Juglandaceae

Headspace Analysis of Volatile Compounds in

Leaves from the Juglandaceae (Walnut) Family
Mohamed A. Farag,
Faculty of Pharmacy, Cairo University, Cairo, P.B. 11562 Egypt. Email: mfarag73@yahoo.com

Abstract
Headspace volatile analysis coupled with software extraction of overlapping GC-seperated components was employed for volatiles profiling in leaves of six Juglans and Carya species. Qualitative and quantitative differences were
observed among species. Sesquiterpenes dominated the volatile blend of all species (J. nigra L. 70%, J. cineara L.
61%, J. regia L. 47%, C. cordiformis, (Wangh.) K. Koch, 50%, C. laciniosa (Michx.) Loud. 41%, and C. illinoinensis
(Wangh.) K. Koch 24%) with germacrene D occurring in the largest amount. Higher levels of monoterpenes were
found in the headspace of J. cineara, J. regia and C. laciniosa leaves (35%, 24% and 18%, respectively). Among the
benzenoids, methyl salicylate was found as the major leaf headspace component (J. regia 17 %, C. cordiformis 15%,
C. laciniosa and C. illinoinensis 10%,).

Key Word Index

Carya cordiformis, Carya illinoinensis, Carya. laciniosa, Juglans cineara, Juglans nigra, Juglans regia, Juglandaceae, headspace volatiles.

Introduction
The Juglandaceae, also known as the Walnut Family, is
a family of trees, or sometimes shrubs, in the order Fagales.
Various members of this family are native to the Americas,
Eurasia, and Southeast Asia. Members of the walnut family
have large leaves that are often aromatic and with a distinctive
fruiting structure (1). There are eight genera in the family,
including the commercially important nut-producing trees
walnut (Juglans), pecan (Carya illinoinensis (Wangh). K.
Koch.), and hickory (Carya) (2). Although chiefly valued for
its nutritive value as major nut crops of the world, the leaves of
the trees are reported to exhibit several medicinal properties.
In regard to its biological activities, Juglans leaves have been
used primarily to treat skin complaints including acne, jock itch,
athletes foot, eczema, scabbing pruritus and varicose ulcers
(35). These effects are attributed to the tannin astringent effect
that makes up to 10% of walnut leaves. Juglone (5-hydroxyalphanapthaquinone) found in J. regia L. and C. illinoinensis
has demonstrated antiviral activities against HSV-1 virus (6), and
is reportedly antifungal due to in vitro inhibition of Candida
albicans and Trichophyton rubrum (7). In addition, walnut
leaves contain up to 3% flavonoids; 0.81.0% ascorbic acid,
and 0.0010.03% volatile oil, mainly germacrene D (8). Most

literature on the bioactivity of Juglans species has focused on

their phenolics with little information on essential oil related
pharmacological effects. This has been circumvented mostly by
scarce reports on volatile composition in family Juglandaceae
with only one report on C. illinoinensis leaves published over
30 years ago. Mody et al. (9) identified 31 compounds including 11 monoterpenes, 10 sesquiterpenes and 9 aromatics with
no relative quantification. Most recent papers on the volatile
composition of Juglandaceae have focused on fresh and roasted
nuts in relation to its fatty acid content (10).
Methodologies most commonly used for plants volatile analysis are based either on steam distillation or headspace volatile
analysis followed by gas chromatography/mass spectrometry
(GC/MS) analysis. Compared with steam distillation, headspace
gives more realistic picture of the volatiles profile. However,
adequate controls need to be considered to avoid interference
of impurities (11). In cases of dynamic headspace analysis, air
is continuously swept over the plant and volatiles are trapped
on an adsorbing matrix which allow for higher enrichment factor especially in case of low volatiles producing plants (11). In
this study, dynamic headspace volatile analysis combined with
GC/MS was utilized for profiling of volatiles in 3 Juglans sp., J.
cineara L. (White walnut), J. nigra L. (Black walnut) and J. regia
Received: March 2007

*Address for correspondence

Revised: April 2007

1041-2905/08/0004-0323$14.00/0 2008 Allured Publishing Corp.
Vol. 20, July/August 2008

Accepted: June 2007

Journal of Essential Oil Research/323

Farag

Table I. Relative percentage of volatile compounds in the headspace of Carya sp.: C. laciniosa; C. illinionensis; C. cordiformis and of
Juglans sp.: J. cineara; J. nigra; J. regia.
RI

Compound

C. cordiformis C. illinoinensis C. laciniosa

Identification

Concentration (%)a
J. cineara J. nigra

J. regia

Aliphatic hydrocarbons
999
decane

1299
tridecane

1399
tetradecane

Total aliphatic hydrocarbons

3.8
0.4
(4.2)

2.3

0.2

(2.5)

0.6

0.3
(0.9)

tr.

MS, RI, STD

MS, RI
MS, RI, STD

Aromatic hydrocarbons
1026
p-cymene
1091
m-cymene
1096
p-cymenene
1179
naphthalene
Total aromatic hydrocarbons

0.5
0.4
0.6
1.3
(2.8)

0.6
0.2

0.4
(1.2)

tr.


0.2
(0.2)

0.5


0.4
(0.9)

0.4


0.5
(0.9)

MS, RI, STD

MS, RI
MS
MS, RI

0.3
4.9

tr.
5.8



3.0
(14.0)

0.1
2.4
0.2
0.5
3.1
8.2

0.2
3.0
(17.7)

3.0
2.9

6.2
0.1
1.8
0.4
19.8
0.1

0.45
(34.7)

0.5
0.6
0.4
0.6
1.8

2.3

0.6
0.1


(6.9)

1.7
3.6

2.1

4.8
0.4
6.8

tr.
4.5
(23.9)

MS, RI
MS, RI, STD
MS, RI, STD
MS, RI
MS, RI, STD
MS, RI
MS, RI, STD
MS, RI, STD
MS, RI, STD
MS, RI, STD
MS, RI
MS

1.0

9.6



4.0


7.4
tr.


2.2



(24.2)

1.4
1.2
2.4
0.7

0.3
5.2

3.4
tr.
8.3

9.4
5.6

2.9

(40.8)

0.4
0.8
0.7

tr.
5.4
7.6

11.8
7.4

20.2

3.3
3.0

(60.6)

tr.
0.3
0.6
0.4

4.9

0.2

3.2


60.3


tr.




(69.9)

0.2
0.1
3.1
3.4
0.7
1.5
0.6
tr.

1.3
0.5

28.6

0.3


6.5


(46.8)

MS, RI
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI, STD
MS, RI, STD
MS, RI, STD
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI, STD
MS, RI
MS, RI

1.5
1.9

2.2
10.3

0.1
0.4
1.0

0.8
0.8

0.6
0.1
tr.
0.4

tr,
0.6
0.3
tr.
0.5
0.2

0.4

0.2
tr.
0.1
0.2

MS
MS
MS, RI, STD
MS, RI
MS, RI, STD
MS, RI
MS, RI
MS, RI

0.5


0.4
(0.9)

Monoterpene hydrocarbons
931
thujene

939
pinene
0.2
980
pinene
0.6
926
cumene

991
myrcene
1.2
1005
phellandrene

1031
limonene
0.7
1040
(Z)ocimene
tr.
1050
(E)ocimene
1.4
1062
terpinene

1088
terpinolene

1125
Unknown monoterpene

Total monoterpene hydrocarbons
(4.1)

Sesquiterpene hydrocarbons
1339
elemene

1376
copaene
0.2
1384
bourbonene
0.9
1391
elemene
2.5
1415
cisbergamotene

1418
caryophyllene
2.3
1436
transbergamotene
tr.
1439
guaiene

1443
(Z)farnesene

1454
humulene
9.6
1458
(E)farnesene

1485
selinene

1490
germacrene-D
22.3
1499
himachalene

1494
selinene

1495
zingiberene

1511
dehydro-ar-himachalene- 4.7
1509
bisabolene
4.7
1524
sesquiphellandrene

1538
cadinene
2.5
Total sesquiterpene hydrocarbons
(48.8)
Alcohols
1013
1030
1032
1070
1098
1110
1139
1183

p-dimethyl-benzyl alcohol
2-ethylhexanol
benzyl alcohol
octanol
linalool
2-phenylethyl alcohol
trans-pinocarveol
cis-pinocarveol

324/Journal of Essential Oil Research

1.0

Vol. 20, July/August 2008

Juglandaceae

Table I. Continued
RI

Compound

Identification

Concentration (%)a
C. cordiformis C. illinoinensis C. laciniosa

J. cineara J. nigra

J. regia

1189
terpineol
1228
citronellol
1564
(E)-nerolidol
1568
caryophyllene alcohol
1574
germacrene D-4-ol
Total alcohols

(1.0)

0.3




(16.2)

0.1


0.6
(3.8)

tr.
0.1

0.2
(1.4)

0.4
tr.
(2.0)

tr.
tr.


(0.9)

MS, RI
MS, RI
MS, RI, STD
MS, RI
MS, RI

Aldehydes/ketones
961
benzaldehyde
962
5-ethyl-2(5H)-furanone
999
2,4-heptadienal *
1001
octanal
1043
phenylacetaldehyde
1102
nonanal
1153
citronellal
1204
decanal
Total aldehydes/ketones

10.6
2.1
0.7

3.2
tr.

0.1
(16.6)

2.7
8.3
1.0
0.1
2.4
0.8
tr.
tr.
(15.3)

2.5
6.1
1.1

1.3
0.4
0.4

(11.8)

0.2
0.2
0.5

0.1
tr.

tr.
(1.0)

0.3
0.9
0.4

0.9
0.7


(3.2)

0.5
0.8


0.4
0.7


(2.4)

MS, RI, STD

MS
MS, STD
MS, RI
MS, RI
MS, RI
MS, RI
MS, RI

Esters
1004
(Z)-3-hexenyl acetate
1186
(Z)-3-hexenyl butyrate
1190
methyl salicylate
1285
bornyl acetate
1297
trans-pinocarvyl acetate
1354 citronellyl acetate
Total esters

1.3

15.1
tr.


(16.4)

0.9

9.6



(10.5)

0.8

10.0


0.7
(11.5)

0.1
0.1
0.7



(0.9)

6.3
tr.
1.5



(7.8)

5.8

16.8
0.1
0.4

(23.1)

MS, RI, STD

MS, RI
MS, RI, STD
MS, RI
MS, RI
MS, RI

Miscellaneous
1356
eugenol
1581
caryophyllene oxide
Total miscellaneous

0.6
tr.


(0.6)

0.1
tr.
0.2

(0.3)

tr.

MS, RI, STD

MS, RI, STD

(89.4)

(89.3)

(91.6)

(98)

Total volatile compounds (%)

(85.2)

(98.8)

MS data for unknown monoterpene RI 1125, m/z (rel. int.): 150(15%), 135(20%), 107(20%), 81(18%), 69(100%), 53(10%);
a
Relative concentration based on duplicate measurements; , not detected; tr, detected but not quantified; * correct isomer not identified; RI, retention index on DB-Wax
column; MS, identification was based on comparison of mass spectra; STD, co-analysis relative to a pure compound matching in retention and mass data.

L. (English walnut) and 3 Carya sp. C. cordiformis (Wangh.)

K. Koch (bitternut hickory), C. illinoinensis (Wangh.) K. Koch
(pecan) and C. laciniosa (Michx.) Loud (Shellbark Hickory).
Differences in chemical composition from a qualitative and
quantitative point of view were detected that would further
assist in species differentiation. Results on volatile composition were also discussed in term of plants reported medicinal
effects. As far as Juglans and Carya species are concerned,
these results provide the first comprehensive volatile profile
of leaves in family Juglandaceae.

Experimental
Plant material: Leaves of Juglans and Carya sp. were
collected from cultivated trees in University of Kentucky
arboretum, authenticated by Robert Pratley with voucher
Vol. 20, July/August 2008

specimens have been deposited at the University of Kentucky

Herbarium.
Headspace isolation: Ten grams of fresh leaves were
placed in a side-arm conical flask (125 ml). Charcoal-purified
air was passed over the plant from the top and volatiles were
collected by pulling vacuum through Tenax (Sigma, St. Louis,
MO) traps located at the flask side arm. Volatiles collected on
the Tenax adsorbent traps for 8 h were eluted with 500 L
hexane and analyzed by GC/MS. A system blank containing
no plant material was run as control.
GC/MS analysis and quantification: GC/MS analysis
was performed on an HP 5890A (HewlettPackard, Palo
Alto, CA) equipped with an HP-5HS column (Agilent)
30-m x 0.32-mm, 0.25-m-thick bonded methyl siloxane.
Injections were made in the splitless mode for 30 sec, and
Journal of Essential Oil Research/325

Farag

the gas chromotograph was operated under the following

conditions: injector 220C, column oven 40C for 3 min, then
programmed at a rate of 12C/min to 180C, kept at 180C
for 5 min and finally ramped at a rate of 40C/min to 250C
and kept for 2 min, He carrier gas linear flow velocity 50 cm/
sec. The transfer line and ion-source temp were adjusted at
230C and 190C, respectively. The HP quadrupole mass
spectrometer was operated in the electron ionization mode
at 70 eV and a source temperature of 180C. Volatile components were deconvoluted using AMDIS software (www.
amdis.net) and identified by its retention indices (relative to
n-alkanes), mass spectrum matching to EPA/NIH database
and with authentic standards (when available). Peaks were
quantified by selected abundant fragments (m/z) to overcome
the problem of co-eluted compounds (12) and relative volatile
abundances were calculated using a custom PEARL script
to extract peak areas of individual ions characteristic of each
component (13,14).

Results and Discussion

The volatile compounds identified from Juglans and Carya
leaves are listed in Table I. Components were categorized
into aliphatic, aromatic, monoterpene and sesquiterpene
hydrocarbons, alcohols, carbonyls (aldehydes/ketones), and
esters for comparative convenience. A total of 70 compounds
were detected including 50 in Juglans and 54 in Carya sp.,
of which only 10 were previously reported from C. illinoinensis leaves. Increase in identification was due in part to
volatile enrichment on Tenax traps, providing the highest
adsorption efficiency among adsorbents (15). GC/MS files
were further processed by AMDIS software that assists in
adjacent peak deconvolution, background subtraction and
increased detection limit (12). Utilizing AMDIS, we were
able to resolve complex volatile blends of several Bacillus
species (14).
Sesquiterpene hyrocarbons: Sesquiterpene hydrocarbons constituted the most dominant chemical group
among Carya and Juglans volatiles: C. cordiformis (50%),
C. illinoinensis (24%), C. laciniosa (41%), J. cineara (61%),
J. nigra (70%) and J. regia (47%). In case of walnut fruit
aroma, aldehydes and ketones were found to be the major
components (10). Sesquiterpenes have been reported to
exhibit a potent anti-inflammatory effect comparable to that
of indomethacin (16-17). The presence of sesquiterpenes in
such high levels in Juglans leaves might account in part for
the reported anti-inflammatory effects. All species released
elemene, caryophyllene, humulene and germacrene
D as previously reported in C. illinoinensis leaves (9). Except
for C. illinoinensis and C. laciniosa, germacrene D was found
to be major volatile component in C. cordiformis (22%), J.
cineara (12%), J. nigra (60%) and J. regia (29%). Salvia sp.
essential oil rich in germacrene D and caryophyllene (up to
50%) are reported to induce sedation (1819). Interestingly,
a study by Girzu et al. (20) has demonstrated that J. regia
chloroform extract containing the naphthoquinone juglone
exhibited a similar sedative effect. Further investigations
on the possible synergism between walnut sesquiterpenes
and juglone should be of interest. Himachalene was only
326/Journal of Essential Oil Research

found among Carya sp., whereas cadinene and selinene

were found exclusively in C. cordiformis and C. laciniosa,
respectively. This compositional variation of sesquiterpene
hydrocarbons among Juglans and Carya sp. could be used
as taxonomic potentialities to help differentiate between
species.
Monoterpene hydrocarbons: High levels of monoterpenes
were only found in J. cineara (35%), J. regia (24%), and C.
laciniosa (18%) with (E)ocimene accounting for up to 50
% among the monoterpene hydrocarbons content. Except for
J. nigra, (E)-and (Z)ocimene represented the most common forms in most species. Other common monoterpenes
found in most species include myrcene and limonene, albeit
at much lower levels.
Oxygenated compounds: A total of 29 oxygenated
compounds were found amounting to 34% in C. cordiformis,
42% C. illinoinensis, 27% C. laciniosa, and 26% J. regia
volatile blends; much lower levels were found in J. cineara
and J. nigra (313%). Compounds were categorized into
carbonyl compounds (aldehydes/ ketones), alcohols and
esters. Aldehydes and ketones were relatively prominent
in Carya species (1216%) and to a lesser extent in Juglans
(13%). Among Carya sp. C. illinoinensis and C. laciniosa
possessed similar carbonyl profiles differing from that
of C. cordiformis. For instance, C. cordiformis had the
highest level of benzaldehyde, whereas C. illinoinensis
and C. laciniosa had comparatively the highest 5-ethyl2(5H) furanone level. The occurrence of benzaldehyde is
in agreement with previous reports on C. illinoinensis (9).
Benzaldehyde, phenylacetaldehyde, 5-ethyl-2(5H) furanone,
2,4-heptadienal and nonanal were found in all species.
Alcohols accounted for 14% of the volatiles in most species except for C. illinoinensis (16%) owing to its relatively
high 2-phenylethylalcohol content (ca. 10%), while it was
present at trace levels in all other species. Another species
with a distinct alcohol composition was J. regia, in which
cis-and trans-pinocarveol. alcohol and trans-pinocarvyl
acetate were unique. Alcohols found in all species include
benzyl alcohol and linalool, with highest levels found in C.
illinoinensis. Linalool found in C. illinoinensis leaves have
been reported to exhibit potent fungitoxic activity against
Fusicladium effusum (21). Hexanol derived volatile which
dominated walnut fresh peel aroma (22), was found at very
low concentration (ca. 1%) in C. illinoinensis, C. lacinosa
and J. nigra.
Next to sesquiterpenoids, esters were the most abundant
compounds in the volatile blend of J. regia (23%), Carya species (1016%) and J. nigra (8%). Esters at such high levels can
contribute for Juglans and Carya leaves aroma. In contrast, aliphatic aldehydes namely hexanal, pentanal, 2-methy-2-pentenal,
not found in this study were found important contributors to
walnut aroma (23). Among esters, methyl salicylate (MeSA)
was the most prominent form (ca. 90%) in most species, except
for J. nigra in which (Z)-3-hexenyl acetate was determined
to be the most abundant ester (78%). MeSA was previously
found in C. illinoinensis leaves (9). It is noteworthy that the
relative high levels of MeSA might mediate for Juglans leaves
reported anti-inflammatory and antimicrobial effects in skin
Vol. 20, July/August 2008

Juglandaceae

diseases. In this study, several volatiles with reported antimicrobial activities were also identified including p-cymene,
naphthalene, benzyl alcohol, benzaldehyde, 2-phenylethanol
and eugenol (24- 25).
Aromatic and aliphatic hydrocarbons: Low emission
levels in aromatic (0.9-2.8%) and aliphatic hydrocarbons
(0.2-0.8%) were observed in all species with p-cymene and
naphthalene being the most common. p-Cymene was common in most essential oils whereas naphthalene was found to
be the most abundant volatile in walnut fruit from Chile (10).
Interestingly, no alkyl benzenes which predominated in walnut
aroma were found in any leaves.
In conclusion, dynamic headspace coupled to GC/MS developed in this work was found suitable for the qualitative and
quantitative investigation of volatiles in Juglandaceae which can
be further used for investigating other factors as geographical
origin and storage on volatile composition.
Acknowledgments

The author thanks George Wagner, Department of Plant Sciences,

University of Kentucky for assistance with GC/MS analysis, and Robert
Pratley, University of Kentucky Herbarium, for plant collection and
authentification.

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