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Thermo-Oxidative Decomposition of Lovage (Levisticum officinale) and Davana (Artemisia pallens) Essential Oils under Simulated Tobacco Heating Product Conditions

Emma Jakab
Emma Jakab
, 
Zoltán Sebestyén
Zoltán Sebestyén
, 
Bence Babinszki
Bence Babinszki
, 
Eszter Barta-Rajnai
Eszter Barta-Rajnai
, 
Zsuzsanna Czégény
Zsuzsanna Czégény
, 
James Nicol
James Nicol
, 
Peter Clayton
Peter Clayton
 oraz 
Chuan Liu
Chuan Liu
   | 23 maj 2020
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Data publikacji: 23 maj 2020
Zakres stron: 27 - 43
Otrzymano: 16 gru 2019
Przyjęty: 30 mar 2020
DOI: https://doi.org/10.2478/cttr-2020-0004
Słowa kluczowe
© 2020 Emma Jakab et al., published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

Figure 1

(a) GC/MS and (b) Py-GC/MS total ion chromatogram of lovage oil (numbered peak identities are given in Table 1 and are shown in square brackets in the text).
(a) GC/MS and (b) Py-GC/MS total ion chromatogram of lovage oil (numbered peak identities are given in Table 1 and are shown in square brackets in the text).

Scheme 1

Proposed conversion reactions of (Z)-ligustilide during low temperature pyrolysis of lovage oil. Compound numbers correspond to those in Table 1. The percentage data indicate the change in composition (area-%) (Table 1).
Proposed conversion reactions of (Z)-ligustilide during low temperature pyrolysis of lovage oil. Compound numbers correspond to those in Table 1. The percentage data indicate the change in composition (area-%) (Table 1).

Figure 2

(a) GC/MS and (b) Py-GC/MS total ion chromatogram of davana oil (numbered peak identities are given in Table 3).
(a) GC/MS and (b) Py-GC/MS total ion chromatogram of davana oil (numbered peak identities are given in Table 3).

Scheme 2

Proposed reactions occurring in davana oil during oxidative pyrolysis. (a) Conversion of bicyclogermacrene and (b) oxidation reactions of davana ether. Compound numbers correspond to those in Table 3. The percentage data indicate the change in composition (area-%) (Table 3).
Proposed reactions occurring in davana oil during oxidative pyrolysis. (a) Conversion of bicyclogermacrene and (b) oxidation reactions of davana ether. Compound numbers correspond to those in Table 3. The percentage data indicate the change in composition (area-%) (Table 3).

Relative intensities (area-%) of the compound classes of lovage oil as received (injection) and after Py-GC/MS experiment (pyrolysis).

Compound classes Injection area-% Pyrolysis area-% Difference in area-%
Monoterpenoids 5.05 4.02 −1.03
Alkyl-, alkenyl-benzenes and cyclohexadienes 7.26 9.01 +1.75
Alkyl-, alkenyl- dihydroisobenzofuranones 65.00 59.60 −5.40
Alkyl-, alkenyl-phthalides 6.57 11.06 +4.49
Alkyl-, alkenyl- tetrahydroisobenzofuranones 2.46 2.58 +0.12
Cyclic anhydrides (benzene, cyclohexadiene) 0.86 1.74 +0.88
Sesquiterpenoids 4.46 5.32 +0.86
Fatty acid and alcohol derivatives 4.36 1.71 −2.65
Alkenes and alkenyl oxo compounds 0.17 0.83 +0.66

Relative intensities (area-%) of the compound classes of davana oil as received (injection) and after Py-GC/MS experiment (pyrolysis).

Compound classes Injection area-% Pyrolysis area-% Difference area-%
Esters 12.56 12.49 −0.07
Bicyclogermacrene 11.68 6.46 −5.22
Other sesquiterpenes 7.59 10.45 +2.86
O-,S-containing sesquiterpenoids 8.09 8.72 +0.63
Davanones 32.95 35.72 +2.77
Hydroxyisodavanones 1.75 2.00 +0.25
Davana ethers 10.43 5.83 −4.60
Other furan derivatives 3.13 4.43 +1.30

Composition of davana oil and pyrolysis products at 300 °C in 9% oxygen / nitrogen atmosphere.

No. tret/min MW Structure Compound Injection /area-% aver. ± std. dev. Pyrolysis /area-% aver. ± std. dev. Difference in area-% Significance levela
1 9.40 130 Ethyl 2-methylbutanoate 0.20 ± 0.03 0 −0.20 ***
2 9.60 130 Ethyl 3-methylbutanoate 0.14 ± 0.02 0 −0.14 ***
3 12.04 144 Propyl 2-methylbutanoate 0.29 ± 0.03 0.06 ± 0.04 −0.23 ***
4 12.18 144 Propyl 3-methylbutanoate 0.21 ± 0.03 0.03 ± 0.03 −0.18 ***
5 13.51 134 p-Cymene 0.41 ± 0.04 0.13 ± 0.09 −0.28 **
6 13.71 106 Benzaldehyde 0.07 ± 0.00 0.18 ± 0.06 +0.11 *
7 15.04 112 5,5-Dimethylfuran-2(5H)-one 0.13 ± 0.01 0.37 ± 0.04 +0.24 ***
8 15.16 154 cis-Arbusculone 0 0.12 ± 0.02 +0.12 ***
9 15.17 172 2-Methylbutyl 2-methylbutanoate 0.46 ± 0.03 0.23 ± 0.10 −0.23 **
10 15.28 172 2-Methylbutyl pentanoate 0.23 ± 0.01 0.10 ± 0.05 −0.13 **
11 15.54 154 trans-Arbusculone 0.03 ± 0.00 0.20 ± 0.02 +0.17 ***
12 15.72 154 Linalool 0.50 ± 0.02 0.28 ± 0.10 −0.22 **
13 16.36 126 5-Ethenyl-5-methyl-dihydrofuran-2(3H)-one 0.13 ± 0.01 0.25 ± 0.03 +0.12 ***
14 16.71 138 4-(Propan-2-ylidene) cyclohexanone 0 0.11 ± 0.03 +0.11 ***
15 16.88 154 Terpinen-4-ol 0.35 ± 0.01 0.24 ± 0.06 −0.11 *
16 18.18 204 Bicycloelemene (isomer 1)b 0 0.37 ± 0.04 +0.37 ***
17 18.19 182 Nordavanoneb 0.24 ± 0.01 0.31 ± 0.03 +0.07 **
18 18.36 204 Bicycloelemene (isomer 2) 0.18 ± 0.01 2.03 ± 0.10 +1.85 ***
19 18.71 164 Methyl 3-phenylpropanoateb 0 0.12 ± 0.01 +0.12 ***
20 18.73 204 Isoledeneb 0.12 ± 0.00 0.04 ± 0.00 −0.08 ***
21 18.81 204 α-Copaene 0.17 ± 0.00 0.18 ± 0.02 +0.01 N
22 18.84 210 4-(5-Ethenyl-5-methyltetrahydrofuran-2-yl)pentan-2,3-dione 0.05 ± 0.01 0.37 ± 0.04 +0.32 ***
23 19.23 204 β-Elemene 0.52 ± 0.01 0.49 ± 0.04 −0.03 N
162 Methyl cis-cinnamate +
24 19.28 204 α-Gurjunene + 0.19 ± 0.09 0.34 ± 0.04 +0.15 *
204 δ-Selinene
25 19.57 196 Geranyl acetate 1.03 ± 0.02 0.82 ± 0.07 −0.21 ***
26 19.63 178 Ethyl 3-phenylpropanoate 0.20 ± 0.00 0.19 ± 0.03 −0.01 N
27 19.69 204 β-Caryophyllene 0.33 ± 0.01 0.33 ± 0.02 0 N
28 19.74 204 Eudesma-3,7(11)-diene 0.06 ± 0.01 0.13 ± 0.01 +0.07 ***
29 19.82 204 Aromadendrene (isomer 1) 0.75 ± 0.03 0.91 ± 0.06 +0.16 **
30 19.85 204 Eudesma-5,11-diene 0.05 ± 0.00 0.23 ± 0.07 +0.18 **
31 19.90 220 Davana furan 0.70 ± 0.01 0.67 ± 0.05 −0.03 N
32 20.10 192 Benzyl isovalerateb 0.20 ± 0.03 0.15 ± 0.05 −0.05 N
33 20.12 204 Aromadendrene (isomer 2)b 0.51 ± 0.08 0 −0.51 ***
34 20.15 176 Ethyl cis-cinnamateb 2.02 ± 0.13 2.45 ± 0.15 +0.43 **
35 20.16 204 α-Humuleneb 0 0.24 ± 0.01 +0.24 ***
36 20.28 204 γ-Muurolene 0.13 ± 0.00 0.10 ± 0.02 −0.03 *
37 20.37 162 Methyl trans-cinnamate 1.02 ± 0.02 1.05 ± 0.04 +0.03 N
38 20.45 204 Isobicyclogermacrene 0.23 ± 0.04 0.66 ± 0.14 +0.43 **
39 20.49 204 Ledene 1.27 ± 0.03 1.48 ± 0.06 +0.21 ***
40 20.57 204 β-Selinene 2.50 ± 0.05 2.30 ± 0.08 −0.20 **
41 20.76 204 Bicyclogermacrene 11.68 ± 0.10 6.46 ± 0.26 −5.22 ***
42 20.81 204 δ-Cadinene + 0.77 ± 0.05 0.96 ± 0.06 +0.19 ***
204 γ-Cadinene
43 20.96 236 Davanone (isomer 1)b 0 0.55 ± 0.01 +0.55 ***
44 20.97 234 Davana ether (isomer 1)b 1.94 ± 0.06 1.10 ± 0.03 −0.84 ***
45 21.08 190 Precocene 0.04 ± 0.00 0.17 ± 0.02 +0.13 ***
46 21.27 234 Davana ether (isomer 2) 5.41 ± 0.20 2.78 ± 0.12 −2.63 ***
47 21.34 176 Ethyl trans-cinnamate 6.34 ± 0.14 7.12 ± 0.04 +0.78 ***
48 21.45 234 Davana ether (isomer 3) 0.24 ± 0.07 0.16 ± 0.04 −0.08 **
49 21.55 234 Davana ether (isomer 4, 5) 2.84 ± 0.07 1.79 ± 0.11 −1.05 ***
50 21.67 224 Geranyl isobutyrate 0.23 ± 0.01 0.16 ± 0.05 −0.07 *
51 21.87 250 Artedouglasia oxide (isomer 1) 0.70 ± 0.02 0.82 ± 0.05 +0.12 **
52 21.95 222 Nerolidol 0.50 ± 0.04 0.45 ± 0.05 −0.05 N
53 22.07 250 Artedouglasia oxide (isomer 2) 0.88 ± 0.03 0.99 ± 0.01 +0.11 ***
54 22.11 236 Davanone (isomer 2) 0.50 ± 0.03 0.61 ± 0.05 +0.11 **
55 22.23 236 Davanone (isomer 3) 1.83 ± 0.15 1.69 ± 0.09 −0.14 N
56 22.43 236 Davanone (isomer 4) 1.11 ± 0.02 1.09 ± 0.10 −0.02 N
57 22.53 220 Spathulenol 3.67 ± 0.18 3.90 ± 0.22 +0.23 N
58 22.58 222 Viridiflorol 0.62 ± 0.08 0.95 ± 0.05 +0.33 ***
59 22.69 236 (+)-Davanone 29.50 ± 0.63 31.77 ± 1.72 +2.27 *
60 22.87 250 Artedouglasia oxide (isomer 3) 0.26 ± 0.02 0.33 ± 0.03 +0.07 **
61 23.05 222 Cadinol (isomer 1) 1.77 ± 0.03 1.77 ± 0.06 0 N
62 23.17 220 Isospathulenol 0.58 ± 0.05 0.62 ± 0.03 +0.04 N
63 23.32 222 Cadinol (isomer 2) + 0.51 ± 0.02 0.49 ± 0.04 −0.02 N
220 4,8a-Dimethyl-6-(prop-1-en-2-yl)-1,2,3,5,6,7,8,8a-octahydronaphthalen-2-ol
64 23.42 222 β-Eudesmol 0.94 ± 0.02 0.99 ± 0.03 +0.05 *
65 23.92 224 Methyl jasmonate 0.28 ± 0.01 0.33 ± 0.03 +0.05 **
66 24.00 202 Desmethoxy encecalin 0.09 ± 0.02 0.20 ± 0.07 +0.11 *
67 24.13 236 Mintsulfide 0.12 ± 0.01 0.18 ± 0.01 +0.06 ***
68 24.72 252 2-Hydroxyisodavanone (isomer 1) 0.18 ± 0.02 0.17 ± 0.03 −0.01 N
69 24.81 252 2-Hydroxyisodavanone (isomer 2) 0.19 ± 0.01 0.18 ± 0.03 −0.01 N
70 24.93 252 2-Hydroxyisodavanone (isomer 3)b 0.14 ± 0.01 0.13 ± 0.01 −0.01 N
71 24.96 268 Hexahydrofarnesyl acetoneb 0.14 ± 0.01 0.18 ± 0.01 +0.04 ***
72 25.11 252 2-Hydroxyisodavanone (isomer 4) 1.08 ± 0.03 1.36 ± 0.15 +0.28 **
73 25.14 252 Hydroxyisodavanone 0.16 ± 0.01 0.15 ± 0.03 −0.01 N
74 26.40 296 Heneicosane 0.12 ± 0.01 0.06 ± 0.05 −0.06 N
75 27.50 296 Phytol 0.31 ± 0.03 0 −0.31 ***
29 unidentified peaks 8.68 11.06 +2.38

Composition of lovage oil and pyrolysis products at 300 °C in 9% oxygen / nitrogen atmosphere.

No. tret/min MW Structure Compound Injection /area-% aver. ± std. dev. Pyrolysis /area-% aver. ± std. dev. Difference in area-% Significance level a
1 10.45 136 α-Pinene 0.74 ± 0.10 0.22 ± 0.08 −0.52 ***
2 11.03 136 Camphene 0.21 ± 0.03 0.10 ± 0.03 −0.11 ***
3 11.74 114 Heptanal 0 0.49 ± 0.10 +0.49 ***
4 11.86 136 β-Pinene 1.23 ± 0.15 0.66 ± 0.18 −0.57 ***
5 13.14 136 d-Limonene 0.22 ± 0.03 0.33 ± 0.06 +0.11 *
6 13.31 136 β-Phellandrene 1.57 ± 0.14 1.42 ± 0.20 −0.15 N
7 13.51 134 p-Cymene 0.07 ± 0.00 0.14 ± 0.02 +0.07 **
8 13.85 136 γ-Terpinene 0.15 ± 0.01 0.29 ± 0.05 +0.14 **
9 14.37 136 Terpinolene 0.29 ± 0.02 0.32 ± 0.04 +0.03 N
10 15.69 150 2-Pentylcyclohexa-1,3-diene 6.00 ± 0.29 6.56 ± 0.52 +0.56 N
11 15.97 148 n-Pentyl-benzene 1.22 ± 0.05 2.12 ± 0.13 +0.90 ***
12 17.12 148 C5-benzene 0.01 ± 0.00 0.13 ± 0.01 +0.12 ***
13 17.28 164 1,3,5-Dodecatriene 0.17 ± 0.01 0.20 ± 0.01 +0.03 *
14 17.30 146 1-Phenyl-1-pentene 0.02 ± 0.00 0.20 ± 0.01 +0.18 ***
15 17.35 154 α-Terpineol 0.08 ± 0.01 0.12 ± 0.01 +0.04 ***
16 18.81 204 α-Copaene 0.20 ± 0.01 0.32 ± 0.03 +0.12 ***
17 19.15 196 α-Terpinyl acetate 0.49 ± 0.03 0.44 ± 0.09 −0.05 N
18 19.22 204 β-Elemene 0.44 ± 0.02 0.55 ± 0.06 +0.11 *
19 19.48 152 2,4-Decadienal 0 0.14 ± 0.01 +0.14 **
20 19.54 204 β-Funebrene 0.10 ± 0.01 0.16 ± 0.02 +0.06 ***
21 19.68 204 γ-Elemene 0.08 ± 0.01 0.17 ± 0.02 +0.09 ***
22 19.83 150 2-Methoxy-4-vinylphenol 0.41 ± 0.09 0.67 ± 0.12 +0.26 **
23 19.91 162 Valerophenone 1.32 ± 0.06 1.77 ± 0.14 +0.45 ***
24 20.03 204 α-Bulnesene 0.23 ± 0.01 0.34 ± 0.02 +0.11 ***
25 20.40 204 2-Isopropenyl-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene 0.12 ± 0.01 0.30 ± 0.03 +0.18 ***
26 20.56 204 β-Selinene 1.00 ± 0.06 1.04 ± 0.11 +0.04 N
27 20.63 204 α-Selinene 0.39 ± 0.02 0.41 ± 0.04 +0.02 N
28 20.83 204 δ-Cadinene 0.66 ± 0.04 0.64 ± 0.05 −0.02 N
29 20.95 148 Phthalic anhydride 0.08 ± 0.00 0.85 ± 0.11 +0.77 ***
30 21.03 204 α-Gurjunene 0.07 ± 0.01 0.12 ± 0.03 +0.05 **
31 21.09 204 β-Himachalene 0.10 ± 0.01 0.15 ± 0.02 +0.05 **
32 21.12 238 Bornyl isovalerate 0.20 ± 0.02 0.19 ± 0.02 −0.01 N
33 21.24 238 Bornyl pentanoate 0.17 ± 0.01 0.19 ± 0.01 +0.02 N
34 21.51 150 1,3-Cyclohexadiene-1,2-dicarboxylic anhydride 0.77 ± 0.04 0.89 ± 0.08 +0.12 *
35 22.14 222 Elemol 0.28 ± 0.03 0.33 ± 0.05 +0.05 N
36 22.44 222 Carotol 0.13 ± 0.01 0.17 ± 0.02 +0.04 *
37 23.02 222 γ-Eudesmol 0.13 ± 0.01 0.12 ± 0.02 −0.01 N
38 23.10 222 τ-Muurolol 0.25 ± 0.02 0.27 ± 0.05 +0.02 N
39 23.33 222 Unidentified sesquiterpene 0.19 ± 0.01 0.18 ± 0.03 −0.01 N
40 23.40 174 3-Propylidenephthalide 0.15 ± 0.01 0.27 ± 0.04 +0.12 **
41 23.42 222 β-Eudesmol 0.29 ± 0.02 0.24 ± 0.05 −0.05 N
42 23.45 222 Unidentified 0.54 ± 0.05 0.43 ± 0.06 −0.11 *
43 23.50 176 3-Propylphthalide 0.06 ± 0.00 0.33 ± 0.05 +0.27 ***
44 24.27 176 (Z)-3-propylidene-4,5-dihydroisobenzofuran-1(3H)-one 1.45 ± 0.12 1.50 ± 0.09 +0.05 N
45 24.49 188 (Z)-3-Butylidenephthalide 4.19 ± 0.30 7.69 ± 0.44 +3.50 ***
46 24.56 192 (Z)-Sedanonic acid lactone 0.20 ± 0.04 0.17 ± 0.03 −0.03 N
47 24.61 190 3-n-Butylphthalide 1.04 ± 0.07 1.22 ± 0.08 +0.18 **
48 25.21 192 (E)-Sedanonic acid lactone 0.20 ± 0.01 0.36 ± 0.03 +0.16 ***
49 25.26 188 (E)-3-Butylidenephthalide 0.94 ± 0.06 1.42 ± 0.08 +0.48 ***
50 25.37 190 (Z)-Ligustilide 58.05 ± 1.90 51.57 ± 2.14 −6.48 **
51 25.47 270 Hexadecanoic acid methyl ester 0 0.20 ± 0.03 +0.20 ***
52 25.54 194 3-Butyl-4,5,6,7-tetrahydroisobenzofuran-1(3H)-one 2.07 ± 0.16 2.05 ± 0.10 −0.02 N
53 25.59 218 Isobenzofuranone derivative 0 0.18 ± 0.02 +0.18 ***
54 25.65 192 Senkyunolide 1.45 ± 0.09 1.29 ± 0.09 −0.16 *
55 26.09 284 Hexadecanoic acid, ethyl ester 0.42 ± 0.03 0.41 ± 0.04 −0.01 N
56 26.36 190 (E)-Ligustilide 4.06 ± 0.24 5.23 ± 0.22 +1.17 ***
57 26.99 186 Ficusin (Furocoumarin) 0.22 ± 0.07 0.21 ± 0.03 −0.01 N
58 27.55 244 Falcarinol 1.02 ± 0.22 0.34 ± 0.10 −0.68 **
59 27.74 218 5-Methoxy-3-butylidenephthalide 0.19 ± 0.01 0.13 ± 0.01 −0.06 ***
60 27.83 308 Linoleic acid ethyl ester 0.79 ± 0.07 0.76 ± 0.11 −0.03 N
61 28.47 280 Linoleic acid 0.37 ± 0.25 0 −0.37 *
62 29.47 224 Unidentified 0.75 ± 0.14 0.31 ± 0.11 −0.44 ***
63 29.72 Fatty acid ester 1.76 ± 0.35 0 −1.76 ***
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