Gas Chromatography–Mass Spectrometry Analysis of Volatile Organic Compounds from Three Endemic Iris Taxa: Headspace Solid-Phase Microextraction vs. Hydrodistillation
Abstract
:1. Introduction
2. Results
2.1. HS–SPME/GC–MS Analysis
2.1.1. PDMS/DVB Fiber
2.1.2. DVB/CAR/PDMS Fiber
2.2. HD Analysis
2.3. PCA Analysis of Major VOCs and EOs Constituents
3. Discussion
4. Materials and Methods
4.1. Plant Material
4.2. Solid-Phase Microextraction (SPME) Fibers and Extraction Procedure
4.3. Hydrodistillation (HD)
4.4. GC–MS Analysis
4.5. Principal Component Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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No. | Compound | RI | RIL | RIL Reference | SI | I. pseudopallida B | I. pseudopallida D | I. pseudopallida T | I. illyrica V | I. illyrica Z | I. adriatica |
---|---|---|---|---|---|---|---|---|---|---|---|
Aliphatic and Aromatic Alcohols and Phenols | |||||||||||
1 | Ethanol | <900 | 448 | [33] | 97% | 2.21 | 1.39 | 6.86 | 4.79 | 3.65 | 2.66 |
5 | Pentan-1-ol | <900 | 779 | [33] | 98% | 0.41 | - | - | - | - | 0.93 |
6 | Butan-2,3-diol | <900 | 802 | [33] | 97% | 1.78 | - | 6.38 | 5.29 | 10.27 | 2.18 |
9 | (Furan-2-yl)methanol | <900 | 864 | [33] | 96% | - | - | - | - | - | 2.75 |
10 | Hexan-1-ol | <900 | 867 | [33] | 96% | 0.18 | - | 0.38 | 0.73 | 1.14 | 1.09 |
11 | 2-Butoxyethanol | 912 | 912 | [33] | 98% | 0.24 | - | - | 0.58 | 0.75 | 0.95 |
14 | 1-Butoxypropan-2-ol | 949 | 945 | [33] | 95% | 0.34 | - | - | 0.31 | 1.27 | 1.39 |
17 | Phenol | 986 | 987 | [33] | 99% | - | - | 0.20 | 0.36 | 0.36 | 0.53 |
24 | 2-Ethylhexan-1-ol | 1035 | 1034 | [33] | 97% | 0.85 | - | 0.40 | 0.49 | 1.82 | 1.66 |
27 | Benzyl alcohol | 1042 | 1042 | [33] | 99% | 2.03 | - | 5.46 | 3.40 | 2.46 | 2.40 |
33 | Octan-1-ol | 1076 | 1076 | [33] | 98% | 0.50 | - | 0.35 | - | 0.34 | 0.47 |
38 | Nonan-2-ol | 1103 | 1102 | [33] | 96% | - | 0.50 | - | - | - | - |
41 | 2-Phenylethanol | 1120 | 1120 | [33] | 99% | 4.67 | - | 1.76 | 1.70 | 4.76 | 0.90 |
69 | Dodecan-1-ol | 1479 | 1478 | [33] | 97% | - | - | 1.40 | - | - | - |
Total identified (%) | 13.21 | 1.89 | 23.19 | 17.65 | 26.82 | 17.91 | |||||
Fatty Acids and Fatty Acid Esters | |||||||||||
2 | Acetic acid | <900 | 600 | [33] | 97% | 2.88 | - | 6.29 | 6.95 | 1.91 | 3.74 |
16 | Hexanoic (caproic) acid | 979 | 977 | [33] | 98% | 0.37 | - | 0.50 | 0.65 | - | - |
42 | Methyl octanoate | 1131 | 1127 | [33] | 97% | - | - | 1.00 | - | - | - |
46 | Octanoic (caprylic) acid | 1181 | 1180 | [33] | 97% | - | - | 2.15 | - | - | - |
49 | Ethyl octanoate | 1198 | 1196 | [33] | 98% | - | - | 1.05 | - | 0.36 | - |
63 | Methyl decanoate | 1330 | 1328 | [33] | 98% | 0.26 | - | 0.57 | - | - | - |
Total identified (%) | 3.51 | - | 11.56 | 7.60 | 2.27 | 3.74 | |||||
Aliphatic and Aromatic Aldehydes | |||||||||||
3 | Pentanal | <900 | 698 | [33] | 98% | - | 3.28 | - | 2.48 | - | - |
7 | Hexanal | <900 | 799 | [33] | 97% | 0.81 | - | 0.71 | 2.57 | 1.14 | 0.96 |
8 | Furfural | <900 | 848 | [33] | 98% | - | - | - | 0.31 | 0.34 | 1.80 |
15 | Benzaldehyde | 971 | 972 | [33] | 99% | 0.68 | - | 1.08 | 0.87 | 0.85 | 1.31 |
22 | 1H-Pyrrole-2-carboxaldehyde | 1014 | 1015 | [33] | 95% | - | - | - | - | - | 1.10 |
28 | Phenylacetaldehyde | 1052 | 1051 | [33] | 98% | - | 1.16 | - | - | - | 0.56 |
29 | 1-Ethyl-2-formyl pyrrole | 1058 | 1046 | [33] | 95% | - | - | - | - | - | 0.82 |
40 | Nonanal | 1109 | 1108 | [33] | 98% | 2.78 | - | 3.25 | 3.55 | 3.10 | 1.22 |
53 | Decanal | 1210 | 1210 | [33] | 99% | 0.62 | - | 2.35 | - | 0.74 | 0.49 |
62 | Undecanal | 1311 | 1309 | [33] | 98% | - | - | 0.76 | - | - | - |
66 | Dodecanal | 1413 | 1412 | [33] | 97% | - | - | 1.01 | - | - | - |
Total identified (%) | 4.89 | 4.44 | 9.16 | 9.78 | 6.17 | 8.26 | |||||
Aliphatic and Aromatic Ketones | |||||||||||
4 | Acetoin | <900 | 720 | [33] | 98% | - | - | 2.84 | 2.86 | 1.39 | 1.04 |
19 | 6-Methylhept-5-en-2-one | 992 | 991 | [33] | 99% | 1.98 | 3.59 | 1.61 | 3.21 | 9.47 | 1.33 |
31 | 2-Acetylpyrrole | 1068 | 1065 | [33] | 96% | - | - | 0.29 | - | - | - |
32 | Acetophenone | 1074 | 1072 | [33] | 96% | 0.16 | - | - | - | - | 0.06 |
36 | Nonan-2-one | 1091 | 1091 | [33] | 98% | - | 4.99 | - | - | - | - |
60 | Undecan-2-one | 1297 | 1296 | [33] | 97% | 0.43 | 2.01 | 1.28 | 1.60 | 0.43 | 0.13 |
70 | Acetovanillone | 1491 | 1491 | [33] | 97% | 0.11 | - | - | 7.12 | - | - |
Total identified (%) | 2.68 | 10.59 | 6.02 | 14.79 | 11.29 | 2.56 | |||||
Lactone | |||||||||||
12 | γ-Butyrolactone | 922 | 925 | [33] | 96% | 0.24 | - | 0.98 | 0.70 | 0.92 | 0.85 |
Monoterpene Hydrocarbons | |||||||||||
13 | α-Pinene | 945 | 942 | [33] | 98% | 4.48 | - | 0.20 | 2.40 | 1.11 | - |
18 | β-Pinene | 986 | 985 | [33] | 98% | 0.75 | - | - | - | - | - |
20 | β-Myrcene | 996 | 997 | [33] | 97% | - | - | 0.50 | - | - | 0.65 |
23 | p-Cymene | 1033 | 1030 | [33] | 98% | 0.85 | 0.18 | - | 0.27 | 0.46 | 0.37 |
25 | Limonene | 1037 | 1035 | [33] | 98% | 1.46 | - | 0.90 | 0.88 | 0.57 | 4.79 |
30 | γ-Terpinene | 1067 | 1064 | [33] | 99% | - | 0.42 | - | - | - | - |
Total identified (%) | 7.54 | 0.60 | 1.60 | 3.55 | 2.14 | 5.81 | |||||
Furan | |||||||||||
21 | 2-Pentylfuran | 997 | 998 | [33] | 97% | 0.53 | 0.84 | - | 0.58 | 1.35 | - |
Oxygenated Monoterpenes | |||||||||||
26 | 1,8-Cineole | 1041 | 1037 | [33] | 98% | 0.68 | - | 2.65 | 0.34 | 1.16 | 3.82 |
34 | Dihydromyrcenol | 1078 | 1075 | [33] | 96% | 0.95 | - | 3.03 | 1.60 | 3.46 | 2.45 |
35 | trans-Linalool oxide | 1080 | 1081 | [33] | 96% | 0.27 | - | - | - | - | - |
37 | 6-Camphenone | 1101 | 1095 | [33] | 95% | 0.43 | - | - | - | - | - |
39 | Linalool | 1104 | 1102 | [33] | 98% | 1.83 | - | 1.91 | 0.75 | 1.64 | 2.57 |
43 | trans-Pinocarveol | 1147 | 1147 | [33] | 97% | 0.85 | - | - | - | - | - |
44 | Camphor | 1152 | 1149 | [33] | 99% | - | - | - | - | - | 3.25 |
45 | Borneol | 1173 | 1172 | [33] | 99% | 0.53 | - | 0.22 | - | - | 0.47 |
47 | Terpinen-4-ol | 1184 | 1184 | [33] | 98% | 0.33 | - | 0.50 | - | - | 0.51 |
48 | α-Terpineol | 1196 | 1195 | [33] | 98% | 3.19 | - | 1.53 | 0.66 | - | 0.76 |
50 | Myrtenol | 1199 | 1198 | [33] | 97% | 6.33 | - | - | - | - | - |
54 | β-Citronellol | 1234 | 1232 | [33] | 97% | - | - | 1.35 | - | - | - |
55 | Carvacrol methyl ether | 1241 | 1246 | [33] | 96% | 0.72 | - | - | - | - | - |
56 | Neryl formate | 1262 | 1261 | [33] | 96% | - | - | 4.02 | - | - | 1.20 |
57 | (E)-Citral | 1276 | 1278 | [33] | 96% | 0.96 | - | 1.43 | - | - | - |
58 | Perilla aldehyde | 1279 | 1279 | [33] | 97% | 20.55 | - | 17.76 | 19.72 | 30.00 | 26.83 |
59 | Bornyl acetate | 1290 | 1288 | [33] | 98% | 0.38 | - | - | - | - | 1.38 |
Total identified (%) | 38.00 | - | 34.40 | 23.07 | 36.26 | 43.24 | |||||
Alkanes | |||||||||||
51 | Dodecane | 1200 | 1200 | [33] | 98% | - | - | 1.72 | - | - | - |
61 | Tridecane | 1300 | 1300 | [33] | 97% | - | - | 1.00 | - | - | - |
65 | Tetradecane | 1400 | 1400 | [33] | 98% | 0.34 | - | 1.20 | 0.25 | 0.25 | 0.52 |
72 | Pentadecane | 1500 | 1500 | [33] | 97% | - | - | - | - | - | 0.52 |
Total identified (%) | 0.34 | - | 3.92 | 0.25 | 0.25 | 1.04 | |||||
Norisoprenoids | |||||||||||
52 | Safranal | 1204 | 1205 | [33] | 98% | 1.46 | - | - | - | 1.69 | - |
75 | cis-α-Irone | 1544 | 1546 | [33] | 97% | - | 45.76 | - | - | - | - |
76 | cis-γ-Irone * | 1551 | - | [24] | 95% | 1.87 | 7.17 | - | - | - | - |
Total identified (%) | 3.33 | 52.93 | - | - | 1.69 | - | |||||
Sesquiterpene Hydrocarbons | |||||||||||
64 | α-Copaene | 1381 | 1376 | [33] | 96% | 5.14 | 1.21 | 2.02 | 3.62 | 2.61 | - |
67 | trans-Caryophyllene | 1424 | 1423 | [33] | 97% | 3.40 | 7.24 | 1.51 | 1.97 | 2.67 | 4.51 |
68 | α-Humulene | 1459 | 1459 | [33] | 98% | 0.73 | 0.27 | 0.42 | 0.66 | 0.80 | 1.13 |
71 | α-Farnesene | 1499 | 1503 | [33] | 97% | 0.81 | 1.09 | 1.19 | 1.99 | 0.98 | 1.94 |
73 | α-Muurolene | 1504 | 1505 | [33] | 96% | 0.62 | 1.73 | - | - | - | - |
74 | δ-Cadinene | 1520 | 1519 | [33] | 98% | - | 1.17 | - | - | - | - |
Total identified (%) | 10.70 | 12.71 | 5.14 | 8.24 | 7.06 | 7.58 | |||||
Aromatic Ester | |||||||||||
77 | Benzyl benzoate | 1769 | 1770 | [33] | 97% | - | - | 0.23 | - | - | - |
Total amount of identified compounds (%) | 84.97 | 84.00 | 96.20 | 86.21 | 96.22 | 90.99 |
No. | Compound | RI | RIL | RIL Reference | SI | I. pseudopallida B | I. pseudopallida D | I. pseudopallida T | I. illyrica V | I. illyrica Z | I. adriatica |
---|---|---|---|---|---|---|---|---|---|---|---|
Aliphatic and Aromatic Alcohols and Phenols | |||||||||||
1 | Ethanol | <900 | 448 | [33] | 97% | 4.75 | 3.22 | 4.70 | 5.23 | 4.34 | 7.01 |
5 | Pentan-1-ol | <900 | 779 | [33] | 97% | - | - | - | 1.70 | - | 0.82 |
6 | Butan-2,3-diol | <900 | 802 | [33] | 97% | 2.41 | - | 7.05 | 7.83 | 11.11 | 2.43 |
9 | (Furan-2-yl)methanol | <900 | 864 | [33] | 96% | - | - | - | - | - | 3.08 |
10 | Hexan-1-ol | <900 | 867 | [33] | 96% | 0.96 | - | 0.14 | 1.29 | 0.30 | 0.89 |
11 | 2-Butoxyethanol | 912 | 912 | [33] | 97% | 0.43 | - | 0.18 | - | 0.42 | 0.38 |
14 | 1-Butoxypropan-2-ol | 949 | 945 | [33] | 95% | 0.29 | - | - | - | 0.81 | 0.80 |
17 | Phenol | 986 | 987 | [33] | 99% | 0.58 | - | - | - | - | - |
23 | 2-Ethylhexan-1-ol | 1035 | 1034 | [33] | 97% | 0.82 | - | - | - | 1.13 | 1.36 |
26 | Benzyl alcohol | 1042 | 1042 | [33] | 99% | 1.52 | - | 5.08 | 1.58 | 1.23 | 1.62 |
30 | Octan-1-ol | 1076 | 1076 | [33] | 98% | 0.59 | - | 0.28 | - | - | 0.27 |
35 | Nonan-2-ol | 1103 | 1102 | [33] | 98% | - | 0.51 | - | - | - | - |
38 | 2-Phenylethanol | 1120 | 1120 | [33] | 99% | 4.31 | - | 1.38 | 0.77 | 3.36 | 0.83 |
65 | Dodecan-1-ol | 1479 | 1478 | [33] | 97% | - | - | 0.93 | - | - | - |
Total identified (%) | 16.66 | 3.73 | 19.74 | 18.40 | 22.70 | 19.49 | |||||
Fatty Acids and Fatty Acid Esters | |||||||||||
2 | Acetic acid | <900 | 600 | [33] | 96% | 14.29 | - | 29.76 | 29.20 | 31.02 | 12.00 |
16 | Hexanoic (caproic) acid | 979 | 977 | [33] | 98% | 0.52 | - | 0.67 | 1.64 | - | - |
39 | Methyl octanoate | 1131 | 1127 | [33] | 97% | - | 0.43 | 1.27 | - | - | - |
42 | Octanoic (caprylic) acid | 1181 | 1180 | [33] | 96% | - | - | 2.35 | - | - | - |
45 | Ethyl octanoate | 1198 | 1196 | [33] | 97% | - | - | 0.61 | - | - | - |
58 | Methyl decanoate | 1330 | 1328 | [33] | 98% | 0.30 | 0.51 | 0.67 | - | - | - |
Total identified (%) | 15.11 | 0.94 | 35.33 | 30.84 | 31.02 | 12.00 | |||||
Aliphatic and Aromatic Aldehydes | |||||||||||
3 | Pentanal | <900 | 698 | [33] | 98% | - | - | - | 2.65 | - | 2.31 |
7 | Hexanal | <900 | 799 | [33] | 97% | 1.46 | - | 1.49 | 4.67 | 1.30 | 1.04 |
8 | Furfural | <900 | 848 | [33] | 98% | - | - | - | 1.03 | 0.11 | 7.91 |
15 | Benzaldehyde | 971 | 972 | [33] | 99% | 0.93 | 0.67 | 1.11 | 0.88 | 0.68 | 1.01 |
21 | 1H-Pyrrole-2-carboxaldehyde | 1014 | 1015 | [33] | 96% | - | - | - | - | - | 0.51 |
27 | Phenylacetaldehyde | 1052 | 1051 | [33] | 98% | - | 0.99 | - | - | - | 0.38 |
28 | 1-Ethyl-2-formyl pyrrole | 1058 | 1046 | [33] | 95% | - | - | - | - | - | 0.92 |
37 | Nonanal | 1109 | 1108 | [33] | 97% | 2.78 | - | 2.71 | 2.07 | 1.24 | 0.90 |
49 | Decanal | 1210 | 1210 | [33] | 99% | 0.50 | - | 1.46 | 0.17 | - | 0.36 |
61 | Dodecanal | 1413 | 1412 | [33] | 98% | - | - | 0.58 | - | - | - |
Total identified (%) | 5.67 | 1.66 | 7.35 | 11.47 | 3.33 | 15.34 | |||||
Aliphatic and Aromatic Ketones | |||||||||||
4 | Acetoin | <900 | 720 | [33] | 98% | - | - | 2.01 | 2.42 | 5.27 | 2.11 |
18 | 6-Methylhept-5-en-2-one | 992 | 991 | [33] | 99% | 2.61 | 9.10 | 1.30 | 3.14 | 5.83 | 0.81 |
29 | Acetophenone | 1074 | 1072 | [33] | 97% | 0.11 | - | - | - | - | - |
33 | Nonan-2-one | 1091 | 1091 | [33] | 96% | - | 5.11 | - | - | - | - |
56 | Undecan-2-one | 1297 | 1296 | [33] | 97% | 0.21 | 1.61 | - | 0.63 | - | 0.12 |
66 | Acetovanillone | 1491 | 1491 | [33] | 98% | 0.41 | - | - | 3.85 | - | - |
Total identified (%) | 3.34 | 15.82 | 3.31 | 10.04 | 11.10 | 3.04 | |||||
Lactone | |||||||||||
12 | γ-Butyrolactone | 922 | 925 | [33] | 96% | 0.41 | - | 0.91 | 1.34 | 0.89 | 0.24 |
Monoterpene Hydrocarbons | |||||||||||
13 | α-Pinene | 945 | 942 | [33] | 96% | 2.46 | - | - | 1.55 | 0.37 | - |
19 | β-Myrcene | 996 | 997 | [33] | 97% | - | - | - | - | - | 0.69 |
22 | p-Cymene | 1033 | 1030 | [33] | 98% | 0.68 | 0.67 | - | - | 0.17 | - |
24 | Limonene | 1037 | 1035 | [33] | 97% | 1.40 | - | 0.42 | 0.60 | 0.20 | 3.52 |
Total identified (%) | 4.54 | 0.67 | 0.42 | 2.15 | 0.74 | 4.21 | |||||
Furan | |||||||||||
20 | 2-Pentylfuran | 997 | 998 | [33] | 96% | 0.80 | 2.37 | - | 0.96 | 0.69 | - |
Oxygenated Monoterpenes | |||||||||||
25 | 1,8-Cineole | 1041 | 1037 | [33] | 98% | 0.12 | - | 0.56 | 0.57 | 0.75 | 2.38 |
31 | Dihydromyrcenol | 1078 | 1075 | [33] | 96% | 1.06 | - | 1.42 | - | 2.09 | 2.07 |
32 | trans-Linalool oxide | 1080 | 1081 | [33] | 96% | 0.30 | - | - | - | - | - |
34 | 6-Camphenone | 1101 | 1095 | [33] | 95% | 0.30 | - | - | - | - | - |
36 | Linalool | 1104 | 1102 | [33] | 98% | 1.31 | - | 0.79 | - | 0.79 | 2.20 |
40 | Camphor | 1152 | 1149 | [33] | 99% | - | - | - | - | - | 2.98 |
41 | Borneol | 1173 | 1172 | [33] | 98% | 0.76 | - | 0.17 | - | - | 0.49 |
43 | Terpinen-4-ol | 1184 | 1184 | [33] | 97% | 0.41 | 0.39 | - | - | - | 0.56 |
44 | α-Terpineol | 1196 | 1195 | [33] | 98% | 3.01 | - | 1.14 | 0.25 | - | 0.64 |
46 | Myrtenol | 1199 | 1198 | [33] | 97% | 6.04 | - | - | - | - | - |
50 | β-Citronellol | 1234 | 1232 | [33] | 97% | - | - | 1.21 | - | - | - |
51 | Carvacrol methyl ether | 1241 | 1246 | [33] | 96% | 0.59 | - | - | - | - | - |
52 | Neryl formate | 1262 | 1261 | [33] | 96% | - | - | 2.52 | - | - | 1.01 |
53 | (E)-Citral | 1276 | 1278 | [33] | 95% | 0.82 | - | 0.52 | - | - | 0.67 |
54 | Perilla aldehyde | 1279 | 1279 | [33] | 98% | 15.63 | - | 8.09 | 6.47 | 17.59 | 20.08 |
55 | Bornyl acetate | 1290 | 1288 | [33] | 97% | 0.27 | - | - | - | - | 1.24 |
Total identified (%) | 30.62 | 0.39 | 16.42 | 7.29 | 21.22 | 34.32 | |||||
Alkanes | |||||||||||
47 | Dodecane | 1200 | 1200 | [33] | 98% | - | - | 1.37 | - | - | - |
57 | Tridecane | 1300 | 1300 | [33] | 99% | - | - | 0.58 | - | - | - |
60 | Tetradecane | 1400 | 1400 | [33] | 98% | 0.05 | - | 0.71 | - | - | 0.35 |
Total identified (%) | 0.05 | - | 2.66 | - | - | 0.35 | |||||
Norisoprenoids | |||||||||||
48 | Safranal | 1204 | 1205 | [33] | 98% | 1.72 | - | - | - | - | - |
70 | cis-α-Irone | 1544 | 1546 | [33] | 96% | - | 43.74 | - | - | - | - |
71 | cis-γ-Irone * | 1551 | - | [24] | 95% | 1.99 | 7.87 | - | - | - | - |
Total identified (%) | 3.71 | 51.61 | - | - | - | - | |||||
Sesquiterpene Hydrocarbons | |||||||||||
59 | α-Copaene | 1381 | 1376 | [33] | 96% | 5.06 | 0.98 | 1.32 | 2.08 | 1.62 | - |
62 | trans-Caryophyllene | 1424 | 1423 | [33] | 97% | 2.70 | 5.50 | 0.61 | 0.82 | 1.37 | 2.79 |
63 | trans-α-Bergamotene | 1441 | 1441 | [33] | 96% | - | - | - | - | - | 0.15 |
64 | α-Humulene | 1459 | 1459 | [33] | 97% | 0.59 | 0.05 | 0.32 | 0.28 | 0.22 | 0.73 |
67 | α-Farnesene | 1499 | 1503 | [33] | 97% | 0.33 | - | - | - | - | 0.83 |
68 | α-Muurolene | 1504 | 1505 | [33] | 95% | 0.39 | 1.41 | - | - | - | - |
69 | δ-Cadinene | 1520 | 1519 | [33] | 98% | - | 0.86 | - | - | - | - |
Total identified (%) | 9.07 | 8.80 | 2.25 | 3.18 | 3.21 | 4.50 | |||||
Total amount of identified compounds (%) | 89.98 | 85.99 | 88.39 | 85.67 | 94.90 | 93.49 |
No. | Compound | RI | RIL | RIL Reference | SI | I. pseudopallida B | I. pseudopallida D | I. pseudopallida T | I. illyrica V | I. illyrica Z | I. adriatica |
---|---|---|---|---|---|---|---|---|---|---|---|
Aliphatic and Aromatic Aldehydes | |||||||||||
1 | Furfural | <900 | 848 | [33] | 98% | 1.07 | 0.05 | - | 0.01 | 0.06 | 0.02 |
4 | Heptanal | <900 | 894 | [33] | 98% | - | 0.08 | - | - | 0.02 | 0.02 |
7 | Benzaldehyde | 971 | 972 | [33] | 99% | - | 0.27 | 0.02 | 0.02 | 0.08 | 0.05 |
13 | Octanal | 1005 | 1004 | [33] | 97% | - | 0.12 | - | - | - | 0.02 |
19 | Phenylacetaldehyde | 1052 | 1051 | [33] | 98% | 0.98 | 0.26 | 0.02 | 0.02 | 0.14 | 0.10 |
21 | 2,6-Dimethylhept-5-enal | 1059 | 1060 | [33] | 97% | 1.01 | 0.14 | - | - | 0.17 | - |
29 | Nonanal | 1109 | 1108 | [33] | 96% | - | - | - | 0.03 | 0.06 | 0.10 |
33 | (E)-Non-2-enal | 1166 | 1161 | [33] | 97% | - | - | - | 0.02 | 0.05 | - |
41 | Decanal | 1210 | 1210 | [33] | 99% | - | 0.09 | - | - | 0.05 | 0.04 |
47 | Undecanal | 1311 | 1309 | [33] | 98% | - | - | - | - | - | 0.03 |
54 | Dodecanal | 1413 | 1412 | [33] | 97% | - | 1.28 | - | - | 0.20 | 0.30 |
Total identified (%) | 3.06 | 2.29 | 0.04 | 0.10 | 0.83 | 0.68 | |||||
Alkanes | |||||||||||
2 | 4-Methyloctane | <900 | 864 | [33] | 95% | - | 0.05 | - | - | - | - |
46 | Tridecane | 1300 | 1300 | [33] | 98% | - | - | - | - | - | 0.05 |
59 | Pentadecane | 1500 | 1500 | [33] | 97% | - | - | - | - | 0.06 | 0.02 |
70 | Heneicosane | 2100 | 1600 | [33] | 98% | - | 1.06 | 0.09 | 0.09 | 0.40 | 0.48 |
72 | Docosane | 2200 | 2200 | [33] | 97% | - | 45.79 | - | 55.45 | 1.04 | 0.21 |
73 | Tricosane | 2300 | 2300 | [33] | 98% | 0.96 | 1.66 | 0.10 | 0.20 | 1.86 | 1.84 |
Total identified (%) | 0.96 | 48.56 | 0.19 | 55.74 | 3.36 | 2.60 | |||||
Aliphatic and Aromatic Alcohols and Phenols | |||||||||||
3 | Hexan-1-ol | <900 | 867 | [33] | 96% | - | - | - | 0.01 | - | 0.02 |
6 | 1-Butoxypropan-2-ol | 949 | 945 | [33] | 95% | - | - | - | - | 0.02 | 0.01 |
9 | Phenol | 986 | 987 | [33] | 99% | - | - | - | 0.02 | 0.04 | - |
15 | 2-Ethylhexan-1-ol | 1035 | 1034 | [33] | 97% | - | - | - | - | 0.02 | 0.03 |
18 | Benzyl alcohol | 1042 | 1042 | [33] | 99% | - | 0.09 | - | - | - | 0.04 |
24 | Octan-1-ol | 1076 | 1076 | [33] | 98% | - | 0.11 | - | 0.01 | 0.02 | 0.04 |
27 | 2-Methoxyphenol | 1093 | 1092 | [33] | 98% | - | 0.11 | - | - | 0.07 | 0.03 |
31 | 2-Phenylethanol | 1120 | 1120 | [33] | 99% | 2.20 | - | - | 0.02 | 0.81 | 0.07 |
35 | Nonan-1-ol | 1176 | 1175 | [33] | 95% | - | - | - | - | - | 0.05 |
48 | 2-Methoxy-4-vinylphenol | 1318 | 1317 | [33] | 99% | 0.96 | 0.12 | 0.02 | 0.08 | 0.33 | 0.08 |
57 | Dodecan-1-ol | 1479 | 1478 | [33] | 97% | - | 0.07 | - | - | 0.13 | 0.30 |
Total identified (%) | 3.16 | 0.50 | 0.02 | 0.14 | 1.44 | 0.70 | |||||
Monoterpene Hydrocarbons | |||||||||||
5 | α-Pinene | 945 | 942 | [33] | 98% | 5.98 | - | 0.01 | 0.16 | 0.08 | - |
10 | β-Pinene | 986 | 985 | [33] | 97% | 0.80 | - | - | - | - | - |
14 | p-Cymene | 1033 | 1030 | [33] | 98% | 0.50 | - | - | 0.01 | 0.02 | - |
16 | Limonene | 1037 | 1035 | [33] | 97% | - | - | - | 0.01 | 0.02 | - |
20 | (E)-β-ocymene | 1055 | 1054 | [33] | 98% | - | - | - | - | - | - |
22 | γ-Terpinene | 1067 | 1064 | [33] | 99% | 1.18 | - | - | - | - | - |
Total identified (%) | 8.46 | - | 0.01 | 0.18 | 0.12 | - | |||||
Fatty Acids and Fatty Acid Esters | |||||||||||
8 | Hexanoic (caproic) acid | 979 | 977 | [33] | 98% | - | - | - | - | 0.02 | 0.06 |
36 | Octanoic (caprylic) acid | 1181 | 1180 | [33] | 96% | - | - | - | 0.03 | 0.11 | 0.16 |
44 | Nonanoic (pelargonic) acid | 1290 | 1290 | [33] | 97% | - | - | - | - | - | 0.34 |
49 | Methyl decanoate | 1330 | 1328 | [33] | 95% | - | - | - | - | 0.13 | - |
51 | Decanoic (capric) acid | 1376 | 1377 | [33] | 98% | 1.41 | - | 0.34 | 0.34 | 2.82 | 0.91 |
53 | Ethyl decanoate | 1399 | 1397 | [33] | 96% | - | - | - | - | 0.42 | - |
63 | Dodecanoic (lauric) acid | 1570 | 1570 | [33] | 96% | 3.78 | - | 1.85 | 1.18 | 2.56 | 3.90 |
64 | Ethyl dodecanoate | 1599 | 1597 | [33] | 97% | - | - | - | - | 0.65 | - |
65 | Tetradecanoic (myristic) acid | 1780 | 1780 | [33] | 98% | 31.92 | 7.27 | 97.01 | 37.12 | 75.11 | 4.20 |
68 | Hexadecanoic (palmitic) acid | 1966 | 1963 | [33] | 99% | - | - | - | - | - | 35.48 |
71 | (Z,Z)-Octadeca-9,12-dienoic (linoleic) acid | 2150 | 2147 | [33] | 98% | - | - | - | - | - | 40.69 |
Total identified (%) | 37.11 | 7.27 | 99.20 | 38.67 | 81.82 | 85.74 | |||||
Aliphatic and Aromatic Ketones | |||||||||||
11 | 6-Methylhept-5-en-2-one | 992 | 991 | [33] | 99% | 0.61 | 1.51 | 0.02 | 0.05 | 0.11 | 0.05 |
23 | Acetophenone | 1074 | 1072 | [33] | 97% | - | - | - | - | - | 0.01 |
30 | 6-Methyl-3,5-heptadien-2-one | 1110 | 1107 | [33] | 96% | - | 0.26 | - | - | - | - |
45 | Undecan-2-one | 1297 | 1296 | [33] | 97% | - | - | - | 0.10 | - | - |
58 | Acetovanillone | 1491 | 1491 | [33] | 98% | - | - | - | - | 0.12 | - |
66 | Hexahydrofarnesyl acetone | 1851 | 1850 | [33] | 97% | - | - | - | - | - | 0.63 |
Total identified (%) | 0.61 | 1.77 | 0.02 | 0.15 | 0.23 | 0.69 | |||||
Furan | |||||||||||
12 | 2-Pentylfuran | 997 | 998 | [33] | 97% | - | - | - | 0.03 | - | 0.05 |
Oxygenated Monoterpenes | |||||||||||
17 | 1,8-Cineole | 1041 | 1037 | [33] | 98% | 0.64 | - | - | 0.03 | 0.12 | - |
25 | Dihydromyrcenol | 1078 | 1075 | [33] | 96% | - | - | - | - | 0.02 | 0.03 |
26 | trans-Linalool oxide | 1080 | 1081 | [33] | 95% | - | 0.11 | - | - | - | - |
28 | Linalool | 1104 | 1102 | [33] | 98% | - | - | - | 0.02 | 0.10 | 0.04 |
29 | Camphor | 1152 | 1149 | [33] | 99% | - | - | - | - | 0.11 | 0.04 |
34 | Borneol | 1173 | 1172 | [33] | 98% | - | - | - | 0.02 | - | - |
37 | Terpinen-4-ol | 1184 | 1184 | [33] | 97% | 7.29 | - | - | 0.02 | 0.07 | 0.07 |
38 | α-Terpineol | 1196 | 1195 | [33] | 98% | 3.38 | - | - | 0.07 | 0.19 | 0.06 |
39 | Myrtenol | 1199 | 1198 | [33] | 97% | 9.60 | - | - | 0.04 | 0.14 | - |
42 | (E)-Citral | 1276 | 1278 | [33] | 95% | 1.49 | 0.15 | - | 0.06 | 0.20 | 0.03 |
43 | Perilla aldehyde | 1279 | 1279 | [33] | 98% | - | - | - | - | 0.16 | 0.07 |
50 | Eugenol | 1363 | 1365 | [33] | 98% | - | - | - | - | - | 0.02 |
56 | (E)-Geranylacetone | 1458 | 1458 | [33] | 98% | - | 0.21 | - | 0.02 | 0.09 | 0.15 |
Total identified (%) | 22.40 | 0.47 | - | 0.28 | 1.20 | 0.51 | |||||
Norisoprenoids | |||||||||||
40 | Safranal | 1204 | 1205 | [33] | 96% | - | - | - | - | 0.20 | - |
60 | trans-α-Irone | 1520 | 1504 | [33] | 97% | - | 0.26 | - | - | - | - |
61 | cis-α-Irone | 1544 | 1546 | [33] | 98% | - | 24.70 | - | - | 0.03 | 0.04 |
62 | cis-γ-Irone * | 1551 | - | [24] | 95% | 8.43 | 4.48 | - | - | 0.08 | 0.03 |
Total identified (%) | 8.43 | 29.44 | - | - | 0.31 | 0.07 | |||||
Sesquiterpene Hydrocarbons | |||||||||||
52 | α-Copaene | 1381 | 1376 | [33] | 97% | - | - | 0.02 | - | - | - |
55 | trans-Caryophyllene | 1424 | 1423 | [33] | 99% | - | 0.12 | - | - | - | - |
Total identified (%) | - | 0.12 | 0.02 | - | - | - | |||||
Aromatic Esters | |||||||||||
67 | Diisobutyl phthalate | 1873 | 1873 | [33] | 98% | 4.13 | - | - | 2.58 | - | 1.15 |
69 | Dibutyl phthalate | 1967 | 1967 | [33] | 97% | 1.51 | 0.39 | - | - | - | 1.93 |
Total identified (%) | 5.64 | 0.39 | - | 2.58 | - | 3.08 | |||||
Total amount of identified compounds (%) | 89.83 | 90.81 | 99.50 | 97.87 | 89.31 | 94.12 |
Taxon | Sample Code | Location | Collection Date | Latitude/Longitude |
---|---|---|---|---|
Iris pseudopallida | I. pseudopallida B | Bast | 28 April 2019 | 43°19′58.4″ N/ 16°59′2.4″ E |
I. pseudopallida D | Dubrovnik | 7 April 2019 | 42°39′36.4″ N/ 18°04′01.7″ E | |
I. pseudopallida T | Topići | 28 April 2019 | 43°21′46.0″ N/ 16°57′28.4″ E | |
Iris illyrica | I. illyrica V | Vir | 23 April 2019 | 44°18′27.3″ N/ 15°1′52.5″ E |
I. illyrica Z | Zaton | 19 April 2019 | 43°46′26.5″ N/ 15°50′10.8″ E | |
Iris adriatica | I. adriatica | Brač | 4 April 2019 | 43°21′30.3″ N/ 16°35′49.6″ E |
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Friščić, M.; Maleš, Ž.; Maleš, I.; Duka, I.; Radonić, A.; Mitić, B.; Hruševar, D.; Jurić, S.; Jerković, I. Gas Chromatography–Mass Spectrometry Analysis of Volatile Organic Compounds from Three Endemic Iris Taxa: Headspace Solid-Phase Microextraction vs. Hydrodistillation. Molecules 2024, 29, 4107. https://doi.org/10.3390/molecules29174107
Friščić M, Maleš Ž, Maleš I, Duka I, Radonić A, Mitić B, Hruševar D, Jurić S, Jerković I. Gas Chromatography–Mass Spectrometry Analysis of Volatile Organic Compounds from Three Endemic Iris Taxa: Headspace Solid-Phase Microextraction vs. Hydrodistillation. Molecules. 2024; 29(17):4107. https://doi.org/10.3390/molecules29174107
Chicago/Turabian StyleFriščić, Maja, Željan Maleš, Ivanka Maleš, Ivan Duka, Ani Radonić, Božena Mitić, Dario Hruševar, Sandra Jurić, and Igor Jerković. 2024. "Gas Chromatography–Mass Spectrometry Analysis of Volatile Organic Compounds from Three Endemic Iris Taxa: Headspace Solid-Phase Microextraction vs. Hydrodistillation" Molecules 29, no. 17: 4107. https://doi.org/10.3390/molecules29174107