The identified volatile components and their peak area percentages of the stems and flowers of
Tanacetumtenuisectumobtained by hydrodistilliation, steam distillation and solvent free microwave extraction are given in
Table 1. The components are listed in order of their elution on the DB-5 column.
As it is shown from the
Table 1, about 96.87% (34 components) of the hydrodistilled oil, 91.32% (46 constituents) of the steam distilled oil and 95.1% (44 components) of the solvent free microwave extraction oil of
T.tenuisectumwere identified. The main components in three oils were camphor (26.91%, 27.23% and 25.52%), borneol (12.61%, 11.48% and 7.62%) and 1,8- cineole (7.93%, 13.23% and 11.26%), respectively. Other notable constituents were in hydrodistilled oil hexadecanoic acid (7.30%), carotol (6.58%) and γ-eudesmol (5.75%); in steam distilled oil camphene (5.44%), hinesol (4.35%) and (E)-sequilavandulol (4.24%) and in solvent free microwave extraction oil hinesol (6.86%), hexadecanoic acid (6.55%) and (E) - sequilavandulol (4.89%).
| No. | Compoundsa | RIb | HD(%) | SD(%) | SFME(%) |
|---|
| 1 | Hexanal | 800 | - | 0.24 | - |
| 2 | Tricyclene | 924 | - | 0.37 | - |
| 3 | -Thujene | 928 | - | 0.19 | t |
| 4 | - Pinene | 935 | - | 1.51 | 1.00 |
| 5 | Camphene | 951 | 0.70 | 5.44 | 3.92 |
| 6 | β- Pinene | 981 | - | 1.04 | 0.68 |
| 7 | Mesitylene | 994 | - | 0.33 | - |
| 8 | p- Cymene | 1024 | t | 1.84 | 1.17 |
| 9 | 1,8-Cineole | 1033 | 7.93 | 13.23 | 11.26 |
| 10 | -Terpinene | 1062 | - | 0.42 | t |
| 11 | Linalool | 1096 | 0.73 | 0.62 | t |
| 12 | Camphor | 1141 | 26.91 | 27.23 | 25.52 |
| 13 | cis-Chrysanthenol | 1160 | 0.82 | - | 1.09 |
| 14 | Pinocarvone | 1162 | - | 0.32 | - |
| 15 | Borneol | 1165 | 12.61 | 11.48 | 7.62 |
| 16 | Terpin-4-ol | 1177 | 1.14 | 0.99 | 0.59 |
| 17 | Naphthalene | 1183 | - | 0.25 | - |
| 18 | -Terpineol | 1188 | 1.20 | 0.84 | 0.58 |
| 19 | Myrtenal | 1191 | - | 0.22 | - |
| 20 | Myrtenol | 1193 | - | 0.24 | - |
| 21 | trans-Carveol | 1217 | 0.64 | 0.78 | 0.54 |
| 22 | cis-Chrysanthenyl acetate | 1260 | t | 0.23 | t |
| 23 | Bornyl acetate | 1285 | 1.66 | 1.40 | 1.12 |
| 24 | 2- methyl Naphthalene | 1292 | - | 1.00 | 0.86 |
| 25 | 1- methyl Naphthalene | 1306 | - | 0.63 | t |
| 26 | -Terpinyl acetate | 1350 | - | 0.3 | - |
| No. | Compoundsa | RIb | HD(%) | SD(%) | SFME(%) |
| 27 | Decanoic acid | 1352 | 2.03 | - | 0.19 |
| 28 | -Copaene | 1376 | - | 0.27 | - |
| 29 | 2,6-dimethyl Naphthalene | 1379 | - | - | 0.57 |
| 30 | (E)-β-Damascenone | 1380 | - | t | - |
| 31 | 1,7- dimethyl Naphthalene | 1397 | - | - | 0.44 |
| 32 | 2,7- dimethyl Naphthalene | 1400 | - | 0.54 | - |
| 33 | 1,3- dimethyl Naphthalene | 1415 | - | 0.46 | - |
| 34 | β-Caryophyllene | 1418 | - | - | 0.73 |
| 35 | Neryl acetone | 1431 | 0.80 | - | 0.88 |
| 36 | isobutyl-n-Butyrate | 1471 | 1.12 | - | - |
| 37 | Pentadecane | 1500 | - | 0.17 | - |
| 38 | β-Bisabolene | 1509 | - | - | 0.56 |
| 39 | Elemol | 1546 | - | - | 0.41 |
| 40 | (E)- Nerolidol | 1564 | 1.07 | 0.36 | 1.37 |
| 41 | (z)-dehydroApofarnesol | 1568 | 0.70 | - | 0.77 |
| 42 | Spathulenol | 1574 | 2.75 | 1.11 | 1.37 |
| 43 | Caryophyllene oxide | 1581 | 3.43 | 1.40 | 2.01 |
| 44 | Carotol | 1594 | 6.58 | - | - |
| 45 | Tetradecanal | 1610 | 1.30 | - | 1.23 |
| 46 | (E)- isoEugenol acetate | 1611 | - | 0.39 | - |
| 47 | -Eudesmol | 1630 | 5.75 | - | - |
| 48 | (E)- Sesquilavandulol | 1632 | - | 4.24 | 4.89 |
| 49 | β- Caryophylla-4(12),8(13)dien-5-ol | 1636 | 1.87 | - | 0.87 |
| 50 | Hinesol | 1638 | - | 4.35 | 6.86 |
| 51 | β-Eudesmol | 1646 | - | 1.58 | 2.33 |
| 52 | -Eudesmol | 1652 | 1.95 | - | - |
| 53 | -Cadinol | 1653 | - | - | 1.41 |
| 54 | 1(5),3-Aromadenedriene | 1660 | - | - | 0.51 |
| 55 | 14- hydroxy-9-epi-β- Caryophyllene | 1664 | 0.97 | 0.27 | - |
| No. | Compoundsa | RIb | HD(%) | SD(%) | SFME(%) |
| 56 | Khusinol | 1674 | - | 0.31 | - |
| 57 | (z)-Nerolidol acetate | 1675 | 0.79 | - | - |
| 58 | 1,6-dimethyl-4-(1-methylethyl) Naphtalene | 1685 | - | 0.30 | 0.98 |
| 59 | Germacrone | 1693 | 0.86 | - | - |
| 60 | 2-Pentadecanone | 1696 | - | - | 0.61 |
| 61 | (E)- Neroliol acetate | 1712 | 0.55 | - | - |
| 62 | (E,E)- Farnesol | 1722 | - | - | 0.38 |
| 63 | Tetradecanoic acid | 1771 | 0.61 | 0.50 | 1.18 |
| 64 | Octadecane | 1800 | t | 0.21 | - |
| 65 | Hexadecanal | 1806 | - | - | 0.64 |
| 66 | 6,10,14-trimethyl-2-Pentadecane | 1872 | 0.80 | 0.44 | 0.88 |
| 67 | Nonadecane | 1900 | 0.67 | 0.18 | - |
| 68 | Hexadecanoic acid | 1973 | 7.30 | 2.76 | 6.55 |
| 69 | Eicosane | 2000 | 0.63 | - | - |
| 70 | Henicosane | 2100 | - | 0.34 | 0.53 |
| Monoterpene hydrocarbons | | 0.70 | 10.81 | 6.77 |
| Oxygenated monoterpenes | | 54.44 | 57.88 | 49.20 |
| Sesquiterpene hydrocarbons | | - | 0.27 | 1.29 |
| Oxygenated sesquiterpenes | | 27.27 | 13.62 | 23.18 |
| Other compounds | | 14.46 | 8.74 | 14.66 |
| Total | | 96.87 | 91.32 | 95.1 |
Compounds listed in order of elution from HP-5 MS column;
Retention indices to C8 - C24 n-alkanes on HP-5 MS column;
According to these results, the composition of the three oils show significant similarity for the concentration of the main components. All three oils were rich in regard tomonoterpenes (55.14%, 68.69%and 55.97%, respectively), while the sesquiterpenes fraction was (27.27%, 13.89% and 24.47%, respectively). The nonterpenoid fraction was relatively small, representing 14.46%, 8.74%, and 14.66%, respectively.
In our pervious investigations on
Tanacetum genus we have identified essential oil compositions of
T. balsamitha,
T. polycephalum,
T.khorassanicum,
T. paradoxum,
T. tabrisianum,
T. elburensisand
T.persicum(
24-
28). The dominant compound in
T. balsamitha was carvone (68.0%) (
24). Camphor (18.2% and 13.9%) and 1,8- cineole (17.0% and 18.6%) were found to be the major components of the oil of
T. polycephalum and
T. lingulatum, respectively (
25,
29).
The major constituents of the aerial partsof
T. khorassanicum were (E)-myroxide (19.8%), camphor (16.4%), isopulegon (13.4%) and 1,8-cineole (11.4%) (
26).
Water distilled oil obtained from the aerial parts of
T. paradoxum and
T.tabrisianum have been the subject of our previous studies. The major components were camphor (23.8%), lavandulyl acetate (19.1%), lavandulol (15.9%) and 1,8- cineole (13.2%) in the former oil, caryophyllene oxide (12.0%)and spathulenol (10.3%) in the latter (
27). Water- distilled oils from the aerial parts of
T. elburensis and
T. persicumgrowing wild in Iran were investigated .
The main constituents of the oil of
T. elburensis were menthylisovalerate (20.0%) and 1,8 cineole (16.6%). The oil of
T. persicum was characterized by higher amounts of borneol (24.3%), menthyl acetate (17.3%), isobornyl 2- methyl butyrate (16.0%) and artedouglasia oxide D (14.3%) (
28).
The oils obtained by hydrodistillation of the leaves and flowers of T.
dumosum growing wild in Iran were investigated. The main constituents of the leaves oil were borneol (27.9%), bornylacetate (18. 4%) and 1,8- cineole (17.5%), while the main components of the flower oil were isobornyl-2-methylbutanoate(41.1%) and
trans-linalyl oxideacetate (11.9%) (
30).
Aerial parts of T. sonbolii, endemic in Iran,contained α- cadinol (35.3%),globulol (20.1%) and 1,8-cineole (8.6%) as major constituents (
31).
Camphor (30.2%), (z)-chrysanthenylacetate (26.5%) and α- farnesene (11.1%) were found to be the major components from the root oil of
T.partheniumfrom Iran. (
32).
The dominant compound in the flower and stem oils of
T. chiliophyllum, from Turkey, was camphor (17.3% and 10.4%) respectively,while root oil of the plant was characterized with hexadecanoic acid (37.5 %) (
37).
The dominant compound in the oil of
T. nitens and
T. argenteum from Turkey was 1,8 cineole (27.57%) and α- pinene (27.86%) respectively (
38).
Baser et al. reported the oils from the flowers of T. zahlbruckneri and flowers and stems of T. tabrisianum from Turkey.
The flower oil of
T. zahlbruckneri was characterised by germacreneD (29.7%) andspathulenol(12.0%).1,8-Cineole (17.6% and 22.5%) and hexadecnoic acid (10.3% and 8.0%) were the major constituents of the flower and stem oil of
T. tabrisianum respectively (
39).
The flower, stem and leaf oils of
T. densum fromTurkey,were characterized with camphor (30.9%,25.7% and 27.7%, respectively) (
40).
Lavandulol (21.5%) and 1,8- cineole (15.2 %) were identified as major components in the oil of
T. gracile from LadakhHimalaya (India) (
41).
Results of the antibacterial activity of the essential oil of
Tanacetumtenuisectumare shown in
Table 2.
| Microorganisms | Inhibition zone(mm) | MICa | MBCb |
|---|
| Staphyloccusaureus(ATCC 5923) | 11 | 625 | 1250 |
| Escherichia coil(ATCC 25922) | 13 | 625 | 1250 |
| Klebsiellapneumoniae(ATCC 27736) | 16 | 625 | 1250 |
| Entobacteraerogenes(ATCC 49469) | 16 | 625 | 625 |
| Bacillus subtilis(ATCC 9372) | 13 | 625 | 625 |
| Bacillus creus(ATCC 6633) | 16 | 1250 | 2500 |
Minimum inhibitory concentration;
Minimum bactericidal concentration .
Anti bacterial activity was determined against six bacteria.
The oil has shown maximum zone of inhibition against Klebsiellapneumoniae, Entobaceraerogenes and Bacillus creus. Staphylococcus aureus, Escherichia coli, Klebsiellapneumoniae, Entobacteraerogenes and Bacillus subtilis were the most sensitive bacteria to the essential oil (having MIC value 625 µg/mL).
Entobacteraerogenes and
Bacillus subtilis have a minimum bactericidal concentration (MBC value 625
µg/mL). 1,8- Cineole and camphor are well- known chemicals having antibacterial potentials (
42,
43).
The antibacterial effects of borneol were also reported (
44). As aresult of these findings, antibacterial activity of
T. tenuisectum oil could be attributed to 1,8 cineol, camphor and borneol. The present study confirms that there is a positive correlation between the chemical content of the oils and their antibacterial activities.