American Journal of Plant Sciences, 2013, 4, 2031-2038
http://dx.doi.org/10.4236/ajps.2013.410254 Published Online October 2013 (http://www.scirp.org/journal/ajps)
2031
Terpene Composition of Three Species of Gymnosperms
from Vietnam
Do N. Dai1, Tran D. Thang2*, Isiaka A. Ogunwande3*
1Faculty of Biology, Vinh University, Vinh City, Vietnam; 2Faculty of Chemistry, Vinh University, Vinh City, Vietnam; 3Natural
Products Research Unit, Department of Chemistry, Faculty of Science, Lagos State University, Lagos, Nigeria.
Received June 15th, 2013; revised July 15th, 2013; accepted August 19th, 2013
Copyright © 2013 Do N. Dai et al. This is an open access article distributed under the Creative Commons Attribution License, which
permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
ABSTRACT
In the present investigation, we studied new essential oil contents and compositions of three individual plants from Cu-
pressaceae family cultivated in Vietnam. The air-dried plants were hydrodistilled and the oils analysed by Gas chroma-
tography (GC) and Gas chromatography couples with Mass spectrometry (GC-MS). The components were identified by
comparison of their retention indices on HP-5 MS capillary column with literature reference and MS pattern with au-
thentic library’s collection.
 -Pinene (36.0%), α-cedrol (18.3%) and thujopsene (5.7%) were the main constituents of
Cupressus tonkiensis Silba. Monoterpenes were the quantitative significant compounds of Sabina chinensis (L.) An-
toine. These are bornyl acetate (19.5%), sabinene (17.3%) and
 -pinene (15.8%). Moreover, the main compounds of
Thuja orientalis L., were identified as
 -pinene (34.1%), α-cedrol (16.5%), β-caryophyllene (5.4%) and β-selinene
(5.2%). The chemotaxonomy implication of these results was also discussed.
Keywords: Cupressus tonkiensis; Sabina chinensis; Thuja orientalis; Bornyl Acetate; α-Cedrol;
 -Pinene; Sabinene
1. Introduction
The genus Cupressus is one of several genera within the
family Cupressaceae that has the common name cypress.
It is considered a polyphyletic group. Based on genetic
and morphological analysis, the Cupressus genus is found
in the Cupressoideae subfamily [1]. As currently treated,
these cypresses are native to scattered localities in mainly
warm temperate regions in the Northern Hemisphere, in-
cluding western North America, Central America, north-
west Africa, the Middle East, the Himalayas, southern
China and northern Vietnam [2]. Cupressus tonkinensis
Silba., is an evergreen, medium-sized tree, up to 15 - 25
cm in height. Bark is grey brown with longitudinal fis-
sures. Leaves are scaly, closely inserted on twigs. Cones
are unisexual, grouped on a stalk. Male cone is subglo-
bular. This is an endangered species in Vietnam, only
found in a narrow area of the Central Region [3]. Little is
known about the chemical constituents and biological po-
tential of this plant. Leaves and stems of C. tonkinensis
produce monoterpene-rich oils whose composition is
α-pinene (23.1%), sabinene (21.0%) and terpinen-4-ol
(14.4%) in the leaf while, α-pinene (42.5%), myrcene
(10.2%) and cedrol (9.0%) were identified in the stem [4].
Another investigation identified sabinene (29.34%), α-pi-
nene (25.4%), 4-terpineol (13.91%) and
 -terpinene (5.5%)
as major compounds of its leaf oil [3].
Sabina chinensis (L.) Antoine is an evergreen tree that
grows up to 20 m high. The leaves are basal while the
yellow flowers are unisexual [5]. S. chinensis is one of
the important species used in Chinese garden and has a
long history. It has many uses and more than 100 culti-
vars. The first report on the main constituents of S. chi-
nensis identified sabinene (46.73%), α-pinene (17. 03%),
terpinen-4-ol (5.34%) and limonene (4.48%) as major con-
stituents [6]. Another analysis [7] reported an abundance
of α-pinene (21.1%), sabinene (18.2%) and limonene
(9.2%) in the oil. Cui et al. [8] demonstrated that the main
substances in volatile oil S. chinensis were bornyl acetate
(38.1%), α-phellandrene (24.0%) and p-menth-l-en-4-o1
(12.4%). Another report [9] described the main composi-
tion of S. chinensis to be sabinene (20.99%), limonene
(19.78%) and bornyl acetate (11.68%).
The oil composition of two other species in the genus
has been documented. The major compounds of S. vir-
giniana [10] from Japan were limonene (32.9%), safrole
(23.0%), asarone (15.9%) and α-pinene (5.2%). S. chi-
*Corresponding author.

Terpene Composition of Three Species of Gymnosperms from Vietnam 2032
nensis cv. Kaizuca leaf oil, as reported by Cui et al. [10]
contained bornyl acetate (46.5%), limonene (30.0%) and
β-pinene (7.9%), while limonene (24.56%) and β-myr-
cene (8.04%) are the prominent compounds from sample
analysed by Hao et al. [9]. The volatile oil from S. chi-
nensis had greater effects of bacteriostasis and air decon-
tamination [7,8,11]. It is also indicated that constituents
such as bornyl acetate, phellandrene, limonene and alpha-
pinene and beta-pinene could also contribute to the anti-
microbial activity of the volatile oils [11].
Thuja occidentalis (syn. Platycladus orientalis (L.)
Franco or Biota orientalis (L.) Endl.) is an evergreen co-
niferous tree, in the cypress family Cupressaceae, which
is native to the northeast of the United States and the
southeast of Canada, but widely cultivated as an orna-
mental plant. T. occidentalis has fan-like branches and
scaly leaves. It is only a small tree, growing to a height
of 10 - 20 m. The bark is red-brown, furrowed and peels
in narrow, longitudinal strips. The cones are slender, yel-
low-green ripening brown, 10 - 15 mm broad, with 6 - 8
overlapping scales. The branches may take root if the
tree falls. Plants are susceptible to attacks by honey fun-
gus [12]. Plants are monoecious, male catkins being pro-
duced at the tips of branches and female cones at the base
[12]. The essential oil from the leaf of P. orientalis is an
important natural product which is used in fragrance, air
freshener, deodorizer, insectifuge, and aromatherapy.
The essential oil composition of the leaf of T. orien-
talis was investigated in Xuzhou, China [13], where its
main components were α-pinene (40.2%), 3-carene (13.2%),
and cedrol (9.3%). The data reported from Iran [14-16]
showed that the main constituents were α-pinene (15.0%
- 30.0%), 3-carene (10.5% - 21.7%), and cedrol (6.1% -
20.3%). Previous studies in China [17-20] had revealed
that the main constituents were α-pinene (8.4% - 24.9%),
3-carene (2.6% - 12.2%), and cedrol (0.7% - 31.4%). In a
recent report [21], a population of T. orientalis afforded
oils whose major compounds were α-pinene (37.6% -
68.1%), cedrol (3.4% - 18.1%), 3-carene (0.1% - 29.4%),
β-caryophyllene (2.0% - 10.2%) and α-caryophyllene
(1.7% - 7.1%) while a sample contained cedrol (15.0%),
3-carene (12.2%) and β-caryophyllene (8.0%), yet an-
other sample had cedrol (19.2%), β-caryophyllene (14.3%)
and α-caryophyllene (11.3%) while the last sample con-
tained cedrol (23.7%), terpinenyl acetate (19.4%), 3-ca-
rene (10.6%) and α-pinene (10.2%). α- and β-Thujone,
fenchone, camphor and sabinene, as well as the diterpen-
es beyerene and rimuene were the main compounds in
the work of Tsiri et al. [22] and Chizzola et al. [23]. In
their own investigation, Guleria et al. [24] identified α-
pinene (29.2%),
 -3-carene (20.1%), α-cedrol (9.8%), ca-
ryophyllene (7.5%), α-humulene (5.6%) and limonene
(5.4%) in the oil of the plant. The dominant constituents
in essential oil of T. orientalis from most localities are a-
pinene, cedrol, and 3-carene. The previous studies also
reveal a large variation in the essential oil composition of
T. orientalis.
In the present paper, we report the essential oil compo-
sitions of three gymnosperms namely Cupressus tonki-
nensis Silba., Sabina chinensis (L.) Antoine and Thuja
occidentalis L., from Vietnam. This is part of our exten-
sive research on the volatile composition of Vietnamese
flora as they are made available [25].
2. Materials and Methods
2.1. Plants Collection
Leaves of C. tonkiensis were collected from Huu Lien
Natural reserve, Lang Son Province, Vietnam, in August
2010. The leaves of S. chinensis and T. orientalis were
collected from Nghe An Province in August 2011. Vou-
cher specimens DND 721, DND 194 and DND 196, re-
spectively have been deposited at the Botany Museum,
Vinh University, Vietnam. Plant samples were air-dried
prior to extraction.
2.2. Isolation of the Volatile Oils
0.5 kg of air-dried sample of each species was shredded
and their oils obtained by hydrodistillation for 4 h at nor-
mal pressure, according to the Vietnamese Pharmacopo-
eia [26]. The plant samples yielded a low content of es-
sential oils: 0.20%, 0.18% and 0.20% (v/w; respectively
for C. tonkiensis, S. chinensis and T. orientalis). Oil sam-
ples were light yellow colored.
2.3. Gas Chromatography (GC) Analysis
Gas chromatography (GC) analysis was performed on an
Agilent Technologies HP 6890 Plus Gas chromatograph
equipped with a FID and fitted with HP-Wax and HP-
5MS columns (both 30 m × 0.25 mm, film thickness 0.25
m, Agilent Technology). The analytical conditions were:
carrier gas H2 (1 mL/min), injector temperature (PTV)
250˚C, detector temperature 260˚C, column temperature
programmed from 40˚C (2 min hold) to 220˚C (10 min
hold) at 4˚C/min. Samples were injected by splitting and
the split ratio was 10:1. The volume injected was 1.0 L.
Inlet pressure was 6.1 kPa.
2.4. Gas Chromatography/Mass Spectrometry
Analysis/(GC-MS)
An Agilent Technologies HP 6890N Plus Chromato-
graph fitted with a fused silica capillary HP-5 MS col-
umn (30 m × 0.25 mm, film thickness 0.25 m) and in-
terfaced with a mass spectrometer HP 5973 MSD was
used for the GC/MS analysis, under the same conditions

Terpene Composition of Three Species of Gymnosperms from Vietnam 2033
as those used for GC analysis. The conditions were the
same as described above with He (1 mL/min) as carrier
gas. The MS conditions were as follows: ionization volt-
age 70eV; emission current 40 mA; acquisitions scan mass
range of 35 - 350 amu at a sampling rate of 1.0 scan/s.
2.5. Identification of Constituents
The identification of constituents was performed on the
basis of retention indices (RI) determined by co-injection
with reference to a homologous series of n-alkanes under
identical experimental conditions. Further identification
was performed by comparison of their mass spectra with
those from NIST 08 Libraries (on ChemStation HP) and
Wiley 9th Version and the home-made MS library built
up from pure substances and components of known es-
sential oils, as well as by comparison of their retention
indices with literature values [27,28].
3. Results and Discussion
The identities of compounds identified in the oil samples
could be seen in Table 1. A total of 33 compounds were
identified in the oil of C. tonkinensis, representing 94.0%
of the oil content. The oil composed largely of monoter-
penes (50.1%) and sesquiterpenes (40.7%) represented
largely by α-pinene (36.0%) and α-cedrol (18.3%), along
with minor quantities of thujopsene (5.7%) and  -3-ca-
rene (3.1%). Monoterpene compounds namely α-pinene,
sabinene, terpinen-4-ol and myrcene were the representa-
Table 1. Terpene composition of the oil samples.
Compoundsa RIb RIc C.p S.c T.o
Butanoic acid 802 763 3.1 - -
Tricyclene 927 921 - 0.5 0.2
α-Thujene 931 924 - 1.1 -
α-Pinene 939 932 36.0 15.8 34.1
Camphene 953 946 0.8 0.8 0.8
Verbenene 962 961 - - 0.3
Sabinene 976 969 0.6 17.3 1.2
 -Pinene 980 974 1.8 0.6 3.1
 -Myrcene 990 988 1.8 5.7 4.3
α-Phellandrene 1006 1002 - 0.1 Tr
 -3-Carene 1013 1008 3.1 - 0.2
α-Terpinene 1016 1014 - 1.9 0.5
p-Cymene 1024 1020 0.3 0.1 0.1
Limonene 1032 1024 - 6.0 4.9
(E)-  -Ocimene 1052 1044 - Tr 0.2
 -Terpinene 1061 1054 - 2.8 0.3
cis-Sabinene hydrate 1070 1065 - 0.2 -
α-Terpinolene 1089 1086 0.4 1.5 3.7
Linalool 1100 1095 1.0 0.2 Tr
n-Nonanal 1106 1100 - - Tr
cis-p-Menth-2-en-1-ol 1117 1118 - 0.2 -
allo-Ocimene 1128 1128 - - 0.1
trans-Pinocarveol 1139 1135 0.5 - -
Camphor 1146 1141 0.6 - -
Terpinen-4-ol 1177 1174 1.0 1.6 0.1
Methyl chavicol 1196 1195 - 0.4 -
Verbenone 1205 1204 0.5 - -
Carvacrol methyl ether 1245 1241 1.7 - -
Linalyl acetate 1257 1254 - - Tr
2-Decenal 1259 1260 - - Tr
1-Decanol 1276 1266 - - Tr
Bornyl acetate 1289 1287 - 19.5 0.7
Linalyl propanoate 1335 1334 - Tr Tr
α-Cubebene 1351 1345 1.2 - -

Terpene Composition of Three Species of Gymnosperms from Vietnam 2034
Continued
Neryl acetate 1362 1359 - - 0.1
α-Ylangene 1375 1373 - - Tr
α-Copaene 1377 1374 - 0.1 0.2
β-Bourbonene 1385 1387 - Tr 0.1
β-Elemene 1397 1398 1.4 0.1 0.3
Methyl eugenol 1407 1410 - 0.3 -
 -Cedrene 1409 1410 - - 0.3
 -Gurjunene 1410 1409 0.6 - -
β-Caryophyllene 1419 1417 0.6 - 5.4
cis-Thujopsene 1431 1429 5.7 - -
β-Gurjunene 1434 1431 - 0.1 -
 -Guaiene 1440 1437 1.0 - -
Aromadendrene 1441 1439 - - 0.6
Widdrene 1444 - - - 0.3
 -Humulene 1454 1452 0.6 - -
trans-β-Farnesene 1455 1454 - - 0.1
allo-Aromadendrene 1460 1458 - - 0.2
 -Acoradiene 1470 1469 - - 0.2
ar-Curcumene 1475 1479 - - 0.1
γ-Gurjunene 1477 1475 - 0.1 -
γ-Muurolene 1480 1478 0.8 - -
Germacrene D 1485 1484 - 0.7 0.9
α-Amorphene 1486 1483 - Tr 0.8
β-Selinene 1490 1489 - - 5.2
Zingiberene 1494 1493 1.8 - 1.6
cis-Cadina-1,4-diene 1496 1495 1.1 - 0.3
 -Selinene 1498 1498 - - 0.5
 -Muurolene 1500 1500 - 0.2 0.2
γ-Patchoulene 1502 1502 - - 0.1
Lepidozene 1502 - - - 0.2
Cuparene 1505 1504 2.2 - -
β-Bisabolene 1506 1505 - - 0.3
(E, E)-α-Farnesene 1506 1505 0.9 - -
 -Cadinene 1514 1513 - 0.1 0.3
trans-  -Bisabolene 1517 1514 - - 0.1
δ-Cadinene 1525 1522 2.1 0.6 0.7
Elemol 1550 1548 0.6 6.4 0.1
3-Hexen-1-ol, benzoate 1551 - - 0.1 0.2
Dodecanoic acid 1567 1565 - - Tr
Germacrene-D-4-ol 1574 1574 - - 0.2
Spathulenol 1579 1577 - - 1.3
Caryophyllene oxide 1583 1582 - 0.1 1.6
α-Cedrol 1601 1600 18.3 - 26.5
β-Oplopenone 1608 1607 - 0.4 -
Tetradecanal 1611 1611 - - Tr
 -Eudesmol 1632 1630 - 0.4 -
 -Muurolol 1646 1640 1.6 1.5 0.3
β-Eudesmol 1651 1649 0.7 - -
α-Cadinol 1654 1652 - - 0.5
α-Bisabolol 1686 1685 0.4 - -

Terpene Composition of Three Species of Gymnosperms from Vietnam 2035
Continued
Franesold 1718 - - - 0.1
Benzyl benzoate 1760 1759 - Tr -
Tetradecanoic acid 1770 - - - -Tr
1,2-Benzenedicarboxylic acid 1917 1917 - 1.0 2.9
16-Hexadecanolide 1928 - - - 0.2
ent-Pimara-8(14),15-diene 1939 - - 0.3 -
Hexadecanoic acid 1970 1959 - Tr Tr
Abietatriene 2050 2055 - 0.7 0.2
Phytol 2125 1942 - - Tr
Totarol 2314 2314 - 0.1 -
cis-Ferruginol 2371 2370 - 0.1 0.1
(Z)-9-Octadecenamide 2398 2396 - - 0.1
Total 94.0 90.0 98.4
Monoterpene hydrocarbons 44.8 53.6 54.2
Oxygenated monoterpenes 5.3 23.5 0.9
Sesquiterpene hydrocarbons 20.0 2.0 19.2
Oxygenated sesq u iterpenes 20.7 8.8 20.6
Diterpenes - 1.2 0.1
Non-terpenes 3.1 1.1 3.4
aElution order on HP-5MS capillary column; bRetention indices on HP-5MS capillary column; cLiterature Retention indi-
ces (see Experimental); dCorrect isomer not identified; - Not identified and not present in Literature; Tr, Trace amount,
<0.1%; C. p = Cupressus tonkinensis; S. c = Sabina chinensis; T. o = Thuja orientalis.
tive compounds of previous studies on C. tonkinensis [3,
4]. The α-pinene content of this oil competes favourably
with previous studies while the contents of other mono-
terpenes above are significantly lower. Cedrol was pre-
viously present in the stem oil but not in the leaf [4].
A total of 45 compounds could be identified from the
leaf oil of S. chinensis, representing 90.0% of the oil con-
tent. Also, monoterpenoids (77.1%) were in abundance
in the oil. The major constituents among the monoter-
penes were bornyl acetate (19.5%), sabinene (17.3%) and
α-pinene (15.8%). The large amount of α-pinene and sa-
binene is in agreement with previous reports [6-9], but
differs from its lower contents of tricyclene, β-myrcene,
α-phellandrene, limonene and p-menth-l-en-4-o1. Ses-
quiterpenes are less common (10.8%) represents mainly
by elemol (6.4%) and
 -muurolol (1.5%) as compounds
above 1%. There seems to be homogeneity in the oil
composition of S. chinensis. Bornyl acetate was among
the main compounds of S. chinensis cv. Kaizuca [10].
Limonene is a common compound of the oil of the genus
Sabina [6-10].
Monoterpenes (55.1%) and sesquiterpenes (39.8%) are
classes of compounds identified in the 69 constituents of
the oil of T. orientalis. The main compounds were α-
pinene (34.1%) and α-cedrol (16.5%). Other significant
compounds were β-caryophyllene (5.4%), β-selinene
(5.2%), limonene (4.9%) and α-terpinene (3.7%). The
predominant compounds were α-pinene and cedrol. This
result was similar to those previously reported [13-21,24,
29,30-32], which revealed that the main constituents
were a-pinene (15.0% - 68.1%), cedrol (3.4% - 39.06%)
and 3-carene (0.1% - 34.55%). However, the content of
3-carene in this sample is too low when compared with
previous studies (Table 2). Other compounds such as β-
caryophyllene, α-caryophyllene and terpinenyl acetate [21],
α-and β-thujone, fenchone, sabinene, camphor, beyerene
and rimuene [22,23], fenchol and β-santalene [32] and
cedrene [19], that are characteristics of previous reports
are either observed in low amounts (e.g.  -3-carene, sabi-
nene) or completely absent (e.g. α- and β-thujone, fen-
chone, fenchol, terpinenyl acetate, β-santalene, α-caryo-
phyllene, cedrene, beyerene and rimuene) in this present
study (Tables 1 and 2).
The previous studies also revealed a large variation in
the essential oil composition of T. orientalis. Therefore,
the oils of T. orientalis could be classified as follows:
1) group characterized by a predominant α-pinene,  -
3-carene and cedrol [13-18,20,21,24,29 and this study]
2) group dominated by cedrol,  -3-carene and β-cary-
ophyllene [21]
3) group with contents of cedrol, β-caryophyllene and
α-caryophyllene
4) α-pinene,  -3-carene and sabinene group [14]
5
) α-thujone, β-thujone and fenchone rich oil [22]

Terpene Composition of Three Species of Gymnosperms from Vietnam 2036
Table 2. Major constituents of essential oils of T. orientalis.
Origin Major Constituents Ref
Vietnam (l) α-cedrol (16.5%),
 -pinene (34.1%), β-caryophyllene
(5.4%) and β-selinene (5.2%) This study
China (l) α-pinene (40.2%), 3-carene (13.2%) and cedrol (9.3%) 13
Iran (w) α-pinene (15.0%), 3-carene (10.5%) and cedrol (20.3%) 14
Iran (l) α-pinene (15.2%), 3-carene (12.0%), cedrol (11.7%) and
sabinene (10.0%) 14
Iran (f) α-pinene (23.5%), 3-carene (23.8%) and sabinene (11.1%) 14
Iran (l) α-pinene (21.9%), α-cedrol (20.3%),
 -3-carene (10.5%)
and limonene (7.2%) 15
Iran (f) α-pinene (52.4%),
 -3-carene (14.2%), α-cedrol (6.5%) and
β-phellandrene (5.1%) 15
Iran (l) α-pinene (30.0%), δ-3-carene (21.7%), β-caryophyllene
(6.9%), and cedrol (6.1%) 16
Iran (st) δ-3-carene (24.3%), α-pinene (15.4%), cedrol (17.7%),
sabinene (8.2%), α-humulene (6.1%) 16
Iran (f) α-pinene (38.7%), δ-3-carene (20.4%) and α-fenchene
(5.0%) 16
China (l) α-pinene (8.4%), 3-carene (12.2%) and cedrol (10.7%) 17
China (l/tw) cedrol (30%) and α pinene (5%) 18
China (l) cedrene (41.25%), cedrol (39.06%), cedrol (31.43%) 19
China (l) α-pinene (24.9%), 3-carene (2.6%) and cedrol (12.7%) 20
China (l)
α-pinene (37.6% - 68.1%), cedrol (3.4% - 18.1%), 3-carene
(0.1% - 29.4%), β-caryophyllene (2.0% - 10.2%) and
α-caryophyllene (1.7% - 7.1%)
21
China (l) cedrol (15.0%), 3-carene (12.2%) and β-caryophyllene
(8.0%) 21
China (l) cedrol (19.2%), β-caryophyllene (14.3%) and
α-caryophyllene (11.3%) 21
China (l) cedrol (23.7%), terpinenyl acetate (19.4%), 3-carene
(10.6%) and α-pinene (10.2%) 21
Poland α- and β-thujone, fenchone, sabinene, beyerene and
rimuenea 22
Austria (tw) camphor (27.8%), fenchone (18.9%), α-thujone (6.8%) and
β-thujone (5.3%) 23
China (l)
α-pinene (29.2%),  -3-carene (20.1%), α-cedrol (9.8%),
caryophyllene (7.5%), α-humulene (5.6%) and limonene
(5.4%)
24
Pakistan (l) α-pinene (40.6%), 3-carene (26.0%) and cedrol(10.7%) 29
Pakistan (f) α-pinene (41.8% - 45.61%), 3-carene (32.69% - 34.55%)
and cedrol (1.82% - 4.50%) 30
Iran (dp) α-pinene, β-pinene, sabinene,
 -3-carene and terpinolenea 31
Nigeria (l) β-santalene (12.19%), cedrol (11.66%), fenchol (10.66%)
and β-elemene (7.81%) 32
aQuantitative data not available; l = leaf; f = fruit; st = stem; dp = different parts; tw = twig.
6) camphor, fenchone and α-thujone group [23]
7) α-pinene, β-pinene and sabinene group [31]
4. Conclusion
Quantitative and qualitative variations were observed be-
tween these oils of Cupressaceae family cultivated in Vi-
etnam and elsewhere. This may be attributed to factors
such as the place of collection, age and nature of the
plant, climatic conditions, handling procedures etc.
5. Acknowledgements
Authors are grateful to Mrs. Ogunwande Musilimat for

Terpene Composition of Three Species of Gymnosperms from Vietnam 2037
the typesetting of the manuscript.
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