An examination of the leaf oils of Tasmanian Kunzea ambigua and other Kunzea species

Abstract

Commercial kunzea oil (Ducane kunzea oil) was analyzed by GC/MS and GC-FID and its composition was compared with that of oils from four individual Kunzea ambigua plants and five other Kunzea spp. A total of 64 components were detected in the studied oils. Ducane kunzea oil contained monoterpenes (70%) including a-pinene (48.3%), 1,8-cineole (14.5%) and a-terpineol (1.9%). Oils from individual K. ambigua plants varied significantly in their content of a-pinene (0.6–62.5%), 1,8-cineole (0–11.2%), bicyclogermacrene (0.4–14%), spathulenol (0.5–12.2%), globulol (0.5–22.6%) and viridiflorol (0.3–38%). The oils from five other Kunzea spp. had significant compositional differences from each K. ambigua oil. Kunzea sp. “Badja Carpet” had a high b-pinene content (56.1%), K. muelleri contained significant levels of allo-aromadendrene (8.0%), spathulenol (7.0%) and, among all the analyzed oils, it had the highest level of bicyclogermacrene (15.7%). Kunzea affinis contained significant levels of p-cymene (26.2%) and g-terpinene (12.2%). Kunzea parvifolia gave an oil rich in g-terpinene (36.5%) and p-cymene (5.0%).

Full text

Vol. 22, September/October 2010 Journal of Essential Oil Research/381
Rec: October 2007
Rev: October 2008
Acc: November 2008
An Examination of the Essential Oils of Tasmanian
Kunzea ambigua, Other Kunzea spp. and
Commercial Kunzea Oil
J. Thomas*, C.K. Narkowicz and G.A. Jacobson
School of Pharmacy, University of Tasmania, Private Bag 26, Hobart, 7001, Tasmania, Australia
N.W. Davies
Central Science Laboratory, University of Tasmania, Private Bag 74, Hobart, 7001, Tasmania, Australia
Abstract
Commercial kunzea oil (Ducane kunzea oil) was analyzed by GC/MS and GC-FID and its composition was
compared with that of oils from four individual Kunzea ambigua plants and five other Kunzea spp. A total of 64 com-
ponents were detected in the studied oils. Ducane kunzea oil contained monoterpenes (70%) including a-pinene
(48.3%), 1,8-cineole (14.5%) and a-terpineol (1.9%). Oils from individual K. ambigua plants varied significantly in
their content of a-pinene (0.6–62.5%), 1,8-cineole (0–11.2%), bicyclogermacrene (0.4–14%), spathulenol (0.5–12.2%),
globulol (0.5–22.6%) and viridiflorol (0.3–38%). The oils from five other Kunzea spp. had significant compositional
differences from each K. ambigua oil. Kunzea sp. “Badja Carpet” had a high b-pinene content (56.1%), K. muelleri
contained significant levels of allo-aromadendrene (8.0%), spathulenol (7.0%) and, among all the analyzed oils, it had
the highest level of bicyclogermacrene (15.7%). Kunzea affinis contained significant levels of p-cymene (26.2%) and
g-terpinene (12.2%). Kunzea parvifolia gave an oil rich in g-terpinene (36.5%) and p-cymene (5.0%).
Key Word Index
Kunzea ambigua, Kunzea affinis, Kunzea muelleri, Kunzea parvifolia, Kunzea baxterii, Kunzea sp. “Badja Carpet,”
Ducane kunzea oil, Myrtaceae, essential oil composition, a-pinene, b-pinene, p-cymene, 1,8-cineole, g-terpinene,
bicyclogermacrene, spathulenol, globulol, viridiflorol, ledol.
1041-2905/10/0005-0381$14.00/0 —© 2010 Allured Business Media
*Address for correspondence: Jackson.Thomas@utas.edu.au
Introduction
Genus Kunzea, (after Gustav Kunze) is indigenous to
Australia and New Zealand, and includes about 42 species
of woody shrubs (1,2). Its Australian distribution is mainly
limited to eastern and southern Australia, with the greatest
representation in the southwest of Western Australia. Kunzeas
grow naturally in coastal or near coastal areas with a few found
some distance inland. Most kunzeas have fairly dense foliage
that is strongly aromatic when crushed due to the volatile oil
content (1,3,4). Kunzea is closely related to Callistemon, Mela-
leuca and Leptospermum, but is differentiated by its stamen
arrangement (2,4).
From the genus Kunzea, the essential oil compositions of
only K. ericoides, K. pulchella, K. pauciflora and K. flavescens
have been previously published (5,6). In this paper the authors
describe the leaf essential oils isolated from one mainland
Australian and three Tasmanian examples of Kunzea ambigua
(Smith) Druce, a species that is native to New South Wales,
Tasmania and Victoria (7). The shrub is also known as “white
kunzea” and “tick bush,” a common name that originated
from its possible tick-repellent properties (1). In this study the
authors have also analyzed the volatile oils isolated from three
Western Australian species: Kunzea baxterii (Klotsch) Schauer,
Kunzea muelleri Benth, and Kunzea affinis S. Moore; Kunzea
parvifolia Schauer, native to New South Wales and Victoria;
Kunzea sp. “Badja Carpet,”, from New South Wales (1,4); and
commercially produced kunzea oil (Ducane kunzea oil).
In recent years there has been considerable interest in the
therapeutic potential of commercially produced myrtaceous
oils such as kanuka (K. ericoides), manuka (Leptospermum sco-
parium), kunzea (K. ambigua), tea tree (Melaleuca alternifolia),
K. ambigua

382/Journal of Essential Oil Research Vol. 22, September/October 2010
and niaoli (M. viridiflora, M. quinquenervia) oils. Kunzea oil
and kanuka oil are currently produced commercially on a small
scale. The commercial production of Ducane kunzea oil is
from bush cutting of natural thickets in northeastern Tasmania.
Steam distilled oil is sold undiluted and is incorporated into
a number of pharmaceutical preparations (8,9). A number of
studies have described the composition and characterization of
kanuka oil constituents (10,11). Commercial kanuka oils vary
in their chemical composition depending on their geographi-
cal origin. Essential oil produced from East Cape was found
to have a lower a-pinene content (55.5%) than oils from the
Coromandel area (67.8%) (10). Oils from K. ericoides exhib-
ited considerable differences in composition between single
plants originating from the same site (5). Recent phytochemical
studies on kanuka oil have shown its antibacterial, antifungal,
spasmogenic and spasmolytic properties (11-15).
Ducane kunzea oil is used in aromatherapy, as a topical
antiseptic and for the treatment of various skin conditions,
including eczema and psoriasis in humans and pastern derma-
titis in animals (8,9). Ducane kunzea oil has been listed as a
therapeutic substance by the Therapeutic Goods Administration
in Australia for topical application for the treatment of vari-
ous dermatological ailments (AUSTL 72143; 1996). However,
there have been no published studies describing in detail its
chemical composition. The main objective of this study was
to analyze the volatile constituents of Ducane kunzea oil and
to examine essential oil compositional variation within a small
selection of Tasmanian and mainland Australian examples of K.
ambigua and between a selection of Kunzea spp. from eastern
and western Australia.
Experimental
Plant collection: The Kunzea spp. extracted for this
study are listed in Table I. Leaves and aerial parts of three K.
ambigua plant examples (B-D) and K. baxterii were collected
from the University of Tasmania, Hobart Campus in 2005.
These included a prostrate form of K. ambigua that originated
from the Freycinet Peninsula area of Tasmania (B), K. ambigua
grown from a cutting taken at Bicheno on the east coast of Tas-
mania (C) and a cultivar from northeast Tasmania propagated
by W Fletcher from Plants of Tasmania Nursery, Ridgeway,
Tasmania (D). Kunzea parvifolia aerial parts were collected
Table I. Australian members of genus Kunzea analyzed in this study.
Species voucher number plant origin oil yield % wt/wt
K. parvifolia JT 021 NSW* 0.19
K. affinis JT 020 WA† 0.11
K. muelleri JT 018 NSW or VIC 0.11
K. baxterii JT 022 WA 0.29
Kunzea sp. “Badja Carpet” JT 023 Mt Badja, NSW 0.08
K. ambigua (pink form, A) JT 024 Cultivar, NSW or VIC‡ 0.22
K. ambigua (prostrate form, B) JT 028 Freycinet Peninsula, TAS§ 0.29
K. ambigua (C) JT 025 Bicheno, TAS 0.31
K. ambigua (D) JT 026 North East TAS 0.30
*New South Wales, † Western Australia, ‡ Victoria, § Tasmania
from a staff member’s garden in Hobart. All remaining plant
specimens were purchased from Redbreast Plant Nursery in
Margate, Tasmania. These included a pink–flowered cultivar
of K. ambigua that originated in New South Wales (NSW)
or Victoria (A), an undescribed Kunzea sp. cultivar selection
“Badja Carpet” from Mt. Badja in NSW and several Western
Australian species. Vouchers were deposited (JT018, JT020-26,
JT028) at the Tasmanian Herbarium (HO), Hobart, Tasmania
for the examined specimens. Ducane kunzea oil (E) (Batch #
010) was obtained from the commercial producer JJ Hood,
Waterhouse, Tasmania.
Isolation of oils: The oils were obtained by hydrodistillation
of the aerial parts of plant material for 4 h on a Clevenger-type
apparatus using approximately 100 g of fresh plant material.
The oil samples collected from the surface of the water in the
sidearm of the apparatus were dried over anhydrous sodium
sulphate and stored in screw cap vials at 4°C until analyzed.
The oil yields quoted in Table I are % wt/wt, based on fresh
plant material.
GC and GC/MS analysis: Quantitative analyses were
performed by GC analysis of the essential oils, using a Varian
3800 gas chromatograph equipped with a FID detector and a
data handling system (Varian Star Version 4). The column used
was a (Varian Factor Four) VF5-ms [30 m x 0.25 mm, 0.25 µm
film thickness]. The samples were dissolved in hexane (5 mg/
mL). A Varian 1177 injector was used in split mode. The car-
rier gas was N2 at a flow rate of 0.4 mL/min in constant flow
mode. The injection temperature was 240°C. Samples (1µL)
were injected split (20:1). The oven temperature profile was
60°C for one min then to 210°C at 6°C/min, then programmed
to 270°C at 25°C/min with a 5 min hold at 270°C. Peak areas
and retention times were measured by electronic integration,
and quantitative composition was obtained by peak normaliza-
tion of GC/FID data. The retention indices of the compounds
were determined relative to n-alkanes obtained from Sigma
Aldrich (Castle Hill, Australia).
Qualitative analyses of the oils were carried out by combined
GC/MS using a Varian 3800 GC connected to a Varian 1200
triple quadruple mass spectrometer. The same column was
used with similar experimental conditions to those described
above except that the carrier gas was He at a flow rate of 1.2
mL/min. The ion source temperature was 220oC and the
transfer line was held at 290oC. The range from m/z 35 to 350
Thomas et al.

Vol. 22, September/October 2010 Journal of Essential Oil Research/383
Table II. Percentage composition of the essential oils isolated from Kunzea spp. determined by GC-FID
Kunzea Kunzea Kunzea Kunzea Kunzea sp. Kunzea ambigua
Compound RI parvifolia affinis muelleri baxterii ‘Badja Carpet’ A B C D E
a-thujene 930 0.1 tr 0.1 tr 0.1 0.1 tr 0.2
a-pinene 938 41.4 47.1 19.2 82.7 14.3 0.6 28.3 62.5 59.2 48.3
camphene 952 0.1 0.1
sabinene 977 2.3 0.5 0.2 tr 0.4
b-pinene 982 0.1 0.1 2.7 56.1 0.4 0.7 0.4 0.6
myrcene 994 tr tr 0.3 tr tr 0.3
a-terpinene 1020 0.5 tr tr tr 0.2
p-cymene 1028 5.0 26.2 1.8 1.1 0.4 0.3 0.2 0.4
limonene 1032 1.3 0.8 0.8 1.1 1.6 0.8 1.0 0.9 1.2
b-phellandrene 1034 tr
1,8-cineole 1036 1.3 11.2 5.9 3.6 14.5
(Z)-b-ocimene 1036 tr
(E)-b-ocimene 1046 1.3 tr 0.1 0.1 0.2 0.3
isoamyl butyrate 1054 0.3 tr 0.1
g-terpinene 1058 36.5 12.2 0.3 0.1 tr tr 0.1
cis-linalool oxide‡ 1071 0.1
terpinolene 1085 0.8 0.2 tr tr tr
linalool 1097 0.3 0.2 0.1 0.5 tr 0.8 0.1 0.1 tr 0.3
isoamyl isovalerate 1102 2.6 0.2 0.1 0.4 0.6 0.5
cis-rose oxide 1108 tr
trans-rose oxide 1125 tr
a-campholenal 1127 0.9 tr tr 0.1 0.1
trans-pinocarveol 1143 0.3 tr 1.5 0.1 tr 0.1
cis-verbenol 1152 0.3
pinocarvone 1165 0.4 tr 0.3
benzenepropanal† 1164 1.1 0.7
terpinen-4-ol 1170 0.3 0.2 1.0 0.7 0.3 0.5
a-terpineol 1197 0.1 0.3 0.3 0.6 2.1 1.1 1.9
myrtenal 1200 0.4
verbenone 1212 0.1
citronellol 1227 0.5 0.6 0.9 1.0
geraniol 1252 0.3 0.1
g-elemene 1333 1.0 0.3
a-cubebene 1352 tr tr 0.1 tr
geranic acid +
a-cubebene 1352 0.2 1.2
a-copaene 1380 0.6 0.1 0.2 tr 0.1 0.1 0.2 0.1
b-elemene 1392 0.4 0.1 tr
a-gurjunene 1412 0.1 0.5 0.2 tr 1.1 0.1 0.1 0.4 0.4
b-caryophyllene 1425 0.9 0.1 3.6 2.1 2.9 0.3 0.1 0.3 0.7
aromadendrene 1444 0.3 0.7 3.0 0.2 0.4 1.2 0.2 0.1 0.2 0.6
a-humulene 1461 0.2 0.3 0.2 0.1 tr tr 0.3
allo-aromadendrene 1466 0.4 0.3 8.0 0.1 0.5 2.4 0.3 0.1 0.3 0.7
germacrene D 1486 2.2 0.9
viridiorene 1497 0.9 0.3 1.4 0.1 0.8 3.0 1.7 0.7 0.3 2.0
bicyclogermacrene 1501 0.6 15.7 0.4 tr 14.0 0.4 1.3 0.4 2.8
d–cadinene 1522 1.1 0.1 0.5 0.1 tr 0.5 0.4
calamenene* 1527 0.6 0.6 1.8 4.6 1.0
cadina-1,4-diene 1537 0.1 tr 0.1 0.1 0.3 tr
epi-globulol 1569 0.2 0.2 tr tr tr
palustrol 1577 0.4 0.1 2.7 0.7 0.3 tr 0.3
spathulenol 1584 0.2 1.4 7.0 tr 2.5 12.2 0.5 1.1 1.7 0.6
caryophyllene oxide 1590 0.1 0.7 2.5 1.4 0.5 tr tr 0.1
globulol 1594 0.5 2.4 4.8 0.9 1.8 22.6 0.5 4.5 16.6 7.9
viridiorol 1603 0.4 2.8 6.4 38.0 11.1 0.3 6.5
viridiorol +
(unknown A) 1604 1.6 4.4 1.4
ledol 1613 0.1 4.8 1.3 1.3
ledol + rosifoliol 1614 0.6 1.0 0.1 9.2 2.2 0.3
K. ambigua

384/Journal of Essential Oil Research Vol. 22, September/October 2010
was scanned three times every second. All the hardware and
software were supplied by Varian Inc (Melbourne, Australia).
The identification of the main components was carried out by
comparison of the MS data against reference spectra from the
NIST (National Institute of Standards and Technology) MS
database and with the use of an in-house library of essential oil
mass spectral data accumulated over many years and through
collaborative links with CSIRO (Commonwealth Scientific
and Industrial Research Organization) and INRA (Institut
National de la Recherche Agronomique). Retention indices
were compared against those calculated from data provided
by Adams (16) for a similar column.
Results and Discussion
The constituents of the oils obtained from the Kunzea spp.
are reported in Table II. The major monoterpene components
of Ducane kunzea oil were a-pinene (48.3%), 1,8-cineole
(14.5%) and terpinene-4-ol (1.9%). The major sesquiterpenes
included the alcohols with the cycloprop[e]azulene skeleton:
globulol (7.9%), viridiflorol (6.5%) and ledol (1.3%), as well
as a minor amount of palustrol (0.3%). Other sesquiterpenes
included bicyclogermacrene (2.0%) and viridiflorene (2.0%).
Most of the medicinally important commercial myrtaceous oils
(tea tree, eucalyptus, niaouli, cajuputi and kanuka) have oil
compositions highly rich in monoterpenes, with the exception
being manuka oil which contains principally sesquiterpenes
(11). Cajuputi, niaouli and eucalyptus oils were found to
be high in 1,8-cineole (52.0–80.1%), kanuka oil was rich in
a-pinene (70.6%). The chief oil components of tea tree oil are
g-terpinene (9–28%) and terpinen-4-ol (28–58%) (17). Manuka
oil was dominated by sesquiterpenes, especially calamenene
(15.9%) and the b-triketones, leptospermone (14.4%) and isolep-
tospermone (3.9%) as well as a-copaene (6.5%) and d-cadinene
(6%). However, none of the commercial oils investigated by
Harkenthal and co-workers (11) contained significant amounts
of globulol or viridiflorol, which were present in Ducane kun-
zea oil. Kanuka oil had a low content of sesquiterpenes (2%)
compared with Ducane kunzea oil, which contained around
25% sesquiterpenes.
The chief monoterpene in all but one of the examined K.
ambigua plants was a-pinene (0.6–62.5%). The exception was
oil A, which was low in a-pinene (0.6%) and contained a slightly
higher level of linalool (0.8%). 1,8-Cineole was the next most
prevalent monoterpene in four of the plant oils (3.6–14.5%)
but was absent in one case (A). Compared to other K. ambigua
oils, leaf oil A, which lacked 1,8-cineole, contained higher levels
of sesquiterpenes: bicyclogermacrene (14.0%), spathulenol
(12.2%), globulol (22.6%) and ledol (4.8%).Only one plant oil
(B) and Ducane kunzea oil had a level of a-terpineol greater
than 1.5%. Fewer monoterpenes were detected in samples A
and D than in the other K. ambigua oils. All the K. ambigua oils
contained globulol (0.5–22.6%) and viridiflorol (0.3–38.0%).
Samples B and C had lower levels of globulol and had the
highest amounts of viridiflorol (38.0% and 11.1% respectively).
However, in plant oils A and D, globulol levels (22.6% and
16.6% respectively) were several times higher compared with
the viridiflorol content (6.4% and 0.3% respectively). Among
the closely related alcohols (ledol and spathulenol), spathulenol
was present in all K. ambigua samples (0.5–12.2%) but ledol
was absent in samples B and C.
Each individual K. ambigua plant extract varied consider-
ably in composition from the Ducane kunzea oil. The Ducane
kunzea oil is produced from a large batch of plant material,
so its composition does not reflect the composition of any
individual plant but rather an average composition. It is likely
that, in common with K. ericoides (5), individual plants used
in its production also vary in their oil composition (16). There
are significant chemical differences between oils from differ-
ent plants analyzed in this study, so it would be possible by
appropriate plant selection and cultivation to produce kunzea
oils with different chemical compositions and potentially dif-
ferent biological activities. A detailed study with an extensive
collection of K. ambigua from different locations is essential
to draw further conclusions about chemotypical variations
within the species.
Table II. Continued
Kunzea Kunzea Kunzea Kunzea Kunzea sp. Kunzea ambigua
Compound RI parvifolia affinis muelleri baxterii ‘Badja Carpet’ A B C D E
leptospermone 1625 1.0 tr tr 0.1 2.1 0.1
C15H26O (unknown B) 1631 0.2 1.0 0.1 1.4 tr tr
isospathulenol§ 1639 0.6 1.7 2.8 tr tr 0.1
T-cadinol 1649 0.2 0.4 tr tr
T-muurolol 1651 0.3 tr 0.4 tr tr
a-muurolol 1654 0.1 0.2 tr tr
a-cadinol 1663 0.5 0.2 tr 0.7 tr tr
RI=retention index; tr=trace < 0.1%; ‡furanoid form; †also known as dihydrocinnamaldehyde; *isomer not identied; §tentative identication; A-K. ambigua pink-owered
form; B-K. ambigua prostrate form; C, D–plant examples of K. ambigua; E-Ducane kunzea oil
Mass Spectral data for unidentied compounds: Unknown A m/z 222 (2%), 163(61), 149(19), 121(24), 109(16), 108(18), 107(100), 105(19), 95(24), 93(42),91(25), 82(20), 81(59),
79(36), 69(21), 67(31), 59(51), 55(24), 43(24), 41(47), 39(14); Unknown B m/z 164 (41%), 149(82), 135(43), 121(28), 108(41), 107(59), 105(19), 95(27), 94(40), 93(54), 91(29),
81(54), 79(39), 77(19), 68(22), 67(29), 59(100), 55(24), 43(52), 41(54)
Thomas et al.

Vol. 22, September/October 2010 Journal of Essential Oil Research/385
The leaf oil of K. parvifolia was abundant in monoterpenes
(86.7%), predominantly
a-pinene (41.4%), g-terpinene (36.5%),
p-cymene (5.0%) and limonene (1.3%). Germacrene D (2.2%)
and d-cadinene (1.1%) were the main sesquiterpene compo-
nents, and modest levels of caryophyllene and viridiflorene
were also present.
Kunzea affinis produced a leaf oil dominated by monoter-
penes (90.2%), with a-pinene (47.1%), p-cymene (26.2%) and
g-terpinene (12.2%). The main sesquiterpene components were
globulol (2.4%), viridiflorol with an unidentified sesquiterpene
(1.6%) and spathulenol (1.4%). Additionally there were lesser
amounts of aromandrene (0.7%), allo-aromandrene (0.3%),
viridiflorene (0.3%) and an unidentified oxygenated sesquit-
erpene C15 H26O (0.2%).
The leaf oil of K. muelleri was found to be rich in sesqui-
terpenes (51.2%), principally bicyclogermacrene (15.7%),
alloaromadendrene (8.0%) and spathulenol (7.0%). The other
sesquiterpene components of note were globulol (4.8%), a
mixture of viridiflorol and an unidentified sesquiterpene (4.4%),
aromadendrene (3.0%) and viridiflorene (1.4%). Additionally
modest levels of rosifoliol together with ledol (1.0%), an un-
identified sesquiterpene C15 H26O (1.0%) and leptospermone
(1.0%) were also detected in the sample.
The leaf oil of K. baxterii was predominately monoterpene
based (90.9%) with a-pinene (82.7%), b-pinene (2.7%), and
(E)-b-ocimene (1.3%) as the main components. The main
sesquiterpene components were b-caryophyllene (3.6%) and
viridiflorol (2.8%) together with lower amounts of calamenene,
caryophyllene oxide and globulol.
The registered cultivar Kunzea sp. “Badja Carpet” gave an
oil which was dominated by monoterpene components (77.5%),
principally b-pinene (56.1%), a-pinene (14.3%), limonene
(1.6%) and trans-pinocarveol (1.5%). These were accompanied
by a range of sesquiterpene components: rosifoliol plus ledol
(9.2%), caryophyllene oxide (2.5%), spathulenol (2.5%) and
b-caryophyllene (2.1%). Although a high b-pinene content is
uncommon in Australian Myrtaceae, it has been previously
reported from K. pauciflora oil (47.4%). Moreover, Kunzea
sp. “Badja Carpet” showed a similar oil profile to that of K.
pauciflora reported previously (6,8).
Each of these 4 different Kunzea spp. oils had significant
compositional differences from each of the oils from K. ambigua
specimens. Of note were the high b-pinene content of “Badja
Carpet,” the high bicyclogermacrene content of K. muelleri,
the high p-cymene and g-terpinene content of K. affinis and
high g-terpinene content of K. parvifolia.
Acknowledgments
The authors thank Joe Brophy for helpful discussions in the initial
assignment of the globulol/viridiflorol/ledol group. JT wishes to thank
Ashok Narayana, Thomas Beattie and Prince Ninan Philip for assistance
with the collection of plant material. This research was supported by
equipment funded by the Australian Research Council.
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K. ambigua