The composition of the essential oils hydrodistilled from the aerial parts of five Achillea biebersteinii Afan samples, collected in central Turkey from Konya, Isparta and Ankara, were analyzed both by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Eighty-four components were identified, representing 87 to 99% of the total oil composition. The identified major components were 1,8-cineole (9-37%), camphor (16-30%) and p-cymene (1-27%). Two samples differed in piperitone (11%) and ascaridol (4%) content. The five A. biebersteinii essential oils were subsequently evaluated for their antifungal activity against the strawberry anthracnose-causing fungal plant pathogens Colletotrichum acutatum, C. fragariae and C. gloeosporioides using the direct overlay bioautography assay. The essential oils showed no antifungal activity at 80 and 160 μg/spot. In addition, A. biebersteinii oils and their major compounds were subsequently investigated against Aedes aegypti first instar larvae in a high throughput bioassay. Among the oils, only one sample from Ankara showed a notable larvacidal effect on Ae. aegypti larvae. The major compounds, 1,8-cineole, camphor and p-cymene, exhibited low mosquito larval activity, and thus the minor compounds are probably responsible for the observed activity against Ae. aegypti larvae. The oils showed weak activity against adult Ae. aegypti.
RadulovicN.S., BlagojevicP.D., SkropetaD., ZarubicaA.R., ZlatkovicB.K., PalicR.M. (2010) Misidentification of Tansy, Tanacetum macrophyllum, as yarrow, Achillea grandifolia: a health risk or benefit?Natural Product Communications, 5, 121–127.
NemethE., BernathJ. (2008) Biological activities of yarrow species (Achillea spp.). Current Pharmaceutical Design, 14, 3151–3167.
4.
SiX.T., ZhangM.L., ShiQ.W., KiyotaH. (2006) Chemical constituents of the plants in the genus Achillea. Chemistry and Biodiversity, 3, 1163–1179.
5.
Kupeli-AkkolE., KocaU., PesinI., YilmazerD. (2009) Evaluation of the wound healing potential of Achillea biebersteini Afan. (Asteraceae) by in vivo excision and incision models. Evidence-Based Complementary and Alternative Medicine (eCAM), 6, 1–7.
6.
DemirciF., DemirciB., GurbuzI., YesiladaE., BaserK.H.C. (2009) Characterization and biological activity of Achillea teretifolia Willd. and A. nobilis L. subsp. neilreichii (Kerner) Formanek essential oils. Turkish Journal of Biology, 33, 129–136.
7.
KonyaliogluS., KaramenderesC. (2005) The protective effects of Achillea L. species native in Turkey against H2O2-induced oxidative damage in human erythrocytes and leucocytes. Journal of Ethnopharmacology, 102, 221–227.
8.
IscanG., KirimerN., KurkcuogluM., ArabaciT., KupeliE., BaserK.H.C. (2006) Biological activity and composition of the essential oils of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica. Journal of Agricultural and Food Chemistry, 54, 170–173.
9.
KaramenderesC., ApaydinS. (2003) Antispasmodic effect of Achillea nobilis L. subsp. sipylea (O. Schwarz) Bässler on the rat isolated duodenum. Journal of Ethnopharmacology, 84, 175–179.
10.
RadulovicN., ZlatkovicB., PalicR., StojanovicG. (2007) Chemotaxonomic significance of the Balkan Achillea volatiles. Natural Product Communications, 2, 453–474.
11.
TrendafilovaA., TodorovaM., VitkovaA. (2010) Essential oil composition of Achillea clusiana from Bulgaria. Natural Product Communications, 5, 129–132.
12.
HoelD., PridgeonJ.W., BernierU.R., ChauhanK., MeepagalaK., CantrellC. (2010) Departments of Defense and Agriculture team up to develop new insecticides for mosquito control. Wingbeats, 21, 19–34.
13.
CopeS.E., StrickmanD.A., WhiteG.B. (2008) The Deployed Warfighter Protection Research Program: Finding new methods to vanquish old foes. The United States Army Medical Department Journal, April-June, 9–20.
14.
DukeS.O., CantrellC.L., MeepagalaK.M., WedgeD.E., TabancaN., SchraderK.K. (2010) Natural toxins for use in pest management, Toxins, 2, 1943–1962.
15.
SokmenA., SokmenM., DafereraD., PolossiouM., CandanF., UnluM., AkpulatH.A. (2004) The in vitro antioxidant and antimicrobial activities of the essential oil and methanol extracts of Achillea biebersteini Afan. (Asteraceae). Phytotherapy Research, 18, 451–456.
16.
BarisO., GulluceM., SahinF., OzerH., KilicH., OzkanH., SokmenM., OzbekT. (2006) Biological activities of the essential oil and methanol extract of Achillea biebersteinii Afan. (Asteraceae). Turkish Journal of Biology, 30, 65–73.
17.
KordaliS., CakirA., AkcinT.A., MeteE., AkcinA., AydinT., KilicH. (2009) Antifungal and herbicidal properties of essential oils and n-hexane extracts of Achillea gypsicola Hub-Mor. and Achillea biebersteinii Afan. (Asteraceae). Industrial Crops and Products, 29, 562–570.
18.
KusmenogluS., BaserK.H.C., OzekT., HarmandarM., GokalpZ. (1995) Constituents of the essential oil of Achillea biebersteinii Afan. Journal of Essential Oil Research, 7, 527–528.
19.
KatayounM.S., MohammadA., KamranM. (2005) The essential oil composition of Achillea biebersteinii Afan. Journal of Essential Oil-Bearing Plants, 8, 200–203.
20.
JaimandK., RezaeeM.B. (2001) Comparative study of the essential oils of three Achillea species from Iran, Journal of Essential Oil Research, 13, 354–356.
21.
RahimmalekM., Sayed-TabatabaeiB.E., EtemadiN., Hossein-GoliS.A., ArzaniA., ZeinaliH. (2009) Essential oil variation among and within six Achillea species transferred from different ecological regions in Iran to the field conditions. Industrial Crops and Products, 29, 348–355.
22.
AziziM., ChizzolaR., GhaniA., OroojalianF. (2009) Composition at different development stages of the essential oil of four Achillea species grown in Iran. Natural Product Communications, 5, 283–290.
23.
GhaniA., AziziM., Hassanzadeh-KhayyatM., Asghar-PahlavanpourA. (2008) Essential oil composition of Achillea eriphora, A.nobilis, A. biebersteinii and A. wilhelmsii from Iran. Journal of Essential Oil-Bearing Plants, 11, 460–467.
24.
AbdolhosseinR., HosseinK., Mercedeh-SaneiS., Jassbi, Amir-RezaJ., MasoudiS. (1998) Comparative study of the essential oils of three Achillea species from Iran. Journal of Essential Oil Research, 10, 207–209.
25.
BaderA., FlaminiG., CioniP.L., MorelliI. (2003) Essential oil composition of Achillea santolina L. and Achillea biebersteinii Afan. collected in Jordan. Flavour and Fragrance Journal, 18, 36–38.
26.
EsmaeiliA., NematollahiF., RustaiyanA., MoazamiN., MasoudiS., BamasianS. (2006) Volatile constituents of Achillea pachycephala, A. oxyodonta and A. biebersteinii from Iran. Flavour and Fragrance Journal, 21, 253–256.
27.
WedgeD.E., DaleN.G. (2000) A new 2D-TLC bioautography method for the discovery of novel antifungal agents to control plant pathogens. Journal of Natural Products, 63, 1050–1054.
28.
TabancaN., DemirciB., BaserK.H.C., AytacZ., EkiciM., KhanS.I., JacopM.R., WedgeD.E. (2006) Chemical composition and antifungal activity of Salvia macrochlamys and Salvia recognita essential oils. Journal of Agricultural and Food Chemistry, 54, 6593–6597.
29.
European Pharmacopoeia, 5th Edition, volume 1 (2005) Council of Europe, Strasbourg. 217.
30.
KoenigW.A., JoulainD., HochmuthD.H. (2004) Terpenoids and related constituents of essential oils. MassFinder 3. HochmuthD.H. (Ed.). Convenient and Rapid Analysis of GC-MS, Hamburg, Germany.
31.
McLaffertyF.W., StaufferD.B. (1989) The Wiley/NBS registry of mass spectral data.J. Wiley and Sons, New York.
32.
JoulainD., KoenigW.A. (1998) The atlas of spectra data of sesquiterpene hydrocarbons.E.B. Verlag, Hamburg.
33.
ESO 2000. (1999) The complete database of essential oils.Boelens Aroma Chemical Information Service, The Netherlands.
34.
JenningsW.G., ShibamotoT. (1980) Quantitative analysis of flavor and fragrance volatiles by glass capillary GC.Academic Press, New York.
35.
TabancaN., WedgeD.E., WangX., DemirciB., BaserK.H.C., ZhouL., CutlerS.J. (2008) Chemical composition and antifungal activity of Angelica sinensis essential oil against three Colletotrichum species. Natural Product Communications, 3, 1073–1078.
36.
WedgeD.E., TabancaN., SampsonB.J., WerleC., DemirciB., BaserK.H.C., NanP., DuanP., LiuZ. (2008) Antifungal and insecticidal activity from two Juniperus essential oils. Natural Product Communications, 3, 1–5.
37.
PridgeonJ.W., BecnelJ.J., ClarkG.G., LinthicumK.J. (2009) A high throughput screening method to identify potential pesticides for mosquito control. Journal of Medical Entomology, 46, 335–341.
38.
PridgeonJ.W., PereiraR.M., BecnelJ.J., AllanS.A., ClarkG.G., LinthicumK.J. (2008) Susceptibility of Aedes aegypti L., Culex quinquefasciatus Say, and Anopheles quadrimaculatus Say to 19 pesticides with different modes of action. Journal of Medical Entomology, 45, 82–87.
