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Chemistry of Natural Compounds

, Volume 44, Issue 3, pp 387–389 | Cite as

Chemical composition and in vitro antibacterial activities of the oil of Ziziphora clinopodioides and Z. capitata subsp. capitata from Iran

  • Z. Aghajani
  • F. Assadian
  • Sh. Masoudi
  • F. Chalabian
  • A. Esmaeili
  • M. Tabatabaei-Anaraki
  • A. RustaiyanEmail author
Article

Keywords

Antibacterial Activity Limonene Linalool Thymol Carvacrol 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

The genus Ziziphora is represented in the flora of Iran by four species [1]. In Iranian and Turkish folk medicine, Ziziphora species have been used as sedative, stomachic, and carminative [2].

The composition of the essential oils of Z. pamiralaica, Z. denticulata, Z. Tenuior [3], Z. bungeana, Z. clinopodioides [4], Z. vychodceviana , Z. pedicelcata, and Z. persica [5] grown under different ecological conditions in Russia was studied by gas chromatography. Pulegone and isomenthone were the major constituents of these oils. Also the antibacterial activity and composition of the essential oil of Z. persica in Turkey have been documented [6]. (+)-Pulegone (79.3%), limonene (6.78%), and piperitenone (4.2%) were the predominant compounds. The major constituent found in the oil of Z. tenuior L. has been reported to be pulegone (87.1%) [7]. The essential oil of Turkish endemic Z. taurica subsp. clenioides was found to contain pulegone (81.9%), limonene (4.5%), and piperitenone (2.3%) [8]. The antibacterial test results showed that the oil had antibacterial activity against a number of bacteria tested. In the previous study on the essential oil and antibacterial activity of Z. clinopodioides subsp. rigida (Boiss.) from Iran, pulegone (45.8%), piperitenone (17.4%), p-menth-3-en-8-ol (12.5%), and thymol (8.0%) were found as the main components [9].

The composition of the oils of Z. clinopodioides Lam. from two different locations and Z. capitata L. subcp. capitata are listed in Tables 1 and 2, respectively, in which the percentage and retention indices of components are given. Twenty components were identified in the oil of Z. clinopodioides, sample A, which represented about 100% of the total composition of the oil. Thymol (53.6%), p-cymene (10.5%), carvacrol (8.7%), γ-terpinene (6.7%), and 1,8-cineole (5.4%) were the major components of the oil of the plant.

Twenty-six components were identified in the oil of Z. clinopodioides, sample B, making up 96.2% of total composition. 1,8-Cineole (21.6%) and terpinen-4-ol (18.2%) were the major components in this oil followed by linalool (7.9%), pulegon (7.7%), and α-terpineol (5.3%).

Thus the oil of Z. clinopodioides, sample A, consists of eight oxygenated monoterpenes (72.1%), nine monoterpene hydrocarbons (24.5%), and three sesquiterpenes (3.4%), while sample B consists of 12 oxygenated monoterpenes (72.1%), 10 monoterpene hydrocarbons (14.1%), three sesquiterpenes (9.1%), and one aliphatic alcohol (0.9%).

As can be seen from the above, both samples are rich in oxygenated monoterpenes (72.1%). In the previous investigation, oxygenated monoterpenes (93.3%) were the predominant portion of the oil of Z. clinopodioides from another location in Iran, with pulegone (45.8%), piperitenone (17.4%), p-menth-3-en-8-ol (12.5%), and thymol (8.0%) as the main constituents [9].

In comparison with the present study, pulegone in sample A cannot be found and, in sample B, pulegone is present in low concentration. Also thymol, which is the main component in sample A, does not exist in sample B and is not even found in high amount in the previous study on the oil of Z. clinopodioides [9]. The oil obtained from Z. clinopodioides grown in Russia was also rich in oxygenated monoterpenes: pulegone (57.0%) and isomenthone (28.6%) [4].

TABLE 1

Percentage Composition of Two Oils of Ziziphora clinopodioides and Z. capitata

   

Z. clinopodioides

   

Z. clinopodioides

Compound

RI

Z. capitata

Aa

Bb

Compound

RI

Z. capitata

Aa

Bb

α-Thujene

 

929

1.2

0.7

α-Terpineol

1179

 

0.3

5.3

α-Pinene

934

0.5

1.1

1.8

Pulegone

1230

 

-

7.7

Camphene

949

 

-

0.6

Bornyl acetate

1280

 

-

3.3

Sabinene

972

 

-

3.9

Thymol

1283

 

53.6

-

βPinene

978

0.7

0.7

2.5

Menthyl acetate

1288

 

-

0.1

Myrcene

989

 

1.9

0.6

Carvacrol

1292

 

8.7

-

3-Octanol

991

 

-

0.9

Geranyl formate

1296

 

-

1.1

α-Phellendrene

1001

 

0.3

-

α-Copaene

1366

0.6

  

α-Terpinene

1012

 

2.0

-

β-Bourbonene

1375

2.0

  

p-Cymene

1020

 

10.5

-

β-Cubebene

1382

0.5

  

Limonene

1026

7.8

  

β-Elemene

1384

2.3

  

1,8-Cineole

1027

 

5.4

21.6

β-Caryophyllene

1410

6.1

  

(Z)-β-Ocimene

1037

15.4

-

1.1

α-Humulene

1447

1.1

2.7

4.5

(E)-β-Ocimene

1046

9.7

-

1.2

Germaerene D

1473

31.1

-

4.0

γ-Terpinene

1056

1.0

6.7

1.5

Bicyclogermacrene

1485

5.2

-

0.6

cis-Sabinene hydrate

1062

 

0.3

2.2

β-Bisabolene

1501

 

0.2

-

Terpinolene

1080

 

0.1

0.2

δ-Cadinene

1518

0.5

  

Linalool

1098

 

1.8

7.9

Spathulenol

1565

2.5

  

p-Menth-3-en-8-ol

1140

 

-

2.7

Caryophyllene oxide

1573

42

0.5

-

Menthone

1148

 

-

0.8

α-Cadinol

1648

1.7

  

Borneol

1160

 

0.9

1.2

Hexadecanoic acid

1969

5.9

  

Terpinen-4-ol

1172

 

1.1

18.2

Total

 

100

100

96.2

a Oil from Lorestan; boil from Qom

TABLE 1

Antibacterial Activity of the Essential Oils of Z. clinopodioides and Z. capitata Oils

  

Z. clinopodioides a

Z. clinopodioides b

 

Microorganisms

Gram +/-

IZ

MIC

IZ

MIC

Gentamicin

Staphylococcus aureus PTCC 1113

+

23.0

1.15

15

1.9

12

Staphylococcus epidermidis PTCC 1349

+

35.5

0.3

22

1.2

20

Staphylococcus saprophyticus PTCC 1379

+

22.5

1.2

17

1.1

15

Shigella flexneri PTCC 1234

-

30.0

0.3

16

2.2

12

Salmonella typhi PTCC 1185

-

28.5

0.6

18

1.2

14

Escherichia coli PTCC 1330

-

35

0.3

21

1.0

15

Pseudomonas aeruginosa PTCC 1310

-

14.0

9.1

9

9.5

15

aOil from Lorestan (Sample A); bOil from Qom. (Sample B). IZ - inhibition zone (mm); MIC - minimum inhibitory concentration (mg/mL);

* Z. capitata: IZ - 14.5, MIC - 9.6.

Although we can see biochemical convergence among the Z. clinopodioides from different locations, due to the frequent occurrence of chemotypes in the family Lamiaceae and environmental factors, different patterns in the composition of the oils are common.

As is shown in Table 1, 19 components were identified in the oil of Z. capitata, which represented about 98.8% of the total composition of the oil.

Germacrene D (31.1%) and (Z)-β-ocimene (15.4%) were the major components in this oil, followed by (E)-β-ocimene (9.7%), limonene (7.8%), β-caryophyllene (6.1%), hexadecanoic acid (5.9%), and bicyclogermacrene (5.2%). Thus the oil of Z. capitata consists of six monoterpene hydrocarbons (35.1%), nine sesquiterpene hydrocarbons (49.4%), three oxygenated sesquiterpenes (8.4%), and one aliphatic acid (5.9%). In the oil of Z. capitata, in contrast to Z. clinopodioides oils, sesquiterpenes (57.8%) predominated over monoterpenes (35.1%).

Antibacterial Activity. The results of the antibacterial screening of the oils (zones of growth inhibition and minimal inhibitory concentration) are shown in Table 2. The antibacterial assays showed that the oils of sample A and B from Z. clinopodioides inhibited the growth of all bacteria. Previous antibacterial study on Z.clinopodioides, with the main compounds of pulegone (nearly half of the total oil, 45.8%), piperitenone (17.4%), p-menth-3-en-8-ol (12.5%), and thymol (8.0%), has shown it to have it moderate activity against Staphylococcus epidermidis and Staphylococcus aureus bacteria compared to our results from sample A, where as, sample B, in which pulegone exists, show the same results for both Grampositive bacteria Staphylococcus epidermidis and Staphylococcus aureus as in previous study of Z. clinopodioides. As thymol has considerable antibacterial activity against Gram-bacteria, [9], the remarkable results of the antibacterial activity of Z.clinopodioides, sample A, in which thymol is the main constituent (53.6%), is explainable.

On the other hand, Z. capatita oil was insensitive against Gram-positive and Gram-negative bacteria except against Shigella flexneri. Gram-negative bacteria with moderate activity with MIC of value 9.6 mg/mL was observed. From our results obtained, it is clear that the activity of the above oils can be associated mainly with significant monoterpene compounds. In sample A, we can see that thymol is the main compound (about half of the total oil, 53.6%) while in sample B 1,8-cineole (21.6%) and terpinen-4-ol (18.2%), linalool (7.9%), and also pulegone in an amount of just 7.7% are found as the main compounds. It may be concluded that some compounds such as 1,8-cineole, terpinen-4-ol, and linalool in sample B contribute to the antibacterial activity of the oil beyond pulegone. In addition, both sample A and B are rich in monoterpenes, while the oil of Z. capitata is rich in sesquiterpenes, and we could not see any sensitivity against Gram- positive and Gram-negative bacteria except against Shigella flexneri bacteria.

Notes

Acknowledgement

We are grateful to Dr. V. Mozaffarian (Research Institute of Forests and Rangelands, Tehran) for helpful assistance in botanical identification.

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Copyright information

© Springer Science+Business Media, Inc. 2008

Authors and Affiliations

  • Z. Aghajani
    • 1
  • F. Assadian
    • 2
  • Sh. Masoudi
    • 2
  • F. Chalabian
    • 3
  • A. Esmaeili
    • 3
  • M. Tabatabaei-Anaraki
    • 3
  • A. Rustaiyan
    • 4
    Email author
  1. 1.Department of Chemistry, Qom BranchI. A. UniversityQomIran
  2. 2.Department of Chemistry, Central Tehran BranchI. A. UniversityTehranIran
  3. 3.Department of Biology and Chemistry, North Tehran BranchI. A. UniversityTehranIran
  4. 4.Department of Chemistry, Science and Research CampusI. A.UniversityTehranIran

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