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Volatile constituents of Haplophyllum buhsei Boiss. flowering aerial parts

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Boshra Azadi
Boshra Azadi
Sepideh Khaef
Sepideh Khaef
Sepideh Khaef
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The essential oil composition of flowering aerial parts of Haplophyllum buhsei Boiss. (Rutaceae) from Iran was analyzed for the first time using gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Thirty six compounds comprising 92.2% of the total oil were characterized. The main components were β-caryophyllene (12.9%), limonene (9.7%), β-pinene (7.9%), linalool (7.4%), α-pinene (6.4%) and 1,8-cineole (5.5%). Volatile oil of Haplophyllum buhsei Boiss. flowering aerial parts was dominated by the high content of monoterpene hydrocarbons (39.2%) and oxygenated monoterpenes (23.2%).
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Bull. Chem. Soc. Ethiop. 2015, 29(2), 327-330. ISSN 1011-3924
Printed in Ethiopia 2015 Chemical Society of Ethiopia
DOI: http://dx.doi.org/10.4314/bcse.v29i2.15
__________
*Corresponding author. E-mail: Azadi.B@iaups.ac.ir ; boshraazadi@yahoo.com
SHORT COMMUNICATION
VOLATILE CONSTITUENTS OF HAPLOPHYLLUM BUHSEI BOISS. FLOWERING
AERIAL PARTS
Boshra Azadi1* and Sepideh Khaef2
1Phytochemistry Department, Faculty of Medicinal Chemistry, Pharmaceutical Sciences Branch,
Islamic Azad University, Tehran, Iran
2Organic Chemistry Department, Faculty of Chemistry, Razi University, Kermanshah, Iran
(Received March 5, 2014; revised May 11, 2015)
ABSTRACT. The essential oil composition of flowering aerial parts of Haplophyllum buhsei Boiss. (Rutaceae)
from Iran was analyzed for the first time using gas chromatography (GC) and gas chromatography–mass
spectrometry (GC–MS). Thirty six compounds comprising 92.2% of the total oil were characterized. The main
components were -caryophyllene (12.9%), limonene (9.7%), -pinene (7.9%), linalool (7.4%), α-pinene (6.4%)
and 1,8-cineole (5.5%). Volatile oil of Haplophyllum buhsei Boiss. flowering aerial parts was dominated by the
high content of monoterpene hydrocarbons (39.2%) and oxygenated monoterpenes (23.2%).
KEY WORDS: Haplophyllum buhsei Boiss., Rutaceae, Essential oil, -Caryophyllene, Limonene
INTRODUCTION
The genus Haplophyllum A. Juss. belongs to Rutaceae family and encompasses approximately
70 species which mainly distributed around the Mediterranean region of Europe and through
western Asia up to Siberia [1, 2]. Eighteen species of Haplophyllum A. Juss. genus are found in
Iran which among them nine species are endemic and Haplophyllum buhsei Boiss. is one of
them [3].
Plants of Haplophyllum A. Juss. genus have long been used in folk medicine for toothache,
stomach and skin diseases, and in the treatment of some types of cancer. The extracts of some
Haplophyllum species exhibit cytotoxic activity [4]. This genus has been shown to possess
alkaloids, lignans, flavonoids, coumarins and essential oils with important biological properties
[5].
A thorough literature review revealed that volatile constituents of many species of the genus
Haplophyllum A. Juss. have been widely investigated in various regions from all over the world
[6-17] but to the best of our knowledge, there was no report on Haplophyllum buhsei Boiss. and
in this article essential oil composition of this endemic species is informed for the first time.
EXPERIMENTAL
Plant material. Flowering aerial parts of Haplophyllum buhsei Boiss. were collected in May
2013 from Dalahu mountain (Dalahu County, Kermanshah Province, Iran).
Essential Oil Isolation. The air-dried crushed flowering aerial parts of Haplophyllum buhsei
Boiss. were subjected to hydrodistillation using a Clevenger-type apparatus for 4 hour. The
obtained essential oil was dried over anhydrous sodium sulphate and stored at 4-6 oC.
Boshra Azad and Sepideh Khaef
Bull. Chem. Soc. Ethiop. 2015, 29(2)
328
GC and GC–MS analyses. Chemical composition of the volatile oil was investigated by gas
chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Haplophyllum
buhsei Boiss. oil was analyzed by GC–MS using a Hewlett-Packard 6890 gas chromatograph
with DB-5 capillary column (30 m х 0.25 mm; film thickness 0.25 μm). The carrier gas was
helium with a flow rate of l mL/min. The column temperature was programmed from 60 oC to
220 oC at 6 oC/min. The gas chromatograph was coupled to a Hewlett-Packard 5973 mass
selective detector. The MS was operated at 70 eV ionization energy. The retention indices were
calculated by using retention times of n-alkanes that were injected after the essential oil at the
same conditions. The components were identified by comparison of retention indices with those
reported in the literatures and also by comparison of their mass spectra with the published mass
spectra or Wiley library [18, 19]. Gas chromatography using flame ionization detection (GC–
FID) analysis was carried out under the same experimental conditions with the same column as
described for the GC–MS. The relative percentage of the identified compounds was computed
from the GC peak area without applying correction factors.
RESULTS AND DISCUSSION
The dried flowering aerial parts of Haplophyllum buhsei Boiss. yielded 0.35% V/W of a pale
yellow volatile oil. Thirty six compounds comprising 92.2% of the total oil were detected which
are presented in Table 1.
Essential oil of Haplophyllum buhsei Boiss. flowering aerial parts was characterized by the high
amount of monoterpene hydrocarbons (39.2%) with limonene (9.7%), -pinene (7.9%), α-
pinene (6.4%), sabinene (4.6%) and myrcene (3.8%) as main components. Oxygenated
monoterpenes represented 23.2% of the volatile oil which dominated by linalool (7.4%) and 1,8-
cineole (5.5%). The sesquiterpene hydrocarbons fraction comprised 22.8% of the oil with -
caryophyllene (12.9%) as the abundant constituent. Oxygenated sesquiterpenes came up to 6.5%
and caryophyllene oxide (3.5%) constituted the major ingredient of this fraction.
Essential oil compositions of numerous species of Haplophyllum A. Juss. genus were previously
reported which depend on many factors such as genetic, geographic distribution, phenological
cycle, seasonal variation, plant organ and analytical method used. Volatile compounds that have
been most commonly reported from Haplophyllum species contain monoterpenoids (e.g.
linalool, α-pinene, -pinene, limonene, α-phellandrene, -phellandrene, α-terpineol, sabinene,
1,8-cineole and myrcene) and sesquiterpenoids (e.g. -caryophyllene, α-humulene, elemol,
caryophyllene oxide and -eudesmol) as the principle constituents in the most of them [6-17].
Regarding to our literature survey, there was no research on essential oil composition of
Haplophyllum buhsei Boiss. and this study describes volatile oil isolation and identification of
this endemic species for the first time.
Table 1. The essential oil composition of Haplophyllum buhsei Boiss. aerial parts.
No. Compound RIa Content (%)
1 α-Pinene 937 6.4
2 α-Fenchene 951 0.9
3 Benzaldehyde 963 Trace
b
4 Sabinene 974 4.6
5 β-Pinene 979 7.9
Short Communication
Bull. Chem. Soc. Ethiop. 2015, 29(2)
329
6 Myrcene 990 3.8
7 n-Decane 1000 0.3
8 α-Phellandrene 1005 2.9
9 p-Cymene 1025 0.4
10 Limonene 1028 9.7
11 1,8-Cineole 1030 5.5
12 (Z)-β-Ocimene 1034 1.8
13 γ-Terpinene 1061 0.8
14 Linalool 1100 7.4
15 α-Thujone 1105 1.5
16 Camphor 1145 2.8
17 Borneol 1165 0.3
18 α-Terpineol 1189 2.5
19 Carvone 1242 0.3
20 Linalyl acetate 1255 2.9
21 α-Ylangene 1372 0.9
22 α-Copaene 1376 0.8
23 β-Elemene 1391 2.7
24 β-Caryophyllene 1419 12.9
25 α-Humulene 1453 2.6
26 γ-Muurolene 1476 Trace
b
27 Bicyclogermacrene 1496 0.2
28 γ-Cadinene 1511 0.1
29 α-Cadinene 1536 2.6
30 Spathulenol 1576 1.3
31 Caryophyllene oxide 1582 3.5
32 β-Eudesmol 1649 1.7
7
33 Tetradecanol 1670 0.1
34 Hexadecanoic acid 1692 Trace
b
35 Pentadecanal 1711 0.1
6 n-Pentadecanol 1777 Trace
b
aRetention indices; relative to n-alkane series on DB-5 capillary column. bTrace (<0.05%).
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... essential oils. [17,18,20,25,26,28,31,39] β-Terpinene H. tuberculatum [37] γ-Terpinene H. robustum H. tuberculatum [28,29,37] δ-3-Carene H. tuberculatum H. virgatum [31,34,39] p-Cymene H. furfuraceum [18] Cis-sabinene hydrate H. perforatum H. robustum [25,28] Isobornyl acetate H. tuberculatum [38] Limonene H. buhsei H. laeviusculum [17,20,25,26,[28][29][30][31][32][33][34]38,39] [19,20,27,32,34,37] Sabinene H. acutifolium H. perforatum H. robustum [16,[25][26][27]29] Trans-β-ocimene H. glaberrimum [19] Non-terpene hydrocarbons [17,[19][20][21][23][24][25]31,32] Aromadendrene H. virgatum [39] Valencene H. virgatum [39] As it can be seen from Tables 2 and 3, the literature data concerning the chemical profiles of the EOs of this valuable medicinal genus are abundant, in particular about its most important species, i.e., H. tuberculatum (Forssk.) A. Juss. From a general survey of these data, it could be clearly observed that the characterized chemical profiles of this species differ widely from one another. ...
... essential oils. [17,18,20,25,26,28,31,39] β-Terpinene H. tuberculatum [37] γ-Terpinene H. robustum H. tuberculatum [28,29,37] δ-3-Carene H. tuberculatum H. virgatum [31,34,39] p-Cymene H. furfuraceum [18] Cis-sabinene hydrate H. perforatum H. robustum [25,28] Isobornyl acetate H. tuberculatum [38] Limonene H. buhsei H. laeviusculum [17,20,25,26,[28][29][30][31][32][33][34]38,39] [19,20,27,32,34,37] Sabinene H. acutifolium H. perforatum H. robustum [16,[25][26][27]29] Trans-β-ocimene H. glaberrimum [19] Non-terpene hydrocarbons [17,[19][20][21][23][24][25]31,32] Aromadendrene H. virgatum [39] Valencene H. virgatum [39] As it can be seen from Tables 2 and 3, the literature data concerning the chemical profiles of the EOs of this valuable medicinal genus are abundant, in particular about its most important species, i.e., H. tuberculatum (Forssk.) A. Juss. From a general survey of these data, it could be clearly observed that the characterized chemical profiles of this species differ widely from one another. ...
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  • Jul 2014
The hydrodistilled volatile oil of flowering aerial parts of Haplophyllum villosum (M. B.) G. Don (Rutaceae) from Iran was analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) for the first time. Thirty eight constituents consisting 97.3 % of the total oil were identified. The monoterpene hydrocarbons had the highest contribution. The main compounds were β-phellandrene (15.6 %), β-caryophyllene (13.1 %), linalool (11.8 %), α-pinene (7.3 %), β-pinene (6.1 %) and α-humulene (5.9 %).
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Essential Oils from Leaves, Stems, Flowers and Fruits of Haplophyllum robustum Bge. (Rutaceae) Grown in Iran
Article
Full-text available
  • Jul 2006
The essential oils obtained by hydrodistillation of the leaves, stems, flowers and fruits of Haplophyllum robustum Bge. (Rutaceae) were analyzed by GC and GC/MS. 1,8-Cineole was the major component (19.1–45.1%) in almost all oils, except for the leaf oil which contained cis-sabinene hydrate (23.2%) as the main constituent. The composition of the oils were mostly quantitatively rather than qualitatively different. All oils consisted mainly of monoterpenes and a small percentage of non-terpenoid compounds.
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Study of the bioactive and fragrant constituents extracted from leaves and aerial parts of Haplophyllum glabrrimum Bge ex Bioss from central Iran by nano scale injection
Article
  • Mar 2010
  • DIG J NANOMATER BIOS
The dried leaves and aerial parts of Haplophyllum glabrrimum which belongs to Rutaceae family and grows in central Iran, were hydrodistilled to produce oils in the yields of 0.08% and 0.14% (w/w), respectively. The oils were analyzed by GC and GC/MS. The amount of the samples injected were 1.0 nL (diluted 1.0 μL of sample in 1000 ml of n-pentane, v/v). Ten and sixteen bioactive, flavour and fragrance molecules were identified, representing 93.86% and 96.89% of the leaves and aerial parts oil, one by one. The main component was Myrcene (52.89%, 65.08%) in leaves and aerial parts oils, respectively.
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The essential oil composition of Haplophyllum laeviusculum C. C. Towns. Aerial parts
Article
  • Jan 2014
In spite of various researches on Haplophyllum A. Juss. species essential oils, there was no report on Haplophyllum laeviusculum C. C. Towns. (Rutaceae) and in this article volatile components of this Iranian endemic species is informed for the first time. The essential oil obtained by hydrodistillation from flowering aerial parts of Haplophyllum laeviusculum C. C. Towns. was analyzed using gas chromatography (GC) and gas chromatography– mass spectrometry (GC–MS). Thirty six constituents constituting 95.7% of the total oil were detected. The major ingredients were β-Pinene (20.1%), α-Phellandrene (11.7%), β-Caryophyllene (7.6%), Myrcene (6.8%), Linalool (6.1%) and Limonene (5.6%). The volatile oil of Haplophyllum laeviusculum C. C. Towns. flowering aerial parts was characterized by high amounts of monoterpene hydrocarbons (56.3%). © 2014, Journal of Chemical and Pharmaceutical Research. All rights reserved.
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Essential Oil of Haplophyllum robustum Bge. from Iran
Article
  • Nov 2004
The essential oil from the aerial parts of Haplophyllum robustum Bge. was isolated by hydrodistillation and was analyzed by GC/MS. Twenty-three compounds representing 86.1% of the total components were detected. The oil consisted mainly of monoterpene hydrocarbons and a small percentage of sequiterpenes. The major compounds were sabinene (30.5%), β-pinene (18.2%) and limonene (12.1%).
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Volatile Oil Constituents of Haplophyllum tuberculatum (Forssk.) A. Juss. (Rutaceae) from Iran
Article
  • Jul 2006
The aerial parts of Haplophyllum tuberculatum (Forssk.) A. Juss. (Rutaceae) were hydrodistilled using a Clevenger-type apparatus to yield an oil of 0.02%. The oil was analyzed by GC and GC/MS; 40 components, representing 91.8% of the oil, were identified. The main components of the oil were linalool (15.5%), α-pinene (7.9%) and limonene (5.3%).
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Essential Oil of Haplophyllum linifolium (L.) G. Don fil. (Rutaceae)
Article
  • Jan 2003
The essential oils from the fruits and the aerial parts of Haplophyllum linifolium harvested in 1994 and 1997 were isolated by hydrodistillation, fractionated by dry column chromatography, and analyzed by GC and GC/MS. The GC of the fruits exhibited 68 peaks from which 50 substances were structurally identified by MS and RI-values, which correspond to 98.8% and 98.2% of the oils, respectively. The main components of these oils were β-phellandrene (25.5% and 35.5%) and β-pinene (23.7% and 21.2%), but the more interesting characteristic is the presence of 4.6% and 2.9% bornyl formate, respectively, a compound rarely found in essential oils. The oil of the aerial parts of the plant exhibited a very similar oil composition differing only in the percentual proportions. β-Phellandrene and β-pinene were the dominating constituents of the herb oils representing 42.6% (30.4%) and 19.8% (22.4%), respectively. Bornyl formate amounted to 2.5% in 1994 and 4.0% in 1997.
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Components of Haplophyllum ramosissimum
Article
  • May 1989
We have investigated the chemical composition of the epigeal part of this plant growing on the Ustyurt plateau. The dry com~ninuted raw material (3 kg) was extracted with methanol. Theevaporated methanolic extract was treated with chloroform. The chloroform solution was shaken with 5% sulfuric acid. The total alkaloids (0.15% on the weight of the dry epigeal part) were obtained from the acid solution in the usual way and their chromatography on silica gel gave robustine (0.05 g), mp 148-149°C (ethanol), dictamnine (0.i g), mp 132-133°C (acetone), skimmianine (0.18 g), mp 175-176°C (methanol), haplopine (0.12 g), mp 203-204°C (methanol), evodine (0.87 g), mp 152-153°C (acetone), methylevoxine (0.5 g), mp I05-I06°C (ether), and evoxine (2.16 g), mp 154-155°C (methanol). The repeated crystallization of the methylevoxine from ether raised its melting point by 20°C [8]. All the substances were identified with authentic samples isolated from other plants of the Haplophyll~ genus [9]. The neutral fraction remaining after the chloroform treatment of the acid solution, when chromatographed on silica gel, yielded two substances: CIOH804 (I), mp 204-205°C (acetone), and CliH1004 (II), mp 143-1450C (water). Both components gave the blue fluorescence in UV light that is characteristic for coumarins. The results of a study of their IR, UV, and mass spectra enabled substance (I) to be identified as 7-hydroxy-6-methoxycoumarine (scopoletin) and~substance (II) as 6,7-dimethoxycoumarin (scoparone) [i0]. The PMR spectrum of (II) was identical with that described for scoparone in [Ii]. Chromatography on silica gel of the polar fraction obtained after the treatment of the methanolic extract with chloroform gave a substance with the composition C12H22OII, mp 190-191°C, [~]D 28 + 65.2 ° (c 1.05; water) which was found to be identical with an authentical sample of sucrose according to a mixed melting point and its IR spectrum.
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