chemical composition and antimicrobial activity of essential oil of achillea cretica ...

This article was downloaded by: [Laurentian University]On: 08 March 2013, At: 10:52Publisher: Taylor & FrancisInforma Ltd Registered in England and Wales Registered Number: 1072954 Registeredoffice: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK

Natural Product Research: FormerlyNatural Product LettersPublication details, including instructions for authors andsubscription information:http://www.tandfonline.com/loi/gnpl20

Chemical composition andantimicrobial activity of essential oil ofAchillea cretica L. (Asteraceae) fromTurkeyF. Zehra Küçükbay a , Ebru Kuyumcu a , Tuçe Bilenler b & BayramYıldız c

a Department of Basic Pharmaceutical Sciences, Division ofAnalytical Chemistry, Faculty of Pharmacy, İnönü University, 44280Malatya, Turkeyb Department of Food Engineering, Faculty of Engineering, İnönüUniversity, 44280 Malatya, Turkeyc Department of Biology, Faculty of Science and Arts, BalikesirUniversity, 10100 Balikesir, TurkeyVersion of record first published: 11 Oct 2011.

To cite this article: F. Zehra Küçükbay , Ebru Kuyumcu , Tuçe Bilenler & Bayram Yıldız (2012):Chemical composition and antimicrobial activity of essential oil of Achillea cretica L. (Asteraceae)from Turkey, Natural Product Research: Formerly Natural Product Letters, 26:18, 1668-1675

To link to this article: http://dx.doi.org/10.1080/14786419.2011.599808

PLEASE SCROLL DOWN FOR ARTICLE

Full terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions

This article may be used for research, teaching, and private study purposes. Anysubstantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,systematic supply, or distribution in any form to anyone is expressly forbidden.

The publisher does not give any warranty express or implied or make any representationthat the contents will be complete or accurate or up to date. The accuracy of anyinstructions, formulae, and drug doses should be independently verified with primarysources. The publisher shall not be liable for any loss, actions, claims, proceedings,

http://www.tandfonline.com/loi/gnpl20

http://dx.doi.org/10.1080/14786419.2011.599808

http://www.tandfonline.com/page/terms-and-conditions

http://www.tandfonline.com/page/terms-and-conditions

demand, or costs or damages whatsoever or howsoever caused arising directly orindirectly in connection with or arising out of the use of this material.

Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

Natural Product ResearchVol. 26, No. 18, September 2012, 1668–1675

Chemical composition and antimicrobial activity of essential oil of

Achillea cretica L. (Asteraceae) from Turkey

F. Zehra Kucukbaya*, Ebru Kuyumcua, Tuce Bilenlerb and Bayram Y|ld|zc

aDepartment of Basic Pharmaceutical Sciences, Division of Analytical Chemistry, Faculty ofPharmacy, _Inonu University, 44280 Malatya, Turkey; bDepartment of Food Engineering, Faculty ofEngineering, _Inonu University, 44280 Malatya, Turkey; cDepartment of Biology, Faculty of Scienceand Arts, Balikesir University, 10100 Balikesir, Turkey

(Received 23 December 2010; final version received 3 May 2011)

Hydrodistilled volatile oil from the aerial parts of Achillea cretica L. (Asteraceae)was analysed by a combination of GC and GC/MS. Seventy-six components wereidentified, constituting 86.4% of the oil. The main constituents of the essential oilwere caryophylladienol-II (13.4%), �-maaliene (6.1%), neo-intermedeol (6.0%),carvone (4.9%), spathulenol (4.5%), palmitic acid (3.3%) and selina-3,11-dien-6�-ol (3.2%). The antimicrobial activity was evaluated by the broth-dilutionmethod on nine microbial strains and showed to be quite strong against theGram-positive bacteria Staphylococcus aureus and Bacillus cereus. The anti-bacterial properties of A. cretica justify its use in traditional medicine for thetreatment of wounds, contaminated through bacterial infections.

Keywords: Achillea cretica; Asteraceae; GC/MS; caryophylladienol-II; antimi-crobial activity

1. Introduction

The genus Achillea L. is a member of the well-known medicinal plant family Asteraceaeand comprises numerous species of wild-growing plants. Fifty of them are considered asEuropean species, mainly as the typical plants of the Mediterranean area (Magiatis,Skaltsounis, Chinou, & Haroutounian, 2002). It is represented with 48 species (54 taxa;including Otanthus Hoffmanns. & Link and Leucocyclus Boiss.) which belong to fivesections in Turkey (Arabaci & Yildiz, 2006a, b; Celik & Akpulat, 2008; Duman, 2000;Ehrendorfer & Guo, 2005; Huber-Morath, 1975; Valant-Vetschera, 1996; Valant-Vetschera & Kastner, 1998). A review on the chemical constituents of Achillea sp. waspublished recently (Si, Zhang, Shi, & Kiyota, 2006). From a phytochemical point of view,the following compound classes were reported as Achillea species metabolites: terpenoids,lignans, flavonoids and amino acid derivatives (Si et al., 2006).

From a wide perspective, Achillea species comprise an important biological resourcein Turkish folk medicine against gastro-intestinal complaints, inflammatory disorders,for wound healing, as emmenagogue, as diuretic, against jaundice and for many othercomplaints (Baytop, 1999; Sezik et al., 2001; Tabata et al., 1994). Also, the essentialoils of several Achillea species from Turkey have been cited in the literature (Aslan,Evren, Konuklugil, Turkoglu, & Kartal, 2009; Bas� er, Demirci, & Duman, 2001;

*Corresponding author. Email: [email protected]

ISSN 1478–6419 print/ISSN 1478–6427 online

� 2012 Taylor & Francis

http://dx.doi.org/10.1080/14786419.2011.599808

http://www.tandfonline.com

Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

F. Demirci, B. Demirci, Gurbuz, Yes� ilada, & Bas� er, 2009; Karamenderes, Karabay-Yavas� oglu, & Zeybek, 2007; Sokmen et al., 2003).

Among the known plants, Achillea cretica L., belonging to the family of Asteraceae, isa perennial, unarmed and white liguled plant occurring in the Southwest of Turkey, Crete,Cyprus and Central and South of Aegean Islands (Huber-Morath, 1975). To the best ofour knowledge, no information is available concerning the antimicrobial activity of theessential oil of A. cretica L. Based on the wide use of A. cretica in the folk medicine as atreatment agent, our study was aimed at evaluating the in vitro antimicrobial activity of theessential oil of A. cretica as well its chemical composition.

2. Results and discussion

2.1. Chemical composition of the essential oil

The composition of the essential oil of A. cretica is given in Table 1. The GC-FID andGC/MS analyses led us to the identification of 76 components, accounting for 86.4% ofthe total oil.

The average yield of the essential oil was 0.05%. The most abundant components(43%) of the oil from the aerial parts of A. cretica were caryophylladienol-II (13.4%),�-maaliene (6.1%), neo-intermedeol (6.0%), carvone (4.9%), spathulenol (4.5%), palmiticacid (3.3%) and selina-3,11-dien-6�-ol (3.2%).

In this study, the essential oil of A. cretica displayed chemical profiles different fromthose observed in many other Achillea species. Generally, eucalyptol, camphor and/or�-terpineol have been found as major compounds in many other Achillea species(Chalchat, Gorunovic, & Petrovic, 1999; Kucukbay, Kuyumcu, & Arabaci, 2010;Rustaiyan, Komeilizadeh, Shariatpanahi, Jassbi, & Masoudi, 1998; Simic, Andjelkovic,Palic, Vajs, & Milosavicevic, 2000). According to a comprehensive work by Nemeth(2005), a variation in the chemical composition of the essential oils within the genusAchillea in different plant parts seems to depend on the investigated species. Themonoterpenes such as 1,8-cineole, camphor, borneol and �- and �-pinene were the mostabundant along with the sesquiterpenes, such as chamazulene, �-caryophyllene and itsoxide. Previous research revealed that the essential oils isolated from some Achillea speciesgrowing in different regions of Turkey were characterised by their high content ofcamphor, �- and �-thujone, piperitone and 1,8-cineole: camphor was found to be thedominant constituent in the oils of Achillea falcata (24.0%) and Achillea phrygia (14.5%)(Bas� er, Demirci, Kaiser, & Duman, 2000; Kurkcuoglu, Tabanca, Ozek, & Bas� er, 2003).Combinations of the monoterpenes camphor, �- and �-thujone were detected in Achilleamultifida oil (3.7%, 60.9% and 9.1%, respectively) (Bas� er et al., 2002). Piperitone wasreported as the main constituent of Achillea teretifolia oil (21.37%). (Aslan et al., 2009).Also, 1,8-cineole (34%), camphor (11%), terpinen-4-ol (8%) and �-thujone (5%) werereported as the main components of the essential oil of the A. teretifolia, and fragnaylacetate (32%), fragranol (24%) and �-eudesmol (8%) for the essential oil of Achilleanobilis subsp. neilreichii (Demirci et al., 2009).

Research studies of recent decades indicated that the chemical compositions of Achilleaspecies are complex and susceptible to variation, but the biologically active componentsare mostly the essential oils and sesquiterpene lactones (Chandler, Hooper, & Harvey,1982).

2.2. Antimicrobial activity

The in vitro results were classified as follows: if the extracts displayed a MIC of less than100 mgmL�1, the antibacterial activity was considered good; from 100 to 500 mgmL�1 the

Natural Product Research 1669

Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

Table

1.GC/M

SanalysisoftheessentialoilofAchilleacretica(yield

percentage0.05%

).

Experim

entalRIa

Literature

RIb

Compound

Composition(%

)Experim

entalRIa

Literature

RIb

Compound

Composition(%

)

1444

1441

Silphiperfol-5-ene,

C15H

24

0.2

1549

1544

�-G

urjunene,

C15H

24

0.9

1453

1450

trans-Linaloloxide,

C10H

18O

20.8

1559

1553

Linalool,C10H

18O

0.3

1454

1452

1-O

cten-3-ol,C8H

16O

0.3

1567

1562

Isopinocamphone,

C10H

16O

0.8

1481

1479

cis-Linaloloxide,

C10H

18O

20.6

1591

1586

Pinocarvone,

C10H

14O

1.0

1485

1482

Longipinene,

C15H

24

0.9

1609

1604

6-M

ethyl-3,5-heptadiene-2-one,

C8H

12O

0.6

1500

1497

�-C

opaene,

C15H

24

0.2

1616

1611

Terpinen-4-ol,C10H

18O

2.4

1502

1499

�-C

amphenal,C10H

14O

20.4

1653

1648

Myrtenal,C10H

14O

0.4

1538

1535

trans-Pinocamphone,

C10H

16O

0.4

1669

1664

trans-Pinocarveol,C10H

16O

0.4

1539

1535

�-Bourbonene,

C15H

24

0.2

1678

1674

p-M

entha-1,5-dien-8-ol,C10H

16O

0.2

1547

–�-M

aaliene,

C15H

24

6.1

2210

2214

Ar-Turm

erol,C15H

22O

1.8

1688

1684

trans-Verbenol,C10H

16O

0.4

2214

2219

�-Cadinol,C15H

26O

2.1

1709

1704

Salicylaldehyde,

C7H

6O

20.2

2230

2237

�-Bisabolol,C15H

26O

0.5

1710

1704

�-M

uurolene,

C15H

24

0.1

2234

2239

Carvacrol,C10H

24O

0.4

1714

1707

�-Terpineol,C10H

18O

0.1

2236

2238

Isospathulenol,C15H

24O

0.1

1726

1719

Borneol,C10H

18O

0.2

2253

2255

�-C

adinol,C15H

26O

3.1

1732

1726

GermacreneD,C15H

24

1.0

2255

2257

�-Eudesmol,C15H

26O

0.5

1747

1740

trans-p-M

enth-2-en-1,8-diol,C10H

18O

20.6

2257

2256

epi-�-Bisabolol,C15H

26O

0.5

1749

1741

�-Bisabolene,

C15H

24

0.2

2265

2264

Neo-interm

edeol,C15H

26O

6.0

1756

1748

Piperitenone,

C10H

14O

0.2

2274

2273

Selina-3,11-dien-6�-ol,C15H

26O

3.2

1759

1751

Carvone,

C10H

14O

4.9

2288

2287

(2Z,6Z)-Farnesol,C15H

26O

0.2

1784

1773

�-Cadinene,

C15H

24

0.2

2293

–Cedr-8-en-13-ol,C15H

24O

1.6

1786

1797

p-M

ethyl-acetophenone,C9H

10O

0.2

2320

2324

Caryophylladienol-II,C15H

24O

13.4

1810

1804

Myrtenol,C10H

16O

0.7

2365

2369

(2E,6E)-Farnesol,C15H

26O

1.1

1824

1827

(E,E)-2,4-D

ecadienal,C10H

16O

0.1

2390

2392

CaryophyllenolII,C15H

24O

0.6

1834

1838

E-�-D

amascenone,

C13H

18O

2.0

2293

2402

Eudesma-4(15)-7-dien-1-�-ol

0.3

1841

1845

trans-Carveol,C10H

16O

0.4

2550

2553

�-C

ostol,C15H

24O

0.5

1864

1867

Thymolacetate,C12H

16O

20.4

2594

2599

14-H

ydroxy-�-m

uurolene,

C15H

24O

0.2

1866

1868

E-G

eranylacetone,

C13H

22O

0.2

2664

2670

Myristic

acid,C14H

28O

20.6

1943

1945

1,5-Epoxy-salvial-4(14)-ene

0.4

2908

2931

Hexadecanoic

acid,C16H

32O

23.3

2005

2008

Caryophylleneoxide,

C15H

24O

0.9

Total

86.4

2026

2029

Perilla

alcohol,C10H

16O

0.2

2034

2037

Salvial-4(14)-en-1-one,

C17H

28O

1.8

2064

2069

HumuleneepoxideII,C15H

24O

0.3

2065

2069

Germacrene-4-ol,C15H

26O

1.2

2077

2080

Cubenol,C15H

26O

1.1

2089

2092

�-O

plopenone,

C15H

24O

0.4

2090

2096

Globulol,C15H

26O

0.8

2102

2104

Viridiflorol,C15H

26O

0.3

1670 F.Z. Kucukbay et al.

Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

2108

2110

trans-Sesquisabinenehydrate,C15H

26O

0.6

2130

2131

Hexahydrofarnesylacetone,

C18H

36O

0.6

2142

2144

Spathulenol,C15H

24O

4.5

2160

2176

Nonanoic

acid,C9H

18O

20.6

2178

2185

�-Eudesmol,C15H

26O

0.5

2180

2186

Eugenol,C10H

12O

20.3

2183

2187

T-C

adinol,C15H

26O

0.3

2195

2198

Thymol,C10H

14O

1.6

2204

2209

T-M

uurolol,C15H

26O

0.3

Note:aRIcalculatedfrom

retentiontimes

relativeto

thatofalkanes

(C7–C29)onthepolarHP-Innowaxcolumn.

bIdentificationwasbasedonthecomparisonofretentionindex

withthose

ofpublished

data

(NIST).


Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

antibacterial activity was considered moderate; from 500 to 1000 mgmL�1 the antibacterialactivity was considered weak; over 1000mgmL�1 the extracts were considered inactive(Pessini, Filho, Nakamura, & Cortez, 2003). The antimicrobial activity of the essential oilof A. cretica expressed as MIC is given in Table 2. The essential oil presented good activityagainst Bacillus cereus with MIC at 62.5mgmL�1 and moderate activity againstStaphylococcus aureus with MIC at 125mgmL�1. These results showed that the essentialoil was particularly active against the Gram-positive bacteria S. aureus and B. cereus. Inanother study, the essential oil of Achillea clavennae exhibited strong antibacterial activityagainst the Gram(�)-ve Haemmophilus influenza and Pseudomonas aeruginosa respiratorypathogens, while Gram(þ)-ve Streptococcus pyogenes was the most resistant to the oil(Skocibusic, Bezic, Dunkic, & Radonic, 2004).

3. Experimental

3.1. Plant material

The plant material of this study was collected in Datca-Knidos, Mugla province ofTurkey, at 2100m, on 19 June 2004. The voucher specimens have been deposited in theHerbarium of Inonu University (INU) in Malatya, Turkey (INU-Collector No: BY15634).

3.2. Analysis of the essential oils

The air-dried aerial parts of plants were submitted for 3 h to steam distillation usingClevenger-type apparatus to produce the essential oils. The percentage yields (%) of theoils calculated on a moisture-free basis are shown in Table 1. Oils were dried overanhydrous sodium sulphate and, after filtration they were stored at 4 �C until tested andanalysed.

GC analysis was performed on an Agilent Technologies 6890N Network system gaschromatograph equipped with an FID and HP-Innowax column (60m� 0.25mm i.d.,0.25mm film thickness). Injector and detector temperatures were set at 250�C. The oventemperature was kept at 60�C for 10min and increased up to 220�C at a rate of 4�C min,then kept constant at 220�C for 10min and increased up to 240�C at a rate of 1�C and thenkept constant at 240�C for 10min. Helium was used as the carrier gas, at a flow rate of1.7mLmin�1.

GC/MS analysis of the essential oil was performed under the conditions with GC(column, oven, temperature and flow rate of the carrier gas) using an Agilent Technologies

Table 2. Antimicrobial activity of Achillea cretica essential oil (MIC in mgmL�1).

Microorganisms Source EO ST

S. epidermidis RSHC No: 95 41000 3.12a 3.12b

S. aureus RSHC NO:1020\06008 125 3.12a 1.5b

S. hominis ATCC 27844 41000 3.12a 1.5b

S. warneri ATCC 27836 41000 3.12a 4100b

B. cereus RSHC NO: 869 62.5 6.2a 1.5b

E. coli Inonu Univ.(TR) 41000 12.25a 6.25b

S. flexneri RSHC NO: 184 41000 50.00a 12.5b

Salmonella Inonu Univ.(TR) 41000 6.25a 50b

C. albicans ATCC 90028 1000 nt

Notes: EO, essential oil of A. cretica; nt, not tested; and ST, standard agent.aAmpicillin.bGentamicin.


Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

6890N Network system gas chromatograph equipped with an Agilent Technologies 5973

inert Mass Selective Detector (Agilent G3180B Two-Ways Splitters with Make up gas) in

the electron impact mode (70 eV). The mass range was between m/z 10 and 425.

3.3. Identification and quantification of essential oils constituents

Retention indices were calculated using retention times of n-alkanes (C7–C29) homologous

series that were injected after the essential oil at the same chromatographic conditions

according to Van den Dool method (Van den Dool & Kratz, 1963). Identification of

individual components of the essential oil was performed by computerised matching of the

acquired mass spectra with those stored in NIST 05/Wiley 7 n (comparison quality490%)mass spectral library of the GC/MS data system and/or by confirmation with the aid of

retention indices from the published sources (NIST, 2008). The relative concentration of

each compound in the essential oil was quantified according to the peak area integrated by

the analysis program.

3.4. Antimicrobial screening

Antimicrobial activities of the essential oil were determined using broth-dilution method

developed by Pessini et al. (2003) with slight modifications. MICs were determined by two-

fold serial dilution of extracts beyond the concentration where no inhibition of the growth

of S. aureus, RSHC NO:1020\06008, Staphylococcus epidermidis RSHC No:95, B. cereus

RSHC NO:869, Shigella flexneri RSHC NO: 184 Staphylococcus hominis ATCC 27844,Staphylococcus warneri ATCC 27836, Salmonella ML, Escherichia coli ML and the yeasts

Candida albicans ATCC 90028, obtained from Refik Saydam Hygiene Center (Ankara,

Turkey) and American Type Culture Collection (Rockville, MD) and the Department of

Microbiology, Faculty of Medicine, Inonu University (Turkey), respectively, wasobserved. Bacterial cultures were maintained on nutrient agar (Merck, Darmstadt,

Germany) at þ4�C, yeast was maintained in Sabouroud dextrose agar (Merck, Darmstadt,

Germany) until use, and the fungi used for growth inhibition tests was grown overnight in

Sabouroud dextrose broth (Merck, Darmstadt, Germany) at 35�C prior to screening tests.

Bacterial cultures were inoculated and incubated at 37�C nutrient broth (Merck,Darmstadt, Germany) for 24 h. Their turbidities matched that of a McFarland no. 0.5

turbidity standard (Hindler, Hochstein, & Howell, 1992). Stock solutions of extract and

standards were prepared in dimethyl sulphoxide (10%, v/v, DMSO) which had no effect

on the microorganisms in the concentrations studied. Dilution series using sterile distilled

water were prepared at 1000, 500, 250, 125, 62.5, 31.25, 15.6, 7.8 and 3.9 mgmL�1 in testtubes containing Mueller Hinton broth (Merck, Darmstadt, Germany). Freshly prepared

bacterial and yeast suspensions that standardised inoculum of the bacteria and yeasts

(106 CFUmL�1) were pipetted into each test tube, in an equal volume, at 0.01mL. Test

tube containing sterile distilled water and medium was used as positive growth control.Ampicillin and Gentamicin (Sigma–Aldrich, USA) were used as antibacterial standards

against all bacteria.Tetrazolium violet was used as an indicator of microbial growth. Growth of the

microorganism reduced the tetrazolium violet to a violet formazan and the test tube was

visibly red coloured (Eloff, 2001). MIC was determined as the lowest concentration ofplant extract inhibiting microbial growth; 0.2mgmL�1 p-iodonitrotetrazolium violet

(INT; Sigma) was added. After further incubation, bacterial growth was indicated by the

red colour of the INT formazan produced (Eloff, 1998).


Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

4. Conclusions

The Achillea genus is widespread all over the world, and many species of this genus havebeen used as conventional herbal medicines by local people. Phytochemical investigationof Achillea species has revealed that many components from Achillea genus are highlybioactive. On the other hand, there are still several aspects of Achillea plants that havereceived little attention so far. Consequently, phytochemical and biological studies of thisgenus should be intensified.

References

Arabaci, T., & Yildiz, B. (2006a). Achillea salicifolia Besser subsp. salicifolia (Asteraceae) in Turkey, with

taxonomic remarks. Turkish Journal of Botany, 30, 171–174.

Arabaci, T., & Yildiz, B. (2006b). Achillea salicifolia Besser subsp. salicifolia (Asteraceae) in Turkey, with

taxonomic remarks. Feddes Repertorium, 117, 459–465.

Aslan, S., Evren, H., Konuklugil, B., Turkoglu, I., & Kartal, M. (2009). Essential oil composition of Achillea

teretifolia from Turkey. Chemistry of Natural Compounds, 45, 274–275.

Bas� er, K.H.C., Demirci, B., & Duman, H. (2001). Composition of the essential oils of two endemic species from

Turkey: Achillea lycaonica and A. ketenoglui. Chemistry of Natural Compounds, 37, 245–252.

Bas� er, K.H.C., Demirci, B., Kaiser, R., & Duman, H. (2000). Composition of the essential oil of Achillea phrygia

Boiss. et Ball. The Journal of Essential Oil Research, 12, 327–329.

Bas� er, K.H.C., Demirci, B., Demirci, F., Kocak, S., Akinci, C., Malyer, H., & Guleryuz, G. (2002). Composition

and antimicrobial activity of the essential oil of Achillea multifida. Planta Medica, 68, 939–941.

Baytop, T. (1999). Turkiye de Bitkiler ile Tedavi Gecmis� ten Bugune (Therapy with Medicinal Plants in Turkey –

Past and Present) (2nd ed.). _Istanbul: Nobel Tip Bas|mevi.

Celik, N., & Akpulat, H.A. (2008). Achillea sivasica (Asteraceae: sect. Babounya (DC.) O. Hoffm.), a new

species from Inner Anatolia, Turkey. Kew Bulletin, 63, 485–489.

Chalchat, J.C., Gorunovic, M.S., & Petrovic, S.D. (1999). Aromatic plants of Yugoslavia. I. Chemical

composition of oils of Achillea millefolium L. ssp. Pannanica(Scheele) Hayak, A. crithmifolia W. et K.,

serbica Nym. and A. tanacetifolia ali. Journal of Essential Oil Research, 11, 306–310.

Chandler, R.F., Hooper, S.N., & Harvey, N.J. (1982). Ethnobotany and phytochemistry of yarrow, Achillea

millefolium, compasitae. Economic Botany, 36, 203–223.

Demirci, F., Demirci, B., Gurbuz, _I., Yes� ilada, E., & Bas� er, K.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.

Duman, H. (2000). Achillea L. In A. Guner, N. Ozhatay, T. Ekim, & K.H.C. Baser (Eds.), Flora of Turkey and

the East Aegean Islands (Supplement) (Vol. 11, pp. 158–159). Edinburgh: Edinburgh University Press.

Ehrendorfer, F., & Guo, Y.P. (2005). Changes in the circumscription of the genus Achillea (Compositae-

Anthemideae) and its subdivisions. Willdenowia, 35(6), 49–54.

Eloff, J.N. (1998). A sensitive and quick microplate method to determine the minimal inhibitory concentration of

plant extracts for bacteria. Planta Medica, 64, 711–713.

Eloff, J.N. (2001). Antibacterial activity of Marula (Sclerocarya birrea (A. Rich.) Hochst. subsp. caffra (Sond.)

Kokwaro) (Anacardiaceae) bark and leaves. Journal of Ethnopharmacology, 76, 305–308.

Hindler, J., Hochstein, L., & Howell, A. (1992). Preparation of routine media and reagents used in antimicrobial

susceptibility testing. Part 1. McFarland standards. In H.D. Isenberg (Ed.), Clinical microbiology

procedures handbook (Vol. 1, pp. 5.19.1–5.19.6). Washington, DC: American Society for Microbiology.

Huber-Morath, A. (1975). Achillea L. In P.H. Davis (Ed.), Flora of Turkey and the East Aegean Islands (Vol. 5,

pp. 241–242). Edinburgh: Edinburg University Press.

Karamenderes, C., Karabay-Yavas� oglu, N.U., & Zeybek, U. (2007). Composition and antimicrobial activity of

the essential oils of Achillea nobilis L. subsp. siplea and subsp. neilreichii. Chemistry of Natural Compounds,

43, 632–634.

Kucukbay, F.Z., Kuyumcu, E., & Arabaci, T. (2010). The essential oil of Achillea boissieri Hausskn. ex Boiss.

Chemistry of Natural Compounds, 46, 824–825.

Kurkcuoglu, M., Tabanca, N., Ozek, T., & Bas� er, K.H.C. (2003). The essential oil of Achillea falcata L. Flavour

and Fragrance Journal, 18, 192–194.

Magiatis, P., Skaltsounis, A-L., Chinou, I., & Haroutounian, S.A. (2002). Chemical composition and

antimicrobial activity of the essential oils of three Achillea species from Greece. Zeitschrift fur

Naturforschung C, 57, 287–290.


Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

Nemeth, E. (2005). Essential oil composition of species in the genus Achillea. Journal of Essential Oil Research,

17, 501–512.

NIST (2008). NIST Standard Reference Database Number 69. P.J. Linstrom and W.G. Mallard (Eds.),

Gaithersburg, MD: National Institute of Standard and Technology, 20899. Retrieved from http://

webbook.nist.gov

Pessini, G.L., Filho, B.P.D., Nakamura, C.V., & Cortez, D.A.G. (2003). Antibacterial activity of extracts and

neolignans from Piper regnellii (Miq) C.DC.var.pallescens (C. DC.) Yunck. Memorias do Instituto

Oswaldo Cruz, 98, 1115–1120.

Rustaiyan, A., Komeilizadeh, H., Shariatpanahi, M.S., Jassbi, A., & Masoudi, S. (1998). Comparative study of

the essential oils of three Achilea Species from Iran. Journal of Essential Oil Research, 10, 207–209.

Sezik, E., Yes� ilada, E., Honda, G., Takaishi, Y., Takeda, Y., & Tanaka, T. (2001). Traditional medicine in

Turkey, X. Folk medicine in Central Anatolia. Journal of Ethnopharmacology, 75, 95–115.

Si, X.-T., Zhang, M.-L., Shi, Q.-W., & Kiyota, H. (2006). Chemical constituents of the plants in the genus

Achillea. Chemistry Biodiversity, 3, 1163–1180.

Simic, N., Andjelkovic, S., Palic, R., Vajs, V., & Milosavicevic, S. (2000). Composition and antibacterial activity

of Achillea chrysacoma essential oil. Journal of Essential Oil Research, 12, 784–787.

Skocibusic, M., Bezic, N., Dunkic, V., & Radonic, A. (2004). Antibacterial activity of Achillea clavennae essential

oil against respiratory tract pathogens. Fitoterapia, 75, 733–736.

Sokmen, A., Vardar-Unlu, G., Polissiou, M., Daferera, D., Sokmen, M., & Donmez, E. (2003). Antimicrobial

activity of essential oil and methanol extracts of Achillea sintenisii Hub.Mor. (Asteraceae). Phytotherapy

Research, 17, 1005–1010.

Tabata, M., Sezik, E., Honda, G., Yes� ilada, E., Fukui, H., Goto, K., & Ikeshiro, Y. (1994). Traditional medicine

in Turkey III. Folk medicine in East Anatolia, Van and Bitlis Provinces. Pharmaceutical Biology, 32, 3–12.

Valant-Vetschera, K.M. (1996). Lectotypification of Achillea santolina L. and Achillea falcata L. (Compositae,

Anthemideae). Botanical Journal of the Linnean Society, 121, 159–168.

Valant-Vetschera, K.M., & Kastner, A. (1998). New combinations and synonyms in Achillea sect. Santolinoideae

(Compositae-Anthemideae) from North Africa and Turkey. Feddes Repertorium, 109, 501–508.

Van den Dool, H., & Kratz, P.D. (1963). A generalization of the retention index system including linear

temperature programmed gas-liquid partition chromatography. Journal of Chromatography, 11, 463–471.


Dow

nloa

ded

by [

Lau

rent

ian

Uni

vers

ity]

at 1

0:52

08

Mar

ch 2

013

chemical composition and antimicrobial activity of essential oil of achillea cretica ...

Documents