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Table 2 Compounds identified by GC–MS of the essential oils of Tripleurospermum disciforme (C.A.Mey.) Sch.Bip., Tanacetum parthenium (L.) Sch.Bip. and Achillea biebersteinii Afan

From: Tripleurospermum disciforme (C.A.Mey.) Sch.Bip., Tanacetum parthenium (L.) Sch.Bip, and Achillea biebersteinii Afan.: efficiency, chemical profile, and biological properties of essential oil

No.

Component

RI Exp

RI Lit

Tripleurospermum disciforme (C.A.Mey.) Sch.Bip

Tanacetum parthenium (L.) Sch.Bip

Achillea biebersteinii Afan

Molecular formula

1

1,3-Cyclopentadiene, 5-(1,1-dimethylethyl)-

800.000

788

 

1.72 ± 0.00a

 

C9H14

2

1-Butanol, 2-methyl-

800.200

762

  

0.13 ± 0.02a

C5H12O

3

Isobutyric acid, isobutyl ester

855.172

908

  

0.07 ± 0.01a

C8H16O2

4

Tricyclene

870.443

921

 

0.57 ± 0.02a

 

C10H16

5

α-Thujene

871.921

924

  

0.40 ± 0.00a

C10H16

6

α-Pinene

880.788

932

 

0.48 ± 0.02b

1.03 ± 0.02a

C10H16

7

Camphene

902.317

953

 

9.40 ± 0.04a

0.19 ± 0.00b

C10H16

8

Sabinene

917.880

969

 

0.12 ± 0.01b

2.17 ± 0.01a

C10H16

9

β-Pinene

921.192

974

 

0.33 ± 0.00a

 

C10H16

10

β-Myrcene

932.119

988

  

1.31 ± 0.00a

C10H16

11

Furan, 2-pentyl-

932.119

996

0.20 ± 0.00a

0.19 ± 0.01a

 

C9H14O

12

α-Phellandrene

944.701

1002

  

1.39 ± 0.01a

C10H16

13

δ-Carene

952.980

1008

 

0.22 ± 0.02b

1.32 ± 0.01a

C10H16

14

p-Cymene

963.245

1020

 

3.27 ± 0.00b

15.31 ± 0.03a

C10H14

15

β-Ocimene

980.463

1032

  

0.96 ± 0.01a

C10H16

16

γ-Terpinene

990.066

1054

 

1.36 ± 0.01b

2.54 ± 0.00a

C10H16

17

Filifolone

1023.809

1082

 

0.27 ± 0.02a

 

C10H14O

18

α-Terpinolene

1012.698

1086

  

1.15 ± 0.00a

C10H16

19

Linalool oxide

1005.820

1093

  

0.39 ± 0.00a

C10H18O2

20

Linalool

1049.735

1095

  

34.49 ± 0.02a

C10H18O

21

2H-Pyran-3(4H)-one, 6-ethenyldihydro-2,2,6-trimethyl-

1026.984

1109

 

0.99 ± 0.05a

 

C10H16O2

22

Chrysanthenone

1041.798

1124

 

0.47 ± 0.01a

 

C10H14O

23

Camphor

1056.084

1141

0.15 ± 0.01b

43.43 ± 0.03a

 

C10H16O

24

(+)-Camphor

1076.984

1142

 

0.38 ± 0.01a

 

C10H16O

25

Borneol

1081.460

1165

 

0.95 ± 0.01a

 

C10H18O

26

Albene

1061.111

1166

0.13 ± 0.00a

  

C12H18

27

Lilac aldehyde D

1062.169

1169

  

0.15 ± 0.00a

C10H16O2

28

Nerol oxide

1067.724

1154

  

0.83 ± 0.00a

C10H16O

30

β-Citronellene

1078.190

1088

  

0.14 ± 0.01a

C10H18

31

Biisobutenyl

1079.894

1032

  

0.28 ± 0.00a

C8H14

32

(-)-Terpinen-4-ol

1086.243

1175

 

1.38 ± 0.04a

 

C10H18O

33

Terpinen-4-ol

1093.650

1177

  

5.04 ± 0.02a

C10H18O

34

α-Terpineol

1108.413

1186

  

7.43 ± 0.01a

C10H18O

35

Cyclofenchene

1099.206

882

 

0.45 ± 0.03a

 

C10H16

36

Sabinol

1113.701

1137

 

0.33 ± 0.00a

 

C10H16O

37

Captan

1113.461

1141

  

0.70 ± 0.00a

C9H8Cl3NO2S

38

cis-Geraniol

1125.240

1231

  

0.75 ± 0.00a

C10H18O

39

Linalool acetate

1131.971

1253

  

4.35 ± 0.02a

C12H20O2

40

Geraniol

1141.346

1249

  

2.70 ± 0.00a

C10H18O

41

Bornyl acetate

1149.759

1287

 

6.76 ± 0.03a

 

C12H20O2

42

(-)-Bornyl acetate

1151.201

1289

  

0.39 ± 0.01a

C12H20O2

43

Silphiperfol-5-ene

1172.355

1330

0.16 ± 0.01a

  

C15H24

44

α-Guaiene

1186.778

1437

0.90 ± 0.00a

  

C15H24

45

α-Terpineol acetate

1191.586

1367

  

1.22 ± 0.03a

C12H20O2

46

Nerol acetate

1197.836

1365

  

1.05 ± 0.00a

C12H20O2

47

γ-Patchoulene

1199.519

1502

 

0.15 ± 0.00a

 

C15H24

48

α-Cubebene

1204.028

1381

 

0.56 ± 0.01a

 

C15H24

49

Geraniol acetate

1210.663

1386

  

2.15 ± 0.02a

C12H20O2

50

Modephene

1213.033

1392

10.00 ± 0.01a

0.37 ± 0.02b

 

C15H24

51

cis-Jasmone

1221.090

1396

  

1.35 ± 0.01a

C11H16O

52

Caryophyllene

1233.886

1418

1.66 ± 0.00a

0.25 ± 0.01c

0.46 ± 0.02b

C15H24

53

Propanoic acid, 2-methyl-, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, exo-

1226.540

1419

 

0.49 ± 0.00a

 

C14H24O2

54

Selina-5,11-diene

1227.962

1447

0.79 ± 0.01a

  

C15H24

55

trans-β-Farnesene

1250.473

1461

  

0.10 ± 0.00a

C15H24

56

cis-β-Farnesene

1255.450

1454

11.94 ± 0.01a

1.29 ± 0.03a

 

C15H24

57

γ-Selinene

1266.113

1492

  

0.16 ± 0.02a

C15H24

58

Germacrene D

1271.327

1484

 

2.43 ± 0.03a

0.22 ± 0.01b

C15H24

59

Bornyl isovalerate

1281.279

1512

 

2.81 ± 0.01a

 

C15H26O2

60

α-Amorphene

1271.563

1483

1.17 ± 0.04a

  

C15H24

61

Aromandendrene

1275.592

1439

  

0.05 ± 0.00a

C15H24

62

β-Bisabolene

1283.649

1506

0.70 ± 0.01a

  

C15H24

63

β-Sesquiphellandrene

1296.445

1525

6.58 ± 0.02a

0.64 ± 0.00b

 

C15H24

64

3H-Pyrazol-3-one, 2,4-dihydro-2-methyl-5-phenyl-

1304.600

1540

  

0.17 ± 0.00a

C10H10N2O

65

Anisole, p-1-cyclohexen-1-yl-

1317.191

1560

55.95 ± 0.03a

4.99 ± 0.01b

 

C13H16O

66

trans-Nerolidol

1318.886

1562

  

0.10 ± 0.01a

C15H26O

67

Bornyl tiglate

1319.128

1615

 

0.44 ± 0.00a

 

C15H24O2

68

Spathulenol

1323.002

1571

 

1.52 ± 0.01a

 

C15H24O

69

Dendrasaline

1324.697

1579

1.14 ± 0.03a

  

C15H22O

70

Benzoic acid, hexyl ester

1329.297

1580

  

0.09 ± 0.00a

C13H18O2

71

Caryophyllene oxide

1334.382

1582

  

0.65 ± 0.00a

C15H24O

72

Mintketone=Salvial-4(14)-en-1-one

1339.467

1599

 

1.05 ± 0.01a

 

C15H24O

73

9-Oxatetracyclo[5.4.0.0(3,10).0(4,8)]undeca-5-en-2-one

1347.215

   

0.83 ± 0.01a

C10H10O2

74

δ-Cadinene

1351.815

1537

 

0.51 ± 0.03a

 

C15H24

75

2-methyl-2-vinyl-5-isopropyltetrahydrofuran

1353.510

1074

  

0.20 ± 0.00a

C10H18O

76

cis-Farnesol

1356.416

1697

 

2.79 ± 0.00a

 

C15H26O

77

γ-Eudesmol

1363.680

1630

 

0.37 ± 0.00b

0.47 ± 0.02a

C15H26O

78

Valencene

1369.007

1496

 

0.83 ± 0.00a

 

C15H24

79

Methyl jasmonate

1370.944

1655

  

0.47 ± 0.01a

C13H20O3

80

Ï„-Cadinol

1372.397

1639

0.81 ± 0.00a

  

C15H26O

81

6-Hydroxy caryophyllene

1376.513

1649

0.42 ± 0.01a

  

C15H24O

82

Neointermedeol

1379.176

1662

 

1.75 ± 0.03a

 

C15H26O

83

β-Eudesmol

1378.934

1649

  

1.18 ± 0.01a

C15H26O

84

2-Norcaranone, 3-methyl-

1387.167

1657

0.54 ± 0.00a

  

C8H12O

85

α-Bisabolol

1391.283

1685

  

0.52 ± 0.01a

C15H26O

86

4-(1,5-Dimethylhex-4-enyl)cyclohex-2-enone

1395.883

1697

1.54 ± 0.01a

  

C14H22O

87

(1R,7S,E)-7-Isopropyl-4,10-dimethylenecyclodec-5-enol

1395.883

1694

 

0.55 ± 0.03a

 

C15H24O

88

γ-Costol

1428.967

1745

  

0.08 ± 0.02a

C15H24O

89

Caparratriene

1439.042

1692

 

0.57 ± 0.02a

 

C15H26

90

15-nor-Prezizaan-7-one

1436.750

1572

0.34 ± 0.04a

  

C14H22O

91

Ascabiol

1443.073

1753

  

0.16 ± 0.00a

C14H12O2

92

(4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone

1444.332

1754

0.83 ± 0.03a

  

C10H11NO2

93

Farnesol

1451.385

1747

0.28 ± 0.02a

  

C15H26O

94

(Z)-8-decen-4,6-diyn-1-yl 3-methylbutanoate

1465.491

1832

0.73 ± 0.01a

  

C15H20O2

95

Phthalic acid, diisobutyl ester

1485.138

1868

0.16 ± 0.05a

  

C16H22O4

96

(Z)-Tonghaosu

1501.842

1891

 

1.18 ± 0.00a

 

C13H12O2

97

Gerany-p-cymene

1524.736

1980

  

0.29 ± 0.01a

C20H30

98

9-Octadecenal, (Z)-

1544.210

1995

  

0.19 ± 0.00a

C18H34O

99

(E)-Tibetin spiroether

1537.368

1888

 

0.22 ± 0.00a

 

C14H14O2

100

Hexadecanoic acid

1546.052

1959

0.75 ± 0.02a

0.63 ± 0.02b

 

C16H32O2

101

cis-1-Chloro-9-octadecene

1547.631

2241

  

0.11 ± 0.03a

C18H35Cl

102

1,15-Hexadecadiene

1580.000

1581

  

0.71 ± 0.00a

C16H30

104

Behenic alcohol

1590.263

2470

  

0.26 ± 0.01a

C22H46O

105

Z-9-Octadecen-1-ol acetate

1635.734

1635

  

0.49 ± 0.01a

C20H38O2

106

Octadecane

1677.811

1789

  

0.08 ± 0.03a

C18H38

107

Tricosane

1686.980

2300

 

0.54 ± 0.01a

 

C23H48

108

Linoleic acid

1634.626

2134

0.53 ± 0.02a

  

C18H32O2

109

Phytan

1688.919

1811

0.38 ± 0.01a

  

C20H42

 

Total

  

98.78

99.55

99.94

 
 

Monoterpenes hydrocarbons

  

0.00

16.2

27.91

 
 

Oxygenated monoterpenes

  

0.15

47.21

51.76

 
 

Sesquiterpenes hydrocarbons

  

34.03

7.15

0.99

 
 

Oxygenated sesquiterpenes

  

2.65

8.03

3

 
 

Others

  

61.95

20.96

16.28

 
  1. Compounds are listed in order of their retention time from a HP-5 column. RI Exp., linear retention indices on HP-5 column, experimentally determined using homologue series of n-alkanes (C8–C20). RI Lit., linear retention index taken from Adams [75], or NIST 14 (2014) and literature. Values with different letters are statistically different (Duncan, P ≤ 0.01), mean (%) ± SD of three cultures were reported