, E. vergrandis L. A. S. Johnson & K. D. Hill, E. suggrandis L. A. S. Johnson & K. D. Hill, E. tenera L. A. S. Johnson & K. D. Hill, E. incerata Brooker & Hopper ined., E. recta L. A. S. Johnson & K. D. Hill, E. balladoniensis Brooker subsp. sedens L. A. S. Johnson & K. D. Hill, E. ‘species P subsp. P’ L. A. S. Johnson & K. D. Hill, E. ‘species T’ L. A. S. Johnson & K. D. Hill, E. ovata Labill. var. ovata, E. yarraensis Maiden & Cambage, E. nova-anglica H. Deane & Maiden, E. smithii R.T. Baker, E. dawsonii R.T. Baker, E. agglomerata Maiden, E. radiata Sieber ex DC. subsp. radiata, E. radiata Sieber ex DC. subsp. robertsonii (Blakely) L. A. S. Johnson & D. F. Blaxell, E. dives Schauer, E. pauciflora Sieber ex Spreng. subsp. pauciflora and E. pauciflora Sieber ex Spreng. subsp. niphophila (Maiden & Blakely) L. A. S. Johnson & D. F. Blaxell, isolated by vacuum distillation, were analysed by GC and GC–MS. Many species contained α-pinene (0–84.3%), limonene (0–6.3%), α-phellandrene (0–16.9%), 1,8-cineole (0–77.5%), p-cymene (0–27.2%), β-caryophyllene (0–10.8%), terpinen-4-ol (0–28.2%), piperitone (0–54.5%), aromadendrene (0–21.9%), bicyclogermacrene (0–65.6%) and torquatone (tr.–3.6%) as principal leaf oil components.

Digestion and absorption ofEucalyptus essential oils in greater glider (Petauroide svolans) and brushtail possum (Trichosurus vulpecula).

Measurements were made of the quantity and composition of the steam-volatile essential oils in gastrointestinal tract contents of greater gliders fedEucalyptus radiata foliage and brushtail possums fedE. melliodora foliage. In both species, there was less oil in the stomach contents than in an equivalent mass of foliage. Only minor losses of leaf oils occurred during mastication by greater gliders, and absorption from the stomach appeared to be the major reason for the difference in the oil content of ingested leaves and of stomach contents. The apparent digestibility of oils over the whole gut was 96–97 %, although oils from the cecum and feces of both species contained compounds not present in the original leaf oils. Absorption of oils before they reach the hindgut should reduce the severity of antimicrobial effects but may involve a metabolic cost to the animal in detoxification and excretion.

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%.

Iridodials and nepetalactone in the defensive secretion of the coconut stick insects,Graeffea crouani

The defensive secretion of the coconut stick insect,Graeffea crouani Le Guillou (Phasmatodea: Phasmatidae) from the Pacific Islands has, as major constituents:trans,trans- andtrans,cis-iridodials and nepetalactone.Cis,trans-iridodial is a minor constituent. A minor iridoid has yet to be identified. Male and female insects yield the same constituents.

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.

Defensive and other secretions of the australian cocktail ant, iridomyrmex nitidiceps

Abstract Iridodial and isovaleric acid were characterized as major components of the total extract, and of the anal gland secretion, of Iridomyrmex nitidiceps . Minor constituents identified from the total extract included iridolactones, dihydronepetalactones, actinidine, 2- and 3-pentenoic acid, and fatty acids. Behaviour experiments demonstrated isovaleric acid to be primarily an alarm substance, developing repellency only at high concentration. Iridodial was deduced to be the basic repellant. Together the two served a defensive function. Their combination as products of one pair of glands showed a high level of social development.

Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part VII. Subgenus Symphyomyrtus, section Exsertaria

The volatile leaf oils of Eucalyptus seeana Maiden, E. bancroftii (Maiden) Maiden, E. parramattensis C. Hall, E. amplifilia Naudin, E. tereticornis J. Smith, E. blakelyi Maiden, E. dealbata A. Cunn. ex. Schauer, E. dwyeri Maiden & Blakely, E. vicina L. A. S. Johnson & K. D. Hill, E. flindersii Boomsma, E. camaldulensis Dehnh. var camaldulensis, E. camaldulensis Dehnh. var. obtusa Blakely, E. rudis Endl., E. exserta F. Muell. and E. gillenii Ewart & L. R. Kerr, isolated by vacuum distillation, were analysed by GC-MS. Most species contained α-pinene (1.5–14%), 1,8-cineole (0–81%), p-cymene (0.6–28%) and aromadendrene/terpinen-4-ol (0.6–24%) as principal leaf oil components.

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 (...