Originalarbeiten Originals

Holz als Roh- und Werkstoff 60 (2002) 356362
Springer-Verlag 2002

DOI 10.1007/s00107-002-0316-y

The composition of volatile extractives from the wood of Juniperus excelsa,

Juniperus foetidissima and Juniperus oxycedrus
G. Uc ar, M. Balaban

356
Over 140 compounds were determined occurring in waterdistillates obtained from the wood chips of three important juniper species of Turkey, J. excelsa, J. foetidissima
and J. oxycedrus. Among the compounds the monoterpenes exist in minor amounts while the sesquiterpenes including their oxygenated members as well as sesquiterpene
alcohols consist of the majority of the whole substances.
The existence of some compounds of the oils might be
attributes of the species and their sap- and heartwood. On
the other side though notable differences, the essential oils
of Turkish juniper woods resemble the commercial cedar
wood oils.

Die Zusammensetzung der fluchtigen Extraktstoffe

im Holz von Juniperus foetidissima
und Juniperus oxycedrus
Mehr als 140 Komponenten wurden bestimmt in Wasserdampfdestillaten der drei wichtigsten Juniperusarten der
Turkei, J. excelsa, J. foetidissima und J. oxycedrus. Monoterpene bilden einen geringen Anteil der Extraktstoffe. Der
Hauptteil besteht aus Sesquiterpenen mit deren Oxy le
dationsprodukten. Das Vorkommen einiger der O
konnte charakteristisch sein fur die jeweilige Art bzw.
le,
deren Splint- und Kernholz Allerdings gleichen diese O
trotz geringer Unterschiede, den wesentlichen
lbestandteilen von Kommerziellen Zedernholzern.
O
1
Introduction
The variety of climate and ecological conditions in Anatolia (Asia Minor) is reflected in the generosity of the
nature which offers an extensive diversity of both fauna
and flora. Many plants have been found here as endemic
species and others are represented by numerous genera
and species. Accordingly, the genus Juniperus occurring
widely all over the northern hemisphere, is represented by
10 taxa in Anatolia, from coastal foredunes of the Mediterranean up to altitudes of 2500 meters on the Taurus
mountains and also in central and northern Anatolia

G. Ucar (&), M. Balaban

Department of Wood Chemistry at the Faculty of Forestry of
Istanbul University, Bahcekoy, 80895 Istanbul, Turkey
e-mail: ucarg@istanbul.edu.tr
This work was supported by the research found of the Istanbul
University. Project nr: 1335/280799.

(Elicin 1977). The species favor dry rocky or sandy soils.

J. excelsa, J. foetidissima and J. oxycedrus, three of ten
juniper species are regarded to grow to tree size reaching
heights of up to 20 meters (J. excelsa) and they are also the
most important ones encountered as pure and mixed
stands in Asia Minor.
The hard juniper wood is esteemed especially for its
durability in timber industry and the associated essential
oils were used for cosmetic and medicinal purposes for
several centuries. Cedar wood oil obtained from steam
distillate of juniper woods is used today to scent soaps,
technical preparations, room sprays, disinfectants and
similar products. Furthermore, the medical use of juniper
is perhaps the one which is most respected in history.
The oils obtained by either steam distillation of cones
(berries) and wood or by dry distillation of heartwood
(cade oil or juniper tar oil) were applied on the treatment
of many diseases from leprosy, typhoid to tape worm. In
modern times, too, the protective and health supporting
reputation of juniper is well known in herbal medicine
(anti fungal, disinfectant, insect repellant properties and
supports the arteries, the heart, the kidneys, the lungs.
Ody 1993).
While juniper forests are quite abundant in many
countries (i.e. North America) and in many parts of the
United States they are even considered noxious trees in
rangelands, particularly in the last decade the juniper
stands in Anatolia decreased considerably due to intensive
harvesting and difficulties were encountered in both the
natural propagation and afforestation. Finally, a short time
ago the Turkish government enacted a law with the aim of
protection of all juniper species in Anatolia.
Some local research has been carried out elucidating
the extracts obtained from leaves and cones (berries) of
sorted Juniperus species in Turkey (Sakar and San Feliciano 1992, Berkman et al. 1994). A few works also
dealt with the wood extracts of these species but only to
limited extent (Avciata and Cengiz 1990, Hafizoglu
1994). This reason gave rise to a detailed study of three
tree forming and high biomass producing juniper species of Turkey, i.e. J. excelsa, J. foetidissima and J.
oxycedrus. In this scope, first the wood extractives isolated by steam distillate were analyzed and will be reported here. The three juniper woods were also subject
to the solvent- (cyclo hexane and ethyl alcohol) and hot
water extractions. In continuity, the chemical characterization of these extracts and their inhibitory effects
against four wood destroying fungi are being under investigation.

alpha-phellandrenol, borneol, p-cymenol, verbenone, carveol were practically found only in the oil of J. excelsa
since they are either absent or just traceable in other
species. J. foetidissima and J. oxycedrus exhibit only a
couple of monoterpenes with the amounts hardly exceeding 0.1%. One of them, the thymoquinone is present
about 1% of the oils from sapwoods of both species and
from heartwood of J. foetidissima. 1.8% of its content
reaches the highest level in the essential oil from the
heartwood of J. oxycedrus. Thymoquinone is obviously a
distinctive compound for the juniper woods and probably
is a rare compound in higher plants. As an example, in the
roots of Inula salicina a thymoquinone derivative, 7-isobutyryloxythymohydroquinone dimethylether was reported (Anthonsen and Kjosen 1971).
Embracing some 90 compounds, the sesquiterpene hydrocarbons and their oxygenated members constitute the
main portion of the oils. Some subsequent sesquiterpenes,
and particularly isomers were not resolved in the chromatogram and therefore integrated together. By changing
the GC parameter an improvement of resolution was
possible at certain places of the chromatogram but at the
same time many compounds were adversely affected from
this practice. It was then unavoidable, even though the
constitutions of adjacent compounds were well established, to give a combined area percent.
Reaching up to 25% in peak areas widdrene, widdrol,
alpha-cedrol and caryophyllene alcohol are the dominating compounds among the sesquiterpenes. Apart from
caryophyllene alcohol the others belong to the major
commercially important components of cedar wood oil
obtained from the juniper woods in the United States in
the same manner. Alpha- and beta-cedrene and cuparene
are other including compounds of commercial oil but they
are usually not present in such large amounts (Adams
1987). Compared to the oils of J. foetidissima and J. oxycedrus, the oil of J. excelsa exhibits the most striking difference with its low widdrene content (2024% vs. ca 3%).
Furthermore, the oils from heartwoods are apparently rich
in alpha- and beta cedrene and other particular sesquiterpene hydrocarbons (cadinene and germacrene isomers,
cuparene, curcumene, and so on.). Similar tendency can
also be observed for certain sesquiterpenoids i.e. sesquiterpene alcohols. The content of widdrol in heartwood oil
from J. oxycedrus is in fact higher but the same content is
as high as fivefold in case of J. foetidissima. Though obtained from sapwood, with ca 22% the oil of J. excelsa has
3
the highest widdrol content. The constitution formulas of
Results and discussion
prevailing and interesting compounds in the oils are preFrom the low boiling monoterpene alpha-pinene to
sented in Fig. 1.
a triterpene squalene, over 140 compounds are listed in
The essential oils investigated here could be of interest
Table 1. The minimum detectable amount and resolution for evaluating as cedar wood oil where, as mentioned
problems of isomer compounds especially hindered the
above, the composition of the commercially important
further rise of the number of compounds, which would
compounds (alpha-and beta-cedrene, widdrene, cuparene,
probably have reached 200.
cedrol and widdrol) is relevant. The area percentage of
The monoterpene region in Table 1 comprises over 30 these compounds are depicted in Fig. 2. Since cedar wood
compounds and the oil of J. excelsa not only has the most oil is produced from steam distillation of juniper heartmonoterpenes (except limonene) but also the greatest
woods the data of J. foetidissima and J. oxycedrus in
amount of monoterpenes (5% vs. 23%). Meanwhile, some Table 1 should be considered and compared with those
monoterpenes, phenyl ethanal, cineole, 1-terpineol,
reported by Adams (1987). Being the amount of cuparene
camphor, pinocarveol, verbenol, pinocarvone,
approximately in the neighborhood of American ceder

2
Experimental
Because of legal protection of all juniper forests in Turkey,
according to the official permission the sampling was restricted to one or two trees for each species. Near Elmali
district (province Antalya) the best juniper stands occur
partly mixed with other conifers. Representative trees
growing in the altitudes between 1300 m and 1600 m from
pure stands were carefully selected and felt in June 2000.
The age and height of trees were determined as follows:
J. excelsa, two trees both without heartwood, 80 and 60
years, 6.7 and 6.5 meters, J. foetidissima, one tree with
heartwood, 225 years, 10.5 meters, J. oxycedrus one tree
with heartwood, 140 years, 6 meters. Beginning 20 to
30 cm above from the soil end and at equal intervals along
the length of stem, four cross-sectional disks were cut from
each tree and tightly packed in plastic bags. The next day
the disks were separated in to sap- and heartwood first and
then chipped in a chopper machine to the sizes between 1
10 mm. Care was exercised in cleaning of the machine
before the chopping of the next wood specimen and about
half kilo of chips obtained at every beginning was discharged. In case of two trees from the same species the
chips were mixed together. About 1 kg of fresh wood chips
and 3 liters of distilled water were placed in a 5 liter round
bottom flask with a wide neck which was connected
through a reduction to a condenser. The water in the flask
was kept boiling until 1 liter distillate was collected. Solvent to solvent extraction was performed with petroleum
benzine (4060 C Merck, suprapure) in a separation
funnel (3 50 mL). The excess of petrol was then carefully
removed down to ca. 10 mL of solution under the light
vacuum. The extracts of each species dissolved in petrol
were then kept in a refrigerator at 0 C until they were
analyzed in GC/MS.
Analyses were carried out on a 30 m silica fused
nonpolar DB-1 column in GC/MS (Shimadzu, QP 5050A).
With the helium flow rate of 1.1 mL min)1 and split of
10/1, following temperature program was maintained:
2 min at 80 C, then 10 C min)1 to 240 C, 20 C min)1
to 280 C, 10 min at 280 C. The identification of most
compounds was based on the libraries Nist 21, Nist 107
and Wiley 229. Some MS-data given in the literature and
the succession of retention times were also helpful for
recognizing some compounds (Fang et al. 1996, Barrero
et al. 1991).

357

Table 1. The composition of volatile wood extracts as percentage of total peak area (bold: main compounds, i.e. >1%, n. d.: not
detected, SI: similarity index *value includes the percent area of following compound)
Tabelle 1. Zusammensetzung der flu chtigen Extraktstoffe als Prozentanteil der gesamten Peakfla che (fett: Hauptkomponente, i.e.
>1%, n. d.: not detected, SI: similarity index *wert schliet die Peakfla che na chster Verbinding ein)
No

358

1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50

Compound

alpha-Pinene
Pseudocumene
Phenylethanal (Hyacinthin)
p-Cymene
Cineole
Limonene
Dehydro-p-Cymene
alpha-Terpinolene
alpha-Campholenal
1-Terpineol
Camphor
Pinocarveol
Verbenol
Pinocarvone
alpha-Phellandren-8-ol
Borneol
p-Cymene-8-ol
4-Terpineol
Myrtenal & alpha-Terpineol
Myrtenol
Verbenone
p-Menthenol
Carveol
Thymoquinone
Myrtanol
Thymil methyl ether
Carvenone
Carvacrol
unidentified (p-vinyl
Guayacol deriv. MW = 162)
2,4-Decadienal
alpha-Cubebene
unidentified Sesquiterpene
(MW = 204)
unidentified (MW = 180)
alpha-Copaene
alpha-Cedrene (isomer SI = 95%)
beta-Elemene (SI = 95%)
Isolongifolene
unident. Sesquiterpene
(Junipene isomer? MW = 204)
unidentified Sesquiterpene
(Farnesene? MW=204)
alpha-Cedrene
beta-Caryophyllene
beta-Cedrene
Widdrene (Thujopsene)
unident. Sesquiterpene
(Cubebene isomer? M = 204)
Dimethoxyacetophenone
(Acetoveratrone)
alpha-Humulene
Dimethoxy phenyl deriv.
(isomer of no. 45, MW=180)
unidentified Sesquiterpene
(MW = 202)
Germacrene or Cubebene
isomer? (SI = 90%)
Cadinene isomer
(delta-Cadinene SI = 93%)

Ret. Time

J. Excelsa
Sapwood

J. Foetidissima

J. Oxycedrus

Sapwood

Heartwood

Sapwood

Heartwood

4.02
4.70
5.10
5.15
5.30
5.32
6.14
6.25
6.65
6.71
6.98
7.01
7.06
7.25
7.36
7.43
7.57
7.63
7.77
7.90
7.95
8.04
8.20
8.52
8.58
8.64
8.74
9.44
9.59

0.10
0.05
0.30
0.01
0.15
n. d.
0.05
0.10
0.11
0.51
0.21
0.24
0.20
0.10
0.17
0.15
0.32
0.22
0.33
0.24
0.35
0.24
0.09
0.15
0.05
0.15
0.09
0.48
0.10

0.55
0.12
n. d.
0.02
n. d.
0.03
0.04
0.17
trace
0.01
0.01
n. d.
n. d.
n. d.
n. d.
n. d.
trace
0.04
0.03
0.03
n. d.
0.04
n. d.
0.69
0.05
0.26
0.03
0.20
trace

0.01
0.02
n. d.
0.10
n. d.
0.01
0.03
0.02
n. d.
0.01
0.03
trace
n. d.
n. d.
n. d.
0.01
0.03
0.08
0.10
0.04
n. d.
0.15
n. d.
0.98
0.18
0.56
0.09
0.38
0.11

0.05
0.02
trace
0.01
n. d.
0.02
0.01
0.05
n. d.
0.01
trace
n. d.
n. d.
n. d.
trace
0.02
0.02
0.03
0.04
0.03
0.03
0.06
n. d.
0.92
0.12
0.22
0.08
0.20
0.03

0.03
n. d.
n. d.
0.03
n. d.
0.02
0.01
0.08
n. d.
0.01
trace
n. d.
n. d.
n. d.
n. d.
0.02
0.01
0.02
0.02
trace
trace
0.02
n. d.
1.80
trace
0.04
0.12
0.06
0.01

9.66
10.61
10.68

0.14
0.03
n. d.

n. d.
0.06
0.07

n. d.
0.05
0.08

0.01
0.05
0.02

n. d.
0.04
trace

10.79
11.05
11.17
11.22
11.28
11.41

0.17
0.06
n. d.
0.05
0.02
0.04

0.05
0.03
0.02
0.16
0.05
0.14

0.09
0.05
0.02
0.40
0.09
0.21

0.05
0.07
0.02
0.22
0.08
0.17

0.03
0.16
0.11
0.16
0.16
0.24

11.46

n. d.

n. d.

trace

0.05

0.07

11.64
11.71
11.74
11.90
12.08

0.35
0.48*

1.21
2.22*

2.72
0.03

19.82
0.06

23.78
0.04

0.74
0.74
0.52
22.09
0.03

21.52
0.10

12.12

0.42

0.14

0.41

0.37

trace

12.18
12.23

0.08
1.40

n. d.
0.30

n. d.
1.55

0.50
1.05

1.04
n. d.

12.26

n. d.

0.23

n. d.

trace

0.12

12.35

n. d.

n. d.

n. d.

trace

0.09

12.43

0.22

0.42

0.54

0.73

1.23

0.37
0.91*

2.26
1.55*

Table 1. (cont.)
No

51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95

Compound

beta-Chamigrene
unidentified Sesquiterpene
(Germacrene SI = 93%)
unidentified Sesquiterpene
(Cedrane? MW = 206)
Cadinene isomer (Selinadiene,
Selinene? SI = 92%)
unidentified Sesquiterpenoide
(MW = 218)
beta Cubebene (SI = 93%)
alpha-Muurolene
Cuperene & Curcumene
unidentified Sesquiterpene
unidentified Sesquiterpene
cis-Calamenene
delta-Cadinene (Cadinene isomer)
Epizonarene? (SI = 90%)
unidentified (Dehydro
Sesquiterpene? MW = 202)
Dehydroisolongifolene
Longipinene isomer
alpha-Calacorene
unidentified Sesquiterpenoide
8,14-Cedranoxide
unidentified Sesquiterpene
epoxid (MW = 220)
Sesquiterpene (Germacrene deriv?)
Caryophylenyl alcohol
unidentified Sesquiterpene
(MW = 220)
unident. Sesquiterpenoide
(MW = 222)
unidentified Sesquiterpenoxide
(MW = 220)
unident. Sesquiterpene alcohol
(MW = 222)
Widdrol
alpha-Cedrol
unidentified Sesquiterpenoide
unresolved Sesquiterpenoides
(MW = 220 & 222)
Cedrol isomer (beta-Cedran-8-ol)
Sesquiterpene ketone? (MW = 218)
Cadinol isomer & Torreyol &
Cubenol
unidentified Sesquiterpene
(MW = 218)
unidentified Sesquiterpenoide
(MW = 218)
Methyl Caryophyllene (MW = 218)
Sesquiterp. alcohols
(T-Muurolol & Torreyol isomer)
Cadinol isomer
unidentified Sesquiterpenoxide
(MW = 220)
alpha-Cadinol & Ledol?
unidentified Sesquiterpenoide
(MW = 218)
Cedr-8-en-15-ol
Caryophyllene alcohol
alpha-Bisabolol
unidentified Sesquiterpenoide
(MW = 222)

Ret. Time

J. Excelsa
Sapwood

J. Foetidissima

J. Oxycedrus

Sapwood

Heartwood

Sapwood
0.73*

Heartwood

12.51
12.53

0.10
n. d.

0.31
n. d.

0.60
n. d.

12.57

0.15

n. d.

0.30

n. d.

n. d.

12.62

n. d.

0.08

0.16

0.10

0.18

12.68

0.14

0.09

0.25

0.45*

0.37*

12.70
12.76
12.82
12.93
12.99
13.02
13.08
13.13
13.17

trace
0.12
0.90
0.26
0.12
0.28
0.90
0.20
0.20

trace
1.82
0.30
0.80
0.10
0.47
0.20
0.40

n. d.
trace
4.79
0.70
0.30
0.50
0.90
0.22
0.70

0.32
3.06
0.15
0.35
0.75
2.29
0.58
0.25

6.86*

13.20
13.22
13.27
13.33
13.41
13.46

0.10
0.15
0.37
0.81
0.65

n. d.
0.25
0.03
0.35
0.37
0.17

0.05
0.05
0.06
0.30
1.34
1.44

n. d.
0.33
0.19
0.21
0.52
0.42

0.85
0.25
0.40
0.32

13.58
13.71
13.78

0.74
0.05
0.20

0.10
trace
0.21

0.50
0.01
0.28

0.50
0.03
0.16

0.17
0.16
0.12

13.87

1.27

0.36

0.36

0.85

1.09

13.92

0.20

0.58

0.18

0.25

n. d.

13.99

0.36

0.81

0.53

0.39

0.11

14.11
14.15
14.25
14.29

22.50
9.00
trace
0.30

3.00
18.80
trace
0.20

15.83
10.00
0.10
0.10

15.88
6.06
0.20
n. d.

19.90
2.00
0.25
n. d.

14.33
14.36
14.46

0.40
0.35
2.59

0.18
0.52
0.35

0.21
0.42
0.25

0.12
0.24
2.50

0.15
trace
7.70

14.54

0.10

0.80

0.20

0.21

trace

14.58

1.69

0.55

1.20

0.92

n. d.

14.66
14.68

4.70
n. d.

2.08
n. d.

4.30
n. d.

5.00
n. d.

n. d.
5.50*

14.70
14.72

n. d.
0.20

n. d.
0.55

n. d.
0.20

n. d.
n. d.

0.20

14.76
14.85

2.00
0.85

0.57
0.93

0.27
0.21

1.24
0.40

1.60
trace

14.92
14.97
15.08
15.15

0.50
14.35
2.68
0.77

0.50
25.00
1.92
0.77

1.82
8.90
1.95
0.40

1.00
8.10
1.78
0.46

0.10
1.00
0.74
0.20

1.38*

n. d.
0.10
1.93
5.76
1.32
n. d.
0.25

359

Table 1. (cont.)
No

96
97
98
99

360

100
101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
137
138
139
140
141

Compound

unident. Sesquiterpene oxide

(MW = 220)
unid. Sesq. (M=220) + Longifolene
rel. alcohol (M = 222)
Juniper Camphor
unidentified Sesquiterpenoide
(MW = 222)
Longipinocarveol
unidentified Sesquiterpenoide
(MW = 220)
unidentified Sesquiterpene
unidentified Sesquiterpene
Caryophylenyl alcohol isomer? &
unidentified
unidentified Sesquiterpenoide
(MW = 220)
unidentified Sesquiterpenoide
(MW = 220)
Dehydroisolongifolene rel. alcohol
(MW = 218)
gamma-Cadinene aldehyde
Caryophyllene rel. Sesquiterpenoide
(MW = 220)
Sesquiterpenoide (MW = 220)
beta-Copaenol
unidentified
unidentified
Sesquiterpene aldehyde?
(MW = 218)
Clovene related alcohol
(MW = 220)
unidentified
unidentified
Sesquiterpene-diol? (MW = 236?)
unidentified (MW = 234)
unidentified (MW = 234)
unidentified (MW = 234)
Cedran-diol,8,13Hexadecanoic acid
Manoyl oxide
Dehydroabietane
9,12 Octadecadienoic acid
9-Octadecenoic acid
unidentified Diterpene
unidentified Diterpene
unidentified Diterpene (MW = 286)
Pimaral? (MW = 286)
unidentified Diterpenoide
(MW = 298)
Unidentified Diterpenoide
(MW = 286)
Unidentified Diterpenoide
(MW = 290)
Totarol isomer
Totarol
Dehydroferruginol
Ferruginol
Diterpene aldehyde
(Me-Ferruginal?)
Unidentified Diterpene
Squalene
Sum

Ret. Time

J. Excelsa
Sapwood

J. Foetidissima

J. Oxycedrus

Sapwood

Sapwood

Heartwood

Heartwood

15.23

0.20

0.30

0.40

0.45

0.90

15.28

2.40*

1.00

0.55

1.76*

0.50

15.30
15.38

0.40

n. d.
0.20

n. d.
0.54*

0.34

0.70
0.10

15.41
15.49

1.89
0.72

1.68
0.33

0.21

4.12
0.30

1.90
0.42

15.58
15.60
15.70

0.50

0.40
0.30

0.20
0.26
0.35

0.07

0.44

0.09
0.07
0.30

0.19

15.87

0.61

0.66

0.29

0.34

0.09

15.93

0.10

0.14

0.08

0.05

0.07

15.98

0.33

0.36

0.14

0.40

n. d.

16.08
16.11

n. d.
0.50

n. d.
0.58

n. d.
0.22

trace
0.41

0.10
0.06

16.19
16.21
16.28
16.33
16.39

0.79

0.16
n. d.
0.05
n. d.
0.10

0.75

0.58

0.18
n. d.
0.39

0.70
0.10
0.15
n. d.
0.35

0.13
0.14
0.25

0.05
0.11
0.10

16.49

0.87

0.20

0.13

0.54

0.88

16.54
16.59
16.67
16.77
16.89
17.16
17.64
18.29
19.03
19.68
20.46
20.54
20.73
20.98
21.23
21.33
21.45

0.11
0.24
0.20
0.42
0.61
0.10
0.05
1.00
0.05
0.04
0.39
0.20
0.18
0.02
0.14
0.08
0.09

0.23
0.16
0.24
0.25
0.23
0.21
0.14
0.02
n. d.
0.06
n. d.
n. d.
n. d.
0.10
0.01
trace
n. d.

0.03
0.08
0.12
0.18
0.38
0.05
0.06
n. d.
n. d.
n. d.
n. d.
n. d.
n. d.
n. d.
n. d.
0.02
n. d.

0.18
0.24
0.30
0.50
0.17
0.13
0.02
0.01
0.01
n. d.
n. d.
n. d.
n. d.
n. d.
0.01
trace

0.10
0.16
0.07
0.01
n. d.
n. d.
trace
n. d.
0.02
0.04
n. d.
n. d.
n. d.
n. d.
n. d.
0.02
trace

21.55

0.10

0.13

n. d.

0.02

n. d.

21.82

0.15

n. d.

n. d.

0.20

0.05

22.18
22.45
22.50
22.60
22.77

0.22
0.20
0.33
0.81
0.23

0.02
0.19
trace
0.13
n. d.

0.01
0.03
n. d.
n. d.
n. d.

0.01
0.03
0.12
0.11
0.02

0.01
trace
0.09
0.07
0.13

22.97
25.07

0.14
0.20
99.34

0.01
n. d.
99.25

n. d.
n. d.
99.23

n. d.
n. d.
99.34

n. d.
n. d.
99.35

361

Fig. 1. The constitutions of essential compounds in the volatile

extracts of juniper woods

Bild 1. Chemische Komponenten der Hauptbestandteile der

fluchtigen Extraktstoffe von Juniperholz

Fig. 2. The composition of the major commercially

important components
Bild 2. Zusammensetzung der kommerziel wichtigen
Komponenten

Turkish oils (2224%) is slightly higher than that obtained

wood oils, the Turkish juniper oils contain as low an
amount of alpha- and beta-cedrene as those from J. ashei, from J. californica, J. occidentalis, but much higher than
that of J. deppeana and J. pinchotii. In American oils, ceJ. erytrocharpa and J. pinchotii. Widdrene content of

362

drol ranged from 5% (J. pinchotii) to 39% (J. occidentalis)

and the 16% respectively 20% cedrol is found in Turkish
oils. 2% widdrol in the oil of J. oxycedrus is as low as that
of many American junipers but with 10% J. foetidissima
has the highest content of this component. At the end the
sum of these six commercial compounds in Turkish oils
comes to about 58% for J. foetidissima and 52% for
J. oxycedrus, where the corresponding values lies between
63% and 87% for most of American juniper species.
Another interesting sesquiterpene alcohol, caryophyllene alcohol appears to be one of the major components of
oils. Regarding the cedar wood oil quality no attention was
paid to this compound or its isomers and also further
information was not given in the work by Adams (1987).
14-hydroxy 9-epi-b-caryophyllene, as a new sesquiterpene
alcohol was reported first by Barrero et al. (1989) in the
essential oil of the wood of J. oxycedrus. In the petroleum
ether extracts of wood from J. oxycedrus, too, caryophyllene alcohol and its derivative were isolated by TLC and
identified by 13 C NMR spectroscopy (Balaban 1997).
Higher yields of caryopyllene alcohol are observed in the
oils from particularly sapwoods, with 25% the sapwood of
J. foetidissima being the highest.
The heartwood oil of J. oxycedrus is apparently rich in
certain cadinol isomers (T-muurolol and torreyol isomers
pk. no. 87,88). Furthermore, existing in larger amounts
longipinocarveol might be another characteristic compound for sapwood oils.
The accumulation of fatty acids in the oil of J. excelsa is
also distinctive. Another noticeable feature of this oil is the
higher content of aromatic diterpenes, like totarol and
ferruginol.

References
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States for New Sources of Cedarwood Oil. Economic Botany 41:
4854
Anthonsen T, Kjosen B (1971) New Thymol Derivatives from
Innula salicina L. Acta Chem Scand. 25: 390392
Avciata U, Cengiz M (1990) Gas Chromatographic Analysis of the
Volatile Compounds of Turkish Juniperus Foetidissima Wild.
Reported at International Conference on Essential Oils for Perfumery and Flavours, held in Antalya-Turkey
Balaban M (1997) Chemical Properties of Some Important, Natural Juniper Species. PhD Thesis, Institute of Natural Sciences of
the Istanbul University. (Turkish)
Barrero AF, Sanchez JF, Ferrol N, Feliciano AS (1989) Conformational Isomers of 14-Hydroxy-9-Epi-b-Caryophyllene Isolated
from the Wood of Juniperus Oxycedrus. Tetrahedron Letters 30:
247250
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A (1991) Oxygenated Sesquiterpenes from the Wood of Juniperus
Oxycedrus. Phytochemistry 30: 15511554
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