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Table 3 Key compounds discriminating Korean and Chinese propolis. The key compounds were selected from key molecular features with VIP > 4, and a fold change ≥ 2 or ≤ − 2 or observed only in each sample

From: UPLC/FT-ICR MS-based high-resolution platform for determining the geographical origins of raw propolis samples

No. RT (min) m/z Formula Error (ppm) VIP Expected compound Feature Class (function)
Fold change (log2) Korea only China only
1 16.60 283.097 C17H14O4 0.247 4.38 5,7-Dimethoxyisoflavone N/A O   Flavonoids (anabolic and anti-catabolic compound)
2 16.86 285.185 C19H24O2 0.228 5.22 Alpha-terpinyl cinnamate N/A O   Cinnamic acid derivatives (flavoring agent)
3 17.89 315.196 C20H26O3 0.216 4.71 Lanugone A N/A O   Terpenes
4 10.83 338.139 C20H19NO4 0.053 5.01 Ficine N/A O   Flavonoidal alkaloid
5 15.60 403.118 C24H18O6 0.275 4.72 Calomelanol I N/A O   Flavonoids (antioxidant activity)
6 13.10 421.128 C24H20O7 0.085 4.70 5-O-Methylhoslundin N/A O   Flavonoids (antioxidant activity)
7 18.67 453.337 C30H44O3 0.490 4.11 Tyromycic acid N/A O   Triterpenoids
8 18.62 475.378 C30H50O4 0.587 4.90 Soyasapogenol A N/A O   Triterpenoids (antibacterial activity) (Rupasinghe et al. 2003)
9 20.67 489.394 C31H52O4 0.366 9.99 1α-hydroxy-2β-(4-hydroxybutoxy) vitamin D3 N/A O   Vitamin D3
10 19.12 491.373 C30H50O5 0.611 4.04 Meliantriol N/A O   Triterpenoids (insecticidal activity)
11 18.36 501.321 C30H44O6 0.578 7.88 Ganolucidic acid D N/A O   Terpenoids
12 18.77 503.337 C30H46O6 0.723 7.35 Esculentic acid N/A O   Triterpenoids
13 14.50 563.168 C28H31ClO10 0.783 7.75 Physalin H N/A O   Physalins
14 16.79 161.060 C10H8O2 0.000 7.05 6-Methylcoumarin 6.2    Benzopyrone (flavoring agent)
15 12.62 329.102 C18H16O6 − 0.079 5.80 Alnetin 5.0    Flavonoids (antifungal activity)
16 12.48 285.075 C16H12O5 0.088 6.81 Genkwanin 4.5    Flavonoids (anticancer activity)
17 14.22 249.112 C14H16O4 − 0.012 8.24 Pyriculol 4.4    Phenylpropanoids (phytotoxin)
18 14.71 285.076 C16H12O5 0.203 4.04 Acacetin 2.9    Flavonoids (anti-inflammatory activity)
19 14.45 343.118 C19H18O6 0.344 6.04 Tetramethoxyflavone 2.7    Flavonoids (anticancer activity)
20 15.48 315.087 C17H14O6 0.133 13.06 Rosinidin 2.4    Anthocyanidins
21 8.26 209.081 C11H12O4 − 0.033 8.44 Dimethylcaffeic acid 2.1    Phenols, caffeic acid derivatives
22 12.89 317.066 C16H12O7 − 0.035 5.18 Rhamnetin 2.0    Flavonoids (anti-inflammatory activity)
23 15.97 285.076 C16H12O5 0.158 7.14 8-C-ethylgalangin 1.6    Flavonoids (anti-inflammatory activity)
24 17.98 357.133 C20H20O6 0.381 6.51 Kievitone 1.4    Flavonoids (phytoalexin)
25 14.83 257.081 C15H12O4 0.086 12.54 Pinocembrin 1.1    Flavonoids (anticancer activity)
26 14.38 315.253 C18H34O4 0.184 4.78 Octadecanedioic acid − 1.1    Long-chain fatty acids
27 16.94 643.419 C36H60O8 0.575 4.09 Fasciculic acid A − 1.2    Triterpenoids (calmodulin antagonist activity)
28 15.03 293.042 C15H10O5 0.198 4.03 Apigenin − 1.5    Flavonoids (anticancer activity)
29 18.45 299.258 C18H34O3 0.478 4.65 Ricinoleic acid − 1.5    Unsaturated fatty acids (anti-inflammatory activity) (Vieira et al. 2000)
30 18.68 297.243 C18H32O3 0.273 5.80 Dimorphecolic acid − 1.8    Fatty acids (antibacterial activity) (Mundt et al. 2003)
31 20.27 310.310 C20H39NO 0.055 8.75 Oleoyl ethyl amide − 2.4    Ethanol amide lipids (analgesic activity)
32 19.51 323.258 C20H34O3 0.121 13.73 (±)5-6E,8Z,11Z-eicosatrienoic acid (HETrE) − 2.9    Unsaturated fatty acids
33 18.86 339.253 C20H34O4 0.363 9.83 Aphidicolin − 3.1    Tetracyclic diterpene antibiotics (Antiviral activity)
34 17.52 463.139 C26H22O8 0.555 5.17 Artomunoxanthentrione epoxide − 3.2    a potential biomarker
35 19.68 325.274 C20H36O3 0.357 6.86 Alchornoic acid − 3.7    Fatty acids
36 18.08 341.269 C20H36O4 0.325 7.18 Thromboxanoic acid skeleton − 3.7    Fatty acids
37 19.86 399.290 C26H38O3 0.073 5.54 Ximaosteroid C − 3.9    Steroids
38 19.68 606.546 C38H71NO4 0.659 6.36 Cer(d16:2(4E,6E)/22:1(13Z)(2OH)) − 4.3    Fatty acids
39 9.39 287.091 C16H14O5 0.066 6.66 Gummiferol N/A   O Polyacetylenic diepoxides (anticancer activity)
40 18.21 321.242 C20H32O3 0.159 4.01 15-Hydroxyeicosatetraenoic acid (HETE) N/A   O Eicosanoids
41 17.83 343.284 C20H38O4 0.303 6.51 Eicosanedioic acid N/A   O Eicosanoids
42 17.27 389.102 C23H16O6 0.239 4.12 Pamoate N/A   O Naphthoic acid derivative
43 16.93 421.128 C24H20O7 0.468 7.29 Glabratephrin N/A   O Flavonoids (antifeedant activity)