Toxic essential oils: Anxiolytic, antinociceptive and antimicrobial properties of the yarrow Achillea umbellata Sibth. et Sm. (Asteraceae) volatiles

Food and Chemical Toxicology

Volumn 50, Issue 6, 2012, Pages 2016-2026

  Radulović, Niko S ^a   Dekić, Milan S ^a,b   Randelović, Pavle J ^a   Stojanović, Nikola M ^a   Zarubica, Aleksandra R ^a   Stojanović Radić, Zorica Z ^a  

^a UNIVERSITY OF NI   (Serbia)

^b STATE UNIVERSITY OF NOVI PAZAR   (Serbia)

Author keywords

Achillea umbellata; Antimicrobial activity; Essential oil; Fragranol; Symptoms; Toxicity

Indexed keywords

ACHILLEA UMBELLATA EXTRACT; BENZALDEHYDE; BENZOIC ACID; BETA PINENE; BORNEOL; CAMPHENE; CAMPHOR; CARVACROL; CINEOLE; COPAENE; ESSENTIAL OIL; EUGENOL; FRAGRANOL; FRAGRANYL ACETATE; HEXANAL; HEXANOL; LIMONENE; LINALOOL; MYRCENE; NONANOL; PARA CYMENE; PHENOL; PINENE; PLANT EXTRACT; SABINENE; TERPINEN 4 OL; TERPINENE; TERPINEOL; THYMOL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACHILLEA; ACHILLEA UMBELLATA; ACUTE TOXICITY; ADULT ANIMAL; ANIMAL EXPERIMENT; ANTIMICROBIAL ACTIVITY; ANTINOCICEPTION; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG ISOLATION; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; LIGHT DARK CYCLE; LOCOMOTION; MALE; MASS FRAGMENTOGRAPHY; MOUSE; NONHUMAN; OPEN FIELD TEST; PROTEUS; PSEUDOMONAS AERUGINOSA; SALMONELLA ENTERITIDIS; STAPHYLOCOCCUS AUREUS; TRANQUILIZING ACTIVITY;

ACHILLEA; ANALGESICS; ANIMALS; ANTI-ANXIETY AGENTS; ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROLYSIS; LETHAL DOSE 50; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; MICE; MICE, INBRED BALB C; MICROBIAL SENSITIVITY TESTS; OILS, VOLATILE; PAIN MEASUREMENT; PLANT LEAVES; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

ACHILLEA; ACHILLEA MILLEFOLIUM; ASTERACEAE; EUKARYOTA; MUS;

EID: 84861441116     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2012.03.047     Document Type: Article

References (55)

1. Adams R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry 2007, Allured Publishing Corporation, Carol Stream. fourth ed.
2. Adorjan B., Buchbauer G. Biological properties of essential oils: an updated review. Flavour Fragr. J. 2010, 25:407-426.
3. Akhila J.S., Deepa S., Alwar M.C. Acute toxicity studies and determination of median lethal dose. Curr. Sci. 2007, 93:917-920.
4. Applequist W.L., Moerman D.E. Yarrow (Achillea millefolium L.): a neglected panacea? A review of ethnobotany, bioactivity, and biomedical research. Econ. Bot. 2011, 65:209-225.
5. Archer J. Test for emotionality in rats and mice: a review. Anim. Behav. 1973, 21:205-235.
6. Bakkali F., Averbeck S., Averbeck D., Idaomar M. Biological effects of essential oils - a review. Food Chem. Toxicol. 2008, 46:446-475.
7. Barra A., Norouzi-Arasi H., Sedaghat-Sharehjini S., Baldovini N. Volatile constituents of Geranium tuberosum L. from Iran. Nat. Prod. Commun. 2006, 1:387-390.
8. Başer K.H., Demirci B., Demirci F., Koçak S., Akinci C., Malyer H., Güleryüz G. Composition and antimicrobial activity of the essential oil of Achillea multifida. Planta Med. 2002, 68:941-943.
9. Bernard A.M., Frongia A., Secci F., Delogu G., Ollivier J., Piras P.P., Salaun J. Stereospecific palladium(0)-catalyzed reduction of 2-cyclobutylidenepropyl esters. A versatile preparation of diastereomeric monoterpenoids: (±)-fragranol and (±)-grandisol. Tetrahedron 2003, 59:9433-9440.
10. Bohlmann F., Jastrow H. Polyacetylenverbindungen, XL die polyine der gattung Achillea L. Chem. Ber. 1962, 95:1742-1747.
11. Bohlmann F., Zdero C., Faass U. Naturally occurring terpene derivatives. XXVI. Constituents of Artemisia fragrans. Chem. Ber. 1973, 106:2904-2909.
12. Bradley P. British Herbal Compendium: A Handbook of Scientific Information on Widely Used Plant Drugs 2006, British Herbal Medicine Association, Bournemouth, pp. 339-344.
13. Candan F., Unlu M., Tepe B., Daferera D., Polissiou M., Sökmen A., Akpulat H.A. Antioxidant and antimicrobial activity of the essential oil and methanol extracts of Achillea millefolium subsp. millefolium Afan. (Asteraceae). J. Ethnopharmacol. 2003, 83:215-220.
14. Chernogorod L.B., Vinogradov B.A. Essential oils of genus Achillea (Asteraceae) species containing fragranol. Rastitel'nye Resursy 2006, 42:61-68.
15. Collier H.O., Dinneen L.C., Johnson C.A., Schneider C. The abdominal constriction response and its suppression by analgesic drugs in the mouse. Br. J. Pharmacol. Chemother. 1968, 32:295-310.
16. Costall B., Jones B.J., Kelly M.E., Naylor R.J., Tomkins D.M. Exploration of mice in a black and white test box: validation as a model of anxiety. Pharmacol. Biochem. Behav. 1989, 32:777-785.
17. Crawley J.N., Goodwin F.K. Preliminary report of a simple animal behaviour for the anxiolytic effects of benzodiazepines. Pharmacol. Biochem. Behav. 1980, 13:167-170.
18. Demirci B., Baser K.H.C. The essential oil composition of Tanacetum macrophyllum (Waldst. et Kit.) Schultz. Bip. J. Essent. Oil Res. 2007, 19:255-257.
19. Demirci F., Demirci B., Gurbuz I., Yesilada E., Baser K.H.C. Characterization and biological activity of Achillea teretifolia Willd. and A. nobilis L. subsp. neilreichii (Kerner) Formanek essential oils. Turk. J. Biol. 2009, 33:129-136.
20. Deraedt R., Jougne S., Delevalcee F., Falhout M. Release of prostaglandin E and F in an algogenic reaction and its inhibition. Eur. J. Pharmacol. 1980, 51:17-24.
21. Dobetsberger C., Buchbauer G. Actions of essential oils on the central nervous system: an updated review. Flavour Fragr. J. 2011, 26:300-316.
22. El-Shazly A.M., Hafez S.S., Wink M. Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt. Pharmazie 2004, 59:226-230.
23. European Scientific Cooperative on Phytotherapy, ESCOP Monographs, 2004. The Scientific Foundation for Herbal Medicinal Products, Thieme, Stuttgart, pp. 452-455.
24. Franzen R. Flavonoid diversification in the Achillea ageratifolia and A. clavennae groups (Asteraceae). Am. J. Bot. 1988, 75:1640-1654.
25. Ghasemi Y., Khalaj A., Mohagheghzadeh A., Khosaravi A. Composition and in vitro antimicrobial activity of the essential oil of Achillea eriophora. Chem. Nat. Compd. 2008, 44:663-666.
26. Hamilton M.A., Russo R.C., Thurston R.V. Trimmed Spearman-Karber method for estimating median lethal concentrations in toxicity bioassays. Environ. Sci. Technol. 1977, 11:714-719.
27. Karabay-Yavasoglu N.U., Karamenderes C., Baykan S., Apaydin S. Antinociceptive and anti-inflammatory activities and acute toxicity of Achillea nobilis subsp. neilreichii extract in mice and rats. Pharm. Biol. 2007, 45:162-168.
28. Karamenderes C., Karabay Yavasoglu N.U., Zeybek U. Composition and antimicrobial activity of the essential oils of Achillea nobilis L. subsp. sipylea and subsp. neilreichii. Chem. Nat. Compd. 2007, 43:632-634.
29. 4 promoted [2+2] cycloaddition of allyl-tert-butyldiphenylsilane and methyl methacrylate. Chem. Commun. 1999, 17:1737-1738.
30. Koster R., Anderson M., DeBeer E.J. Acetic acid for analgesic screening. Fed. Proc. 1959, 18:412-417.
31. Kuesmenoglu S., Baser K.H.C., Ozek T., Harmandar M., Goekalp Z. Constituents of the essential oil of Achillea biebersteinii Afan. J. Essent. Oil Res. 1995, 7:527-528.
32. Kundaković T., Fokialakis N., Kovačević N., Chinou I. Essential oil composition of Achillea lingulata and A. umbellata. Flavour Fragr. J. 2007, 22:184-187.
33. Kuropka G., Neugebauer M., Glombitza K.W. Essential oils of Achillea ptarmica. Planta Med. 1991, 57:492-494.
34. Nassir-Ahmadi A., Rustaiyan A., Jassbi A.R. Chemical analysis of the essential oil of Artemisia haussknechtii Boiss. DARU 1994, 4:39-49.
35. Nemeth E., Bernath J. Biological activities of yarrow species (Achillea spp.). Curr. Pharm. Des. 2008, 14:3151-3167.
36. Opdyke D.L. Monographs on fragrance raw materials. Food Cosmet. Toxicol. 1975, 13:683-923.
37. Pires J.M., Mendes F.R., Negri G., Duarte-Almeida J.M., Carlini E.A. Antinociceptive peripheral effect of Achillea millefolium L. and Artemisia vulgaris L.: both plants known popularly by brand names of analgesic drugs. Phytother. Res. 2009, 23:212-219.
38. Polatoglu K., Goren N., Baser K.H.C., Demirci B. The variation in the essential oil composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey. J. Essent. Oil Res. 2009, 21:97-100.
39. Radulović N., Blagojević P. Plant volatiles providing additional evidences to the occurrence of a wild-growing population of Calamintha vardarensis (Greuter et Burdet) Šilić outside of its natural habitat. Chem. Biodiversity 2010, 7:2856-2868.
40. Radulović N., Blagojević P., Skropeta D., Zarubica A., Zlatković B., Palić R. Misidentification of tansy, Tanacetum macrophyllum, as yarrow, Achillea grandifolia: a health risk or benefit?. Nat. Prod. Commun. 2010, 5:121-127.
41. Radulović N.S., Dekić M.S., Stojanović-Radić Z.Z., Zoranić S.K. Geranium macrorrhizum L. (Geraniaceae) essential oil: a potent agent against Bacillus subtilis. Chem. Biodiversity 2010, 7:2783-2800.
42. Richardson I.K.B. Achillea L. Flora Europaea 1976, vol. 4:159-165. Cambridge University Press, Cambridge.
43. Senatore F., Napolitano F., Apostolides A.N., Bruno M., Herz W. Composition and antimicrobial activity of the essential oil of Achillea falcata L. (Asteraceae). Flavour Fragr. J. 2005, 20:291-294.
44. Si X.-T., Zhang M.-L., Shi Q.-W., Kiyota H. Chemical constituents of the plants in the genus Achillea. Chem. Biodiversity 2006, 3:1163-1180.
45. Skaltsa H.D., Demetzos C., Lazari D., Soković M. Essential oil analysis and antimicrobial activity of eight Stachys species from Greece. Phytochemistry 2003, 64:743-752.
46. Stojanović G., Asakawa Y., Palić R., Radulović N. Composition and antimicrobial activity of Achillea clavennae and Achillea holosericea essential oils. Flavour Fragr. J. 2005, 20:86-88.
47. Stojanović G., Radulović N., Hashimoto T., Palić R. In vitro antimicrobial activity of extracts of four Achillea species: the composition of Achillea clavennae L. (Asteraceae) extract. J. Ethnopharmacol. 2005, 101:185-190.
48. Stojanović-Radić, Z., Čomić, Lj., Radulović, N., Blagojević, P., Denić, M., Miltojević, A., Rajković, J., Mihajilov-Krstev. T., Antistaphylococcal activity of Inula helenium L. root essential oil: eudesmane sesquiterpene lactones induce cell membrane damage. Eur. J. Clin. Microbiol. Infect. Dis. http://dx.doi.org/10.1007/s10096-011-1400-1.
49. Tzakou O., Loukis A. Chemical composition of the essential oil of Achillea umbellata growing in Greece. Nat. Prod. Res. 2009, 23:264-270.
50. Valant-Vetschera K.M., Wollenweber E. Exudate flavonoid aglycones in the alpine species of Achillea sect. Ptarmica: chemosystematics of A. moschata and related species (Compositae-Anthemideae). Biochem. Syst. Ecol. 2001, 29:149-159.
51. Van den Dool H., Kratz P.D. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr. 1963, 11:463-471.
52. Weyerstahl P., Kaul V.K., Weirauch M., Marschall-Weyerstahl H. Volatile constituents of Artemisia vestita oil. Planta Med. 1987, 53:66-72.
53. Wollenweber E., Valant-Vetschera K.M., Ivancheva S., Kuzmanov B. Flavonoid aglycones from the leaf surfaces of some Achillea species. Phytochemistry 1987, 26:181-182.
54. Woolf A. Essential oil poisoning. Clin. Toxicol. 1999, 37:721-727.
55. Young R., Johnson D.N. A fully automated light/dark apparatus useful for comparing anxiolytic agents. Pharmacol. Biochem. Behav. 1991, 40:739-743.