Growth Regulating Properties of Isoprene and Isoprenoid Based Essential Oils

Growth regulating properties of isoprene and isoprenoid based essential oils

Andrew Maxwell P. Jones1Ϯ, Mukund R. Shukla1Ϯ, Sherif M. Sherif1,2, Paula B. Brown3, Praveen K. Saxena1*

ϮThese authors contributed equally to this work

1 Gosling Research Institute for Plant Preservation, Department of Plant Agriculture, University of Guelph, Guelph, ON, Canada, N1G 2W1

2 Department of Horticulture, Faculty of Agriculture, Damanhour University, Al-Gomhuria St., PO Box 22516, Damanhour, Al-Behira, Egypt.

3 British Columbia Institute of Technology, Burnaby, British Columbia, Canada V5G 3H2

*Corresponding author:

Praveen K. Saxena

Gosling Research Institute for Plant Preservation

Department of Plant Agriculture

University of Guelph

Guelph, ON, Canada, N1G 2W1

e-mail:

Phone: (519)824-4120 ext. 52495

Fax: (519)767-0755

Supplementary Table 1: Chemical composition of essential oils used in this study.

Species name / RT (min) / % of total peak area / Identification by mass spectra matching* / % Match quality
Artemisia annua / 10.5 / 0.2 / 2-methylbutanoic acid ethyl ester / 95
Artemisia annua / 14.1 / 0.2 / santolinatriene / 97
Artemisia annua / 14.5 / 0.1 / tricyclene / 96
Artemisia annua / 15 / 0.1 / α-thujene / 93
Artemisia annua / 15.4 / 12.4 / α-pinene / 95
Artemisia annua / 16 / 2.3 / camphene / 95
Artemisia annua / 16.1 / 0.2 / 2-methylbutanoic acid propyl ester / 83
Artemisia annua / 17.3 / 1.9 / sabinene / 93
Artemisia annua / 17.3 / 1.4 / β-pinene / 97
Artemisia annua / 18 / 0.1 / 2,3-dehydro-1,8-cineole / 74
Artemisia annua / 18.1 / 1 / β-myrcene / 95
Artemisia annua / 18.6 / 1 / artemesiatriene / 91
Artemisia annua / 19.1 / 0.3 / α-terpinene / 97
Artemisia annua / 19.5 / 0.9 / ρ-cymene / 97
Artemisia annua / 19.8 / 8.8 / eucalyptol / 95
Artemisia annua / 20.1 / 0.5 / trans-β-ocimene / 93
Artemisia annua / 20.5 / 0.1 / α-ocimene / 97
Artemisia annua / 20.8 / 0.7 / γ-terpinene / 94
Artemisia annua / 21.2 / 22.6 / artemisia ketone / 90
Artemisia annua / 21.3 / 0.2 / (E)-sabinene hydrate / 96
Artemisia annua / 21.8 / 1.6 / artemesia alcohol / 90
Artemisia annua / 21.9 / 0.2 / terpinolene / 97
Artemisia annua / 22.3 / 0.1 / γ-terpinene isomer / 96
Artemisia annua / 22.4 / 0.2 / linalool / 81
Artemisia annua / 22.5 / 0.8 / E,E-cosmene / 90
Artemisia annua / 22.9 / 0.1 / thujone / 96
Artemisia annua / 23.1 / 0.1 / (+)-4-carene / 76
Artemisia annua / 23.2 / 0.1 / campholenic aldehyde / 87
Artemisia annua / 23.7 / 2.1 / (E)-verbenol / 86
Artemisia annua / 23.9 / 5.7 / camphor / 95
Artemisia annua / 24.3 / 0.6 / 2,6-dimethylocta-1,5,7-trien-3-ol / 86
Artemisia annua / 24.5 / 1.2 / pinocarvone / 86
Artemisia annua / 24.5 / 0.5 / borneol / 95
Artemisia annua / 24.8 / 0.2 / pinocamphone / 96
Artemisia annua / 24.9 / 0.7 / (-)-terpinen-4-ol / 94
Artemisia annua / 25.3 / 0.4 / α-terpineol / 86
Artemisia annua / 25.5 / 0.8 / (-)-myrtenal / 93
Artemisia annua / 26.6 / 0.1 / cis-3-hexenyl isovalerate / 83
Artemisia annua / 26.7 / 0.1 / trans carveol / 53
Artemisia annua / 27.2 / 0.1 / δ-carvone / 95
Artemisia annua / 27.7 / 0.1 / piperitone / 93
Artemisia annua / 28.1 / 0.2 / 2,4-pentadiynylbenzene / 96
Artemisia annua / 28.3 / 0.1 / 1-tridecene / 96
Artemisia annua / 28.9 / 0.1 / thymol / 99
Artemisia annua / 30.1 / 0.7 / α-longipinene / 95
Artemisia annua / 30.2 / 0.2 / eugenol / 98
Artemisia annua / 30.5 / 0.1 / (+)-cycloisosativene / 98
Artemisia annua / 30.6 / 2.2 / longicyclene / 99
Artemisia annua / 31.1 / 0.9 / γ-muurolene / 99
Artemisia annua / 31.6 / 4.8 / (+)-longifolene / 96
Artemisia annua / 32 / 6.5 / caryophyllene / 99
Artemisia annua / 32.8 / 1.9 / (E)-β-farnesene / 95
Artemisia annua / 33.3 / 0.1 / γ-selinene / 93
Artemisia annua / 33.5 / 5.1 / germacrene D / 96
Artemisia annua / 33.6 / 1.7 / β-selinene / 95
Artemisia annua / 33.8 / 1 / acenaphthene / 99
Artemisia annua / 33.8 / 0.4 / germacrene B / 64
Artemisia annua / 34.4 / 0.3 / δ-cadinene / 70
Artemisia annua / 35.2 / 0.1 / aristolene epoxide / 96
Artemisia annua / 35.7 / 0.1 / spathulenol / 62
Artemisia annua / 35.9 / 0.1 / caryophyllene oxide ISOMER / 55
Artemisia annua / 35.9 / 0.7 / caryophyllene oxide / 95
Artemisia annua / 36.7 / 0.2 / (-)-α-cedrene / 95
Artemisia annua / 36.9 / 0.2 / alloaromadendrene oxide / 95
Artemisia annua / 37 / 0.3 / 1-(4-cyclohexylphenyl) ethanone / 94
Artemisia annua / 37.6 / 0.1 / β-maaliene / 50
Artemisia annua / 41.4 / 0.1 / fitone / 89
Artemisia annua / 42 / 0.3 / bis(2-methylpropyl)1,2-benzenedicarboxylic acid ester / 99
Artemisia annua / 42.5 / 0.2 / nonadecane / 78
Artemisia annua / 43.2 / 0.1 / 4,5,6,7-tetramethylphthalide / 99
Artemisia annua / 43.4 / 0.1 / cyclopentane / 68
Artemisia annua / 43.6 / 0.1 / (+)-cuparene / 50
Artemisia annua / 46.3 / 0.1 / heneicosane / 50
Artemisia annua / 46.6 / 0.1 / (-)-(E)-pinane / 97
Artemisia annua / 49.8 / 0.1 / heptadecane / 70
Artemisia annua / 53 / 0.1 / heneicosane isomer / 95
Citrus limon / 15 / 0.6 / α-thujene / 91
Citrus limon / 15.2 / 2.9 / α-pinene / 95
Citrus limon / 17.4 / 15 / β-pinene / 95
Citrus limon / 18.2 / 2 / β-myrcene / 95
Citrus limon / 19.2 / 0.3 / α-terpinene / 96
Citrus limon / 20.1 / 60.9 / δ-limonene / 94
Citrus limon / 20.5 / 0.1 / α-ocimene / 94
Citrus limon / 21 / 11 / γ-terpinene / 94
Citrus limon / 21.9 / 0.5 / (+)-4-carene / 95
Citrus limon / 27.1 / 0.9 / nerol (z-Citral) / 64
Citrus limon / 28 / 1.5 / citral / 97
Citrus limon / 30.3 / 0.9 / neryl propionate / 95
Citrus limon / 30.8 / 0.7 / geranyl acetate / 90
Citrus limon / 31.9 / 0.5 / caryophyllene / 95
Citrus limon / 32.2 / 0.9 / α-farnesene / 98
Citrus limon / 33.7 / 0.1 / valencene / 99
Citrus limon / 33.9 / 0.1 / α-caryophyllene / 50
Citrus limon / 34.1 / 1.3 / β-bisabolene / 96
Cuminumcyminum / 14.9 / 0.2 / α-thujene / 94
Cuminumcyminum / 15.2 / 0.6 / α-pinene / 97
Cuminumcyminum / 17.3 / 8.6 / β-pinene / 97
Cuminumcyminum / 18.1 / 0.7 / β-myrcene / 94
Cuminumcyminum / 19.5 / 4.6 / p-cymene / 95
Cuminumcyminum / 19.6 / 0.4 / β-phellandrene / 87
Cuminumcyminum / 19.7 / 0.2 / eucalyptol / 99
Cuminumcyminum / 20.9 / 8.2 / γ-terpinene / 87
Cuminumcyminum / 21.1 / 0.1 / 3-carene / 89
Cuminumcyminum / 22.2 / 0.2 / γ-terpinene isomer / n/ap
Cuminumcyminum / 24.9 / 0.2 / terpinen-4-ol / 90
Cuminumcyminum / 25.4 / 1.6 / allylidene cyclohexane / 80
Cuminumcyminum / 27.1 / 46.4 / cuminaldehyde / 98
Cuminumcyminum / 27.9 / 0.1 / perillaldehyde / 97
Cuminumcyminum / 28.2 / 4.9 / (3Z,5E)-1,3,5-undecatriene / 60
Cuminumcyminum / 28.5 / 22.5 / α-methylbenzenemethanol / 56
Lavandulaangustifolia / 15.2 / 0.6 / α-pinene / 95
Lavandulaangustifolia / 15.9 / 0.5 / camphene / 97
Lavandulaangustifolia / 17.3 / 0.9 / β-pinene / 95
Lavandulaangustifolia / 17.7 / 0.4 / 1-octen-3-ol / 86
Lavandulaangustifolia / 17.9 / 0.4 / 3-octanone / 94
Lavandulaangustifolia / 18.1 / 0.7 / β-myrcene / 90
Lavandulaangustifolia / 19.1 / 0.5 / m-cymene / 95
Lavandulaangustifolia / 19.8 / 9.3 / eucalyptol / 95
Lavandulaangustifolia / 20.1 / 2.2 / trans-β-ocimene / 95
Lavandulaangustifolia / 20.5 / 2.9 / α-ocimene / 95
Lavandulaangustifolia / 20.8 / 0.1 / γ-terpinene / 96
Lavandulaangustifolia / 21.1 / 0.2 / unresolved mixture / 80
Lavandulaangustifolia / 21.3 / 0.2 / cis-linalool oxide / 90
Lavandulaangustifolia / 21.9 / 0.5 / terpinolene / 90
Lavandulaangustifolia / 22.7 / 28 / linalool / 95
Lavandulaangustifolia / 22.9 / 0.5 / octen-1-ol acetate / 90
Lavandulaangustifolia / 24 / 9.4 / camphor / 95
Lavandulaangustifolia / 24.7 / 3.9 / borneol / 95
Lavandulaangustifolia / 25 / 1.4 / terpinen-4-ol / 95
Lavandulaangustifolia / 25.2 / 0.1 / α,α-4-trimethylbenzenemethanol / 52
Lavandulaangustifolia / 25.4 / 1.7 / α-terpineol / 92
Lavandulaangustifolia / 25.5 / 0.2 / trans-(-)5-methyl-3-(1-methylethenyl)cyclohexene / 91
Lavandulaangustifolia / 26.5 / 0.1 / isobornyl propionate / 90
Lavandulaangustifolia / 26.7 / 0.1 / 2-methylbutanoic acid hexyl ester / 90
Lavandulaangustifolia / 26.9 / 0.1 / hexyl n-valerate / 58
Lavandulaangustifolia / 27.5 / 23.6 / 1,3,3-trimethyltricyclo[2.2.1.02,6]heptane / 91
Lavandulaangustifolia / 28.2 / 0.1 / l-bornyl acetate / 98
Lavandulaangustifolia / 28.3 / 1.3 / neryl acetate / 86
Lavandulaangustifolia / 29.5 / 0.3 / isobutyl tiglate / 65
Lavandulaangustifolia / 30.3 / 0.3 / neryl propionate / 90
Lavandulaangustifolia / 30.8 / 0.8 / geranyl acetate / 90
Lavandulaangustifolia / 31.5 / 0.1 / zingiberene / 50
Lavandulaangustifolia / 31.7 / 0.1 / α-bergamotene / 98
Lavandulaangustifolia / 31.9 / 1.4 / santalene / 98
Lavandulaangustifolia / 31.9 / 2.6 / caryophyllene / 95
Lavandulaangustifolia / 32.2 / 0.3 / α-farnesene / 98
Lavandulaangustifolia / 32.5 / 0.1 / β-bisabolene / 93
Lavandulaangustifolia / 32.6 / 0 / β-santalene / 95
Lavandulaangustifolia / 32.7 / 1.3 / (E)-β-farnesene / 93
Lavandulaangustifolia / 32.9 / 0.1 / geranyl butyrate / 78
Lavandulaangustifolia / 33.1 / 0.1 / α-cubebene / 83
Lavandulaangustifolia / 33.5 / 0.8 / germacrene D / 46
Lavandulaangustifolia / 33.9 / 0.1 / helminthogermacrene / 98
Lavandulaangustifolia / 34 / 0.6 / linalyl butyrate / 96
Lavandulaangustifolia / 34.2 / 0.3 / γ-muurolene / 95
Lavandulaangustifolia / 35.9 / 0.3 / caryophyllene oxide / 72
Lavandulaangustifolia / 37.2 / 0.2 / 2-Isopropyl-5-methyl-9-methylenebicyclo[4.4.0]dec-1-ene / 95
Lavandulaangustifolia / 38.1 / 0.1 / di-epi-α-cedrene / 97
Menthaspicata / 15.2 / 1.2 / α-pinene / 95
Menthaspicata / 17.2 / 0.8 / sabinene / 93
Menthaspicata / 17.3 / 1.1 / β-pinene / 95
Menthaspicata / 18.1 / 2.5 / β-myrcene / 95
Menthaspicata / 18.4 / 1.3 / 3-octanol / 83
Menthaspicata / 19.1 / 0.4 / α-terpinene / 97
Menthaspicata / 19.8 / 14.8 / δ-limonene / 95
Menthaspicata / 20.1 / 0.2 / trans-β-ocimene / 95
Menthaspicata / 20.5 / 0.1 / α-ocimene / 97
Menthaspicata / 20.8 / 0.6 / γ-terpinene / 94
Menthaspicata / 21.1 / 1.2 / E-sabinene hydrate / 96
Menthaspicata / 21.9 / 0.2 / terpinolene / 96
Menthaspicata / 22.2 / 0.1 / γ-terpinene isomer / 94
Menthaspicata / 23 / 0.1 / β-terpinene / 70
Menthaspicata / 24.9 / 1.4 / terpinen-4-ol / 93
Menthaspicata / 25.6 / 3 / (+)-dihydrocarvone / 98
Menthaspicata / 25.8 / 1 / dihydrocarveol / 92
Menthaspicata / 26.7 / 0.6 / trans-carveol / 95
Menthaspicata / 27.5 / 59.5 / δ-carvone / 96
Menthaspicata / 27.6 / 0.2 / piperitone / 97
Menthaspicata / 28 / 0.1 / cis-carvone oxide / 87
Menthaspicata / 28.2 / 0.1 / anethole / 98
Menthaspicata / 28.5 / 0.2 / dihydroedulan / 92
Menthaspicata / 29.5 / 0.7 / neodihydrocarveol / 90
Menthaspicata / 30.3 / 0.6 / L-carvyl acetate / 91
Menthaspicata / 31 / 2.3 / (-)-β-bourbonene / 96
Menthaspicata / 31.3 / 0.5 / jasmone / 97
Menthaspicata / 31.9 / 1.5 / caryophyllene / 95
Menthaspicata / 32.1 / 0.4 / b-cubebene / 96
Menthaspicata / 32.5 / 0.2 / germacrene D / 90
Menthaspicata / 32.7 / 1 / (E)-β-farnesene / 95
Menthaspicata / 33.1 / 0.2 / α-cubebene / 91
Menthaspicata / 33.5 / 1.1 / germacrene D / 97
Menthaspicata / 34.4 / 0.1 / β-cadinene / 97
Menthaspicata / 36.1 / 0.5 / γ-gurjunene / 97
Origanumvulgare / 15.2 / 1.4 / α-pinene / 95
Origanumvulgare / 19.4 / 0.4 / p-cymene / 97
Origanumvulgare / 19.6 / 2 / δ-limonene / 95
Origanumvulgare / 19.7 / 1.8 / eucalyptol / 95
Origanumvulgare / 20.8 / 0.3 / γ-terpinene / 97
Origanumvulgare / 22.4 / 2 / linalool / 64
Origanumvulgare / 26 / 0.7 / α-terpineol / 86
Origanumvulgare / 26.1 / 0.2 / myrtenol / 93
Origanumvulgare / 27.3 / 0.4 / cuminaldehyde / 98
Origanumvulgare / 28 / 0.3 / myrcene / 80
Origanumvulgare / 28.7 / 41.2 / thymol / 95
Origanumvulgare / 29.1 / 44.5 / carvacrol / 95
Origanumvulgare / 29.5 / 0.2 / (-)-myrtenyl acetate / 64
Origanumvulgare / 30.1 / 0.3 / bornylene / 91
Origanumvulgare / 30.9 / 0.2 / neryl acetate / 86
Origanumvulgare / 31.4 / 0.1 / methyl eugenol / 96
Origanumvulgare / 31.9 / 0.6 / caryophyllene / 95
Origanumvulgare / 32.8 / 0.2 / α-caryophyllene / 97
Origanumvulgare / 34.1 / 0.5 / β-bisabolene / 95
Origanumvulgare / 34.4 / 0.5 / 2,5-dimethoxybenzaldehyde / 53
Origanumvulgare / 34.5 / 0.1 / (+)-δ-cadinene / 96
Origanumvulgare / 35.8 / 0.2 / spathulenol / 80
Origanumvulgare / 36 / 0.5 / caryophyllene oxide / 96
Origanumvulgare / 41.4 / 0.1 / fitone / 99
Origanumvulgare / 43.4 / 0.2 / cembrene / 99
Pimpinellaanisum / 17.3 / 0.1 / β-pinene / 97
Pimpinellaanisum / 19.6 / 0.4 / δ-limonene / 95
Pimpinellaanisum / 22.3 / 0.2 / 4-carene / 60
Pimpinellaanisum / 25.6 / 0.3 / 1-methoxy-4-(2-propenyl)benzene / 99
Pimpinellaanisum / 27.9 / 0.1 / 4-methoxybenzaldehyde / 97
Pimpinellaanisum / 28.9 / 98.6 / anethole / 98
Pimpinellaanisum / 31.7 / 0 / α-bergamotene / 99
Pimpinellaanisum / 31.9 / 0.1 / caryophyllene / 99
Pimpinellaanisum / 32.3 / 0.1 / α-farnesene / 98
Syzygiumaromaticum / 29.1 / trace / carvacrol / 93
Syzygiumaromaticum / 30.9 / 84.1 / eugenol / 97
Syzygiumaromaticum / 32.1 / 10.3 / caryophyllene / 98
Syzygiumaromaticum / 32.9 / 3.7 / α-caryophyllene / 97
Syzygiumaromaticum / 34 / 0.1 / linalyl butyrate / 78
Syzygiumaromaticum / 34.5 / 0.6 / δ-cadinene / 93
Syzygiumaromaticum / 35.2 / 0.3 / camphene / 45
Syzygiumaromaticum / 35.9 / 0.3 / (E)-β-farnesene / 78
Syzygiumaromaticum / 36 / 0.7 / caryophyllene oxide / 97

* Mass spectra libraries NIST98 and NBS97

Supplementary Table 2: Headspace analysis of essential oils used in this study

Species name / RT (min) / % of total peak area / Identification by mass spectra matching* / % Match quality / Kovats RI¤
Artemisia annua / 8.9 / 46.8 / α-pinene / 95 / 876
Artemisia annua / 9.4 / 13.2 / camphene / 95 / 897
Artemisia annua / 10.5 / 6.9 / α-phellandrene / 95 / 940
Artemisia annua / 11.2 / 0.7 / β-myrcene / 95 / 965
Artemisia annua / 12.2 / 0.3 / cymene / 95 / 997
Artemisia annua / 12.5 / 0.3 / ρ-cymene / 95 / 1008
Artemisia annua / 12.7 / 11.5 / eucalyptol / 95 / 1016
Artemisia annua / 14.1 / 17.7 / 3,3,6-trimethyl-1,5-heptadien-4-one / 55 / 1060
Artemisia annua / 17.1 / 1.7 / camphor / 95 / 1148
Artemisia annua / 17.8 / 0.2 / borneol / 95 / 1166
Artemisia annua / 18.4 / 0.1 / γ-terpinene (90% MQ) / 90 / 1180
Artemisia annua / 25.3 / 0.1 / α-cubebene / 70 / 1383
Artemisia annua / 26.3 / 0.3 / longifolene / 99 / 1411
Artemisia annua / 26.7 / 0.3 / caryophyllene / 95 / 1428
Artemisia annua / 28.6 / 0.1 / germacrene D / 85 / 1495
Citrus limon / 8.9 / 7.7 / α-pinene / 95 / 876
Citrus limon / 10.6 / 25.3 / β-pinene / 95 / 942
Citrus limon / 11.2 / 2 / β-myrcene / 95 / 965
Citrus limon / 12.2 / 0.1 / α-terpinene / 95 / 997
Citrus limon / 12.8 / 58.5 / limonene / 95 / 1019
Citrus limon / 13.9 / 6.1 / γ-terpinene (94% MQ) / 95 / 1055
Citrus limon / 15 / 0.2 / 4-carene / 95 / 1090
Cuminumcyminum / 8.9 / 6.9 / α-pinene / 95 / 875
Cuminumcyminum / 10.6 / 57.5 / β-pinene / 95 / 943
Cuminumcyminum / 11.2 / 2.2 / α-phellandrine / 99 / 965
Cuminumcyminum / 12.5 / 11.7 / ρ-cymene / 95 / 1007
Cuminumcyminum / 13.9 / 13.7 / γ-terpinene / 95 / 1055
Cuminumcyminum / 20.7 / 6 / cuminaldehyde / 95 / 1249
Cuminumcyminum / 22.2 / 0.7 / (3Z,5E)-1,3,5-undecatriene / 70 / 1296
Cuminumcyminum / 22.5 / 1.2 / 2,2-dimethyl-1-phenyl-1-propanol / 72 / 1304
Lavandulaangustifolia / 16.7 / 1.7 / (E,Z)-2,6-dimethyl-2,4,6-octatriene / 95 / 1136
Lavandulaangustifolia / 39.7 / 0.1 / 2,2-dimethoxy-1,2-diphenylethanone / 95 / 1895
Lavandulaangustifolia / 19 / 0.2 / 2-methylpropanoic acid octyl ester / 78 / 1195
Lavandulaangustifolia / 15.6 / 15.7 / 3-carene / 92 / 1105
Lavandulaangustifolia / 18 / 0.8 / borneol / 95 / 1169
Lavandulaangustifolia / 21.3 / 6.9 / C10H16 monoterpene / 93 / 1268
Lavandulaangustifolia / 9.4 / 4.9 / camphene / 95 / 899
Lavandulaangustifolia / 17.1 / 6.5 / camphor / 95 / 1148
Lavandulaangustifolia / 26.7 / 0.4 / caryophyllene / 99 / 1428
Lavandulaangustifolia / 12.7 / 34.9 / cineol / 95 / 1016
Lavandulaangustifolia / 22.5 / 0.3 / neryl acetate / 95 / 1305
Lavandulaangustifolia / 16.1 / 0.3 / oct-1-en-3-yl-acetate / 80 / 1119
Lavandulaangustifolia / 15 / 0.5 / terpinolene / 95 / 1090
Lavandulaangustifolia / 13.5 / 6 / α-ocimene / 95 / 1043
Lavandulaangustifolia / 8.9 / 6.4 / α-pinene / 95 / 876
Lavandulaangustifolia / 11.2 / 3.1 / β-myrcene / 95 / 965
Lavandulaangustifolia / 13.1 / 5 / β-ocimene / 95 / 1029
Lavandulaangustifolia / 10.6 / 5.9 / β-pinene / 93 / 941
Lavandulaangustifolia / 18.4 / 0.4 / γ-terpinene / 95 / 1180
Menthaspicata / 19.1 / 0.5 / (+)-dihydrocarvone / 98 / 1196
Menthaspicata / 15.1 / 0.2 / 1-methyl-4-(1-methylethylidene) cyclohexene / 94 / 1090
Menthaspicata / 7.5 / 2.1 / 2,5-diethyltetrahydrofuran / 95 / 812
Menthaspicata / 13.5 / 0.1 / 3,7-dimethyl-1,3,7-octatriene / 95 / 1043
Menthaspicata / 8.3 / 1.7 / 3-ethylidene-1-methylcyclopentene / 95 / 849
Menthaspicata / 26.7 / 0.1 / caryophyllene / 95 / 1428
Menthaspicata / 39.3 / 0 / dibutylphthalate / 78 / 1878
Menthaspicata / 27.8 / 0.1 / dimethylphthalate / 91 / 1468
Menthaspicata / 12.7 / 46.1 / limonene / 95 / 1015
Menthaspicata / 8.6 / 0.8 / sabinene / 74 / 863
Menthaspicata / 25.6 / 0.3 / S-bourbonene / 95 / 1391
Menthaspicata / 18.4 / 0.3 / terpinen-4-ol / 99 / 1180
Menthaspicata / 23.8 / 0.1 / trans-isolimonene / 98 / 1341
Menthaspicata / 8.9 / 12.7 / α-pinene / 95 / 876
Menthaspicata / 12.2 / 0.9 / α-terpinene / 97 / 997
Menthaspicata / 11.2 / 9.1 / β-myrcene / 91 / 966
Menthaspicata / 10.6 / 9.9 / β-pinene / 95 / 941
Menthaspicata / 13.9 / 1.3 / γ-terpinene / 95 / 1054
Menthaspicata / 20.9 / 13.3 / δ-carvone / 95 / 1254
Origanumvulgare / 8.9 / 61.1 / α-pinene / 95 / 876
Origanumvulgare / 10.5 / 0.7 / β-pinene / 95 / 899
Origanumvulgare / 11.3 / 0.8 / β-myrcene / 93 / 941
Origanumvulgare / 12.2 / 0.6 / 4-carene / 95 / 965
Origanumvulgare / 12.5 / 1.1 / ρ-cymene / 95 / 1016
Origanumvulgare / 12.7 / 25.7 / limonene / 95 / 1029
Origanumvulgare / 13.9 / 2.1 / γ-terpinene / 95 / 1043
Origanumvulgare / 15.1 / 0.1 / α-terpinene / 95 / 1090
Origanumvulgare / 15.5 / 0.5 / 3-carene / 92 / 1105
Origanumvulgare / 22.6 / 5.3 / thymol / 80 / 1119
Origanumvulgare / 22.9 / 1.8 / carvacrol / 95 / 1136
Origanumvulgare / 26.7 / 0.1 / caryophyllene / 95 / 1148
Origanumvulgare / 39.7 / 0.1 / 2,2-dimethyl-1,2-diphenylethanone / 95 / 1169
Pimpinellaanisum / 10.6 / 4.9 / α-pinene / 95 / 943
Pimpinellaanisum / 12.7 / 8.2 / limonene / 95 / 1013
Pimpinellaanisum / 22.3 / 86.9 / anethole / 99 / 1299
Syzygiumaromaticum / 24.7 / 41.2 / eugenol / 95 / 1368
Syzygiumaromaticum / 26.7 / 47.7 / caryophyllene / 95 / 1428
Syzygiumaromaticum / 27.8 / 8.1 / α-caryophyllene / 95 / 1466
Syzygiumaromaticum / 39.3 / 0.7 / dibutylphthalate (78% MQ) / 78 / 1877
Syzygiumaromaticum / 39.8 / 2.3 / 2,2-dimethoxy-1,2-diphenylethanone / 64 / 1895

* Mass spectra libraries NIST98 and NBS97

¤Kovats retention index calculated based on n-alkane standard

Supplementary Table 3: Description of genes and primers used for qrt-PCR analysis.

Supplementary Figure 1: Expression of nine wound inducible genes in Arabidopsis after 1 hourof exposure (10 μl/ 300 cc vessel) to methyl jasmonate (MeJA), isoprene (ISO), cuminaldehyde (CuAl), as well as plants that were mechanically wounded (wound) or not treated (Con).

Supplementary Figure 2: Expression of nine wound inducible genes in Arabidopsis after 6 hours of exposure (10 μl/ 300 cc vessel) to methyl jasmonate (MeJA), isoprene (ISO), cuminaldehyde (CuAl), as well as plants that were mechanically wounded (wound) or not treated (Con).