Development of the Volatile Fingerprint of Qu Aurantii Fructus by HS-GC-IMS
Abstract
:1. Introduction
2. Results
2.1. Volatile Compounds and Semi-Quantitative Analysis of Qu Aurantii Fructus
2.2. Comparative Analysis of Unique Volatile Compounds in Different Samples
2.2.1. Comparative Analysis of Volatile Compounds between Qu Aurantii Fructus and Aurantii Fructus
2.2.2. Comparative Analysis of Volatile Compounds of Qu Aurantii Fructus and the Common Adulterants
2.3. Stoichiometric Analysis
2.3.1. Principal Component Analysis (PCA)
2.3.2. Cluster Analysis (CA) for Qu Aurantii Fructus and Aurantii Fructus
2.3.3. Partial Least Square-Discriminant Analysis (PLS-DA)
2.4. Establishment of Characteristic Fingerprint of Qu Aurantii Fructus
3. Discussion
4. Materials and Methods
4.1. Materials
4.2. HS-GC-IMS Methods
4.3. Data Analysis
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | CAS | Formula | MW | RI | Dt (RIP Rel.) | Area Percentages (n = 8) | Range | Comment |
---|---|---|---|---|---|---|---|---|
limonene | 138-86-3 | C10H16 | 136.2 | 1025.2 | 1.68 | 6.93% | 5.93–8.29% | monomer |
limonene | 138-86-3 | C10H16 | 136.2 | 1026.2 | 2.17 | dimer | ||
α-farnesene | 502-61-4 | C15H24 | 204.4 | 1520.0 | 1.45 | 10.41% | 6.88–14.46% | monomer |
α-farnesene | 502-61-4 | C15H24 | 204.4 | 1551.4 | 1.43 | dimer | ||
γ-terpinene | 99-85-4 | C10H16 | 136.2 | 1066.9 | 1.21 | 6.24% | 5.62–7.07% | monomer |
γ-terpinene | 99-85-4 | C10H16 | 136.2 | 1065.6 | 1.70 | dimer | ||
linalool | 78-70-6 | C10H18O | 154.3 | 1118.7 | 1.222 | 5.51% | 4.20–8.20% | monomer |
linalool | 78-70-6 | C10H18O | 154.3 | 1117.3 | 1.76 | dimer | ||
linalool | 78-70-6 | C10H18O | 154.3 | 1118.7 | 2.24 | trimer | ||
α-terpineol | 98-55-5 | C10H18O | 154.3 | 1209.5 | 1.22 | 5.07% | 4.30–5.84% | monomer |
α-terpineol | 98-55-5 | C10H18O | 154.3 | 1211.2 | 1.78 | dimer | ||
camphene | 79-92-5 | C10H16 | 136.2 | 959.8 | 1.64 | 4.50% | 3.65–5.37% | monomer |
camphene | 79-92-5 | C10H16 | 136.2 | 959.1 | 2.19 | dimer | ||
α-ocimene | 13877-91-3 | C10H16 | 136.2 | 1048.3 | 1.71 | 4.38% | 2.62–5.91% | monomer |
β-ocimene | 13877-91-3 | C10H16 | 136.2 | 1049.7 | 2.14 | dimer | ||
methyleugenol | 93-15-2 | C11H14O2 | 178.2 | 1436.2 | 1.47 | 4.19% | 3.38–6.08% | |
linalool oxide | 60047-17-8 | C10H18O2 | 170.3 | 1081.1 | 1.26 | 2.92% | 1.56–3.70% | monomer |
linalool oxide | 60047-17-8 | C10H18O2 | 170.3 | 1082.4 | 1.81 | dimer | ||
α-thujene | 2867-05-2 | C10H16 | 136.2 | 916.0 | 1.67 | 2.80% | 2.23–3.20% | |
nerol | 106-25-2 | C10H18O | 154.3 | 1239.4 | 1.31 | 2.33% | 1.62–3.85% | monomer |
nerol | 106-25-2 | C10H18O | 154.3 | 1238.4 | 1.75 | dimer | ||
β-pinene | 127-91-3 | C10H16 | 136.2 | 979.8 | 1.72 | 2.15% | 1.93–2.33% | monomer |
β-pinene | 127-91-3 | C10H16 | 136.2 | 982.1 | 2.17 | dimer | ||
linalyl acetate | 115-95-7 | C12H20O2 | 196.3 | 1337.0 | 1.22 | 2.09% | 1.53–3.41% | monomer |
linalyl acetate | 115-95-7 | C12H20O2 | 196.3 | 1337.4 | 1.69 | dimer | ||
linalyl acetate | 115-95-7 | C12H20O2 | 196.3 | 1338.2 | 1.89 | trimer | ||
tricyclene | 508-32-7 | C10H16 | 136.2 | 905.0 | 1.66 | 2.01% | 1.01–2.55% | |
α-terpinene | 99-86-5 | C10H16 | 136.2 | 1006.7 | 1.22 | 1.97% | 1.22–2.55% | monomer |
α-terpinene | 99-86-5 | C10H16 | 136.2 | 1009.3 | 1.72 | dimer | ||
terpinen-4-ol | 562-74-3 | C10H18O | 154.3 | 1163.6 | 1.22 | 1.61% | 1.12–2.49% | monomer |
terpinen-4-ol | 562-74-3 | C10H18O | 154.3 | 1164.2 | 1.72 | dimer | ||
(Z)-β-farnesene | 28973-97-9 | C15H24 | 204.4 | 1489.7 | 1.45 | 1.50% | 0.76–2.18% | |
coumarin | 91-64-5 | C9H6O2 | 146.1 | 1520.6 | 1.22 | 1.46% | 0.79–3.05% | |
2-methoxy-4-methylphenol | 93-51-6 | C8H10O2 | 138.2 | 1163.6 | 1.19 | 1.09% | 0.53–1.94% | |
geraniol | 106-24-1 | C10H18O | 154.3 | 1267.9 | 1.22 | 1.08% | 0.75–1.48% | |
decanal | 112-31-2 | C10H20O | 156.3 | 1261.4 | 1.55 | 1.06% | 0.55–1.98% | monomer |
decanal | 112-31-2 | C10H20O | 156.3 | 1260.6 | 2.06 | dimer | ||
propan-2-one | 67-64-1 | C3H6O | 58.1 | 485.7 | 1.12 | 0.96% | 0.42–1.82% | |
trans-p-menth-2-en-1-ol | 29803-81-4 | C10H18O | 154.3 | 1137.0 | 1.70 | 0.95% | 0.54–2.07% | |
myrcene | 123-35-3 | C10H16 | 136.2 | 994.9 | 1.68 | 0.83% | 0.16–1.32% | |
γ-octalactone | 104-50-7 | C8H14O2 | 142.2 | 1298.5 | 1.31 | 0.80% | 0.31–2.08% | monomer |
γ-octalactone | 104-50-7 | C8H14O2 | 142.2 | 1299.3 | 1.80 | dimer | ||
acetic acid | 64-19-7 | C2H4O2 | 60.1 | 576.3 | 1.16 | 0.64% | 0.39–0.98% | |
α-pinene | 80-56-8 | C10H16 | 136.2 | 931.1 | 1.21 | 0.63% | 0.18–0.96% | |
2-methylprop-2-enal | 78-85-3 | C4H6O | 70.1 | 581.9 | 1.21 | 0.57% | 0.42–0.92% | |
borneol | 507-70-0 | C10H18O | 154.3 | 1184.3 | 1.90 | 0.57% | 0.44–0.76% | |
citral | 5392-40-5 | C10H16O | 152.2 | 1309.3 | 1.05 | 0.55% | 0.42–0.83% | monomer |
citral | 5392-40-5 | C10H16O | 152.2 | 1310.1 | 1.61 | dimer | ||
benzothiazole | 95-16-9 | C7H5NS | 135.2 | 1229.2 | 1.16 | 0.49% | 0.25–0.77% | |
1-(furan-2-yl)ethanone | 1192-62-7 | C6H6O2 | 110.1 | 893.5 | 1.12 | 0.49% | 0.21–0.69% | monomer |
1-(furan-2-yl)ethanone | 1192-62-7 | C6H6O2 | 110.1 | 893.5 | 1.44 | dimer | ||
3-methylbut-2-enal | 107-86-8 | C5H8O | 84.1 | 766.6 | 1.36 | 0.49% | 0.32–0.65% | |
3-methylbutyl hexanoate | 2198-61-0 | C11H22O2 | 186.3 | 1281.4 | 1.53 | 0.46% | 0.20–1.10% | monomer |
3-methylbutyl hexanoate | 2198-61-0 | C11H22O2 | 186.3 | 1280.5 | 2.15 | dimer | ||
ethyl octanoate | 106-32-1 | C10H20O2 | 172.3 | 1256.1 | 1.49 | 0.45% | 0.16–0.61% | |
methanol | 67-56-1 | CH4O | 32 | 393.2 | 0.99 | 0.44% | 0.05–0.86% | |
furfural | 98-01-1 | C5H4O2 | 96.1 | 812.1 | 1.08 | 0.43% | 0.32–0.63% | monomer |
furfural | 98-01-1 | C5H4O2 | 96.1 | 814.2 | 1.33 | dimer | ||
methyl acetate | 79-20-9 | C3H6O2 | 74.1 | 537.0 | 1.19 | 0.42% | 0.23–0.88% | |
2-methylbutanal | 96-17-3 | C5H10O | 86.1 | 657.6 | 1.40 | 0.31% | 0.17–0.60% | |
butanoic acid | 107-92-6 | C4H8O2 | 88.1 | 788.9 | 1.17 | 0.30% | 0.13–0.57% | |
propanal | 123-38-6 | C3H6O | 58.1 | 526.6 | 1.15 | 0.28% | 0.16–0.42% | |
ethanol | 64-17-5 | C2H6O | 46.1 | 441.8 | 1.05 | 0.27% | 0.11–0.70% | monomer |
ethanol | 64-17-5 | C2H6O | 46.1 | 442.1 | 1.14 | dimer | ||
vanillin | 121-33-5 | C8H8O3 | 152.1 | 1408.6 | 1.27 | 0.27% | 0.20–0.43% | |
butan-2-one | 78-93-3 | C4H8O | 72.1 | 582.7 | 1.25 | 0.27% | 0.11–0.46% | |
octanal | 124-13-0 | C8H16O | 128.2 | 998.2 | 1.82 | 0.24% | 0.04–0.93% | |
isopentanol | 123-51-3 | C5H12O | 88.1 | 715.4 | 1.25 | 0.24% | 0.02–0.41% | monomer |
isopentanol | 123-51-3 | C5H12O | 88.1 | 716.7 | 1.50 | dimer | ||
benzaldehyde | 100-52-7 | C7H6O | 106.1 | 945.4 | 1.15 | 0.24% | 0.21–0.29% | monomer |
benzaldehyde | 100-52-7 | C7H6O | 106.1 | 946.7 | 1.47 | dimer | ||
acetophenone | 98-86-2 | C8H8O | 120.2 | 1073.1 | 1.19 | 0.23% | 0.15–0.31% | |
butane-2,3-dione | 431-03-8 | C4H6O2 | 86.1 | 572.1 | 1.18 | 0.22% | 0.17–0.26% | |
propan-1-ol | 67-63-0 | C3H8O | 60.1 | 493.4 | 1.18 | 0.21% | 0.08–0.47% | |
ethyl decanoate | 110-38-3 | C12H24O2 | 200.3 | 1411.3 | 1.61 | 0.21% | 0.19–0.23% | |
(Z)-dec-4-enal | 21662-09-9 | C10H18O | 154.3 | 1191.1 | 1.34 | 0.20% | 0.17–0.25% | |
(methyldisulfanyl)methane | 624-92-0 | C2H6S2 | 94.2 | 726.4 | 0.99 | 0.18% | 0.09–0.45% | |
(E)-hex-2-en-1-ol | 928-95-0 | C6H12O | 100.2 | 833.9 | 1.18 | 0.17% | 0.02–0.57% | monomer |
(E)-hex-2-en-1-ol | 928-95-0 | C6H12O | 100.2 | 832.0 | 1.52 | dimer | ||
pentanoic acid | 109-52-4 | C5H10O2 | 102.1 | 892.7 | 1.22 | 0.14% | 0.05–0.23% | |
ethyl acetate | 141-78-6 | C4H8O2 | 88.1 | 609.7 | 1.34 | 0.14% | 0.11–0.18% | |
heptan-2-one | 110-43-0 | C7H14O | 114.2 | 870.2 | 1.26 | 0.14% | 0.05–0.26% | monomer |
heptan-2-one | 110-43-0 | C7H14O | 114.2 | 870.2 | 1.63 | dimer | ||
benzyl propionate | 122-63-4 | C10H12O2 | 164.2 | 1347.4 | 1.36 | 0.14% | 0.08–0.29% | |
methylpropanal | 78-84-2 | C4H8O | 72.1 | 554.7 | 1.28 | 0.14% | 0.06–0.20% | |
4-methyl-3-penten-2-one | 141-79-7 | C6H10O | 98.1 | 778.5 | 1.44 | 0.13% | 0.03–0.19% | |
hexanal | 66-25-1 | C6H12O | 100.2 | 779.6 | 1.56 | 0.13% | 0.03–0.41% | dimer |
2-methylbutanoic acid | 116-53-0 | C5H10O2 | 102.1 | 879.9 | 1.20 | 0.12% | 0.07–0.16% | |
citronellol | 106-22-9 | C10H20O | 156.3 | 1266.1 | 1.85 | 0.11% | 0.09–0.14% | |
heptanal | 111-71-7 | C7H14O | 114.2 | 879.9 | 1.35 | 0.11% | 0.03–0.37% | monomer |
heptanal | 111-71-7 | C7H14O | 114.2 | 882.1 | 1.70 | dimer | ||
ethyl propanoate | 105-37-3 | C5H10O2 | 102.1 | 693.4 | 1.45 | 0.11% | 0.03–0.17% | |
hexan-2-ol | 626-93-7 | C6H14O | 102.2 | 766.6 | 1.29 | 0.10% | 0.04–0.16% | |
pent-1-en-3-one | 1629-58-9 | C5H8O | 84.1 | 672.5 | 1.31 | 0.10% | 0.02–0.28% | |
(E)-hept-2-enal | 18829-55-5 | C7H12O | 112.2 | 929.7 | 1.26 | 0.09% | 0.06–0.13% | monomer |
(E)-hept-2-enal | 18829-55-5 | C7H12O | 112.2 | 942.3 | 1.67 | dimer | ||
3-methylbutanal | 590-86-3 | C5H10O | 86.1 | 643.4 | 1.41 | 0.09% | <0.01–0.17% | |
pentan-1-ol | 71-41-0 | C5H12O | 88.1 | 748.1 | 1.26 | 0.08% | 0.04–0.13% | |
1-hydroxypropan-2-one | 116-09-6 | C3H6O2 | 74.1 | 640.2 | 1.22 | 0.08% | 0.05–0.11% | |
6-methyl-5-hepten-2-one | 110-93-0 | C8H14O | 126.2 | 972.7 | 1.17 | 0.08% | 0.02–0.18% | |
ethyl benzoate | 93-89-0 | C9H10O2 | 150.2 | 1179.4 | 1.27 | 0.08% | 0.05–0.13% | |
1-penten-3-ol | 616-25-1 | C5H10O | 86.1 | 678.0 | 1.34 | 0.07% | 0.02–0.16% | |
hexan-1-ol | 111-27-3 | C6H14O | 102.2 | 855.0 | 1.33 | 0.07% | 0.06–0.09% | monomer |
hexan-1-ol | 111-27-3 | C6H14O | 102.2 | 855.6 | 1.64 | dimer | ||
isovaleric acid | 503-74-2 | C5H10O2 | 102.1 | 879.9 | 1.23 | 0.07% | 0.04–0.10% | |
benzeneacetaldehyde | 122-78-1 | C8H8O | 120.2 | 1028.1 | 1.26 | 0.06% | 0.05–0.07% | |
3-hydroxybutan-2-one | 513-86-0 | C4H8O2 | 88.1 | 702.5 | 1.33 | 0.06% | 0.03–0.08% | |
butanal | 123-72-8 | C4H8O | 72.1 | 597.3 | 1.29 | 0.05% | 0.02–0.06% | |
pyrrole | 109-97-7 | C4H5N | 67.1 | 743.2 | 0.97 | 0.05% | 0.02–0.08% | |
3-methylpentan-1-ol | 589-35-5 | C6H14O | 102.2 | 831.3 | 1.60 | 0.04% | 0.02–0.07% | |
3-methylpentan-2-one | 565-61-7 | C6H12O | 100.2 | 753.8 | 1.49 | 0.04% | 0.03–0.05% | |
hexan-2-one | 591-78-6 | C6H12O | 100.2 | 768.7 | 1.20 | 0.04% | 0.02–0.06% | monomer |
hexan-2-one | 591-78-6 | C6H12O | 100.2 | 768.2 | 1.51 | dimer | ||
(E)-pent-2-enal | 1576-87-0 | C5H8O | 84.1 | 739.2 | 1.36 | 0.04% | 0.02–0.10% | |
3-methylsulfanylpropanal | 3268-49-3 | C4H8OS | 104.2 | 887.8 | 1.09 | 0.04% | 0.02–0.06% | |
2-methylfuran-3-thiol | 28588-74-1 | C5H6OS | 114.2 | 871.4 | 1.14 | 0.04% | 0.01–0.09% | |
2-oxopropyl acetate | 592-20-1 | C5H8O3 | 116.1 | 848.3 | 1.04 | 0.03% | <0.01–0.12% | |
ethyl 2-methylbutanoate | 7452-79-1 | C7H14O2 | 130.2 | 853.2 | 1.23 | 0.03% | 0.02–0.04% | |
pentanal | 110-62-3 | C5H10O | 86.1 | 688.3 | 1.42 | 0.03% | 0.01–0.07% | |
ethyl 2-methylpropanoate | 97-62-1 | C6H12O2 | 116.2 | 753.4 | 1.56 | 0.02% | <0.01–0.05% | |
2-methylbutan-1-ol | 137-32-6 | C5H12O | 88.1 | 736.7 | 1.48 | 0.02% | 0.01–0.03% | |
2-ethyl pyrazine | 13925-00-3 | C6H8N2 | 108.1 | 918.8 | 1.12 | 0.02% | 0.01–0.04% | |
(E)-2-methylpent-2-enal | 623-36-9 | C6H10O | 98.1 | 818.3 | 1.49 | 0.02% | 0.01–0.03% | |
2,5-dimethylfuran | 625-86-5 | C6H8O | 96.1 | 705.0 | 1.36 | 0.02% | 0.01–0.03% | |
propanol | 71-23-8 | C3H8O | 60.1 | 540.0 | 1.24 | 0.02% | <0.01–0.04% | |
furan-2-ylmethanol | 98-00-0 | C5H6O2 | 98.1 | 846.7 | 1.38 | 0.02% | 0.01–0.03% | |
(Z)-3-hexen-1-ol | 928-96-1 | C6H12O | 100.2 | 844.0 | 1.52 | 0.02% | 0.01–0.05% | |
isopropyl acetate | 108-21-4 | C5H10O2 | 102.1 | 652.2 | 1.48 | 0.01% | 0.01–0.03% | |
isoamyl acetate | 123-92-2 | C7H14O2 | 130.2 | 854.9 | 1.75 | 0.01% | 0.01% | |
ethyl 2-methylbutanoate | 7452-79-1 | C7H14O2 | 130.2 | 826.9 | 1.65 | 0.01% | 0.01% | |
methyl 3-methylbutanoate | 556-24-1 | C6H12O2 | 116.2 | 756.1 | 1.53 | 0.01% | 0.01 |
No. | Name | Species | Place of Origin |
---|---|---|---|
1 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
2 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
3 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
4 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
5 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
6 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
7 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
8 | Qu Aurantii Fructus | Citrus changshan-huyou Y.B.Chang | Quzhou City, Zhejiang Province |
9 | Aurantii Fructus | Citrus aurantium L. | Qijiang County, Sichuan Province |
10 | Aurantii Fructus | Citrus aurantium L. | Chongqing City |
11 | Aurantii Fructus | Citrus aurantium ‘Huangpi’ | Yuanjiang City, Hunan Province, |
12 | Aurantii Fructus | Citrus aurantium cv. Xiucheng | Jiujiang City, Jiangxi Province |
13 | Aurantii Fructus | Citrus aurantium cv. Xiucheng | Zhangshu City, Jiangxi Province |
14 | Aurantii Fructus | Citrus aurantium cv. Xiucheng | Sanhu Town, Xingan County, Jiangxi Province |
15 | Aurantii Fructus | Citrus aurantium ‘Daidai’ | Quzhou City, Zhejiang Province |
16 | Aurantii Fructus | Citrus aurantium ‘Chuluan’ | Dongtou, Wenzhou City, Zhejiang Province |
17 | adulterants | Citrus wilsonii Tana-ka, | Hanzhong City, Shanxi Province |
18 | adulterants | Citrusreticulata ‘Unshiu’ | Wenzhou City, Zhejiang Province |
19 | adulterants | Citrussinensis (Linn.) Osbeck | Quzhou City, Zhejiang Province |
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Fang, C.; He, J.; Xiao, Q.; Chen, B.; Zhang, W. Development of the Volatile Fingerprint of Qu Aurantii Fructus by HS-GC-IMS. Molecules 2022, 27, 4537. https://doi.org/10.3390/molecules27144537
Fang C, He J, Xiao Q, Chen B, Zhang W. Development of the Volatile Fingerprint of Qu Aurantii Fructus by HS-GC-IMS. Molecules. 2022; 27(14):4537. https://doi.org/10.3390/molecules27144537
Chicago/Turabian StyleFang, Cuifen, Jia He, Qi Xiao, Bilian Chen, and Wenting Zhang. 2022. "Development of the Volatile Fingerprint of Qu Aurantii Fructus by HS-GC-IMS" Molecules 27, no. 14: 4537. https://doi.org/10.3390/molecules27144537