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Journal of the Chilean Chemical Society

versión On-line ISSN 0717-9707

J. Chil. Chem. Soc. vol.62 no.3 Concepción set. 2017

http://dx.doi.org/10.4067/s0717-97072017000303581 

Article

GC-MS ANALYSIS OF THE ESSENTIAL OIL FROM ARTEMISIA aucheri BOISS. FRUITS

MAHSA AMINKHAH1  2 

JINOUS ASGARPANAH3  * 

1Herbal Medicines Research Center, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran – Iran (HMRC)

2Department of Phytochemistry and Essential Oil Technology, Faculty of Pharmaceutical Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran – Iran (IAUPS)

3Department of Pharmacognosy, Faculty of Pharmacy, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran – Iran (IAUPS)

ABSTRACT

The essential oil content in the fruits of Artemisia aucheri growing wild in south of Iran was found to be 2.4% (v/w). The essential oil was analyzed by gas chromatography (GC) and GC–mass spectrometry (GC–MS). Characterization of individual components was performed using a commercial mass spectrometry library, and twenty nine components, representing 89.0% of the fruits essential oil were identified. This analysis showed the presence of three volatile components, including camphor (46.5%) and 1,8-cineol (23.4%) as the main compounds.

Keywords: Artemisia aucheri; fruits; Essential oil; GC/MS

INTRODUCTION

The genus Artemisia (Asteraceae) is one of the largest and most widely distributed genera comprising a variable number of species, ranging from 200 to over 400 and is predominantly distributed in the northern temperate region of the world [1]. 29 species are reported in Iran of which some are endemic [2,3]. Numerous reports on essential oil compositions of different Artemisia species, especially on those used in flavor industry and in medication have been published [4].

Artemisia aucheri is a native plant which is found in some parts of Iran including the south regions. This plant is extensively exploited as a medicinal plant and locally called “Dermaneh Koohi” [5]. The flowering aerial parts and the fruits have been commonly used in Iranian traditional medicine as antiseptic, analgesic and to treat painful menstruation, dyspepsia, arthralgia, fever, headache, common cold and healing wound [1]. Literature survey revealed reports just on the essential oil composition of the aerial parts of A. aucheri and there was no attempt to study the essential components of A. aucheri fruits up to now. Regarding it and significant pleasant odor of the fruits, we were prompted to investigate the essential oil composition of this part of A. aucheri for the first time.

EXPERIMENTAL

Plant material

Fresh fruits of A. aucheri were collected in June 2015 Genow protected area, Bandar Abbas, Hormozgan Province, Iran: (27°26′44″N 56°18′18″E, 500 m). Specimens were identified by R. Asadpour and voucher was deposited in the Herbarium of Pharmaceutical Sciences Branch, Islamic Azad University (IAUPS), Tehran under code number 220-PMP/A. Fruits were submitted to hydrodistillation in a Clevenger-type apparatus for 3 hours. At the end of distillation the oil was collected, dried with anhydrous Na2SO4, measured, and transferred to clean glass vial and kept at a temperature of −18°C for further analyses.

Analysis of the essential oil

Oil sample analysis was performed on a Hp-6890 gas chromatograph (GC) equipped with a FID and a DB-5 capillary column, 30 m × 0.25 mm, 0.25 μm film thickness, temperature programmed as follows: 60°−240°C at 4°C/min. The carrier gas was N2 at a flow of 2.0 ml/min; injector port and detector temperature were 250°C and 300°C, respectively. Sample was injected by splitting and the split ratio was 1:10. GC/MS analysis was performed on a Hewlett-packard 6890 /5972 system with a DB-5 capillary column (30 m × 0.25 mm; 0.25 μm film thickness. The operating conditions were the same conditions as described above but the carrier gas was He. Mass spectra were taken at 70 eV. Scan mass range was from 40-400 m/z at a sampling rate of 1.0 scan/s. Quantitative data were obtained from the electronic integration of the FID peak areas. The components of the oil were identified by their retention time, retention indices, relative to C5-C28 n-alkanes, computer matching with the WILEY275.L library and as well as by comparison of their mass spectra with data already available in the literature [6,7]. The percentage of composition of the identified compounds was computed from the GC peaks areas without any correction factors and was calculated relatively. The analysis of the essential oil is the average of three replicates.

RESULTS AND DISCUSSION

The hydrodistillation of A. aucheri fruits gave pale yellow oil with pleasant odor and yield of 2.4% (v/w) based on the fresh weight. Figure 1 shows the gas chromatogram of A. aucheri fruits essential oil. Table 1 demonstrates the list of compounds whose GC/MS concentration is not less than 0.1% of total peak concentration. According to the Table 1, twenty nine components were identified in the fruits essential oil which presented about 89.0% of the total composition. The major constituents of A. aucheri fruits oil were characterized as camphor (46.5%) and 1,8-cineol (23.4%). The studied essential oil comprised one hydrocarbon (0.1%), twenty one monoterpenoids (85.0%), three sesquiterpenoids (1.7%) and three phenylpropanoid (1.5%).

Figure 1 Gas chromatogram of A. aucheri fruits essential oil. 

Table 1 GC-MS analysis of A. aucheri fruits essential oil. 

Compounda KIb KIc Percentage
1. Tricyclene 931 927 0.4
2. α-Pinene 942 939 0.1
3. Camphene 950 954 4.8
4. β-Pinene 976 979 0.1
5. α-Terpinene 1011 1017 0.2
6. ρ-Cymene 1028 1026 2.1
7. 1,8-Cineol 1036 1033 23.4
8. γ-Terpinene 1060 1062 0.1
9. Artemisia alcohol 1080 1084 0.8
10. Hotrienol 1100 1101 0.4
11. β-Thujone 1119 1114 2.6
12. Camphor 1143 1146 46.5
13. Sabina ketone 1162 1159 0.2
14. Borneol 1166 1169 0.4
15. Terpinene-4-ol 1179 1177 1.3
16. ρ-Cymene-8-ol 1188 1183 0.1
17. Myrtenal 1194 1193 0.3
18. Myrtenol 1198 1196 0.2
19. Piperitol 1204 1198 0.2
20. Carvone 1241 1243 0.7
21. Bornyl acetate 1286 1289 0.3
22. Carvacrol 1300 1298 0.3
23. Hydrocinnamic acid, ethyl ester 1331 1335 0.2
24. Cinnamic acid, methyl ester 1366 1370 1.0
25. Jasmone 1399 1394 0.5
26. α-Calacorene 1552 1548 0.1
27. Spathulenol 1581 1577 1.1
28. Caryophyllene oxide 1587 1583 0.5
29. 6,10,14-trimethyl-2-pentadecanone 1844 1840 0.1
Total 89.0

aCompounds listed in order of elution.

bKI (Kovats index) measured relative to n-alkanes (C9-C28) on the non-polar DB-5 column under condition listed in the Materials and Methods section.

cKI, (Kovats index) from literature.

Camphor as the major component of the studied oil is a monoterpenoid ketone and is familiar to many people as a principal ingredient in topical home remedies for a wide range of symptoms, and its use is well consolidated among the population of the whole world, having a long tradition of use as antiseptic, antipruritic, rubefacient, abortifacient, aphrodisiac, contraceptive and lactation suppressant [8]. Presence of high amount of camphor in A. aucheri fruits oil is considerable and demonstrates that the studied essential oil could be a good source of this compound and could possess the related biological properties including insecticide, antibacterial, analgesic and antiinflammatory activities. 1,8-cineol is the other main component of A. aucheri fruits oil and is characterized as a monoterpenoid ether and has a fresh camphor-like smell and a spicy, cooling taste. Because of its pleasant spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics.

Four reports on the analysis of Artemisia species fruits oils have been published [9,10]. Table 2 shows the main compounds of A. aucheri fruits oil and those of four other species. Presence of camphor as the main component of the studied oil in the fruits oil of A. annua from Iran and absence of it in other fruits oils is characteristic. 1,8-cineol as the other major compound of A. aucheri fruits oil has been reported in the fruits oil of A. absinthium and A. annua which were collected from Iran. The fruit oils of A. tschernieviana and A. annua (from China) are completely different from that of A. aucheri and the absence of both major components in A. aucheri in their fruits oils is noticeable.

Table 2 Essential oil main components of the fruits of five Artemisia species (>5%). 

Compounds A. aucheri A. absinthium A. tschernieviana A. annuaa A. annuab
Camphor
1,8-Cineol
β-Thujone
Sabinene
β-Pinene 13.7
cis-Chrysanthenol
Limonene 7.7
o-Cymene 5.8
Bornyl acetate 5.6
Nerolidol 10.4
Spathulenol 10.0
Cubenol 15.4
Artemisia 9.8
ketone 9.7
Pinocarveol 7.2 9.0
Caryophyllene 8.2
oxide
(E)-β- 6.9
farnesene
Caryophyllene

aA. annua fruits collected from Iran.

bA. annua fruits collected from China.

This paper presents the essential oil composition of A. aucheri fruits for the first time. Regarding to the essential oil major components, further biological studies are suggested to investigate the pharmacologic and therapeutic properties of the fruits.

ACKNOWLEDGMENTS

Supports from the Pharmaceutical Sciences Branch, Islamic Azad University are gratefully acknowledged.

REFERENCES

1 Tan, R. X.; Zheng, W. F.; Tang, H. Q. Planta Med. 1998, 64, 295-302. [ Links ]

2 Rechinger, K. H., in: Flora Iranica. Akademische Druck-u. Verlagsanstalt. Graz, 1986. [ Links ]

3 Mozafarian, V., in: Study and Recognition of Iranian Artemisia spp. Tehran University of Sciences Press, Tehran, 1988. [ Links ]

4 Gilemeister, E,; Hoffmann, F. in: Die Aetherischen Ole. 4th ed. vol VII. Academic Verlag. Berlin, 1961. [ Links ]

5 Mozaffarian, V., in: A Dictionary of Iranian Plant Names, Farhang Moaser Press, Tehran, 2006. [ Links ]

6 Swigar, A. A.; Silverstein, R. M., in: Monoterpenes. WI: Aldrich Chemical Company Publ., Milwaukee, 1981. [ Links ]

7 Adams, R. P., in: Identification of essential oil components by gas chromatography/mass spectroscopy. Allured publishing Co. Carol Stream, Illinois, 1995. [ Links ]

8 Zuccarini, P. J. Appl. Sci. Environ. Manage. 2009, 13(2), 69-74. [ Links ]

9 Pasha Zanousi, M. B.; Aberoomand Azar, P.; Raeesi, M. J. Med Plants Res. 2012, 6(42), 5489-5494. [ Links ]

10 Wang, R. L. D.; Liao, H. Zhongnan Yaoxue. 2007, 5, 230–232. [ Links ]

Jinous Asgarpanah Postal address: Pharmaceutical Sciences Branch, Islamic Azad University, Yakhchal Ave., Shariati Ave., Tehran, Iran, e-mail: asgarpanah@iaups.ac.ir

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