FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fragr. J. 2001; 16: 239–240

DOI: 10.1002/ffj.983

Volatile constituents of Hymenocrater incanus Bunge, an

Iranian endemic species
M. Mirza,∗ L. Ahmadi and M. Tayebi
Research Institute of Forests and Rangelands, PO Box 13185-116, Tehran, Iran
Received 8 August 2000
Revised 22 November 2000
Accepted 23 November 2000

ABSTRACT: The volatile constituents of the aerial parts of Hymenocrater incanus Bunge growing in Iran, isolated
by hydrodistillation, was analysed by GC–MS. The oil was found to contain 35 components. The oil was rich in
ˇ-caryophyllene (17.6%) and 1,8-cineole (16.9%). The other major constituents were ˛-pinene (9.2%), ˇ-pinene
(7%), trans-ˇ-ocimene (5.4%), germacrene-D (4.5%) and caryophyllene oxide (3.9%). Copyright  2001 John
Wiley & Sons, Ltd.
KEY WORDS: Hymenocrater incanus Bunge; Lamiaceae; essential oil; ˇ-caryophyllene; 1,8-cineole; ˛-pinene;
ˇ-pinene

Introduction Gas Chromatography–Mass Spectrometry

Nine species of the genus Hymenocrater (Lamiaceae)
are found in Iran, of which four are endemic.1,2 One
of them is H. incanus, which occurs in west, south and
central parts of Iran. Hymenocrater spp. are low shrubs
and perennial herbs.3 The essential oil obtained from this
genus has not previously been chemically investigated.
We report in this paper the chemical composition of the
essential oil obtained by hydrodistillation from the leaves
and flowers of H. incanus.
(GC–MS)
GC–MS analysis was carried out on a Varian 3400
apparatus equipped with a DB-1 fused silica column
(60 m ð 0.25 mm, film thickness 0.25 µm) and inter-
faced with a Varian ion trap detector. Column tempera-
ture was programmed at 50–270 ° C at 4 ° C/min; injector
and transfer line temperatures were 280 ° C and 290 ° C,
respectively; carrier gas, helium, with a linear velocity
of 31.5 cm/s; split ratio, 1/60; ionization energy, 70 ev;
scan time, 1 s; mass range, 40–450.

Experimental
Plant Material
The leaves and flowering tops of H. incanus were col-
lected in May 2000 at an altitude of 2300 m, near Abadeh
in Fars province, and a voucher specimen was deposited
at the Herbarium of TARI in Tehran, Iran.
Identification of the Components
The identity of the components was based on comparison
of their GC retention indices on the column as well as
their mass spectra with corresponding data of authentic
compounds or of reference oils4 – 6 and computer match-
ing with the WILEY 5 and TRP libraries.

Isolation of the Essential Oil Results and Discussion

The volatile oil of the aerial parts of Hymenocrater
The yellow essential oil of Hymenocrater incanus was
incanus was obtained by hydrodistillation using a Cle-
obtained in a yield of 0.6% (w/w), based on the dry
venger-type apparatus for 3.5 h, dried over anhydrous
weight of the sample. GC–MS analysis led to the identi-
sodium sulphate and stored under nitrogen in a sealed
fication of the components, listed in Table 1 according to
vial until required.
their order of elution on the DB-1 column, with their per-
centages. Thirty five components, which make up 99%
Ł Correspondence to: M. Mirza, Research Institute of Forests and
of the total composition of the oil, were identified.
Rangelands, PO Box 13185-116, Tehran, Iran.
Contract/grant sponsor: Research Institute of Forests and Rangelands, The oil contains about 60% monoterpenes, with 1,8-
Iran. cineole (16.9%), ˛-pinene (9.2%), ˇ-pinene (7%) and

Copyright  2001 John Wiley & Sons, Ltd.

240 M. MIRZA, L. AHMADI AND M. TAYEBI

Table 1. Chemical composition of the essential oil of leaves and

flowers of Hymenocrater incanus Bunge

Method of
Compound (%) (RIŁ ) identificationŁŁ
Tricyclene 0.1 933 a, b, c
˛-Thujene 0.5 935 a, b, c
˛-Pinene 9.2 942 a, b, c
Camphene 3.0 952 a, b, c
Sabinene 1.3 972 a, b, c
ˇ-pinene 7.0 976 a, b, c
Myrcene 0.66 985 a, b, c
˛-Terpinene 0.1 1010 a, b, c
p-Cymene 0.9 1012 a, b, c
1,8-Cineol 16.9 1021 a, b, c
(Z)-ˇ-Ocimene 1.6 1025 a, b, c
(E)-ˇ-Ocimene 5.3 1036 a, b, c
-Terpinene 1.7 1047 a, b, c
trans-Sabinene hydrate 0.3 1061 a, b, c
Terpinolene 0.1 1076 a, b, c
Linalool 1.7 1080 a, b, c
Camphor 1.9 1116 a, b, c
Borneol 3.7 1145 a, b, c
Terpinene-4-ol 0.2 1157 a, b, c
˛-Terpineol 1.1 1167 a, b, c
Bornyl acetate 2.8 1264 a, b, c
cis-Jasmone 0.4 1360 a, b, c
˛-Copaene 0.2 1371 a, b, c
ˇ-Bourbonene 3.1 1380 a, b, c
ˇ-Elemene 0.9 1384 a, b, c
ˇ-Caryophyllene 17.7 1415 a, b, c
ˇ-Cubebene 1.1 1422 a, b, c
(Z)-ˇ-Farnesene 1.8 1440 a, b, c
˛-Humulene 0.6 1445 a, b, c
Germacrene-D 4.5 1471 a, b, c
Bicyclogermacrene 1.7 1486 a, b, c
ˇ-Bisabolene 0.8 1495 a, b, c
υ-Cadinene 0.6 1509 a, b, c
Spathulenol 2.7 1559 a, b, c
Caryophyllene oxide 3.9 1505 a, b, c
ŁRI: retention indices relative to C9 –C24 alkanes on the DB-1 column.
ŁŁ
a, compared with retention time of authentic samples or of components of reference oils;
b, retention indices relative to C9–C24 n-alkanes on the DB-1 column; c, compared with mass
spectra.

trans-ˇ-ocimene (5.4%) as the major constituents. The References

sesquiterpene fraction amounted to 39.5% of the oil.
The main sesquiterpenes were ˇ-caryophyllene (17.6%),
germacrene-D (4.5%) and caryophyllene oxide (3.9%),
approximately 26% of the total oil. Other compounds
present in appreciable amounts are borneol (3.7%),
ˇ-bourbonene (3.1%), camphene (3%), bornyl acetate
(2.8%) and spathulenol (2.7%).
Acknowledgements—The authors would like to thank the Research
Institute of Forests and Rangelands for financial support.
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2. Rechinger KH. Flora Iranica, No. 150. 1982; 241–242.
3. Davis PH. Flora of Turkey, Vol. 7. Edinburgh, 1982; 293.
4. Sandra P, Bicchi C. Capillary Gas Chromatography in Essential
Oil Analysis. Alfred Huethig Verlag: New York, 1987.
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penes and sesquiterpenes on methyl silicon and Carbowax ð20M
phases. J. Chromatogr. 1990; 503: 1–24.
6. Adams RP. Identification of Essential Oils by Ion Trap Mass Spec-
troscopy. Academic Press: San Diego, CA, 1989.

Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 239–240