Achillea millefolium L.

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1 (9) (Achillea millefolium L.) * * souri97@gmail.com : : 90 : 9 : 9 Achillea millefolium L. (Asteraceae) (GC) (GC/MS). % % % % % %5 % (%/7/) 8 (%7/78/5) D (%/7) (%8) (%/6/) (%/69/) : (Achillea millefolium L.).D (Yavari et al., 00) DOI:

2 Talwar & ) (Trumbeckaite et al., 0 (Bozin et al., 008 Srivastava, 006 Talwar & ).(Srivastava, //5...(Rehus & Neugebauerova, 0) (Tricolporate).. (Colpus) Azani et ).(al., (Bimbiraitė et al., 008)..(Bimbiraitė et al., 008) (00) Azizi (00) Azizi. 8. % (Achillea) (Azizi et al., 00) 00 Kiumarsi et ).(al., (Azani et al., 009).(Calmasur et al., 006) Kiumarsi et ) (Ethnopharmacology) (al., 009 Rehus & ).(Neugebauerova, 0 Rehus & ).(Neugebauerova, 0 (Karaalp et al., 009).. Trumbeckaite et al., ).(0. Bozin et al., 008)

3 0 5. (Cissabinene hydrate).. 8.(Azizi et al., 00) 9 5 %5 (v/w) %0/069 (v/w). 8..(Gudaityte & Venskutonis, 007) %9 (v/w) 0 ) Gudaityte &.(Venskutonis, 007 D.(Rohloff, 00) % (v/w).(zheljazkov & Astatkie, 0). D (Guaiazulene).(Suleimenov et al., 00) Suleimenov (00) %9/) (. 8. Jaimand (999). SPMEGC/MS 8 D. Paduch (008) Achillea millefolium L. 90 ) ( ) ( ) ( ) ( ) (

4 5... ).(. (m) ( C) (mm) 8 09 E 5 / 6/ 5 5 E 5 7/ E 5 7/ N 7 E 5 /7 9/ 6 E 5 /6 6/ E 5 5/9 8/ E 5 /6 6/8.. ) Sefidkon &.(RahimiBidgoly, ) British pharmacopoeia,.(988.. (GC) Varian CP VF FID ) (. (GC/MS) CP800GC 000. / (C6C)

5 0 5...(Shibamoto, 987) A. millefolium L. (%) (%) ).( %9/8 %9/ %97/ %9/ %96/ %9/5 %9/6. A. millefolium L. : 8 (%6/) (%9/) (%7/09) D (%6/6) (%/) (%/) (%8/0) 8 (%7/7) (%/) 8 (%5/) (%6/5) (%6/) (%5/8) 8 (%5/) (%6/) D (%5/) (%/6) (%9/) (%8/5) 8 (%7/7) 8 (%8/5) D (%) (%0/0) (%6/) (%) 8 (%/6) (%6/9) (%5/9) ).( %/7 %. 7 (CisCadinen7ol) (%/8) (Zvalerenyl acetate) (%) (%/). (Transcarvyl acetate) (%8) (Methylchavicol) (%). (Cischrysanthenol) (%).

6 5... RI αthujene 96 0/07 αpinene 96 9/ /8 6/ 9/ /6 6/9 camphene 95,(0)thujadien sabinene 975 /8 / / 6 βpinene 98 6/ /9 / /7 / 7 dehydro,8cineole 99 8 αterpinene 00 9 ortho, cymene 08 0/7 / 0,8Cineole 08 6/ 7/7 5/ 5/ 7/7 8/5 /6 artemisia ketone 059 /7 gammaterpinene 06 cissabinene hydrate 07 artemisia alcohol 08 / 5 linalool 0 6 transsabinene hydrate 06 7 cispmenthenol /0 0/7 8 αcampholene aldehyde 9 cissabinole 7 / / 0 transverbenol 5 / / 8/5 camphor 5 0/7 / cischrysanthenol 59 Pinocarvone 70 6/ 5/ / /8 / borneol 80 6/5 /6 /6 / 5 terpineneol 87 / / 6 αterpineol 0 / / /5 / / / 7 myrtenol 0 / 8 methyl chavicol 0 9 verbenol 7 0 isogeraniol cischrysanthenyl acetate 58 / / / /7 neryl formate 8 /7 /8 / 5/9 /6 bornyl acetate 8 0/7 thymol 9 0/09 5 transcarvyl acetate 6 eugenol 55 0/7 7 αcopaene 78 0/07

7 0 55 RI 8 transcaryophyllene 5 /7 /8 /8 /8 6/ / 9 allo aromadendrene 6 /5 / / /5 /8 0 βchamigrene 77 / αamorphene 80 0/08 0/06 Germacrene D 87 6/6 5/ /8 5/ 7/ /7 bicyclogermacrene 500 cisalphabisabolene 5 5 γcadinene 58 6 δcadinene 5 7 Zvalerenyl acetate 56 8 βvetivenene 55 9 elemol transnerolidol 57 / / 6/ / /9 /9 /6 5 spathulenol 59 / /5 /6 / 5 caryophyllene oxide 599 / /7 /5 /5 0 /9 5 guaiol 6 / 5 hinesol ciscadinen7ol 67 /8 56 δcadinol 69 7 / / 5/8 /6 /7 57 βeudesmol 65 / / 58 αeudesmol 668 /8 8 6/ 5/5 /0 / 5/9 59 Khusinol 689 /0 /6 / / /9 60 β sinensa 69 /5 5/6 /8 /0 6 (Z,E)farnesol 70 6 (E,E)farnesol 75 6 chamazulen 70 /7 (%) 8/8 8/ 7/97 /6 7/ / (%) 9/ / /5 5/6 6/5 / /9 (%) /7 8 7/6 8 5/ / 7/8 (%) / 58/ 6/8 / / 8/9 (%) 96/ 97/ 9/6 9/8 9/ 9/5 9 SAS () () () () ().

8 Yavari et al., ).(00 (Mockute & Judzentiene, 00) (%). (%/7). ( ).(Bocevska & Sovova, 007).. Azani, N., Sheidai, M. and Attar, F., 009. Morphological and palynological studies in some Achillea L. species (Asteraceae) of Iran. Iranian Journal of Botany, 5(): 6. Azizi, M., Chizzola, R., Ghani A. and Oroojalian, F., 00. Composition at different development stages of the essential oil of four Achillea species grown in Iran. Natural Product Communications, 5(): Bimbiraitė, K., Ragažinskienė, O., Maruška, A. and Kornyšova, O., 008. Comparison of the chemical composition of four yarrow (Achillea millefolium L.) morphotypes. Biologia, 5(): 08. Bocevska, M. and Sovova, H., 007. Supercritical CO extraction of essential oil from yarrow. The Journal of Supercritical Fluids, 0(): Bozin, B., MimicaDukic, N., Bogavac, M., Suvajdzic, L., Simin, N., Samojlik, I. and Couladis, M., 008. Chemical composition, antioxidant and antibacterial properties of Achillea collina Becker ex Heimerl s.l. and A. pannonica Scheele essential oils. Molecules, (9): %5 (007) Venskutonis Gudaityte %55 7 %0/ (0) Nadim (%0/7) D. 8 %5/ %6/ %8/5 ) (%/6 %5/ %7/7 ).(%7/7 %/ %/) (% %7/09 %/6 %5/8 ).(%/7 (%/) (%/0) 8 (%7/58) Nadim et ) (al., 0 8.

9 57 0 millefolium agg. cultivated in conventional and organic way. Acta Fytotechnica et Zootechnica Special Number, : 5. Rohloff, J., 00. Cultivation of Herbs and Medicinal Plants in Norway Essential Oil Production and Quality Control. Norwegian University of Science and Technology, NTNU. Ph.D Thesis NTNU Trondheim, Norway. Sefidkon, F. and RahimiBidgoly, A., 00. Quantitative and qualitative variation of essential oil of Thymus kotschanus by different methods of distillation and stage of plant growth. Iranian Medicinal and Aromatic Plants Research, 5:. Shibamoto, T., 987. Retention indices in essential oil analysis: 5975, In: Sandra, P. and Bichi, C., (Eds). Capillary Gas Chromatography in Essential Oil Analysis. Alfred Heuthig, New York, 5p. Suleimenov, Y.M., Atazhanova, G.A., Ozek, T., Demirci, B., Kulyyasov, A.T., Adekenov S.M. and Baser, K.H.C., 00. Essential oil composition of three species of Achillea from Kazakhstan. Chemistry of Natural Compounds, 7: 750. Talwar, G.P. and Srivastava, L.M., 006. Text Book of Biochemistry and Human Biology. Published by Asoke, 8p. Trumbeckaite, S., Benetis, R., Bumblauskiene, L., Burdulis, D., Janulis, V., Toleikis, A., Viškelis, P. and Jakštas, V., 0. Achillea millefolium L. s.l. herb extract: antioxidant activity and effect on the rat heart mitochondrial functions. Food Chemistry, 7(): Yavari, A.R., Nazeri, V., Sefidkon, F. and Hassni, M.E., 00. Chemical composition of Thymus migricus Klokov & Desj.Shost. essential oil from different regions of West Azerbaijan province. Iranian Medicinal and Aromatic Plants Research, 6():. Zheljazkov, V.D. and Astatkie, T., 0. Effect of residual distillation water of 5 plants and three plant hormones on Scotch spearmint (Mentha gracilis Sole). Industrial Crops and Products, (): British Pharmacopoeia, 988. British Pharmacopoeia (Vol. ). Her Majesty's Stationery Office, London. Calmasur, O., Kordali, S., Kaya, O. and Aslan, I., 006. Toxicity of essential oil vapours obtained from Achillea spp. to Sitophilus granarius (L.) and Tribolium confusum (Jacquelin du Val). Journal of Plant Diseases and Protection, (): 7. Gudaityte, O. and Venskutonis, P.R., 007. Chemotypes of Achillea millefolium transferred from different locations in Lithuania to the controlled environment. Biochemical Systematics and Ecology, 5(9): Jaimand, K., Rezaee, M.B. and Barazandeh, M.M., 999. Investigation on essential oil composition of Achillea millefolium L. subsp millefolium. Medicinal and Aromatic Plant Research, : 78. Karaalp, C., Yurtman, A.N. and Yavasoglu, N.U.K., 009. Evaluation of antimicrobial properties of Achillea L. flower head extracts. Pharmaceutical Biology, 7(): 869. Kiumarsi, A., Abomahboub, R., Rashedi, S.M. and Parvinzadeh, M., 009. Achillea millefolium, a new source of natural dye for wool dyeing. Progress in Color, Colorants and Coatings, (): 879. Mockute, D. and Judzentiene, A., 00. Variability of the essential oils composition of Achillea millefolium ssp. millefolium growing wild in Lithuania. Biochemical Systematics and Ecology, (9): 005. Nadim, M.M., Malik, A.A., Ahmad, J. and Bakshi, S.K., 0. The Essential oil composition of Achillea millefolium L. cultivated under tropical condition in India. World Journal of Agricultural Sciences, 7(5): Paduch, R., NowakKryska, M., Niedziela, P. and KandeferSzerszeń, M., 008. Essential oil composition and in vitro biological activity of Achillea millefolium L. extracts. Journal of Pre Clinical and Clinical Research, (): Rehus, L. and Neugebauerova, J., 0. The comparison of the content of essential oil and flavonoids in selected species of genus Achillea

10 Iranian Journal of Medicinal and Aromatic Plants, Vol. 0, No., 0 58 Chemical composition of Achillea millefolium L. essential oil from different regions of Eest Azerbaijan province M. Ghanbari and M.K. Souri * MSc. Student, Department of Horticultural Sciences, Faculty of Agriculture, Tarbiat Modares University, Tehran, Iran * Corresponding author, Department of Horticultural Sciences, Faculty of Agriculture, Tarbiat Modares University, Tehran, Iran, Souri97@gmail.com Received: January 0 Revised: January 0 Accepted: February 0 Abstract Genus Achillea millefolium L. (Asteraceae) consists of about 00 species. Nineteen species grow naturally in Iran of which seven are endemic. In this study, chemical composition of the essential oils of seven Achillea populations growing wild in northwest Iran, during the flowering period were investigated. The aerial parts were collected from Zonoz, Basmenj, Pirbala, Bonab, Shabestar, Kondlaj and Jolfa regions from Eest Azerbaijan province in May and June 0. The essential oils were obtained by hydrodistillation method and analyzed by combination of GCFID and GCMS. Mean essential oil yield was calculate to be 0.%, 0.%, 0.%,0.%, 0.%, 0.5% and 0.% (w/w) for Zonoz, Basmenj, Pirbala, Bonab, Shabestar, Kondlaj and Jolfa, respectively. Overall, 5, 8, 8,, 5, 7 and compounds were identified from Zonoz, Basmenj, Pirbala, Bonab, Shabestar, Kondlaj and Jolfa, respectively. The main constituents of the oils were δcadinol (..7%),,8cineole (8.57.7%), transnerolidole (.6.%), germacrene D (.70.9%), alphapinene (.069.%), borneole ( %) and pinocarvone (.86.%). According to the obtained results, Basmenj and Zonoz are recommended as two suitable regions for the extraction of,8cineol and δcadinol. Key words: Achillea millefolium L., essential oil, δcadinol,,8cineole, germacrene D.

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