Chemical Composition of Oil from Eremostachys Macrophylla

Chemical Composition of anele from Eremostachys MacrophyllaChemical composition of the essential vegetable cover from windy partof Eremostachys macrophylla Montbr. Auch.from Northeast of IranAkhlaghi HAbstractThe essential oil obtained by hydrodisstillation of the frolicsome 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 machine 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 set. The main comp nonpareilnts of the oil were hexadecanoic acid (27.5%), ethyl group linoleate (8.5%), 6-methyl--ionone (8.0%), isobutyl phthalate (5.8%), -cadinol (4.7%) and germacrene D (4.3%). The oil was well-off in nonterpenoids (56.0%) and among them, oxygenated nonterpenes (53.2%) predominated over nonterpene hydrocarbons (2.8%).Key Word IndexEremostachys macroph ylla Montbr. Auch., Lamiaceae, essential oil composition, hexadecanoic acidIntroductionThe genus Eremostachys of the family Lamiaceae (alt. Labiatae) contains 15 species of perennial in Iran, and five of them be 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 odorous aerial parts of Eremostachys laciniata Bunge from Jordan (3), flowers, stems, and roots of Eremostachys laevigata from Iran (4), flower, foliage 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 Eremostachy s revealed the presence of vicarin, a new isoflavone from Eremostachys vicaryi (10), eremosides A-C, immature 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 muse dealt with the analysis of the essential oils of aerial parts of Eremostachys macrophylla Montbr. Auch grown wild in northeastern Iran.ExperimentalPlant material The plant material was collected during the anthesis 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. all important(p) oil isolation. Air-dried aerial parts of E. macroph ylla (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, outfit with a HP-5MS fused silica column (30 m0.25 mm i.d., film thickness 0.25 m). 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 toter gas with a linear speeding 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 tube column (30m0.25 mm film thickness 0.32 m) . 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 property 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 discussionBecause of the variable results obtained in front 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--ionone (8.0%), isobutyl phthalate (5.8%), -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 oxyge nated diterpene (0.4%) were detected in this oil. The data lead to a rank order of constituent groups NHSHOSOMDHODMH for the aerial parts oil. The main components in this oil were hexadecanoic acid (27.5%), ethyl linoleate (8.5%), 6-methyl--ionone (8.0%), isobutyl phthalate (5.8%), -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%), -elemene (9.1%), myr cene (6.7%), -elemene (2.7%), and -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 -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 earthshaking 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 withal be differences related to environment al conditions such as climate, altitude, collection time, ground composition of the sampling area and different growth stages such as pre- blossom, fresh flowering and air-dried-flowering stages.ConclusionThe 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--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 sorting of conditions, including climate, time of collection, and the ground composition of the sampling area besides of growth stages of plant.AcknowledgmentWe are grateful to Dr. V. Mozaffarian (Research Institute of Forests and Rangelands, Tehran) for identifying the plant materials.Table 1. Constitue nts of the essential oils from aerial parts of Eremostachys macrophylla obtained by hydrodistillation aNo.compoundFormulaPercentageRRIbClass1LimoneneC10H160.11031MHc24-TerpineolC10H18O0.11179OMd3Fenchyl acetateC12H20O20.41223OM4AnetholeC10H12O0.11285OM5-CopaeneC15H240.21364SHe6- BourboneneC15H240.81385SH7-CubebeneC15H240.11390SH8TetradecaneC14H300.11400NHf9-CaryophylleneC15H240.31418SH10-GuaieneC15H240.11439SH11AromadendreneC15H240.61442SH12-HumuleneC15H242.01452SH13(E)--FarneseneC15H240.11457SH14Germacrene DC15H244.31480SH15-IononeC13H20O0.21488OM16BicyclogermacreneC15H240.71500SH17-CadineneC15H240.61515SH186-Methyl--iononeC14H22O8.01518OM19-CadineneC15H243.51522SH20Cadina-1,4-dieneC15H240.11533SH21Germacrene D-4-olC15H26O0.61574OSg22SpathulenolC15H24O1.51578OS23Caryophyllene oxideC15H24O0.51583OS24Humulene epoxide IIC15H24O1.71608OS25-MuurololC15H26O1.41643OS26-CadinolC15H26O4.71656OS27Tetradecanoic acidC14H28O21.81760NH28OctadecaneC18H380.41800NH296,10,14-Trimethyl-2-Pentadecanon e,C18H36O1.71848NH302-Hydroxy-CyclopentadecanoneC15H28O20.41853NH31Pentadecanoic acidC15H30O20.31867NH32Isobutyl phthalateC16H22O45.81877NH33CyclohexadecaneC16H320.31883NH3416-methyl-Oxacyclohexadecan-2-one,C16H30O20.31943NH35Sandaracopimara-8(14),15-dieneC20H322.51969DHh36di-ButylphthalateC16H22O40.91973NH37Hexadecanoic acidC16H32O227.51977NH38EicosaneC20H422.02000NH39Heptadecanoic acidC17H34O20.42065NH40Methyl linoleateC19H34O20.62084NH41PhytolC20H40O0.42111ODi42(Z,Z)-9,12-Octadecadienoic acidC18H32O22.72136NH43Ethyl linoleateC20H36O28.52164NH44Octadecanoic acidC18H36O22.32172NHTotal identified91.6a The compounds have been arranged according to their retention indices on an HP-5 MS capillary columnb Kovatz retention indices given in the literaturec Monoterpene hydrocarbonsd Oxygenated monoterpenee Sesquiterpene hydrocarbonsf Nonterpene hydrocarbonsg Oxygenated sesquiterpenehDiterpene hygrocarboniOxygenated diterpeneReferences1. 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