Chemical Composition of Oil from Eremostachys Macrophylla

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30 Nov 2017

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Chemical composition of the essential oil from aerial parts of Eremostachys macrophylla Montbr. & Auchfrom Northeast of Iran

  • Akhlaghi H

Abstract

The essential oil obtained by hydrodisstillation of the aerial parts of Eremostachys macrophylla Montbr. & Auch., grown wild in Iran, was analyzed by GC and GC/MS. The colorless oils were obtained by hydrodistillation, using a Clevenger-type apparatus for three hours, from aerial parts in 0.18% yield (w/w). Fourty-four compounds representing 91.6% of aerial parts oil of Eremostachys macrophylla were identified. The main components of the oil were hexadecanoic acid (27.5%), ethyl linoleate (8.5%), 6-methyl-α-ionone (8.0%), isobutyl phthalate (5.8%), α-cadinol (4.7%) and germacrene D (4.3%). The oil was rich in nonterpenoids (56.0%) and among them, oxygenated nonterpenes (53.2%) predominated over nonterpene hydrocarbons (2.8%).

Key Word Index

Eremostachys macrophylla Montbr. & Auch., Lamiaceae, essential oil composition, hexadecanoic acid

Introduction

The genus Eremostachys of the family Lamiaceae (alt. Labiatae) contains 15 species of perennial in Iran, and five of them are endemic (1,2). During the past decade, seven investigations have been carried out on the chemical composition of the essential oils of the genus Eremostachys. These studies analyze the fresh aerial parts of Eremostachys laciniata Bunge from Jordan (3), flowers, stems, and roots of Eremostachys laevigata from Iran (4), flower, leaf and stem of Eremostachys macrophylla Montbr. & Auch., and aerial part and stem of Eremostachys labiosa from Iran (5), aerial parts of Eremostachys adenantha and Eremostachys macrophylla from Iran (6), aerial parts of Eremostachys macrophylla from Central Iran (7), aerial parts of Eremostachys laevigata Bge. From Iran (8) and aerial parts of Eremostachys laciniata Bge. from Iran (9).

Phytochemical investigation on a few species of Eremostachys revealed the presence of vicarin, a new isoflavone from Eremostachys vicaryi (10), eremosides A-C, New Iridoid Glucosides from Eremostachys loasifolia (11), loasifolin, a new flavonoid from Eremostachys loasifolia (12), a new acidic iridoid glucoside (13), furanolabdane diterpene glycosides from Eremostachys laciniata (14), new iridoid glucosides from Eremostachys moluccelloides Bunge (15) and Eremostachiin: a new furanolabdane diterpene glycoside from Eremostachys glabra (16).

Our study dealt with the analysis of the essential oils of aerial parts of Eremostachys macrophylla Montbr. & Auch grown wild in northeastern Iran.

Experimental

Plant material: The plant material was collected during the flowering stage in May 2012 from northern Sabzevar in Khorasan Province, Iran, at an altitude of 1580 meters. A voucher specimen has been deposited in the herbarium of Research Center of Natural Resources, Sabzevar, Iran.

Essential oil isolation. Air-dried aerial parts of E. macrophylla (100 g) were subjected to hydrodistillation in a Clevenger-type apparatus for three hours to produce colorless oils. The yield of total volatiles was 0.18% (w/w). The oils were dried over anhydrous sodium sulfate and stored in sealed vials at 4 °C before analysis.

GC analysis. GC analysis was performed using a Shimadzu GC-9A gas chromatograph, equipped with a HP-5MS fused silica column (30 m×0.25 mm i.d., film thickness 0.25 µm). The oven temperature was held at 50 °C for five minutes and then programmed to 250 °C at a rate of 3 °C/min. The injector and detector (FID) temperatures were 290 °C . Helium was used as carrier gas with a linear velocity of 32 cm/s.

GC/MS analysis. GC/MS analysis was carried out on a Hewlett-packard 6890 gas chromatograph fitted with a fused silica HP-5MS capillary column (30m×0.25 mm ; film thickness 0.32 µm) . The oven temperature was programmed from 60 °C to 220 °C at 6 °C/min . Helium was used as carrier gas at a flow rate of 1 mL/min. The chromatograph was coupled to a Hewlett-Packard 5973 mass selective detector with an ionization voltage of 70 eV.

Qualitative and quantitative analyses. Constituents of the volatile oils were identified by comparison of their retention indices relative to C9-C21 n-alkanes and of their mass spectral fragmentation pattern with those reported in the literature (17) and stored in a MS library (Wiley 275). The quantification of the components was performed on the basis of their GC peak area data from the HP-5MS column separation.

Results and discussion

Because of the variable results obtained in previous studies and as a part of on-going work on the chemical analysis of oils obtained from the wild plants of Iran, we decided to re-investigate the oils of this specific plant. Hydrodistilled volatile oils from the crushed dry aerial parts of Eremostachys macrophylla Montbr. & Auch. (Lamiaceae) from Sabzevar (Iran) was studied by GC and GC/MS. The air-dried aerial parts of the plant yielded 0.18% (w/w) oil. The oil was clear and colorless. Fourty-four components were identified in the aerial parts oil that contained 91.6% of the compounds. Table 1 lists formulas, percentages, and retention indices of identified compounds in the oil. As evident from the table , the main components are hexadecanoic acid (27.5%), ethyl linoleate (8.5%), 6-methyl-α-ionone (8.0%), isobutyl phthalate (5.8%), α-cadinol (4.7%) and germacrene D (4.3%).

In this study, GC and GC/MS analysis method revealed monoterpenoid hydrocarbon (MH), oxygenated monoterpenes (OM), sesquiterpenoid hydrocarbons (SH), oxygenated sesquiterpenes (OS), nonterpenoid hydrocarbons (NH), diterpene hydrocarbon (DH) and oxygenated diterpene (OD) in the oil from the aerial parts of Eremostachys macrophylla. One monoterpene hydrocarbon (0.1%), five oxygenated monoterpenes (8.8%), thirteen sesquiterpene hydrocarbons (13.4%), six oxygenated sesquiterpenes (10.4%), seventeen nonterpene hydrocarbons (56.0%), one diterpene hydrocarbon (2.5%) and one oxygenated diterpene (0.4%) were detected in this oil. The data lead to a rank order of constituent groups: NH>SH>OS>OM>DH>OD>MH for the aerial parts oil. The main components in this oil were hexadecanoic acid (27.5%), ethyl linoleate (8.5%), 6-methyl-α-ionone (8.0%), isobutyl phthalate (5.8%), α-cadinol (4.7%) and germacrene D (4.3%).

The oil consisted mainly of nonterpenes and relatively small fractions of other terpenoids. Also, oxygenated nonoterpenes (53.2%) predominated over nonterpene hydrocarbons (2.8%).

However, in a previous study on volatile oil from aerial parts of Eremostachys macrophylla, among the thirty-five identified compounds that have been compromised to 92.9% of the oil, spathulenol (23.4%), hexadecanoic acid (13.5%) and caryophyllene oxide (9.3%) were the major ones (6), while in other report on the aerial parts of this plant, among the sixteen identified compounds that have been compromised to 96.4% of the oil; germacrene-D (47.1%), germacrene-B (17.8%), γ-elemene (9.1%), myrcene (6.7%), β-elemene (2.7%), and β-phellandrene (2.6%) have been the major ones (7). Also, we reported analysis of the essential oils from flowers, leaves and stems of Eremostachys macrophylla (5). The specimen had been collected at different place, time and altitude from current study. The major compounds in the flower oil of E. macrophylla were 1,8-cineol (19.0 %) and germacrene D-4-ol (10.6 %), whereas the leaf oil contained α-pinene (30.0 %), 1,10-di-epi cubenol (22.7 %), elemol (13.3 %) and bornyl acetate (11.0 %). The stem oil of the plant consisted mainly of 1,10-di-epi cubenol (34.4%) and elemol (24.0 %).

Evident from the above data, there are significant differences in the results of the current study with previous studies (6,7) for the aerial parts of E. macrophylla . These discrepancies are not entirely unexpected since hydrodistillation relates to the interactions of the oil constituents with water vapor. Of course, there may also be differences related to environmental conditions such as climate, altitude, collection time, ground composition of the sampling area and different growth stages such as pre-flowering, fresh flowering and air-dried-flowering stages.

Conclusion

The chemical composition of the essential oil of aerial parts from Eremostachys macrophylla Montbr. & Auch. (Lamiaceae) growing in Sabzevar was investigated. This study showed considerable amounts of hexadecanoic acid (27.5%), ethyl linoleate (8.5%), 6-methyl-α-ionone (8.0%). These major constituents were different from previous studies on the same species 5-7. These results demonstrated that the chemical composition of the essential oil of the same species can change depending on a variety of conditions, including climate, time of collection, and the ground composition of the sampling area besides of growth stages of plant.

Acknowledgment

We are grateful to Dr. V. Mozaffarian (Research Institute of Forests and Rangelands, Tehran) for identifying the plant materials.

Table 1. Constituents of the essential oils from aerial parts of Eremostachys macrophylla obtained by hydrodistillation a

No.

compound

Formula

Percentage

RRIb

Class

1

Limonene

C10H16

0.1

1031

MHc

2

4-Terpineol

C10H18O

0.1

1179

OMd

3

Fenchyl acetate

C12H20O2

0.4

1223

OM

4

Anethole

C10H12O

0.1

1285

OM

5

α-Copaene

C15H24

0.2

1364

SHe

6

β- Bourbonene

C15H24

0.8

1385

SH

7

β-Cubebene

C15H24

0.1

1390

SH

8

Tetradecane

C14H30

0.1

1400

NHf

9

β-Caryophyllene

C15H24

0.3

1418

SH

10

α-Guaiene

C15H24

0.1

1439

SH

11

Aromadendrene

C15H24

0.6

1442

SH

12

α-Humulene

C15H24

2.0

1452

SH

13

(E)-β-Farnesene

C15H24

0.1

1457

SH

14

Germacrene D

C15H24

4.3

1480

SH

15

β-Ionone

C13H20O

0.2

1488

OM

16

Bicyclogermacrene

C15H24

0.7

1500

SH

17

γ-Cadinene

C15H24

0.6

1515

SH

18

6-Methyl-α-ionone

C14H22O

8.0

1518

OM

19

δ-Cadinene

C15H24

3.5

1522

SH

20

Cadina-1,4-diene

C15H24

0.1

1533

SH

21

Germacrene D-4-ol

C15H26O

0.6

1574

OSg

22

Spathulenol

C15H24O

1.5

1578

OS

23

Caryophyllene oxide

C15H24O

0.5

1583

OS

24

Humulene epoxide II

C15H24O

1.7

1608

OS

25

τ-Muurolol

C15H26O

1.4

1643

OS

26

α-Cadinol

C15H26O

4.7

1656

OS

27

Tetradecanoic acid

C14H28O2

1.8

1760

NH

28

Octadecane

C18H38

0.4

1800

NH

29

6,10,14-Trimethyl-2-Pentadecanone,

C18H36O

1.7

1848

NH

30

2-Hydroxy-Cyclopentadecanone

C15H28O2

0.4

1853

NH

31

Pentadecanoic acid

C15H30O2

0.3

1867

NH

32

Isobutyl phthalate

C16H22O4

5.8

1877

NH

33

Cyclohexadecane

C16H32

0.3

1883

NH

34

16-methyl-Oxacyclohexadecan-2-one,

C16H30O2

0.3

1943

NH

35

Sandaracopimara-8(14),15-diene

C20H32

2.5

1969

DHh

36

di-Butylphthalate

C16H22O4

0.9

1973

NH

37

Hexadecanoic acid

C16H32O2

27.5

1977

NH

38

Eicosane

C20H42

2.0

2000

NH

39

Heptadecanoic acid

C17H34O2

0.4

2065

NH

40

Methyl linoleate

C19H34O2

0.6

2084

NH

41

Phytol

C20H40O

0.4

2111

ODi

42

(Z,Z)-9,12-Octadecadienoic acid

C18H32O2

2.7

2136

NH

43

Ethyl linoleate

C20H36O2

8.5

2164

NH

44

Octadecanoic acid

C18H36O2

2.3

2172

NH

 

Total identified

 

91.6

   

a The compounds have been arranged according to their retention indices on an HP-5 MS capillary column

b Kovatz retention indices given in the literature

c Monoterpene hydrocarbons

d Oxygenated monoterpene

e Sesquiterpene hydrocarbons

f Nonterpene hydrocarbons

g Oxygenated sesquiterpene

hDiterpene hygrocarbon

iOxygenated diterpene

References

1. Mozaffarian, V. (1996), A Dictionary of Iranian plant names, Frhang Moaser, Tehran, pp. 207-208.

2. Rechinger,K.H. (1982). Eremostachys, in: Flora Iranica, Labiatae No. 150. Edits., K.H. Rechinger and I.C. Hedge, Pp 290-292, Akademische Druck and Verlagsanstalt, Graz, Austria.

3. Al-Jaber, H.I., Al-Qudah, M.A., Barhoumi, L.M., Abaza, I.F., Afifi, F.U. (2012). Variation in the essential oil composition of Eremostachys laciniata from Jordan at different flowering stages, J. Essent. Oil Res. 24(3): 289-297.

4. Esmaeili, A. (2012). Biological activities of Eremostachys laevigata Bunge. grown in Iran, Pak. J. Pharm. Sci., 25(4): 803-808.

5. Rustaiyan, A., Masoudi, S., Ezzatzadeh, E., Akhlaghi, H., Aboli, J. (2011). Composition of the Aerial Part, Flower, Leaf and Stem Oils of Eremostachys macrophylla Montbr. & Auch. and Eremostachys labiosa Bunge. from Iran, J Essent. Oil Bear. Pl., 14(1): 84-88.

6. Javidnia, K., Miri, R., Soltani, M., Khosravi, A.R. (2008). Essential oil composition of two species of Eremostachys from Iran (E. adenantha Jaub. et spach and E. macrophylla Montbr. et auch.

J. Essent. Oil Res., 20(3): 226-228.

7.Nori-Shargh D., Kiaei, S.M., Deyhimi, F. (2007). The volatile constituents analysis of Eremostachys macrophylla Montbr. & Auch. from Iran, Nat. Prod. Res., 21(8):733-5.

8. Amiri, H., Meshkat Al Sadat, M.H., Lari Yazdi, H. (2007). Chemical composition of the essential oil of Eremostachys Laevigata bung, DARU J.Pharm. Sci., 15(1):34-40.

9. Navaei, M.N., Mirza, M. (2006). Chemical composition of the oil of Eremostachys laciniata (L.) Bunge from Iran, Flavour. Frag. J., 21(4): 645-646.

10. Imran, M., Mehmood, R., Mughal, U.R., Ali, B., Malik, A. (2012). Vicarin, a new isoflavone from Eremostachys vicaryi, J. Asian Nat. Prod. Res., 14(3): 293-296.

11. Ali, B., Mehmood, R., Mughal, U.R., Malik, A., Safder, M., Hussain, R., Imran, M., Tareen, R.B. (2012). Eremosides A-C, New Iridoid Glucosides from Eremostachys loasifolia, Helv. Chim. Acta, 95(4): 586-593.

12. Mughal, U.R., Fatima, I., Malik, A., Tareen, R.B. (2010). Loasifolin, a new flavonoid from Eremostachys loasifolia, J. Asian Nat. Prod. Res., 12(4): 328-330.

13. Calis, I., Guevenc, A., Armagan, M., Koyuncu, M., Gotfredsen, C.H., Jensend, S.R. (2008). Secondary metabolites from Eremostachys laciniata, Nat. Prod. Commun., 3(2): 117-124.

14. Delazar, A., Modarresi, M., Nazemiyeh, H., Fathi-Azad, F., Nahar, L., Sarker, S.D. (2008). Furanolabdane diterpene glycosides from Eremostachys laciniata, Nat. Prod. Commun., 3(6): 873-876.

15. Calis, I., Guvenc, A., Armagan, M., Koyuncu, M., Gotfredsen, C.H. Jensen, S.R. (2007). Iridoid glucosides from Eremostachys moluccelloides Bunge, Helv. Chim. Acta, 90(8): 1461-1466.

16. Delazar, A., Modarresi, M., Shoeb, M., Nahar, L., Reid, R.G., Kumarasamy, Y., Majinda, R.R.T., Sarker, S.D. (2006). Eremostachiin: a new furanolabdane diterpene glycoside from Eremostachys glabra, Nat. Prod. Res., 20(2): 167-172.

17. R.P. Adams, (2007). Identification of Essential Oil Components by Gas Chromatography/ Mass Spectrometry, 4th Edition. Allured Publishing Corporation, Carol Stream, IL, USA.



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