I. HS-SPME/GC-MS analysis of VOCs emitted from pine and spruce litter into the gas phase
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- Ἀριδαίος Γεωργίου
- 5 χρόνια πριν
- Προβολές:
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1 Supplementary information For the first time, one of the authors of this paper came across the discussed problem in the late autumn of 1976 while determining VOCs content in the urban atmosphere. Six monoterpene hydrocarbons were identified by GC-MS in the air samples collected in the sorption tube in the park zone of Leningrad. Because the sampling was conducted after the growing season, it was concluded that the most probable source of these compounds were fallen poplar leaves remaining at the testing site (Ioffe, B.V., Isidorov, V.A. and Zenkevich, I.G.: Gas chromatographic mass spectrometric determination of volatile organic compounds in an urban atmosphere, J. Chromatogr., 142, , 1977). I. HS-SPME/GC-MS analysis of VOCs emitted from pine and spruce litter into the gas phase Figure 1S presents some of the HS-SPME chromatograms of VOCs emitted from pine litter during its decomposition in natural conditions. Despite numerous advantages of the HS-SPME method over conventional methods of VOCs concentration in sorption tubes, including thermodesorption and cryofocusing of analytes, in some aspects it cannot rival especially the latter of the two mentioned. Primarily, this is related to the possibilities of simultaneous quantitative determination of the most and the least volatile VOCs. For instance, the registered traces of 2- butanone is not tantamount to extremely low emission of this substance, because small surface under the peaks on the chromatogram is a consequence of the low value of the substance s air-tofiber partition coefficient (K fg = 251 at 22 o C, whereas for limonene the same coefficient at the same temperature K fg = 10,965) (Isidorov and Vinogorova, 2005). On the other hand, HS-SPME is not appropriate for quantitative determination of sesquiterpenes, because the equilibrium distribution between air and PMDS phase requires several dozen hours. For this reason, in that stage of the experiment, the task was limited to evaluation of the emission rate of monoterpenes from pine and spruce litter. 1
2 Fig. 1S. Typical HS-SPME/GC-MS chromatograms from pine needle litter emissions concentrated on PDMS (100 μm) fiber. 2
3 Tables 1S 4S present the total the results of semi-quantitative GC-MS analysis. The ion current depends on the chemical structure of analyte and it is not a true quantification. Table 1S. VOCs composition pine and spruce needle litter emissions (%) according to HS-SPME/GC-MS analysis with using of Carboxen/PDMS fiber coating Pine litter Spruce litter LTPRI Days of incubation Compound Ethanol Acetone Ethyl formate trace 2 Dichloromethane trace - Methylene chloride Methyl acroleine trace trace 2-Butanone trace trace trace Hexane Methyl furan Ethyl acetate trace 3-Methylfuran trace trace Trichloromethane Benzene Pentanal Pentanone Trichloroethylene trace 0.6 trace Pyridine trace trace Toluene Hexanone Octane trace Hexanal trace Ethyl butanoate Butyl acetate trace Ethyl benzene 854 trace 0.1 Santene Tricyclene α-thujene trace trace α-pinene Camphene Benzaldehyde trace Verbenene trace Sabinene Octanone β-pinene trace Phenol Octanone trace 6-Methyl-5-hepten trace one 0.1 trace trace Myrcene trace trace trace α-phellandrene
4 3-Carene trace α-terpinene trace trace p-cymene D-Limonene Benzyl alcohol trace Ethyl-1-hexanol trace β-(z)-ocimene β-(e)-ocimene γ-terpinene Isopentyl butanoate p-mentha-2,4(8) trace diene Terpinolene trace 0.2 trace Nonanal Camphor trace 0.1 trace trace Camphene hydrate Borneol 1160 trace trace α-terpineol 1171 trace trace 0.1 trace Myrtenol 1190 trace trace Decanone 1195 trace 0.2 trace Verbenone 1203 trace trace Thymol, methyl ether 1230 trace trace 0.3 Bornyl acetate 1278 trace trace α-longipinene Cubebene 1341 trace trace α-terpinyl acetate 1344 trace Ylangene trace Copaene trace β-bourbonene 1374 trace trace trace β-cubebene β-elemene 1383 trace Sesquiterpene 1386 trace D-Longifolene trace β-(e)-caryophyllene trace trace Aromadendrene 1428 trace trace trace α-humulene 1445 trace trace trace γ-muurolene 1467 trace Germacrene D trace β-selinene 1475 trace trace α-selinene α-muurolene 1491 trace γ-cadinene δ-cadinene Cadina-1,4-diene trace trace trace 0.2 α-cadinene α-calacorene trace Caryophyllene oxide τ.-cadinol α-cadinol trace 4
5 1 not registered; 2 below 0.1 % of TIC. II. Changes in the chemical composition of the extractive organics in the litter Fig. 2S. Analysis flow chart On the chromatograms of each of the extracts (hexane, ether and water extracts) one could observe peaks representing hundreds of substances of various classes, and for some of them it was impossible for us to find either the value of retention index in literature or their mass spectra in the available databases. In such cases individual identification is extremely difficult, if at all possible. As a result, in the presented tables there are different levels of structure specification for the analytes: chemical name (individual identification), homologous series (e.g. sesquiterpene alcohol C 15 H 24 O; resin acid; etc.), or substance class (e.g. sesquiterpenes, diterpenes, disaccharides). Table 2S. Relative composition (%) of the hexane extracts from the pine and spruce litter on various stages of decomposition 5
6 Pine litter Spruce litter Compound (TMS derivative) LTPRI Days of incubation Toluene trace trace 3-Hexanone 788 trace trace trace 2-Hexanone 791 trace trace 3-Hexanol 795 trace trace trace trace 2-Hexanol 799 trace trace trace Hexanal 798 trace trace trace trace 0.1 Santene 880 trace trace trace Heptanal 899 trace Tricyclene trace trace trace 0.1 trace 0.1 trace trace α-thujene trace trace trace α-pinene Camphene trace Thuja-2,4(10)-diene 946 trace trace α-fenchene 953 trace trace Benzaldehyde 956 trace 0.2 trace trace trace Verbenene 963 trace trace trace Sabinene trace trace trace trace β-pinene trace Methyl-5-hepten-2-one 983 trace trace trace trace β-myrcene trace α-phellandrene 999 trace trace trace Octanal 1000 trace trace trace 3-Carene trace trace trace trace α-terpinene 1011 trace trace trace trace trace p-cymene 1019 trace trace trace trace trace trace Limonene Eucalyptol β-(z)-ocimene trace trace trace trace trace γ-terpinene trace 0.1 trace trace trace trace cis-sabinenehydrate Terpinolene trace trace trace 0.1 trace α-pinene oxide 1090 trace trace 0.1 trans-sabinenehydrate trace trace Linalool trace trace Terpenoid trace trace Nonanal 1100 trace trace 0.1 trace endo-fenchol 1107 trace trace trace α-campholenal 1120 trace trace trace trace trace trace trans-pinocarveol 1131 trace trace trace trace trace trace trace Camphor trace trace cis-verbenol trace 0.1 trace 0.1 Camphenehydrate Isoborneol 1149 trace trace trace 6
7 Pinocarvone 1155 trace trace trace trace trace Borneol 1159 trace trace trace trace cis-pinocamphone 1166 trace trace trace trace trace 4-Terpineol 1171 trace trace trace trace trace trace m-cymene-8-ol 1178 trace trace trace trace p-cymene-8-ol 1181 trace trace trace trace α-terpineol trace trace trace Myrtenal 1189 trace trace trace Myrtenol 1191 trace trace trace trace Verbenone trace trace trace trace Fenchyl acetate 1214 trace trace Citronellol trace Thymol, methyl ether 1232 trace trace trace Piperitone trace trace Linalool acetate 1252 trace trace 2-(E)-Decenal 1258 trace trace 2.5-Bornanedione trace trace Bornyl acetate trace trace Undecanone 1290 trace trace trace trace trace Tridecane trace trace trace 0.1 trace trace (E.E)-2,4-Decadienal 1312 trace trace trace trace δ-elemene trace 0.2 trace trace trace α-terpenyl acetate 1334 trace trace exo-2-hydroxycineole trace acetate α-longipinene trace trace α-cubebene Citronellyl acetate 1350 trace trace trace Ylangene trace 0.1 trace trace α-copaene trace β-bourbonene trace 0.1 trace trace β-cubebene trace β-elemene Sesquiterpene Isolongifolene Longifolene trace Methyl eugenol 1401 trace trace β-(e)-caryophyllene Sesquiterpene trace trace trace Sesquiterpene 1428 trace 0.2 trace trace Aromadendrene trace Sesquiterpene trace trace α-humulene Geranyl acetone 1448 trace trace trace β-farnesene trace trace Sesquiterpene trace 0.1 7
8 Alloaromadendrene γ-muurolene Germacrene D trace trace 0.1 ar-curcumene 1479 trace trace trace 0.1 β-selinene Sesquiterpene trace α-selinene Valencene trace trace 2-Tridecanone α-muurolene γ-cadinene δ-cadinene NN Cadina-1,4-diene Sesquiterpenoid C 15 H 26 O α-cadinene α-calacorene trace trace trace trace β-calacorene trace 0.2 trace trace (E)-Nerolidol Germacrene D-4-ol Spathulenol Caryophyllene oxide Humulene epoxide II ,10-di-epi-Cubenol Cubenol trace trace τ.-cadinol τ.-muurolol trace α-muurolol (δ-cadinol) trace trace α-cadinol Sesquiterpene alcohol Cadalene trace trace Pentadecanal (Z)-Tetradecenoic acid Oplopanone Tetradecanoic acid Sesquiterpenoid C 15 H 24 O trace Khusinol acetate Neophytadiene trace Hexahydrofarnesyl acetone trace (E)-2-Hexadecenal trace (Z)-Hexadecenoic acid Manoyl oxide epi-Manoyl oxide trace NN Diterpenoid NN
9 Manool NN epi-manool NN Phytol trace Sterol trace NN Diterpenoid Oxomanoyl oxide? Sclareol Diterpenoid trace 2.5 Verticiol? Dehydroabietal Diterpenoid Diterpenoid trace trace Larixol trace trace Diterpenoid trace trace Diterpenoid Methyldehydroabietate trace Torulosol? NN Methyl neoabietate trace 0.9 trace NN Diterpenoid NN(retinoic acid, methyl ester?) NN Hexacosane Tetracosanal trace Heptacosane Lanost-7-en-3-one? All-trans-squalene? trace Tetracosanol acetate Squalene NN trace 0.2 Nonacosane NN trace trace NN Sterol Sterol γ-sitosterol Sterol NN trace 1-Octacosanal trace Sitostenone trace Nonacosanal
10 α-tocopherol Ergosterol Squalene derivative trace NN Squalene oxide? trace trace 0.6 trace Ergosta-4,22-dien-3-one Sarsasagenone Stigmastan-7-one? Sterol trace trace β-saccharostenone? Sterol Methylenecycloartan-3- one Sterol (sitostenone?) Fucostenone? Triterpenoid Sterol Triterpenoid Phytol derivative? Stigmastane-3,6-dione? NN Squalene derivative trace NN Triterpenoid (betulin?) NN trace trace 2.3 NN trace 0.2 Octadecyl oleate? Table 3S. Relative composition (%) of the ether extracts from the pine and spruce litter on various stages of decomposition Pine litter Spruce litter Compound (TMS LTPRI Days of incubation derivatives) Ethylene glycol ,2-Propylene glycol trace trace trace trace trace Cadaverine 1061 trace trace trace trace trace trace trace Lactic acid trace 0.1 trace Hexanoic acid trace trace trace trace 0.1 trace trace 0.1 Glycolic acid trace trace trace trace trace trace Pyruvic acid 1097 trace trace trace trace trace trace n-butylamine trace trace trace trace Levulinic acid 1138 trace trace trace Methyl-2-hydroxy butyric acid 3-Hydroxypropanoic acid 1154 trace trace trace trace trace 10
11 3-Hydroxybutyric acid 1168 trace trace trace 1-Octanol trace trace Dithioerythritol? 1206 trace trace 0.1 NN 1227 trace trace Benzoic acid trace trace trace trace trace Octanoic acid 1267 trace trace trace 0.1 Phosphoric acid trace trace trace 0.1 trace Glycerol trace trace Succinic acid trace trace 0.1 Methylsuccinic acid 1333 trace trace Fumaric acid 1356 trace trace trace 0.1 Nonanoic acid 1363 trace trace trace trace trace trace 4-Hydroxybenzaldehyde 1369 trace 0.1 trace Hydroquinone 1406 trace trace trace trace trace Glutaric acid 1411 trace trace trace 3-Methylglutaric acid 1432 trace trace Decanoic acid 1459 trace Hydroxyacetophenone trace NN NN trace NN Vanillin Cinnamic acid 1539 trace trace trace NN Dodecanol Hydroxybenzoic acid trace 4-Hydroxybenzoic acid Vanillyl alcohol Dodecanoic acid trace trace trace NN Tridecanol NN Octanedioic acid trace 0.1 trace 0.1 NN trace 11-(Z)-Tetradecenoic acid trace trace Arabinitol trace Hydroxyhydrocinnamic acid Vanillic acid NN Azelaic acid trace trace trace 3-Vanilpropanol Methylphosphonic acid? Shikimic acid 1848 trace trace Tetradecanoic acid myo-inositol, penta-tms
12 11-(Z)-Hexadecenoic acid trace NN NN NN p-coumaric acid trace Pentadecanoic acid trace trace 1-Hexadecanol trace Undecanedioic acid trace Dimethyl hydroxyglutaric acid Palmitelaidic acid trace Hexadecanoic acid Ferulic acid i-heptadecanoic acid NN NN Heptadecanoic acid trace Caffeic acid trace trace 1-Octadecanol Phytol trace trace trace NN Linolenic acid NN Linoleic acid Oleic acid NN Octadecenoic acid trace trace Octadecanoic acid Resin acid Resin acid Tetradecanedioic acid Pimaric acid Isopimaric acid NN trace Palustric acid Isopimara-8,15-dienoic acid trace trace NN Dehydroabietic acid Labda-8(20),13-dien-15- oic acid Abietic acid NN Resin acid Eicosanoic acid trace trace 0.1 Resin acid Diterpenoid
13 Neoabietic acid Diterpenoid Diterpenoid Diterpenoid Pinocembrin NN Diterpenoid Oxodehydroabietic acid? Hydroxydehydroabietic acid NN trace Docosanoic acid Diterpenoid NN NN Diterpenoid NN Tetracosanoic acid trace NN trace α-hydroxytetracosanoic acid, methyl ester trace trace Catechin NN β-tocopherol NN trace NN α-tocopherol NN Triterpenoid Matairesinol Triterpenoid NN trace β-sitosterol NN trace Sterol (β-saccharostenone?) Sterol (sitostenone?) NN NN Glucoside NN Table 4S. Relative composition (%) of the water extracts from the pine and spruce litter on various stages of decomposition Compound (TMS derivative) LTPRI Pine litter Spruce litter Days of incubation 13
14 Carbodiimide trace trace trace Ethylene glycol trace 1,2-Propylene glycol ,3-Butanediol trace Cadaverine 1061 trace trace trace trace Lactic acid Hydroxyisobutyric acid 1072 trace trace Glycolic acid Valine. mono-tms trace trace Pyruvic acid n-butylamine 1108 trace trace trace Alanine 1116 trace trace trace trace Glycine 1128 trace 4.0 Laevulic acid? trace Butanoic acid, 2-methyl trace hydroxy- Oxalic acid 1146 trace trace 0.2 trace trace 3-Hydroxypropanoic acid 1154 trace trace Leucine, mono-tms Hydroxybutyric acid 1161 trace trace trace 0.1 trace trace trace Hydroxyisobutyric acid trace trace Isoleucine, mono-tms trace Octanol trace trace trace Dithioerythritol? trace trace Malonic acid 1215 trace trace Butanoic acid, 3-methyl trace trace trace hydroxy- Valine, di-tms 1225 trace 0.1 trace trace Benzoic acid trace trace trace trace Urea 1255 trace 0.1 trace trace trace Serine, di-tms trace Leucine, di-tms 1283 trace trace Phosphoric acid Glycerol Benzeneacetic acid 1296 trace trace Threonine, di-tms Proline 1301 trace trace trace trace trace Isoleucine, di-tms 1303 trace trace 0.2 trace Maleic acid trace trace Succinic acid Methylsuccinic acid trace trace trace trace Glyceric acid Fumaric acid trace 4-Hydroxybenzaldehyde trace
15 Serine, tri-tms 1370 trace 0.1 trace trace 2(3H)-Furanone, dihydro-3, trace trace 0.1 NN NN Threonine, tri-tms 1404 trace trace Hydroquinone NN Methionine NN α-pinene, 3-hydroxy-? Hydroxyacetophenone 1466 trace NN trace Homoserine, tri-tms Malic acid Salicylic acid Pyroglutamic acid trace Vaniline trace trace Threitol trace trace trace Glycine, tri-tms trace NN Erythronic acid NN Threonic acid Asparagine trace NN Hydroxybenzoic acid Hydroxybenzoic acid Phenylalanine, di-tms Glutamic acid trace α-arabinofuranose trace trace trace β-arabinopyranose trace trace Arabinonic acid, γ-lactone Dodecanoic acid trace trace 0.1 trace Rhamnose α-ribofuranose NN trace Xylonic acid, γ-lactone β-ribopyranose Carbohydrate (pentose) trace α-ribopyranose Carbohydrate Carbohydrate Suberic acid NN
16 Carbohydrate Carbohydrate Xylitol D-Xylose Carbohydrate acid NN Arabinitol Ribitol Vanillic acid Carbohydrate acid Gentisic acid trace β-xylopyranose Carbohydrate acid trace Glycerophosphoric acid trace Carbohydrate NN Arabinoic acid Azelaic acid trace Ribonic acid Vanilpropanol trace Protocatechuic acid Carbohydrate α-d-fructofuranose Shikimic acid α-d-mannopyranose trace β-d-fructofuranose Tetradecanoic acid Citric acid myo-inositol, penta-tms Adenine trace NN trace 0.6 β-d-glucofuranose trace trace NN Quinic acid Carbohydrate acid Gluconic acid, δ-lactone trace Galactonic acid, γ-lactone trace trace 0.4 NN α-d-glucopyranose Glucaric acid, γ-lactone p-coumaric acid NN L-Ascorbic acid Glucitol
17 Gallic acid Saccharic acid trace 0.2 Inositol. isomere Undecandioic acid β-d-glucopyranose D-Gluconic acid Vanillylmandelic acid derivative Hexadecanoic acid Glucuronic acid trace 0.3 Glucaric acid NN trace Glucuronic acid trace 0.4 Dodecanedioic acid trace Ferulic acid Carbohydrate myo-inositol, hexa-tms trace trace n-acetyl-d-glucosamine trace n-acetyl-d-glucosamine trace Carbohydrate Uridine Thymol glucopyranoside NN NN Oleic acid NN Octadecanoic acid trace Carbohydrate alcohol Disaccharide/glucoside NN Carbohydrate Carbohydrate NN NN Uridine, di-tms Carbohydrate NN Disaccharide NN Disaccharide NN NN Adenosine trace α-lactulose β-lactulose
18 Sucrose NN α-cellobiose Disaccharide NN Maltose Trehalose (mycose) Leucrose trace 0.6 Disaccharide Catechin, (+)-2.3-trans trace trace 0.5 trace β-melibiose? NN Gentibiose trace NN Taxifolin Disaccharide NN NN trace NN Matairesinol trace trace NN NN α-tocopherol Trisaccharide Trisaccharide trace 0.8 Trisaccharide (cellotriose?) Tetrasaccharide trace 1.0 Tetrasaccharide trace
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