Studies on the chemistry of 's native flora and fauna

My first involvement in natural products chemistry was during my Honours year in chemistry at UNSW in 1964 where, like so many other chemists before me, I set to work on my bag of sawdust obtained from some Australian tofind ou t what organic compounds could be extracted from it. The involved was Sophora tomentosa and under the supervision of Associate Professor Ron Eade I obtained some isoflavone and pterocarpin derivatives. That experience whetted my interest in the chemicals contained living systems and sparked an interest in why they were there. Sophora tomentosa is a member of the Leguminosae and it is only within this family that isoflavones had been found. The work described in this thesis has been carried out at the School of Chemistry, University of New South Wales over a period of, approximately, 25 years. During this time at the University I have been responsible for providing the routine mass specti'ometry service within the School of Chemistry, though the work described herein is not part of that work. GC/MS was initiated within the School in 1969. In 1970, as a postdoctoral fellow, I used the technique for the first time in the my work on chemistry. After a period of 5 years at Monash University I returned to UNSW in 1976 to run the routine mass spectrometry service. My involvement with insect chemistry continued and several years later I commenced work on essential oils chemistry. Like a lot of other people who spend their lives in doing chemical research, I got into essential oils research more or less by accident, though in my case this accident was once removed. In my case the route to essential oils was via insect chemistry. This was an area that was very challenging and enjoyable and one in which I was able to make some significant contributions. Professor Ken Cavill was head of the Department of Organic Chemistry at UNSW in the 1960's and 1970's. His research interests at the time were in the area of insect chemistry. Professor Cavill's group at UNSW was interested in the chemistry of the volatile secretions of Australian and this is the area in which I was involved, both during the time I spent as a research fellow and postdoctoral associate with him. Afterwards, while running the routine mass spectrometry service at the University of New South Wales I made some contributions in this area. My first contributions had been earlier, however, when as a postgraduate student I had helped collect, by the thousand, the Australian bull Myrmecia gulosa (a task not for the faint heaited).

Page 1 My first contribution to insect chemistry was an investigation of the volatile hydi-ocarbons of the formicine ant Camponotus intrepidus where we found the 4-methyl alkane series for the first time in [24]. The references are listed at the end of this introduction and aie contained in the body of the thesis. Fuither work in this area was directed primarily into the two subfamilies Dolichoderinae, in which Professor Cavill was primarily interested, and Ponerinae (in which my interest was increasing).

In the Dolichoderinae we made contributions to the knowledge of the chemistry of nitidiceps [25], /. purpureas [26], the cuticular hydrocarbons of I. humilis, I. purpureiis and /. nitidiceps [27]. Later on, with Professor Clezy and Dr Phyllis Robertson, we determined the structure of some secondary amines isolated from the venom gland of the dolichoderine ant Technomyrmex albipes [28]. The compounds were synthesised by Mr Chris Leung. This was unusual chemistry as amines had not been isolated from the venom gland of ants of this sub-family before The work in the field of dolichoderine chemistry also led to work on the Fijian stick insect, Graejfae crouani [29], where Mr Noel Davies and myself determined its defensive secretion. The secretion was supplied by Dr Roger Smith at that time of the University of the South Pacific. We also designed an efficient apparatus for collection of crawling [30].

My own interest in ants was in the more primitive subfamily Ponerineae and in paiticular the pyrazines that they contained in their mandibular glands. We also found them in the formicine ant Notoncus ectatommoides [31]. The majority of work on ponerine ants in which I was involved was on the Rhytidiponera, a wide ranging genus in Australia. We were able to demonstrate the presence of 2,5-dimethyl-3-isopentyl pyrazine in a series of Rhytidoponera species [32,33,34] as well a further pyrazine from the head of the bull ant Myrmecia gulosa [35].

Work of which I am particularly satisfied is that on the secretions of Rhytidoponera metallica in which we found twelve pyrazines, a record for the time, and were able to suggest structures for ten of these compounds which were subsequentiy synthesised by Drs Berhane Tecle and Chang-Ming Sun under the direction of Dr Robert Toia [34]. The remaining two oxygenated pyrazines contained in this ant still await structural elucidation. Later we were able to demonstrate that the E- and Z- isomers of these pyrazines gave different mass spectra, presumably due to steric effects, a featui'e exceptionally raie in mass specti'ometiy [36]. This research led to biosynthetic studies on some of the aromatic compounds contained in the gasters of tliese ponerine ants by students of Dr Robert Toia. My conuibution to this work were in the determination of the structures in question [37,38]. I was also involved in determination of the compounds present in the dolichoderine ml Iridomyrmex discors [39].

Page 2 As a consequence of my interest in pyrazines from natural sources I have been able to contiibute reviews on naturally occurring pyrazines and their mass specti-al characterisation (with Prof. Cavill) [40] and later a review on the pyrazines obtained from insect sources [41].

Contributions to the area of mass spectrometry which I have made over the years include showing that reductions of nitro compounds can take place in the CI source of a mass spectrometer [8], study of the EI and CI mass spectra of aryl ureas [9], contributions to the study of low energy, low temperature mass spectra [10,11,12] and publication of new mass spectra of 2,2-disubstituted benzodioxoles [13], aryl sulphenamides [14] and the rare naturally occun ing p-triketones [15].

I contiibuted as part of a team which used microprocessors to contiol mass spectrometers (when microprocessors were in their infancy) [16, 17], perfected a method of obtaining elemental compositions from low resolution mass spectrometers [18] and demonstrated one of the first LC/MS systems in the world, certainly the first in Australia [19].

Published work on synthetic chemistry includes studies in organophosphorus chemistry (for my Ph. D. under Assoc. Professor Michael Gallagher) [1-7], a synthesis of aryl cyclopropanol derivatives (postdoctoral work with Professor Garry Griffin) [20] and my subsequent further work on these systems [21], the synthesis of 3-arylbenzothiophenes [22] and a minor contribution in pyrrole chemistry [23]. The papers in this and the preceding three paiagraphs[l-23] do not form part of this thesis.

The main part of the work submitted for the degree, in which I was the senior author or an equal participant, concems my work on the essential oils of Australian native flora. Australia is blessed with a vast variety of native flora and fauna, throughout the continent. A chemist interested in the volatiles of the native flora is almost overwhelmed with the large number of families present on this continent which contain volatile oils in their , wood, bark and roots.

The research in which I have been involved has been mainly undertaken in the family , which contains two subfamilies, Leptospermoideae and Myrtoideae. This is not surprising as this is the largest oil bearing family, containing over 140 genera in two sub- families. My work in this area is listed in the Table 2. Quite a significant number of species from both sub-families have been investigated and where possible conclusions about their chemotaxonomy have been reached. Work on other families has also been carried out and this is also included in this thesis. The families are described in alphabetical order in the following sections and Table 2.

Page 3 The sub-family Leptospermoideae contains many of the large genera within the Myrtaceae, ie. , , and Leptospermum, as well as many other smaller genera. This sub-family is well represented in AustraUa. The other sub-family, Myrtoideae, is not so strongly represented within the Australian region. Within this sub-family, though with the exception of Syzygium, a significant number of genera with the major ones being Austromyrtus, Rhodamnia, Rhodomyrtus, Uromyrtus, Archirhodomyrtus, have been investigated, the vast majority being examined for the first time. Table 1, adapted from Briggs and Johnson and also Wrigley and Fagg 1993, below, gives the major divisions of the Myrtaceae and includes the genera which occur in Australia, while Figure 1 shows the major divisions within the eucalyptus alliance. A summary of the genera on which work has been published is given in Table 2 and the results of this work ai'e briefly discussed in the text following this table.

Table 1 Major Divisions of the Myrtaceae

Subamily Taxa: Distribution Aust. genera LEFTTOSIPEIRMOIIIIDIEAIE 85:42 SE Asia, Australia, Pacific, outliners in S Africa and Chilie 1 METROSIDEROS 29:11 Pacific, , N. & E. Austraia ALLIANCE i. Kania suballiance (4):1 Lyscicarpus ii. Meterosideros suballiance (11):3 Metrosideros, Tristania, m.Xanthostemon suballiance (3):1 Xanthostemon Lindsayomyrtus, , iv. suballiance (12):6 Welchiodendron, Lophostemon, Syncarpia, Ristantia 2 HETEROPYXIS ALLIANCE 1 S.E. Africa 3 BACKHOUSIA ALLIANCE 2:2 E. Australia Backhousia, Choricarpia EUCALYPTOPSIS 2:1 N. Australia & PNG ALLIANCE Allosyncarpia

Page 4 EUCALYPTUS ALLIANCE 10:10 Major concentration in Aust., some species of (i) (ii) in E, Malesia, Arillastrum (i) in New Caledonia

Angophora suballiance (4):4 AriUastrum, Angophora, Blakella, Corymbia

Symphyomyrtus, Telocalyptus, Symphyomyrtus suballiance (3):3 Eudesmia

Eucalyptus s. str. suballiance (3):3 Idiogenes, Eucalyptus, Gaubaea LEPTOSPERMUM 17 Major concentration in SW Aust., ALLIANCE well represented in E. & S. Aust., a few genera also in W. Pacific and SE Asia

i. Leptospermum suballiance (7):7 Leptospermum, Agonis, Kunzea, Neofabricia, Angasomyrtus, Percalymma,

ii. suballiance (10):9

a. Melaleuca infra-aUianace (4): 4 Callistemon, Melaleuca, Conothamus, Lamarchea

b. Calothamnus infra-alliance (5):5 Calothamnus, , Regelia, Phymatocarpus,

CHAMEL AUCIUM 22:12 Aust., major concentration in SW ALLIANCE Aust.: Baeckea also with a few subsp. to SE Asia and New Calidonia

i. Baeckea suballiance (7):7 Baeckea, Astartea, Scholtzia, Balaustion, Hypocalymma, Ochosperma, Rinzia

ii. suballiance (15):5 Calytrix, Aclythropsis, Homalocalyx, Wehlia, Pileanthus, Thryptomene, Micromyrtus, Chamelaucium, , Homoranthus, Rylestonia, , , Corynanthera, Malleostemon

B Subfamily MTOTOHIDIEAIE 83:14 Major concentrations in S & C. America, SE Asia, E. Aust.,W. Pacific; Eugenia pantropical, Myrtus Mediterranean to Iran, mtns to Sahara.

MYRCIA ALLIANCE 7:0 S. & C. America

Page 5 MYRTUS ALLIANCE 29:9 S. & C. America, E. Aust., NZ, New Calidonia, Malesia, a few sp. to S. China, Myrtus isolated in MediteiTanean. Austromyrtus, Uromyrtus, Rhodomyrtus, Archirhodomyrtus, Myrtella, Rhodamnia, Decaspermum, Myrtus, Fenzlia CRYPTORHIZA 7:1 S. & C. America, E. Aust. ALLIANCE Pilidiostigma 4 OSBORNIA ALLIANCE 1:1 N. Aust., E. Malesia: on sea coasts Osbornia 5 ACMENA ALLIANCE 8:4 S. & SE Asia, Malesia, N. & E. Aust., islands of W. Pacific: Syzygium ssp. also in Hawaiian islands and Africa. i. Syzygium suballiance (4):2 Cleistocalyx, Syzygium ii. Acmena suballiance (4):2 Acmenosperma, Acmena EUGENIA ALLIANCE 20:1 Mostly S. & C. America, Eugenia also from Africa to S. & N. Asia and NE Aust.; Meteoromyrtus in India, Stereocayum in New Calidonia.

* Genera on which I have worked, either in part or in full, are listed in bold type.

My early work with Mr Doug Boland of CSIRO, Division of Forestiy, led to the production of a well received book. Eucalyptus Oils - use, chemistry, distillation and marketing [42]. Along with Dr Alan House, we edited the book and I wrote over half of the material published therein. A second book has appeared as part of the ACIAR monograph series. This was co-authored with Dr John Doran of CSIRO Forestry on the essential oils of tropical Melaleuca, Callistemon dsid. Asteromyrtus species [43]. I was responsible for the chemistry in this book. With Mr Lyn Craven and Brendan Lepschi, I have been studying the oils of the genus Melaleuca. This has been in conjunction with Craven's revision of the genus for a forthcoming volume of the series. Cuiiently the leaf oils of approximately 170 species have been investigated, but because of the large number of species involved (approximately 230) and the lai'ge number of new species which have only just been described [Aust, Syst. Bot„ 12, 819-927 (1999)], little published work on this genus has so

Page 6 far arisen. It is anticipated, however, that a further book on the leaf oils of this genus will be produced. The papers on species of Melaleuca included herein are akeady recognised species.

The family has been investigated in a much more selective manner. Several of the investigations have been undertaken to try and help botanical subdivisions while others (the majority) have been undertaken to examine the sole (Australian) species within a genus. Other families, paiticularly those with limited Australian representatives, have yielded some interesting and in some cases useful, chemistries which are set out below.

Within all this work, unless the chemistry of a species was unusual and warranted separate publication, eveiy effort has been made to examine all species of a particular genus so that any chemical trends within the genus could be discemed (if they existed).

The work described in the accompanying publications, particularly those on essential oils, has been cai'ried out with the help of a significant number of botanists, to whom I owe a large debt of gratitude. Starting early in my investigations with Mr Doug Boland, Drs Alan House and John Doran of CSIRO, Division of Forestry and continuing with Mr Lyn Craven and Mr Brendan Lepschi of the Australian National Herbarium, Mr John Clarkson and particularly Mr Paul Forster of the Herbarium have allowed this work to be not only chemically interesting but also systematically useful. I owe a tremendous debt of gratitude to Paul Forster whose many trips up to the rain forest areas of Cape York have led to a large number of rare and unusual species being investigated. Without his indefatigable collecting of species, a large body of work would not have seen the light of day. In the papers arising from these collaborations the majority of the botanical input has come from these collaborators.

My good friend Dr Bob Goldsack has been responsible for the majority of the literature work which has gone into the papers described herein, as well as some of the laboratory work itself. Bob's knowledge of has been invaluable to an interdiciplinary project such as this. It was Bob who introduced me to Paul Forster, the only one of my collaborators whom I have never met in person, and for this introduction alone he deserves a special debt of gratitude. In papers with Drs Ian Southwell and Erich Lassak, we have all made significant contributions to the work. The task of writing the main parts of the manuscripts and dealing with the Joumal editors has been shared amongst us.

Ian Southwell and I have written a paper, soon to be published, listing the new and unusual or useful compounds discovered in our work over the past 11 years [44]. A previous paper in this series by Ian Southwell {Flavour and Fragrance Journal 2,21 (1987)] listed a lot of the significant compounds detected in my work in the previous 10 years. I was not an author of this latter paper. Mrs Arapachorn Punruckovng, as a Honorary Research Fellow, worked

Page? with me for several years and her contribution to isolating the oil from a large number of species, particularly Melaleuca, is most gratefully acknowledged. Her name appears on some of the papers and will appear on more, particularly those involving the genus Melaleuca, when that body of work is written up.

The analyses described in this work result mostly from gas chromatography and combined gas chromatography/mass spectrometiy. They have been canied out originally on an AEI MS 12 mass spectrometer and more recently a VG Quatti-o machine. Where needed, NMR spectroscopy was used to help in structural elucidation and there is even one X-ray crystal structure (my only one). In some of the papers Dr Chris Fookes appears as a co-author. In these papers the NMR results are down to Chris and he has provided the majority of analyses based on these results.

Twenty two of the papers have been with Dr Peter Dunlop and Ms Caroline Bignell of Adelaide University (125-147 ). Peter developed a method that, in effect, is a vacuum distillation of the oil directly from the leaf. I devised the analytical method for examining the oil from these distillations and check-analysed a considerable number of samples in this series of papers. The results reported in these papers on the eucalypts represents analyses of over 300 species of southern and Western Australian eucalypts, a large number for the first time. Although not applicable to large scale oil extraction, this method undoubtedly gives a more accurate idea of what volatile oils are actually present in the leaf.

Table 2 Family, genera and species examined for this thesis

Family: ANNONACEAE Genus Species Comments References

Fitzalania keteropetala monotypic genus 45

Haplostichanthus johnsonii unusual chemistry 45

Page 8 Xylopia macrceae, sp. nov. sole Australian species 47

Family: ARAUCARIACEAE

Agathis 7 species includes all Australian species 48

Araiicatia 10 species includes all Australian species 48

Wollemia nobilis monotypic genus 48

Family: AUSTROBAILEYACEAE

Austrobaileya scandens sole member of family 49

Family: IDIOSPERMACEAE

Idiospermum aiistraliense sole member of family 50

Family: LAMIACEAE

Hyptis suaveolens Malaysian origin 51

pectinata Fijian origin 52

Mentha grandifolia 1 of 4 Australian species 53

diemenica 1 of 4 Australian species 54

Ocimurn tenuifolium Australian occurrence 55

basilicum Fijian source 56

sanctum Fijian source 57

Family: LAURACEAE

Cryptocarya cmninghamii unusual chemistry 58

Undera queemlandica sole Australian member 59

Family: MONIMIACEAE

Austrormtthaea elegans monotypic genus 60

Doryphora aromatic a, sassafras s complete genus examined 61

Page 9 Dryadodaphne sp(Mt Lewis BP Hyland sole Australian species 62 RFK1496) Kibara rigidifolia sole Australian species 62 Levieria accwninata sole Australian species 62

Family MYRTACEAE Acmenosperma claviflorum only Australian representative 63 Actinodium cunninghamii monotypic genus 64 Angasomyrtiis salina monotypic genus 65 Archirhodomyrtiis beckleri complete Australian genus 66 examined Asteromyrtus 6 species complete Australian genus 67 examined Austromyrtus 4 species lasioclada group 68 23 species bidwillii group, (Complete 69,70 Australian genus now examined) dulcis, tenuifolia unusual chemistry 71 Backhousia 9 species complete genus examined 12,13 J A Callistemon 37 species complete genus examined 75 viminalis 76,77 Choticarpia 2 species complete genus examined 78 Homoranthus montanus.flavescens unusual chemistry 79 Leptospermum 3 Western Australian species 3 out of 15 species examined 80 60 + species most (55) eastern Australian 81,82,83,84,85,86, species 87,88 Lindsayomyrtus racemoides monotypic genus Lophostemon 5 species complete Australian genus 90 examined Lysi carp us angustifolius monotypic genus 91 Melaleuca 4 species central and northern Australian 92 species 7 species broad leaf 93 8 species Western Australian species 94

Page 10 14 species tropical species 43,95,88

acacioides, alsophila unusual chemistry 96

alternifolia, linariifolia, 97,98,99 dissitiflora

citrolens 4 chemotypes 100

leucadendra 2 chemotypes 101,43

squamophloia, new species, unusual chemistry 102 stypheliioides

Metrosideros sclerocarpa, nervulosa all Australian species examined 103

Micromyrtus striata unusual chemistry 104

Neofabricia 3 species complete genus examined 105

Osbornia octodonta monotypic genus 106

Pilidiostigma 6 species complete genus examined 107

Rhodamnia 17 species complete Australian genus 108 examined

Rhodomyrtus 7 species complete Australian genus 109 examined

Syncarpia 3 species complete genus examined 110,111

Thaleropia queetisla/uUca monotypic genus 112

Thryptomene hexandra, parvifolia, complete Queensland species 113 oligofuira examined

Tristania neriifolia monotypic genus 114

Tristaniopsis complete Australian genus 114 3 species examined

Uromyrtus complete Australian genus 115 4 species examined

Welchiodendron monotypic genus 89 longivalve

Tribe: Eucalytpeae

Arillastrum gummiferum monotypic genus 116

"Stockwellia" sp. monotypic genus 117

Allosyncarpia (emata monotypic genus 118

Page 11 Angophora -17 species 8 species examined 119

Corymbia 12 species complete yellow bloodwood 120 group examined

Corymbia dallachiana unusual chemistry 121,122

Subgenus Idiogenes

Eucalyptus cloeziana monotypic, unusual chemistry 123

Subgenus Gaubaea

Eucalyptus curtisii, tenuipes complete subgenus examined 124

Subgenus Eudesmia

Eucalyptus 22 species 10 species examined 125,126

Subgenus Monocalyptus

Eucalyptus -230 species >75 species examined 127,121,128,129

deuaensis newly described species 130

delegatensis 131

youmanii, macrorhyncha 132

Subgenus Symphyomyrtus

Eucalyptus -500 species >250 species examined 133,134,135,136, 137,138,139,140, 141,142,143,144, 145,146,147,148

camaldulensis 149,150

urophylla, pellita, scias extra-Australian species 151

pellita Indian origin 152

jensenii unusual chemistry 153

nova-anglica unusual chemistry 154

pulverulenta 155

brassiana growing in India 156

Page 12 bridgesiana growing in India 157 bakeri 158 fusiformis newly described species 159 central Australian species 160 Western Australian species 161 species growing in 162 Vietnam

Family: RUTACEAE Boronia latipima unusual chemical form 163 Bouchardatla newococca monotypic genus 164 Coleonetm pulchellum initial investigation of species 165 Crowea exalata, saligna, complete genus examined 166 angiistifolia Eriostemon chemical and botanical 167 banksii, australasius separation of species different chemical form 168 Euodia hortensis Geleznowia monotypic genus 169 Lunasia armra sole Australian member 170 Melicope melanophloia three chemical varieties found 171 Murraya paniculata chemical separation of two 172 types Sarcomelicope simplicifolia sole Australian member 170 Zanthoxylum 7 species Complete Australian genus 173 examined

Family: SANTALACEAE Santalum spicatum further investigation of the 174 species

Family: VERBENACEAE Vitex trifolia Fijian origin 52

Page 13 trifolia Thai origin limonifolia Thai origin 176

Family: WINTERACEAE Tastmnnia 7 species complete genus examined 177 Zygogynum 3 species complete genus examined 178

ANNONACEAE: In Australia this primitive family is represented by approximately 19 genera containing some 40 species. The two AustraUan species of Xylopia differ from their African and Asian counterparts in possessing oils which are low in monoterpenes, with X. maccreae having bicyclogermacrene as principal component and X. sp. nov. containing spathulenol and globulol as major components [47].

The monotypic genus Fitzalania, is endemic to Australia. F. heteropetala contains p- caryophyllene and aromadendrene as principal components of its leaf oil [45]. Haplostichanthus is a genus with one described and several undescribed species. H. johnsonii, the only species so far documented, gave an oil in which 2,3,4,5-tetramethoxyallylbenzene was by far the principal component. This was its first report from nature [46]. We have, in fact, completed work on all the Australian species within the family Annonaceae. The majority of this work awaits writing up. ARAUACRIACEAE: In 1994 a new monotypic genus of auracaroid was discovered in the Wollemi National Park north-west of Sydney. The leaf oil of this species {Wollemia nobilis) has been found to consist principally of a-pinene, germacrene-D and (+)-16-kaurene. The leaf oil of W. nobilis has been compared with all the Australian species of the two other genera (Agathis, Araucaria) within the family Araucariaceae. A large variation in oil content was found, though the oil of W. nobilis appeared to be closest to species within the genus Agathis [48]. AUSTROBAILEYACEAE: Aust?-obaileya scandens is the only species within this family and is one of the most primitive of all living angiosperms. The essential oil, with p- pinene as the principal component and p-caryophyllene as a significant component, is unusual only in having the p-pinene present at approx. 10 times the concentration of a-pinene, the reverse usually being true [49].

Page 14 IDIOS PERM ACE AE: Idiospemium australieme is the sole species in this primitive angiosperm family. By far the major component of the leaf oil of this species is bicyclogermacrene, followed by p-caryophyllene and viridiflorol [50].

LAMIACEAE: Australia possesses 4 species of the menus Mentha within this family. M. grandifolia gives an oil in which /ra/i5-piperitone oxide, piperitenone oxide, pulegone and menthone are the major components, and in this respect it differs from the other 2 species so far examined [53]. The other species that we have examined, M. diemenica, gave an oil in which menthone, pulegone, neomenthyl acetate and neomenthol were the principal components [54]. The oil of this species has similarities to the other species, M. satureioides, previously investigated by chemists.

The genus Ocimum occurs both in Australia and overseas. In Australian samples of O. tenuifolium we have identified methyl chavicol as the principal component [55] while from Fijian O. basilicum methyl eugenol and E-methyl cinnamate were the major components [56]. From O. sanctum we identified strains in which methyl eugenol, p-caryophyllene or eugenol were the principal components [57].

We have also examined members of the genus Hyptis from Malaysia and Fiji. H. suaveolens from Malaysia contains p-caryophyllene as its major component [51], while H. pectinata from Fiji also presents |3-caiyophyllene, together with germacrene-D as principal components [52].

LAURACEAE: The leaf oil of Cryptocarya ciinninghamii has been examined and the lactone responsible for its apricot/coconut odour was identified [58], while Lindera queenslandica gives a sesquiterpenoid oil in which the principal components are a-copaene and p-elemene [59]. The Australian members of the genus Neolitsea have been examined as well as those of Cinnamomum. This work has not yet been written up.

MONIMIACEAE: Australia possesses approximately 12 genera containing 27 species. Austromatthea elegans, a monotypic genus, gave an oil in which with benzyl benzoate or benzyl salicylate were by far the major components [60] making this a particularly convenient natural source of these compounds.

The genus Doryphora contains two species, both endemic to Australia. D. sassafras contains camphor, safrole and methyl eugenol as piincipal components in leaf, bark and seed oil, while in D. aromatica the major components were elemol, guaiol, bulnesol and p-eudesmol [61].

Page 15 Other genera within this primitive family which are monotypic in Australia are Dryadodaphne, Levieria and Kibara. For Dryadodaphne sp. (Mt Lewis BP Hyland RFK1496) guaiol and bulnesol were the principal components, for L. accuminata n-dodecanal and 5- cadinene were the principal components, while for K. rigidifolia Z-p-ocimene, germacrene-D and bicyclogeiTnacrene accounted for a significant part of the oil [62].

MYRTACEAE: The genus Eucalyptus is by far he lai-gest genus in this family, with some 790 species, within the family Myitaceae and as such has played a prominent role in my study of the essential oils of the Austi-alian flora.

Vaiious attempts at classification of this large genus have been made over the years, culminating in Hill and Johnson's splitting of Corymbia from the rest of Eucalyptus [Telopea, 6,185-504 (1995)]. While my interest in the essential oils of the eucalypts has allowed opportunistic study of the genus, it has always been carried out with a view to trying to discem a pattern in the oils which may be reflected in the phylogeny of the genus [121. Since the publication of this paper and our book on Eucalyptus oils [42], much more work has been done. It is summarised in a chapter by Ian Southwell and myself in a chapter on eucalyptus oil chemistry in a book which is yet to be published[199, not included in this thesis]. No further attempt has been made to examine the oils in the light of the phylogeny. In the following section I shall briefly mention my contributions to the knowledge of the essential oils of this genus.

The Arillastrum group contains 5 species in 4 genera. Arillastrum gummiferum from New Caledonia, gives an oil rich in (-)-limonene (the opposite enantiomer form that present in citrus oils) and unlike any oil so far investigated in the Myrtaceae [116]. The informal genus "Stockwellia" gives an oil in which the overwhelming principal component is 2,4,6- trimethoxytoluene [117]. This is the only report of the natural occurrence of this compound.

The Eucalyptopsis group contains 2 genera: Eucalyptopsis, with two species from Papua- and neither at the moment investigated, and Allosyncarpia. A. ternata, the only species of this genus, gave an oil in which sesquiterpenes predominated, even though a- pinene was the principal component [118].

Angophora (17 species) and Corymbia (113 species) forni a clade and are reported to beai- closer relationship to each other than to the remaining Eucalyptus species. My published contribution to Angophora has been with Peter Dunlop and Caioline Bignell where we have examined 8 species (usually from single ). The oil was obtained by Dunlop's method of vacuum distillation from the powdered leaf, not steam distillation [119].

Page 16 -Arillastrum Group (4 genera-5 species)

Angophora (17) Corymbia Fundoria (1) Corymbia Apteria (1) Corymbia Rufaria (67) — Corymbia Ochraria (17) — Corymbia Blakearia (27) Odontocalyptus O Eudesmia s.str. si Fibridia (20+) Leprolaena Baileyanae <-i ^ o ^ (t> 13- =r "Leprolaena Miniatae o3n « .h - o rt> -Gaubaea (2) 3 c diogenes (1) vOtvoET. .Monocalyptus (170+) -Symphyomyrtus (500+)

Telocalyptus (4)

Nothocalyptus (1) I have reported on the essential oils of the 12 "Yellow Bloodwoods" {Corymbia section Ochraria). The majority of species in this section give an oil with a-pinene as principal component. Where this was not the case, there was a variation between guaiol, globulol, the 3 eudesmols and p-pinene as major component [120]. While compiling the above report a check on the oils of other Corymbia species was also undertaken. This showed some variation in the oils, though most showed a-pinene as principal component, though there were a significant exceptions with some species producing no oil (C. confertiflora, C. flavescens) and C. dallichiana produced the p-triketone, papuanone as its principal component [121,122]. My contribution to [122] was in the structural elucidation of papuanone, not its synthesis. C. citriodora, of course, stands out because of its lemon scented oils; C. curtipes, spathulenol; C. hamersleyana, bicyclogemiacrene; C. setosa, globulol; C. umbonata, the 3 eudesmols and the aromatic ketone torquatone [129].

The subgenus Idiogenes contains only 1 species. Eucalyptus cloeziana. This has been shown to occur in two chemical forms, one of which contains a-pinene as, by far, the major component. The second chemical form, only found in trees from Lappa, Queensland, contains the p-triketone, tasmanone, as virtually its only component. This compound was not found in the other chemotype [123].

The subgenus Gaubaea contains only two species, E. curtisii and E. tenuipes. Both are unusual and are isolated from the other Eucalyptus species by floral and leaf characters. Even so, the oils that these species present are not remarkable, with E. curtisii containing E-p- ocimene and globulol as major components in a multi-component oil and E. tenuipes having p- pinene and a-terpineol as its principal components, once again in multi-component oils [124].

The subgenus Eudesmia contains 22 species, 10 of which have had their oils examined [125,126,199] These species present variable oils, with principal components varying among bicyclogermacrene, a-pinene, a-terpineol and 1,8-cineole. Highlighting the difficulty of correlating oils with their species groups is the oil of E. miniata which contains either two or nine aromatic ketones contributing 40% of the oil, something not found in any other member of the subgenus. The structures of these compounds have now been elucidated and have been submitted for publication (Brett Ireland, B.Sc Honours thesis, UNSW, 1999, [210]). These ketones are not found in E. gigantangion, recedntly split from E. miniata and sould seem to lend support for its recognition as a descrete taxon. In its oil, the closest relative to E. miniata would be E. conglomerata in the subgenus Eucalyptus sens, strict, (see below).

The subgenus Eucalyptus sens, strict. (Monocalyptus) contains some 230 species in three unequal sections. E. rubiginosa is the sole member of section Islaria, but its oil, with a-

Page 18 pinene as principal component, is not atypical [124]. In section Hesperia, coming from Westem Australia, are a group of species which contain the p-triketones tasmanone and lateriticone. These come from four separate series [127]. In the largest section, Renantheria, more p-triketones occur in series Marginatae from Westem Australia [127] and in series Capitellatae from eastem Australia [199], these being the only occuiTences of these compounds in the eucalypts [121].

Apait from this, the oils usually contain 1,8-cineole as major component if the oil yield is high (>2%). Sesquiterpenes occur in all oils, with a-, p- and y-eudesmol usually the predominant compounds. Within this section (Renantheria) is a group of over 70 species which contain cis- and rr<3/2S-menth-2-en-l-ol and cis- and trans-piperitol as significant components. This is the only place in the genus Eucalyptus sens. lat. where this occurs [121,199].

The Backhousia alliance contains 2 genera, Backhousia (9 species) and Choricarpia (2 species). Within Backhousia there is quite a variety of oil types from aromatic oils (B. anisata, B. myrtifolia), p-triketone containing oils {B. ongustifolia), terpenoid oils {B. citriodora, B. hughesii, B. kingii, B. sciadophora) and oils containing aliphatic alcohols {B. bancroftii, B. sp. (Didcot, PI Forster 1267) [72,73,74]. Chemotypes were found within these species. The genus Choricarpia contains two species which both contain oils rich in a-pinene, limonene and 1,8-cineole. They are more similar to the oils of B. sciadophora and kingii than any of the other species yNiihin Backhousia [78].

Within the Metrosideros alhance, the genus Metrosideros is not represented in mainland Australia, occurring only on Lord Howe Island where two species, M. sclerocarpa and M. nervulosa occur. Both produced oils in poor yield which were sesquiterpenic in character, though the latter species also contained significant amounts of n-hexadecanol [103]. A close relative of Metrosideros, the monotypic genus Thaleropia queenslandica, fi om Queensland, gave an oil high in monoterpenes, with a-pinene by far the major component [112].

Within the Leptospermum sub-alliance, occurs the genus Syncarpia which contains three species, one with 2 subspecies. In this genus S. hillii stands out in that its leaf oil is dominated by two tetrahydrochroman derivatives that do not occur in any of the other species of the genus. They are related to the p-triketone, syncarpic acid found in the bark of 5. glomulifera by Hodgson et al. in 1960 [Austr. J. Chem.,13, 385 (I960)]. The oil of the remaining species are qualitatively similar in the mono- and sesquiterpenes that they contain, and ai-e usually dominated by a-pinene [110, 111].

Page 19 Two monotypic genera occuning within this alliance are Welchioclendron longivalve and Lindsayomyrtus racemoides. Both these species give poor yields of predominantly sesquiteipenic oils, with p-caryophyllene and humulene as major components [89].

The genus Lophostemon contains five species all of which occur in eastem Australia. The oils of these species all contain aromadendrene as a major component, together with globulol and spathulenol. Three of the species, L. suaveolens, L. lactifluus and L. grandiflorus subsp. ripariiis also contain a-pinene in major amounts [90].

Three species of Tristaniopsis occur in Australia (the remainder of the approximately 30 species occuning in New Caledonia, Malesia and Indochina). These thi*ee species gave quantitatively variable oils, with mixtures of mono- and sesquiterpenes being present. Apart from one sample of T. laurina with 80% of a-pinene, no one compound dominated the oils [114]. Allied to Tristaniopsis is the monotypic genus Tristania. Tristania neriifolia gave an oil rich in a-pinene and a-, p- and 7-eudesmol [114]. Lysicarpus angustifalius, another monotypic genus in this alliance, gave an oil in which a- and p-pinene, in approximately amounts, were the principal components [91].

The Leptospemium alliance contains a diverse group of 24 genera of which numerically the most important is the genus Leptospejinum. This genus of approximately 80 species is predominantly an eastem-Australian genus, with some 65 species occurring on the eastem side of the continent. There are also 3 species which occur outside Australia. We have been investigating the species in eastem-Austi-alia, trying to detennine ti-ends, so far with little success. Certain species do stand out for their chemical composition: L. petersonii and L. liversidgei for thek lemon scented fonns [87, L. morrisonii for the presence of the p-triketone, grandiflorone [86], L. myrtifolium for the presence of 2 farnesal isomers, E,£-famesol and 2,3-dihydi'ofaniesol in one chemotype [85]. The majority of species, however, contain unremarkable oils which are either rich in a-pinene or rich in sesquiterpenes, with a-, p- and y- eudesmol or globulol, viridiflorol and spathulenol as major components [81-88]. Several species from Westem Australia have also been examined and produced oils rich in monoterpenes, with a-pinene as principal component [80]. More work is required on the remaining Westem Australian species.

Neofabricia, a close relative of Leptospermum has also been investigated. The three species of this genus gave terpenoid oils without any trend discerned. They contain a-pinene or p-caryophyllene as principal components [105]. The oils from this genus are, however, quite similai- to a significant number of Leptospermum oils. The monotypic genus Angasomyrtus salina, from Westem Australia has also been investigated and its oil shown to contain principally a-pinene [65].

Page 20 Species from several genera of the Chamelaucium alliance have also been examined. The three Queensland species of the genus Thryptomene have been examined, showing that two species T. hexandra and T. parvifolia give oils rich in 1,8-cineole while the third species, T. oligandra has y-terpinene as its principal component [113].

Actinodium cunninghamii, a species from used in the cut market gave both leaf and flower oils which were overwhelmingly rich in a-pinene [64], Two species of the genus Homoranthm, H. montanus and H.flavescens have been shown to produce an unusual oil containing large quantities of Z-p-ocimene [79].

Within the Melaleuca sub-alliance the principal genera are Melaleuca and Callistemon. These two genera are at present under investigation by Lyn Craven for a forthcoming volume of "Flora of Australia". There are approximately 230 species of Melaleuca, the greater number of which occur in Westem Australia. Callistemon is predominantly an eastern-Australian genus containing approximately 37 species. Craven has proposed that the genus Callistemon be subsumed into Melaleuca (Craven, pers. comm.)

A large amount of work has been directed at the oil oi Melaleuca alternifolia, M. linariifolia and M. dissitiflora, the three species commonly used for "Tea Tree Oil" production. Although I have made some contributions in this area [97-99, my interests have lain in the more numerous and less commonly known species of this genus. Some of this work is summarised in a book [43] with additional material in the book chapters [88,95].

I have so far examined the oils of some 170 species of the genus Melaleuca. The morphological paper describing the complete genus has just been published [L.A. Craven and B.J. Lepschi, Aust. Syst. Bot., 12, 819-927 (1999)]. It is hoped to complete the analyses of the remaining species in the genus and describe the oils in an all embracing book.

Some of this work, primarily on eastem-Australian species has been published to document the variation in oils between members of this large genus and some examples are given here. M. leucadendra from eastem-Australia gives an aromatic oil with either methyl eugenol or E-methyl isoeugenol as principal components [101]. However, the same species from the westem parts of its range give a completely terpenoid oil. The boundary is towards the middle of the Northem Territory where both forms co-exist [43].

Other published work details the chemotype variations in Melaleuca citrolens [100] and its close relatives M. acacioides and M. alsophila [96] as well as other broad leaved melaleucas [62] and some species from Westem Australia [94] and central and northem Australia [92].

Page 21 The latter paper details the oil from M. uncinata, an arid country species, which is of "Tea Tree Oil" quality. A comparison of the oils from the newly created species M. squamophloia and its close relatives M. styphelioides andM. bracteata has also been documented [102].

The genus Callistemon contains approximately 37 species with all but one, C. viminalis, having rather limited distiibution and the vast majority occuning in eastern Australia. We have examined the leaf oil of all the known species and found that the leaf oils fall into two groups: the majority (approx. 30 species) gave oils in which 1,8-cineole was the major component with a-pinene, limonene and a-terpineol each being approximately 1/10 that of the major component. These species also had oil yields of 0.1-1%. The remaining species (approximately 7) contained virtually no oil and this oil was sesquiterpenoid in nature with very little in the way of monoterpenes present [75].

The oil of C. viminalis was examined in gi'eater detail over its entire range and found to vary quantitatively over this range. The more southerly latitude oils contained higher amounts of 1,8-cineole (60-80%), while the more northern oils contained less cineole (0.5-47%) [77]. Using all the oil components it was found that partial least squares analysis allowed the latitude to be calibrated from the leaf oil concentrations. The statistics for this paper were provided by Professor Brynn Hibbert. The oil analyses of several cultivars of C. viminalis has also been undertaken [76].

The genus Asteromyrtus, comprising six Australian and one Indonesian (known only from a herbarium voucher) species has recently been reinstated to accommodate species previously included in either Sinoga or Melaleuca. The leaf oils of the six Australian species (which occur in northern Australia and extend into Papua-New Guinea) are rich in monoterpenes of which a-pinene or 1,8-cineole are the principal components. The oil of A. symphyocarpa oil is being produced in Papua-New Guinea as a 'Cajuput' type oil. There is the possibility for several other members of this genus being exploited in a similar manner [67].

The sub-family Myrtoideae is not so strongly represented within the Australian region as the sub-family Leptospermoideae. Within the Myrtus alliance of this sub-family, genera that have so far been examined include Uromyrtus, Archirhodomyrtus, Rhodomyrtus, Austromyrtus and Rhodamnia.

The genus Uromyrtus with four species gives vaiied oils ranging fi-om U. australis which gives a sesquiterpenoid oils with p-caryophyllene and the eudesmols as principal components. U. sp. (Tinaroo Range G.P.Guymer 2034) has bicyclogemiacrene as principal

Page 22 component, whereas U. metrosideros and U. sp. (McPherson Range G.P. Guymer 2000) both of which give mono terpenoid oils [115]. Archirhodomyrtus beckleri is the only member of this genus to occur in Australia. It exists in two chemical forms one of which contains an overwhelming amount of E-jS-ocimene as principal component while the second chemotype contains major amounts of (3- cai'yophyllene, a- and p-eudesmol. The ocimene chemotype comes only from southern populations of the species [66].

Rhodomyrtus, with seven species in Australia gave variable oils. R. canescens, R. pervagata, R. psidioides and R. sericea produced monoterpenoid oils while R. ejfusa, R. macrocarpa and both subspecies of/?, trineura gave sesquiterpenoid oils [109].

Austromyrtus is a genus at present under taxonomic revision and there are plans to split it into three genera (P. Forster, pers. commun.). The two species that will constitute Austromyrtus sens, strict.aiQ A. dulcis and A. tenidfolia. Both species give oils which are rich in the phenol, isobaeckeol. This compound is not present in any other species in Austromyrtus sens. lat. There is also a 'ridge' form of A. dulcis and this form is entuely terpenoid in content, with major amounts of a-pinene and 1,8-cineole [71].

The second group of Austromyrtus sens lat. contains four species, only one of which {A. lasiocladd) has been formally described. These species all present sesquiterpenoid oils [130]. The third group of species, the A. bidwillii group comprises 23 species with variable oil types within both monoterpenoid and sesquiterpenoid oils. Notable among these oils were those from two species (A. sp. (Danbulla L.S.Smith 10123) and A. sp. (Spencer Creek P.I.Forster 13701) both of which contain £;-p-ocimene in amounts up to 80% [69,70].

The genus Rhodamnia contains seventeen species within Australia. Once again these species present oils which are either monoteipenoid, with a major component of a-pinene, or sesquiterpenoid oils, with no outstanding component [108].

Pilidiostigma, a member of the Cryptorhiza alliance is endemic to Australia. This is the only member of the alliance which has been examined and the only member not to occur in either Central of South America. The genus contains sk species all of which give sesquiteipenoid oils with aromadendi'ene or ^^//o-aromadendrene being principal components in all the oils [107].

Osbornia octodonta, the only member of the Osbornia alliance is notable for being the only member of the Myrtaceae that is a mangi'ove species It is a monotypic genus which has

Page 23 been placed in a subfamily of its own. The oil of this species was notable for being constant throughout the large range over which it was collected (well over 1000km), Its principal components were a-pinene, 1,8-cineole and a-terpineol [106]. Leaves of this species, when crushed and rubbed on the skin, are used by fishermen as an insect repellent.

Acmenosperma claviflonm, the only member of the Acmena alliance that I have been able to study. It gave an oil which was entirely sesquiterpenoid in nature, with bicyclogermacrene being by far the largest component [63].

RUTACEAE: The family Rutaceae is well represented in Australia by approximately 41 genera and over 320 species and some of these are known to produce some interesting and unusual essential oils. My interest in this family has been primaiily in chemotaxonomy and I have, in a number of cases, been able to help in the of some genera.

Eriostemon banksiii has recently been reinstated from a subspecies of E. australasius to species level, partly on the basis of their essential oil contents. E. banksii contained both Z-and £'-methyl 4-isoprenoxycinnamate which were lacking in E. australasius. Likewise there were significant differences in the amounts of p-elemene, p-caryophyllene, and unidentified sesquiterpene hydrocarbon, a-pinene, (3-pinene and limonene. These differences are regarded as significant and together with other morphological differences have led to the raising to species level of E. banksii [167].

Murraya paniculata is another species which has been shown to be differentiated by essential oils. At present there are two entities known as the "big leaf and "small leaf' forms which grow in different ecosystems. They contain statistically significantly different amounts of p-caryophyllene, bicyclogermacrene, germacrene-D and E-nerolidol. Paul Forster, the botanist involved in this work, is of the opinion that based on vaiious morphological and habitat differences as well as the essential oil differences they represent two distinct species [172].

The genus Crowea contains 3 species, two of which occur on the east coast of Austi-alia and the third,which has two varieties, in the south-west of Western Australia. The genus does not occur in the intervening country. One species, C. saligna had been previously investigated and only the major component, croweacin, identified. In the course of my work on this genus we have identified 5 chemical varieties of C. exalata, provided a detailed examination of the contents of the oil of C. saligna and for the first time examined C. angustifolia from Western Australia. The oils of these species all contain aromatic ethers, some highly substituted, and while it is possible to distinguish amongst them all, there is an obvious communality running through the genus [166].

Page 24 Examination of the leaf oil chemistry of Melicope melanophloia (now Dinosperma melanophloid) has shown the existence of three chemical varieties in which methyl chavicol and methyl eugenol (absent in the other two chemotypes), a-pinene, E-p-ocimene combined with 2- hydroxy-4,6-dimethoxyacetophenone are marker compounds. This species is noted for its 'aniseed' smell and this work has shown that this chemical variety occurs only in the southern part of its range. The 2-hydroxy-4,6-dimethyacetophenone only occurs in material originating from the Mt Windsor Tableland in north Queensland [1711.

Bouchardtia neurococca and Geleznovia verrucosa are both the sole members of their respective genera within the family Rutaceae. B. neurococca, from eastem Australia, contains major amounts of p-caryophyllene, humulene and caryophyllene oxide in its essential oil [164]. G. verrucosa, a Western Australian species used in the cut flower market, gave an oil from both leaves and which was rich in a-pinene. The major difference in the oils of this latter species was the presence of eugenyl acetate in the flower oil and its viitual absence in the leaf oil [169].

Two genera within the family Rutaceae which are represented in Australia and Lord Howe Island by a single species are the monotypic genus Lunasia amara and Sarcomelicope simplicifolia. In the case of L. amara the essential oil contained y-elemene, p-caryophyllene and bicyclogermacrene as principal components while for S. simplicifolia the main components were p-caryophyllene and bicyclogermacrene. The Lord Howe Island oil was qualitatively similar but quantitatively different [166]. A reinvestigation of Fijian Euodia hortensis leaves and flowers showed a major amount of menthofuran and lesser amounts of evedone. In this species the presence of compounds such as hmonene-lO-ol, perillyl alcohol, p-isopropylbenzaldehyde and the lack of pulegone (the previously proposed precursor of menthofuran) in the oil leads to the postulate that a different biosynthetic pathway to menthofuran may be occurring in this species [168].

An initial investigation of the ornamental species Coleonema pulchellum showed that its aromatic foliage contained a- and p-pinene, myrcene and p-phellandrene as major components and presumably were the compounds responsible for its pleasant perfume [165]. The Grampians boronia, Boronia latipinna, contained bomyl acetate as ,by far, its principal component [163].

The genus Zanthoxylum is represented in Australia by 6 species and there is also one species on Lord Howe Island. The species, apart from Z. ovalifolium, which produces oil in 1- 2% yield, gave poor oil yields. The species produced oils that were usually sesquiterpenoid in nature, though several species gave either significant or major amounts of alkan-2-ones. Z.

Page 25 pinnatlim, from Lord Howe Island, contained undecan-2-one and tridecan-2-one as principal comstituents [173]. SANTALACEAE: Santalmi spicatum oil was reinvestigated and found to consist of a complex mixture of sesquiterpenes in which the alcohols E.E-famesol, epi-a-bisabolol (anymol), a-santalol, Z-nuciferol and cw-p-santalol predominated. This considerably enlarged the number of known components in the oil of this species [174].

VERBENACEAE: Vitex trifolia, from Fiji, gave an oil in which p-caryophyllene was the major component [51], while fi'om Thailand, two varieties of this species gave oils in which 1,8-cineole, a-pinene and terpinyl acetate were the major component for var. simplicifolia and 1,8-cineole and p-caryophyllene were significant components [175]. V. limonifolia, also from Thailand, produced an oil in which both p-caryophyllene and caryophyllene oxide were significant components [176].

WINTERACEAE: The primitive vessel-less family Winteraceae contains two genera that occur in Australia, Zygogynum, a genus containing 3 species in Australia and Lord Howe Island, and Tasmannia, which contains 7 species in Australia. The three species of Zygogynum contain different oils, with Z. howeanum (endemic to Lord Howe Island) giving an oil in which p-caryophyllene was by far the major component. Z. semicarpoides oil had a significant amount of monoterpene hydrocarbons but with spathulenol being the major component. The two subspecies of Z. queenslandianum presented complicated oils with no one compound dominating and there appeared to be significant differences between the subspecies [178].

The genus Tasmannia, not surprisingly, produces different oils in its 7 species. T, glaucofolia had saffrole and terpinen-4-ol as major components; T. insipida had viridiflorol; T. lanceolata, 1,8-cineole and a-pinene; T. membanea, either viridiflorol or a-, p- and 7-eudesmol; T. purpurescens, limonene; T. stipitata, a-pinene and linalool; T. xerophila, a-phellandrene and a-pinene [177]. This is one case where chemotaxonomy can distinguish between the species. Not suiprisingly the steam distilled oils differed from those obtained by solvent extraction, which included more polar sesquiterpenes. Croweacin, previously only encountered in members of the genus Crowea (Rutaceae) was also identified in T. glaucophila.

Projects have also been undertaken with chemists outside Australia. Polyscias fruticosa (Araliaceae) gave oils in which the principal components differed depending on the source of the oil; being germacrene-D in oil from Fiji and either a-bergamotene or E-a-bisabolene in oil from growing in Thailand [179]. Eugenia javanica (Myrtaceae) also from Thailand gave an oil in which a-pinene, y-terpinene and p-cymene were principal components [180]. This was a quantitative difference from the other species previously examined.

Page 26 Collaborative work with overseas chemists have resulted in identification of essential oils of the following species:- Dacrydium nitidum andD. nausurense [181], Schinus terebinthifolium [182], Colophospermwn mopane (leaf, seed and bark [183], Erechtites valerianifolia Acacia spiwbis [185], Zingiber cassumunar [186], Pandanuspyroformis [187], Citrus lemon cv "Pant Lemon-1" [188], the majority being the first analyses of the essential oils of these species.

With other Australian scientists the following exotic and Australian species have also been examined. Piper methysticum [189], Piper nigram [190], Annona atemoya [191], Pistacia lentiscus [192], Granny Smith apples [103], Kippistia suaedifolia [194], Liquidamber styraciflora [195] ond Polygonum odoratum [196], the majority being examined for the first time. There has also been an examination of the oil excreted by the greater glider possum and brushtail possum which had been fed a diet of Eucalyptus radiata and E. melliodora leaves [197]. I have also been involved with identification of the compounds, subsequently identified as the monoterpene hydrocarbons A-3-carene and terpinolene, responsible for causing skin damage in mangos [198].

The remaining manuscripts listed in the Publications [199-21 l]have either been submitted or are accepted for publication, as opposed to 'in press'. They have not been made part of this thesis

Page 27 PUBLICATIONS

Ph.D. Work

1. Brophy, JJ. and Gallagher, MJ., The cleavage of bis-phosphonium salts by sodium hydride. Chem Commun., 531-532 (1966).

2. Brophy, J.J. and Gallagher, M.J., Proton magnetic resonance spectra of some organophosphorus compounds. Aust. J. Chem., 20: 503-513 (1967).

3. Brophy, J.J. and Gallagher, M.J., The hydrolysis of bis-phosphonium salts. Chem. Commun., 344-345 (1967).

4. Brophy, J.J. Freeman, K.L. and Gallagher, M.J., Some phenyl migrations in organophosphorus compounds. J. Chem. Soc. (C). 2760-2765 (1968).

5. Brophy, J.J. and Gallagher, M.J., The alkaline hydrolysis of bis-phosphonium salts. Aust. J. Chem., 22: 1385-1398(1969).

6. Brophy, J.J. and Gallagher, M.J., The reaction of bis-phosphonium salts with metal hydrides. Aust. J. Chem., 22: 1399-1404 (1969).

7. Brophy, J.J. and Gallagher, M.J., The action of cyanide ion and other nucleophiles on some phosphonium salts. Aust. J. Chem., 22: 1405-1413 (1969).

Mass Spectrometry Work

8. Brophy, J.J., Diakiw, V., Goldsack, R.J., Nelson, D. and Shannon, J.S., Anomalous ions in the chemical ionisation mass spectra of aromatic nitro and nitroso compounds. Org. Mass Sprectrom., 14: 210-203 (1979).

9. Brophy, J.J., Middleton,S., Nelson, D. and Shannon, J.S., Electron inpact and chemical ionisation mass spectra of aryl ureas. Org. Mass Spectrom., 14: 379-386 (1979).

10. Brophy, J.J.and Maccoll, A., Low energy, low temperaturemass spectra #9, the linear undecanols. Org. Mass Spectrom. 22: 659-662 (1988).

70. Brophy, J J., Shannon, J.S., Maccoll, A. and Mruzek, M.N. Low energy, low temperature mass spectra. Part 12* The identification of the isomers of the menthol and menthol methyl ethers by low energy, low temperature mass spectrometry. Int. J. Mass Spec, and Ion Phys. 92: 9-13 (1989).

12. Brophy, J.J. and Maccoll, A. Low energy, low temperature mass spectra. Part 15. The mass spectra of some monoterpene hydrocarbons. Org. Mass Spec. 27: 1042-1951 (1992).

13 Brophy, J.J., Crank, G., Minh, H. and Nelson, D., The electron impact and chemical ionisation mass spectra of 2,2-disubstituted-l,3-benzodioxoles. Org. Mass Spectrom., 15: 435-436 (1980).

14. Chan, L.K., Brophy, J.J., Cole, E.R., Southwell-Keely, P.T., Duffield, A.M. and Lidgard, R.O., Mass spectra of aryl sulphenamides. Org. Mass Spectrom., 22: 697-698 (1987).

15. Brophy, J.J., Goldsack, R.J., Forster. P.I., Clarkson, J.R. and Fookes, C.J.R. Mass spectra of some p-triketones from Australian Myrtaceae. J. Essent. Oil Res. 8: 465-470 (1996).

16. Brophy, J.J., Morgan, J.T., and Nelson, D., Linear mass scale from a magnetic mass spectrometer using a microprocessor. Computers and Chem., 3: 65-69 (1979).

17. Brophy, J.J., Kingston, E.E., Morgan, J.T. and Nelson, D., Microprocessor controller for linked scans of electric sector voltage and magnetic field in a magnetic double-focussing mass spectrometer. Int. J. Mass Spectrom. and Ion Phys., 35: 319-334. (1980).

16. Brophy, J.J., Goldsack, R.J., Lidgard, R.O., Melley, D.P. and Nelson, D., Elemental compositions from low resolution magnetic mass spectrometers. Lab. Practice. 28, 615-619 (1979).

Page 28 19. Brophy, J J., Nelson, D. and Withers, M.K. A packed microbore liquid chromatography column used as a direct probe inlet for a chemical ionisation mass spectrometer. Int. J. Mass Spectrom. and Ion Phys., 36: 205-323 (1980).

Synthetic Chemistry Work

20. Brophy, J J. and Griffin, G. W., A convenient route to cyclopropanol derivatives. Tetrahedron Lett., 493- 496 (1970).

21. Brophy, J.J., The di-7C-methane rearrangement of 1,3,3-triarylprop-l-enes. Aust. J. Chem., 29: 2445- 2457 (1976).

22. Blatt, H., Brophy, J.J., Colman, L.J. and Tairych, W.J., Reaction of diarylcarbinols and diarylolefins with thionyl chloride: A synthesis of 3-arylbenzothiophenes. Aust. J. Chem., 29: 883-890 (1976).

23. Atkinson, E.J., Brophy, J,J. and Clezy, P.S. Chemistry of pyrrolic compounds LXII. The oxidative cyclization of bilenes-b: Identification of the expelled carbon fragment. Aust. J. Chem. 43:383-391 (1990).

Insect Chemistry Publications

24. Brophy, J.J., Cavill, G.W.K. and Shannon, J.S., Constituents of the Dufour's and venom gland of the ant Camponotus intrepidus. J. Insect Physiol., 12:791-798 (1973).

25. Cavill, G.W.K., Robertson, P.L., Brophy, J.J., Duke, R.K., Orton, C.J., and , W.D., Defensive and other secretions of the Australian cocktail ant, Iridomyrmex nitidiceps. Tetrahedron, 32: 1931-1938 (1982).

26. Cavill, G.W.K., Robertson, P.L., Brophy, J.J., Duke, R.K., McDonald, J.A. and Plant, W.D., Chemical ecology of the meat ant,/r/dowtyrmejc purpMreMs sens strict. Insect Biochem., 14:505-513 (1984).

27. Brophy, J.J., Cavill, G.W.K., Davies, N.W., Gilbert, T.D., Philp, R.P. and Plant, W.D., Hydrocarbon constituents of three species of dolichoderine ants. Insect Biochem., 13: 381-389 (1983).

28. Brophy, J.J., Clezy, P.S., Leung, C.W.F. and Robertson, P.L. Secondary amines from the venom gland of the Dolichoderine ant Technomyrmes albipes. J. Chem. Ecol. 19: 2183-2192 (1993).

29. Smith, R.M., Brophy, J.J., Cavill, G.W.K. and Davies, N.W. Iridodials and nepetalactone in the defensive secretion of the coconut stick insect, Graffae crounai. J. Chem. Ecol., 5: 727-735 (1979).

30. Brophy, J.J., Nelson, D. and Paille, R.R., A vacuum aspiration apparatus for the effecient collection of ants. J. Aust. Ent. Soc., 21: 303-305 (1982).

31. Brophy, J.J., Cavill, G.W.K., MacDonald, J.A., Nelson, D. and Plant, W.D., Volatile constituents of two species of Australian Formicine ants of genera w\<\Polyrhachus. Insect Biochem., 12: 215- 219 (1982).

32. Brophy, J.J., Cavill, G.W.K. and Plant, W.D., Volatile constituents of an Australian ponerine ant, Rhytidoponera chalaebya. Insect Biochem., 11: 307-311 (1981).

33. Brophy, J.J., Cavill, G.W.K. and Duke, R.K., Volatile constituents of the ponerine ant Rhytidoponera aciculata{Sm\\h). Insect Biochem., 13:503-506(1983).

34. Tecle, B., Sun, C.M., Brophy, J.J. and Toia, R.F., Novel pyrazines from the head of the Australian ponerine mi Rhytidoponera metallica. J. Chem. Ecol, 13: 1811-1822 (1987).

35. Brophy, J.J. and Nelson, D., 2,5-Dimethyl-3-n-propylpyrazine from the head of the bull ant, Myrmecia gulosa {Fabt.). Inset Biochem., 15:363-365 (1985).

36. Brophy, J.J., Sun C.-M., Tecle, B. and Toia, R.F. Mass spectrometric fragmentations of isomeric 5- methyl-3-alkyl-2-alkenylpyrazines. Org. Mass Spectrom, 24: 609-614 (1989).

Page 29 37. Tecle, B., Brophy, J.J. and Toia, R.F., Biosynthesis of 2-hydroxy-6-methylacetophenone in the Australian ^nQn\\QmiRhytidoponeraaciculata{Sm\ih). Insect Biochem., 16:333-336 (1986).

38. Brophy, J.J., Sun, C.M., Tecle, B. and Toia, R.F., Chemistry of Australian ants: 2,5-dimethylchromone from Rhytidoponera metallica, J. Nat. Prods. 51: 99-102 (1988).

39. Cox, M.F., Brophy, J.J. and Toia, R.F., Chemotaxonomy of the Australian Dolichoderinae: Volatile constituents oi [ridomyrmex ?discors. J. Nat. Prods. 52: 75-80 (1989).

40. Brophy, J.J. and Cavill, G.W.K., Naturally occurring pyrazines and their mass spectral characterisation. Heterocycles, 14: 477-504 (1980).

41. Brophy, J.J. Pyrazines obtained from insects: their source, identification, synthesis and function, in Atta- Ur-Rahman (Ed.) Studies in Natural Products Chemistry 5: Structure Elucidation - Part B, pp 221-273 (1989).

Essential Oils Publications

42. Boland, D.J., Brophy, J.J. and House, A.P.N. (Eds.) Eucalyptus oils: Use, Chemistry, Distillation and Marketing. Inkata I*ress, Melbourne. 1991.

43. Brophy, J.J. and Doran, J.C. Essential Oils of Tropical Asteromyrtus, Callistemon andMelaleuca Species. ACIAR Monograph No. 40. 144pp (1996).

44. Southwell, I.A. and Brophy, J.J. Essential oil isolates from the Australian flora. Part 3. J. Essent. Oil Res., in press.

45. Brophy, J.J,, Goldsack, R.J. and Forster. P.I. The leaf essential oil of Fitzalania heteropetala F. Muell. (Annonaceae). J. Essent. Oil Res. 9:93-94 (1997).

46. Brophy, J.J., Fookes, C.J. R. and House, A.P.N. The leaf essential oil of Haplostichanthus johnsonii F. Muell. J. Essent. Oil Res. 4 : 315-316 (1992).

47. Brophy, J.J., Goldsack, R.J. and Forster. P.I., The essential oils of the Australian species of Xylopia (Annonaceae). J. Essent. Oil Res., 10, 469-472 (1998).

48. Brophy, J.J., Goldsack, R.J., Wu., M.Z., Fookes, C J.R. and Forster, P.I. The chemistry of the Australian Gymnosperms. The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae. Biochem. Syst. Ecoi, 28, 563-578 (2000).

49. Brophy, J.J., Goldsack, R.J. and Forster, P.I. The leaf essential oil of Austrobaileya scandens C. White. J. Essent. Oil Res., 6: 301-303 (1994).

50. Brophy, J.J. and Goldsack, RJ. The leaf essential oil of Idiospermum australiense (Diels) S.T. Blake (Idiospermaceae). Flavour and Fragr. J. 7:79-80(1992).

51. Laily Bin Din, Zuriata Zakaria, Mohd Wahid Aamusudin, Brophy, J.J. and Toia, R.F., Composition of the steam volatile ois from//yp/w Poit. Pertanika, 11:239-242(1988).

52. Brophy, J.J. and Lassak, E. V., The volatile leaf oils of Hyptis pectinataa (L.) Point, and Vitex trifolia L. \dS.bicolor. (Willd.) Moldenke from Fiji. Flavour and Fragr. J., 2: 41-43 0987).

53. Brophy, J.J., Goldsack, R.J., Forster, P.I. and Fookes, C.J.R., The leaf essential oil of Mentha grandiflora Benth. (Lamiaceae). J. Essent. Oil Res. 9, 459-461 (1997).

54. Brophy, J.J., Goldsack, R.J., Lawrence, B.M. and Forster, P.I. The esssential oil of Mentha diemenica (Lamiaceae). J. Essent. Oil Res. 8: 179-181 (1996).

55. Brophy, J.J., Clarkson, J.R. and Goldsack, R.J. The essential oil of Ocimum tenuiflorum L, (Lamiaceae) growing in northern Australia. J. Essent. Oil Res. 5: 459-461 (1993).

Page 30 56. Brophy, J.J. and Jogia, M.K. Essential oils from Fijian Ocium basilicum. Flavour and Fragr. J., 1: 53- 55 (1986). 57. Brophy, J.J. and Jogia, M.K., Essential oils from two varieties of Fijian Ocimum sanctum (Tulsi), Fiji Agric. J., 46: 21-26 (1984). 58. Brophy, J.J., Goldsack, R.J. and Forster. P.I. The leaf essential oil of Cryptocarya cunninghamii Meissner (Lauraceae). J. Essent. Oil Res. 10, 73-75 (1998). 59. Brophy, J.J., Goldsack, R.J. and Forster, P.I., The essential oil of Lindera queenslandica (Lauraceae). J. Essent. Oil Res. 11, 453-455 (1999). 60. Brophy, J.J., Goldsack, R.J. and Forster, P.I, The essential oil of Austromatthaea elegans L.S. Smith (Monimiaceae). J. Essent. Oil Res. 7:585-588 (1995), 61. Brophy, J,J., Goldsack, R J., House, A,P.N. and Lassak, E.V, The essential oils of the genus Doryphora. J. Essent. Oil Res. 5: 581-586 (1993). 62. Brophy, J.J., Goldsack, R.J. and Forster. P.I., The essential oils of some Australian Monimiaceae. Flavour Fragr. J., 13: 273-276 (1998). 63. Brophy, J.J., Goldsack, R.J. and Forster. P.I. The essential oil of Acmenosperma claviflorum (Myrtaceae). J. Essent. Oil Res., 11, 162-164 (1999). 64. Brophy, J.J. ^d Goldsack, R.J., The essential oil of the leaves and flowers of Actinodium cunninghamii Schauer (Myrtaceae). J. Essent. Oil Res. 6: 639-640 (1994). 65. Brophy, J.J., Goldsack, R.J. and Craven, L.A. The leaf essential oil of Angasomyrtus salina Trudgen & Keighery. J. Essent. Oil Res. 6: 69-71 (1994) 66. Brophy, J.J,, Goldsack, R,J, and Forster. P.L Variation in Archirhodomyrtus beckleri (Myrtaceae): evidence from volatile oils. Flavour Fragr. J. 11: 11-14 (1996). 67. Brophy, J.J,, Clarkson, J.R., Craven, L.A. and Forrister, P.I. The essential oils of the Australian members of the g^ms Asteromyrtus (Myrtaceae). Biochem. Sys. EcoL, 22: 409-417 (1994). 68. Brophy, J.J., Goldsack, R.J. Fookes and Forster, P.I. The Essential oils of Australian Austromyrtus sens, lat. Part 2. IhQ A. lasioclada Flavour Fragr. J. 10:293-296(1995). 69. Brophy, J.J., Goldsack, R.J. and Forster, P.I. E-P-ocimene from two species of Austromyrtus (Myrtaceae). J. Essent. Oil Res. 7: 1-4 (1995), 70. Brophy, J.J., Goldsack, R.J. Fookes, C,J.R. and Forster. P.I. The Essential oils of Australian Austromyrtus sens Aat. Partffl. The A. bidwillii group. Flavour Fragr. J. 11,275-287 (1996). 71. Brophy, J.J., Goldsack, RJ., Fookes, CJ.R. and Forster, P.I. The Essential oils of Australian Austromyrtus sens. lat. Part 1. The A. dulcis group. Flavour Fragr. J. 10: 69-73 (1995). 72. Brophy, J.J., Clarkson, J.R. and Fookes, C.J.R. Angustifolenone, a new ketone from Backhousia angustifolia. Fhytochemistry, 28: 1259-1261 (1989). 73. Brophy, J.J. and Boland, D.J. The leaf essential oil of two chemotypes of Backhousia anisata Vickery. Flavour Fragr. J., 6: 187-188 (1991). 74. Brophy, J.J., Goldsack, R.J. Fookes, C.J.R. and Forster, P.I. The leaf essential oils of the genus Backhousia (Myrtaceae). J. Essent. Oil Res. 7: 237-254 (1995). 75. Brophy, J,J., Goldsack, R.J., Forster, P.I., Craven, L.A. and Lepschi, B.J. The leaf essential oils of the Australian members of the genus Callistemon (Myrtaceae). J. Essent. Oil Res., 10, 595-606 (1998). 76. Brophy, J.J., Lassak, E.V. and Toia, R.F., The volatile leaf oils of Callistemon viminalis. J. & Proc. Royal Soc. N.S.W.. 118: 101-104 (1985).

Page 31 77. Brophy, J.J., Forster, P.I., Goldsack, R.J., Hibbert, D.B. and Punruckvong A. Variation in Callistemon viminalis (Myrtaceae): New evidence from volatile oils. Aust. Syst. Bot., 10, 1-13 (1997).

78. Brophy, J.J., Goldsack, R.J. and Forster, P.I. The essential oils of Choricarpia leptopetala (F. Muell.) Domin and C. subargentea (C. White) L.A.S. Johnson (Myrtaceae). Flavour Fragr. J.. 9: 7-10 (1994).

79. Brophy, J.J., Goldsack, R.J., Comwell, C.P., Leach, D.N., Wyllie, S.G., Forster, P.I. and Fookes, C.J.R., Z-P-Ocimene from two species of Homoranthus (Myrtaceae). J. Essent. Oil Res. 10: 229-233 (1998).

80. Brophy, J.J., Goldsack, R.J. and Lassak, E.V. Leaf essential oils of some Leptospermum (Myrtaceae) species from southern and Western Australia. J. Essent. Oil Res., 11, 1-5 (1999).

81. Brophy, J.J., Goldsack, R.J., Forster, P.I., Bean, A.R., Clarkson, J.R. and Lepschi, B.J. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 1, L. brachiandrum and L. pallidum groups. Flavour Fragr. J. 13,19-25 (1998).

82. Brophy, J.J., Goldsack, R.J., Forster, P.I., Bean, A.R. and Lepschi, B.J. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 2, L. blakelyi and its allies. Flavour Fragr. J. 13: 353-358 (1998).

83. Brophy, J.J., Goldsack, R.J., Forster, P.I., Bean, A.R. and Lepschi, B J. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 3, L. arachnoides and its allies. Flavour Fragr. J. 14, 85-91 (1999).

84. Brophy, J.J., Goldsack, R.J., Forster, P.I., Bean, A.R. and Lepschi, B.J. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 4, Leptospermum deanei and allies. Flavour Fragr. J., 14, 92-97 (1999).

85. Brophy, J.J., Goldsack, RJ., Forster, P.L, Bean, A.R. and Lepschi, B.J. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 5, L. continentale and its allies. Flavour Fragr. J. 14, 98-104 (1999).

86. Brophy, J.J., Goldsack, RJ., Forster, P.I., Bean, A.R. and Lepschi, B.J. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 6, L. polygalifolium and its allies. Flavour Fragr. J. in press.

87. Brophy, J.J., Goldsack, R.J., Punruckvong, A., Forster, P.L, Bean, A.R. Lepschi, B.J., Doran, J.C. and Rozefelds, A.C. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 7, L. petersonii, L. liversidgei and their allies. Flavour Fragr. J. accepted for publication.

88. Brophy, J.J., Boland, D.J. and Lassak, E.V., Survey of the Leaf essential oils of Melaleuca and Leptospermum species from tropical Australia, in Trees For The Tropics - Growing Australian multipurpose trees and shrubs in developing countries, ed. Boland, D.J. ACIAR, pp 193-203 (1989)

89. Brophy, J.J., Goldsack, R.J., Forster, P.I. and Clarkson, J.R. The essential oils of Welchiodendron longivalve and Lindsayomyrtus racemoides (Myrtaceae) leaves. Flavour Fragr. J. 11: 67-70 (1996).

90. Brophy, J.J., Goldsack, R.J. and Forster, P.I., Esssential oils of the genus Lophostemon (Myrtaceae). Flavour Fragr. J. 15, 17-20 (2000).

91. Brophy, J.J., Goldsack, R.J. and Forster, P.L The essential oil of Lysicarpus angustifolius (Hook.) Druce (Myrtaceae). J. Essent. Oil Res., 6: 139-143 (1994).

92. Brophy, J.J., Lassak, E.V. and Boland, D.J., Steam volatile oils of Melaleuca globifera, M. lateriflora, M. symphyocarpa and M. uncinata. Flavour Fragr. J. 5:43-48(1990).

93. Brophy, J.J., Lassak, E.V. and Boland, D.J., Volatile leaf oils of six northern Australian broad-leaved melaleucas. J. & Proc. Roy. Soc. N.S.W. 121: 29-33 (1988).

94. Brophy, J.J. and Lassak, E.V.L. Steam volatile leaf oils of some Melaleuca species from Western Australia. Flavour Fragr. J. 7: 27-31 (1992).

Page 32 95. Brophy, JJ. Potentially Commercial Melaleucas, in Medicinal and Aromatic Plants - Industrial Profiles: Tea Tree, The G&nv&Melaleuca. ed by Southwell, LA. and Lowe R., Harwood Academic Publishers, Netherlands. pp247-274 (1999).

96. Brophy, J.J., Lassak, E.V. and Boland, D.J., Volatile leaf oils of the two subspecies of Melaleuca acacioides F. Muell. J. & Proc.Roy. Soc. N.S.W. 120: 135-139 (1987).

97. Brophy, J.J. and Lassak, E.V. The volatile leaf oils of Melaleuca armillaris, M. dissitiflora and M. trichostachya. J. & Proc. Royal Soc. N.S.W.. 116: 7-10)1983).

98. Brophy, J.J., Davies, N.W., Southwell, I.A., Stiff, LA. and Williams, L.R. Gas chromatogrpahic quality control for oil of Melaleuca - terpinen-4-ol type (Australian Tea Tree). J. Agric. Food. Chem. 37: 1330- 1335 (1989).

99. Southwell, LA., Stiff, LA. and Brophy, J.J. Terpinolene varieties of Melaleuca. J. Essent. Oil Res. 4: 363-367 (1992).

100. Brophy, J.J. and Clarkson, J.R. The essential oils of four chemotypes of Melaleuca citrolens. J. & Proc. Roy. Soc. N.S.W., 122: 11-18 (1989).

101. Brophy, J.J. and Lassak, E.V., The leaf oil of Melaleuca leucadendra. L., Two phenylpropanoid chemotypes. Flavour Fragr. J., 3:43-46(1988).

102. Brophy, J.J., Goldsack, R.J., Doran, J.C., Craven, L.A. and Lepschi, B.J. A comparison of the leaf oils of Melaleucd squamophloia with those of its close relatives M. styphelioides and M. bracteata. J. Essent. Oil Res., 11, 327-332 (1999).

103. Brophy, J.J., Goldsack, R.J. and Goldsack, G. The essential oils of the indigenous Myrtaceae of Lord Howelsalnd. Flavour Fragr. J., 8: 153-159(1993).

104. Southwell LA. and Brophy J.J. /^o-Amyl wo-valerate from the essential oil of Micromyrtus striata J.W, Green. J. Essent. Oil Res. 3: 281-283 (1991).

105. Brophy, J.J. and Clarkson, J.R. The essential oils of the genus Neofabricia. Biochem. Sys. Ecol. 20: 689-696 (1992).

106. Brophy, J.J., Clarkson, J.R. and Goldsack, R.J. The essential oil of Osbornia octodonta F. Muell. J. Essent. Oil Res. 5: 1-5 (1993).

107. Brophy, J.J., Goldsack, R.J., Punruckvong, A. and Forster. P.L, Leaf essential oils of Pilidiostigma. Flavour Fragr. J. 14, 143-146(1999).

108. Brophy, J.J., Goldsack, R.J. and Forster. P.L The essential oils of Australian species of Rhodamnia (Myrtaceae). Flavour Fragr. J. 12: 345-354 (1997).

109. Brophy, J.J., Goldsack, R.J. and Forster. P.L The leaf essential oils of Australian species of Rhodomyrtus (Myrtaceae). Flavour Fragr. J. 12: 103-108(1997).

110. Brophy, J J., Craig, D.C., Goldsack, R.J. and Fookes, C.J.R., Hillyl acetate, a keto-acetate from the leaf steam volatiles of 5j;icflrp/A M/K Bailey. Phytochemistry 37: 1645-1647 (1994). 111. Brophy, J.J., Goldsack, R.J., Bean, A.R., Forster. P.L, and Fookes, C.J.R. The leaf essential oil of the genus Syncarpia Ten. (Myrtaceae). Flavour Fragr. J. 11: 361-366 (1996).

112. Brophy, J.J., Goldsack, R.J. and Forster. P.L The essential oil of Thaleropia queenslandica (Myrtaceae). J. Essent. Oil Res. 9: 587-588 (1997).

113. Brophy, J.J., Goldsack, R.J., Forster, P.L and Clarkson, J.R., The essential oils of the Queensland species of Thryptomene (Myrtaceae). J. Essent. Oil Res. 12, 11-13 (2000).

114. Brophy, J.J., Goldsack, R.J. and Forster, P.L, The essential oil of Australian species of the genera Tristaniopsis and Tristania J. Essent. Oil Res. 11, 661-665 (1999).

Page 33 115. Brophy, J.J., Golcisack,RJ. and Forster, P.I. The essential oils of the Australian species of Uromyrtus (Myrtaceae). Flavour Fragr. J. 11:133-138(1996).

116. Boland, D.J., Brophy, J.J. and Goldsack, R.J. The leaf essential oil of Arillastrum gummiferum (Brongriart & Gris) Pancher ex Baillon. Flavour Fragr. J., 9: 47-49 (1994).

117. Brophy, J.J., Fookes, C-J.R. and House, A.P.N.H. 2,4,6-Trimethoxytoluene from a plant of genus "Stockwellia". Phytochemistry 31: 324-325 (1992).

118. Brophy, J.J. Jind Boland, D.J. The leaf essential oil of Allosyncarpia ternata. Flavour Fragr. J. 7: 117-119 (1992).

119. Dunlop, P.J., Bignell, C.M., Brooker, M.I.H., Brophy, J.J. and Hibbert, D.B., Use of gas chromatograms of essential leaf oil to compare eight taxa of genus Angophora (Myrtaceae): possible relationships to the genus Eucalyptus. Biochem. Syst. Ecol. 27, 815-830 (1999).

120. Brophy, J.J., Forster, P.I., Goldsack, R.J. and Hibbert, D.B., The essential oils of the yellow blood eucalypts (Corymbia section Ochraria, Myrtaceae). Biochem. Syst. Ecol., 26: 239-249 (1998).

121. Boland, D.J. and Brophy, J.J. A search of chemical trends in the essential ols of the Eucalypts and related genera. Ch7, pp71-87, in Volatile Attractants from Plants, Eds Buttery, R.G., Sugisawa H. and Teranishi, R. ACS Symposium Series No. 525 (1993).

122. Van Klink, J.W., Brophy, J.J., Perry, N.B. and Weavers, R.T., p-Triketones from Myrtaceae: Isoleptospermone from Leptospermum scoparium and papuanone from Corymbia dallachiana. J. Nat. Prods., 62, 487-489 (1999).

123. Brophy, J.J. and Boland, D.J. Leaf essential oil of two chemotypes of J^wca/ypto J.Essent. Oil Res., 2: 87-90 (1990).

124. Brophy, J.J., Goldsack, R.J. and Forster. P.I., The essential oils of three unusual eucalypts: Eucalyptus curtisii, E. rubiginosa and£. tenuipes (Myrtaceae). Flavour Fragr. J. 13, 87-89 (1998).

125. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part XII. A - Subgenus Eudesmia. B - Subgenus Symphyomyrtus, (a) Section Exsertaria, (b) Series Globulares. Flavour Fragr. /., 11, 145-151 (1996).

126. Bignell, C.M., Dunlop, P.J. and Brophy, J J. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XIX. Flavour Fragr. /., 13, 131-139 (1998).

127. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Fookes, C.J.R. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XIV - Subgenus Monocalyptus. Flavour Fragr. J., 12, 177-183 (1997) .

128. Bignell, C.M., Dunlop, P.J. and Brophy, J.J. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XV - Subgenus Symphyomyrtus, Section Bisectaria, Series Levispermae. Flavour Fragr. J., 12,185-193 (1997).

129. Bignell, C.M., Dunlop, P.J. and Brophy, J.J. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XVIIl. A - Subgenus Monocalyptus. B - Subgenus Symphyomyrtus, (i) Section Guilfoyleanae, (ii) Section Bisectaria, Series Accedentes, Series Occidentales, Series Levispermae, Series Loxophlebae, Series Macrocarpae, Series Orbifoliae, Series Calycogonae, (iii) Section Dumaria, Series Incrassatae and Series Ovulares. Flavour Fragr. J., 12,423-432 (1997).

130. Boland, D.J., Gilmore, P.M. and Brophy, J.J., Eucalyptus deuaensis (Myrtacae), a new species of Mallee from Deua National Park, South Coast of New South Wales. Brunonia., 9: 105-112 (1986).

131. Boland, D.J., Brophy, J.J. and Lassak, E.V., Steam volatile seedling oils of Eucalyptus delegatensis. Phytochemistry, 21: 2467-2469 (1982).

132. Brophy, J.J., Lassak, E.V., Soe Win and Toia, R.F., The volatile leaf oils of Eucalyptus youmanii and Eucalyptus niacrorhyncha. J. Sci. Soc. Thailand. 8: 137-145 (1982).

Page 34 133. Bignell, C.M., Dunlop, P.J., Brophy, J.J, and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part I - Subgenus Symphyomyrtus, Section Dumaria, Series Incrassatae. Flavour Fragr. J., 9,113-117 (1994).

134. Bignell, C.M., Dunlop, P.J., Brophy, JJ. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part II - Subgenus Symphyomyrtus, Section Dumaria, Series Torquatae. Flavour Fragr. J., 9,167-171 (1994).

135. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part III - Subgenus Symphyomyrtus, Section Bisectaria, Series Macrocaipae. Flavour Fragr. J., 9, 309-313 (1994).

136. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part IV - Subgenus Symphyomyrtus, Section Dumaria, Series Dumosae. Flavour Fragr. J., 10,85-91 (1995).

137. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part V - Subgenus Symphyomyrtus, Section Bisectaria, Series Oleosae. Flavour Fragr. J., 10,313-317 (1995).

138. Bignell, C.M., Dunlop, P.J., Brophy, J J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part VI - Subgenus Symphyomyrtus, Section Adnataria. Flavour Fragr. J., 10, 359-364 (1995).

139. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part VII - Subgenus Symphyomyrtus, Section Exsertaria. Flavour Fragr. /., 11,35-41 (1996).

140. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part VIII - Subgenus Symphyomyrtus, (a) Section Bisectaria, Series Comutae and Series Bakeranae and (b) Section Dumaria, unpublished Series Furfuraceae group. Flavour Fragr. J., 11, 43-47 (1996).

141. Bignell, C.M., Dunlop, P.J., Brophy, J J. and Jackson, J.F, Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part IX - Subgenus Symphyomyrtus, Section Bisectaria, (a) Series Elongatae, (b) unpublished Series Stricklandiae, (c) Series K^seanae and (d) Series Orbifoliae. Flavour Fragr. J., 11,95-100 (1996).

142. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part X - Subgenus Symphyomyrtus, Section Bisectaria, (a) unpublished Series Erectae, (b) Series Contortae and (c) Series Decurvae. Flavour Fragr. J., 11, 101-106 (1996).

143. Bignell, C.M., Dunlop, P.J., Brophy, J J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus. Part XI - Subgenus Symphyomyrtus. A - Section Bisectaria, (a) Series Occidentales, (b) unpublished Series Annulatae, (c) Series Micromembranae, (d) Series Obliquae, (e) Series Dundasianae, (f) Series Cooperianae, (g) Series Halophilae, (h) Series Salmonophloiae and (i) Series Pubescentes. B - Section Dumaria, (a) Series Merrickianae. Flavour Fragr. J., 11,107-112 1996).

144. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XIII - (a) Series Subulatae, (b) Series Curviptera, (c) Series Contortae, (d) Series Incognitae, (e) Series Terminaliptera, (0 Series Inclusae, (g) Series Microcorythae and (h) Series Cornutae. Flavour Fragr. J., 11,339-347 (1996).

145. Bignell, C.M., Dunlop, P.J., Brophy, J.J. and Jackson, J.F. Volatile leaf oils of some Queensland and northern Australian species of the genus Eucalyptus (Series II). Part I - Subgenus Symphyomyrtus, Section Adnataria, (a) Series Oliganthae, (b) Series Ochrophloiae, (c) Series Moluccanae, (d) Series Polyanthemae, (e) Series Paniculatae, (f) Series Melliodorae and (g) Series Porantheroideae. Flavour Fragr. J., 12,19-27 (1997).

Page 35 146. Bignell, C.M., Dunlop, P.J. and Brophy, J J. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XVI - Subgenus Symphyomyrtus, Section Bisectaria, Series Cneorifoliae, Series Porantherae and Series Falcatae. Flavour Fragr. J., 12, 261-267 (1997).

147. Bignell, C.M., Dunlop, PJ. and Brophy, JJ. Volatile leaf oils of some south-western and southern Australian species of the genus Eucalyptus (Series I). Part XVII - Subgenus Symphyomyrtus, (i) Section Bisectaria, Series Calycogonae and (ii) Section Dumaria, Series Dumosae, Series Rigentes and Series Ovulares. Flavour Fragr. /., 12, 269-275 (1997).

148. Bignell, C.M., Dunlop, P.J. and Brophy, J.J. Volatile leaf oils of some Queensland and northern Australian species of the genus Eucalyptus (Series II). Part II - Subgenera (a) Blakella, (b) Corymbia, (c) unnamed, (d) Idiogenes, (e) Monocalyptus and (0 Symphyomyrtus. Flavour Fragr. J., 12, 277-284 (1997).

149. Doran, J.C., Caruhapattana, B., Brophy, J.J. and Namsavat S. Effect of time of harvest on yield of leaves and essential oils of Eucalyptus camaldulensis. J. Essent. Oil Res. 7: 627-632 (1995).

150. Doran, J.C. and Brophy, J J. The tropical red gums - A source of high cineole eucalyptus oils. New Forests. 4: 157-178 (1991).

151. Doran, J.C., Williams, E.R. and Brophy, J.J. Patterns of variation in the leaf oils of Eucalyptus urophylla, E. pellita and E. scias. Aust. J. Bot. 43: 327-336 (1995).

152. Singh. A.K., Gupta, K.C. and Brophy, J.J. Chemical constituents of the essential oil of Eucalyptus pellita. Benth. J. Essent. Oil Res. 2: 147-148 (1990).

153. Boland, D.J. , Brophy, J.J. and Fookes, C.J.R. Jensenone, a new ketone from Eucalyptus jensenii Maiden. Fhytochemistry 31: 2178-2179 (1992).

154. Brophy, J. J., Lassak, E.V. and Boland, DJ. The leaf essential oils of Eucalyptus nova-anglica. J. Essent. Oil Res. 4: 29-32 (1992).

155. Brophy, J.J., Lassak, E.V. and Toia, R.F., Thtsltam \o\2Li\\& oiloiEucalyyptus pulverulenta. Flanta Medica., 170-171 (1985).

156. Singh. A.K., Gupta, K.C. and Brophy, J.J. Chemical constituents of the leaf essential oil of Eucalyptus brassiana S.T.Blake. J. Essent. Oil Res. 3: 45-47(1991).

157. Singh, A.K., Gupta, K.C. and Brophy, J.J. Volatile constituents of the essential oil of Eucalyptus bridgesiana growing in India. J. Essent. Oil Res. 3:449-450(1991).

158. Brophy, J.J. and Boland, D.J., 'Lq2£ oi\ oi Eucalyptus bakeri Maiden. inTrees For The Tropics - Growing Australian multipurpose trees and shrubs in developing countries, ed. Boland, D.J. ACIAR, pp 205-207,(1989)

159. Boland, D.J., Kleinig, D.A. and Brophy, J.J., Eucalyptus fusiformis (Myrtaceae), a new species of ironbark (series Faniculatae) from north-eastern New South Wales, Brunonia, 10: 210-215 (1987).

160. Brophy, J.J. and Lassak, E.V., The volatile leaf oils of some central Australian species of Eucalyptus. J. iSc Proc. Royal Soc. N.S.W.. 119: 103-108 (1986).

161. Brophy,J.J. and Lassak, E.V. Steam volatile oils of some Western Australian JEwca/jprMj species. Flavour Fragr. J. 6: 265-269 (1991).

162. Hang, Nguyen Thai, Dung, Nguyen Xuan, Lo, Vu Ngoc, Do, Nguyen Than, Brophy, J.J., Thuan, Pho Due, Thin, Nguyen Thi, and Khang, Nguyen Duy. Study of the essential oils of Eucalyptus cultivated in Vietnam. ACGC Chem. Res. Commun., 5: 5-10 (1996).

163. Brophy, J.J., Southwell, I.A, and Stiff, I.A., Volatile constituents of Boronia latipinna. J. Nat. Prods., 49: 174-177 (1986).

164. Brophy,J.J., Goldsack,R.J. andForster.P.I. The essential oil of BoMc/za/t/az/a neurococca (Rutaceae) leaves. J. Essent. Oil Res. 6, 505-506 (1994).

Page 36 165. Brophy, JJ. .'ind Lassak, E,V., Volatile leaf oil of pw/c/je/ZM/n (Rutaceae). Flavour and Fragrance J., 1.155-157(1986).

166. Brophy, J.J., Goldsack, R.J., Punruckvong, A., Forster. P.I. and Fookes, C.J.R. The essential oils of the genus Crowea (Rutaceae). J. Essent. Oil Res. 9, 401-409 (1997).

167. Bayly, M.J., Brophy, J.J., Forster, P.I., Goldsack, R.J. and Wilson, P.O. Reinstatement of Eriostemon banksii (Rutaceae), with a report on the composition of leaf essential oils in E. banksii and E. australasius s. s(r. Aust. Syst. Bot. 11: 13-22 (1998).

168. Brophy, J J., Croft, K.D., Lassak, E.V„ Rahmani, M. and Tioa, R.F., The volatile oil of Euodia hortensis., Flavour Fragr. J., 1: 17-20(1985).

169. Brophy, J.J. and Goldsack, R.J., The essential oil of the leaves and flowers of Geleznowia verrucosa Turcz. (Rutaceae). J. Essent. Oil Res. 7: 663-665 (1995).

170. Brophy, J.J., Goldsack, R.J., Forster. P.I. and Hutton, I. The leaf essential oils of Lunasia amara var. amara and Sarcomelicope simplicifolia subsp. simplicifolia (Rutaceae) from Australia. J. Essent. Oil Res. 9: 141.144 (1997).

171. Brophy, J.J., Goldsack, R.J. and Forster. P.I. Chemotype variation in the leaf essential oils of Melicope melanophloia C.T. White (Rutaceae). J. Essent. Oil Res. 9: 279-282 (1997).

172. Brophy, J.J., Forster, P.I. and Goldsack, R.J. Diversity in Australian populations of Murraya paniculata (Rutaceae): New evidence from volatile leaf oils. Aust. Sys. Bat., 7: 409-418 (1994).

173. Brophy, J.J., Goldsack, R.J., Forster. P.I. and Hutton, I. The essential oils of the Australian and Lord Howe Island species of Zanthoxylum (Rutaceae). J. Essent. Oil Res., in press.

174. Brophy, J.J., Fookes, C.R.J. and Lassak, E.V. Constituents of Santalum spicatum (R.Br.) A. DC. Wood oil. J. Essent. Oil Res. 3: 381-385 (1991).

175. Suksamrarn, A., Werawattanametin, K. and Brophy, J.J. Variation of essential oil constituents in the Vitex trifolia species. Flavour Fragr. J., 6: 97-99 (1991).

176. Suksamrarn, A., Aphaijitt, S. and Brophy, J.J. The volatile leaf oil of Vitex limonifolia Wall. Flavour Fragr. J., 5: 53-55 (1990).

177. Southwell, I.A. and Brophy, JJ. Differentiation within the Australian Tasmannia by essential oil comparison. Phytochemistry 31: 3073-3081 (1992).

178. Brophy, J.J., Goldsack, R.J., Goldsack, G. and Forster, P.I. Leaf essential oil of the Australian members of the genus Zygogynum. J. Essent. Oil Res. 6: 353-361 (1994).

179. Brophy, J.J., Lassak, E.V. and Suksamrarn, A. Volatile leaf oils olPolyscias fruticosa. Flavour Fragr. /., 5: 179-182 (1990).

180. Suksamarain, A. and Brophy, J J., The volatile leaf oil of ^M^ewa yavawca. Flavour Fragr. J., 2:37-40 (1987).

181. Brophy, J.J. and Jogia, M.K., Major constituents of the essential oils of Fijian Dacrydiums. J. Nat. Prods.. 49: 730-732 (1986).

182. Singh, A.K., Singh, J., Gupta, K.C. and Brophy, J.J., Essential oil of leaves and inflorescence of Schinus terbinthifolius: An exotic plant of India. J. Essent. Oil Res., 10, 697-699 (1998).

183. Brophy, J.J., Boland, D.J. and van der Lingen, S. Essential oils in the leaf, bark and seed of Mopane {Colophospermum mopane). South African Forestry J. #161, 23-25 (1992).

184. Brophy, J.J. and Lassak, E.V., The volatile leaf oil of Erechities valerianifolia (Asteracae). South Pacific J. Natural Sci., 8: 78-85 (1986).

Page 37 185. Brophy, J.J.. Lassak, E.V. and Sevenet, T,, The volatile phyllode oil of Acacia spirobis (Mimosaceae). Phytochemistry, 26: 3071-3072 (1987).

186. Taroeno, Brophy, J.J. and Zwaving, J.H. Analysis of the essential oil of cax^wmMAZflr Roxb. from Indonesia. Flavour Fragr. J. 6: 161-163 (1991).

187. Brophy, J.J. and Lassak, E.V., The odorous principle of ripe Panc/a/ziw pyw/orwij fruit. South Pacific J. Natural Sci., 9: 41-47 (1987).

188. Kumar, U., Ram, B., Pant, A.K., Gupta, K.C. and Brophy, J.J. Volatile constituents of the distilled leaf and peal oils of Citrus limon Burn Cv. "Pant Lemon - 1". J. Essent. Oil Res. 4: 643-644 (1992).

189. Cheng, D., Lidgard, R.O., Duffield, P.H., Duffield, A.M. and Brophy, J.J. Identification by methane CI GCMS of the products obtained by steam distillation and aqueous acid extraction of commercial Piper methysticum. Biomed. Environ. Mass Spectrom., 17:371-376 (1988).

190. Buckle, K.A., Rathnananthie, M. and Brophy, J.J., Compositional differences of black, green and white pepper {Piper nigram, L) oil from three cultivars. J. Food Tech., 20: 599-613 (1985).

191. Wyllie, S.G., Cook, D., Brophy, J.J. and Richter, K., Volatile flavour components of Annona atemoya (Custard Apple). J. Agric. Food. Chem., 35: 768-770 (1987).

192. Wyllie, S. G., Brophy, J.J., Sarafis, V. and Hobbs, M. Flavour volatiles of the fruit Pistacia lentiscus. J. Food Sci., 55: 1325-1326 (1990).

193. Stanley, G., Algie, J.E. and Brophy, J.J., l,3,3-Trimethyl-2,7-dioxabicyclo-(2,2,l)-heptane, a volatile oxidation product of a-famesene in apples. Chem. and Ind., 556 (1986).

194. Brophy, J.J., Rynn, T.M., Lassak, E.V. and Pickard, J., The volatile herb oil of Kippistia suaedifolia. Phytochemistry. 21: 812-814 (1982).

195. Wyllie, S.G. and Brophy, J.J., The leaf oil of Liquidambar styraciflua. Planta Medica, 55: 316-317 (1989).

196. Hunter, M.V., Brophy, J.J., Ralph, B.J. and Bienvenu, F.E. Composition of Polygonum odoratum Lour, from southern Australia. J. Essent. Oil Res. 9:603-604 (1997).

197. Foley, W.J., Lassak, E.V. and Brophy, J.J., Digestion and adsorption of Eucalyptus essential oil in the Great Glider {Petavroides volans ) and the Bmshtail Possum (Trichosurus vulpecula ). J. Chem. EcoL, 13: 2115-2130 (1987).

198. Loveys, B.R., Robinson, S.P., Brophy, J.J. and Chacko, E.K. Mango sapbum: Components of fruit sap and their role in causing skin damage. Aust. J. Plant Physiol., 19: 449-457 (1992).

Papers not included in this thesis

199. Brophy, J.J. and Southwell, I.A., Eucalyptus Chemistry, in Medicinal and Aromatic Plants - Industrial Profiles: Eucalyptus, ed by Coppen, J,J.W., Harwood Academic Publishers, Netherlands, accepted for publication

200. Brophy, J.J., Goldsack, RJ., Fookes, C.J.R. and Forster, P.I., Essential Oils of Australian Gymnosperms Part 1, The leaf essential oil of Sundacarpus amarus (Blume)C.N. Page (). J. Essent. Oil Res. accepted for publication

201. Doran, J.C., Brophy, J.J., Lassak, E.V. and House, A.P.N. Backhousia citriodora F. Muell. - Re- discovery and chemical characterisation of the /-citronellal form and aspects of its breeding system. Flavour Fragr. J., submitted.

202. Brophy, J.J., Goldsack, R.J. and Forster, P.I., Leaf essential oils of the Australian species of Gyrocarpus and Hernandia (Hernandiaceae). J. Essent. Oil Res., accepted for publication.

Page 38 203. Brophy, J J., Goldsack, RJ. and Forster, P.I., The leaf oils of the Australian species of Polyalthia (Annonaceae). /. Essent. Oil Res., accepted for publication.

204. Brophy, J.J., Goldsack, R.J., Fookes, C.J.R. and Rozefelds, A.C., The chemistry of Australian Gymosperms. Part III. The leaf essential oils of the genus Microstrobos (Podocarpaceae). /. Essent. Oil Res., accepted for publication

205. Brophy, J.J., Goldsack, RJ., Forster, P.I. and Southwell. I.A., The leaf essential oil of the genus Acradenia (Rutaceae). J. Essent. Oil Res., accepted for publication.

206. Southwell, I.A., Brophy, J J. and Tucker, D J., Darwinia citriodora (Myrtaceae), a new source of methyl myrtenate and methyl geranate. J. Essent. Oil Res., accepted for publication.

207. Asante, K.S., Brophy, J.J., Doran,. J.C., Goldsack, R.J., Hibbert, D.B. and Larmour, J.S., A comparitive study of the seedling leaf oils of the Spotted Gums (species of the Corymbia [MyrtaceaeJ, section Folitaria). Aust. J. Bot., submitted.

208. Brophy, J.J., Goldsack, R.J. and Forster, P.I., The leaf essential oils of the Australian species of Citrus (Rutaceae). J. Essent. Oil Res., submitted.

209. Brophy, J.J., Goldsack, R.J. and Forster, P.I., The leaf oils of Dinosperma erythrococca and D. stipitata (Rutaceae). J. Essent. Oil Res., submitted.

210. Ireland, B.F., Goldsack, R.J., Fookes, C.J.R., Clarkson, J.R. and Brophy, J.J., The leaf essential oil of Eucalyptus miniata and£^. gigantangion. Aust. J. Chem., submitted.

211. Brophy, J.J., Goldsack, R.J., Fookes, C.J.R. and Forster, P.I., The Essential Oil of Pentaceras australe (Rutaceae). J. Essent. Oil. Res., submitted.

212. Brophy, J.J., Goldsack, R.J. and Forster, P.I.., The leaf oils of the Australian species of Desmos (Annonaceae). J. Ess. Oil Res., submitted.

Page 39 The publish articles number 24 to 198 listed from page 28 to 38 have been removed from the digital copy of this thesis. Please see the print copy of the thesis for a complete manuscript.