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Table 2 Key compounds discriminating Korean and Brazilian 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 Brazil only
1 16.79 161.060 C10H8O2 0.118 5.69 6-Methylcoumarin N/A O   Benzopyrone (flavoring agent)
2 8.26 209.081 C11H12O4 0.053 7.84 Dimethyl caffeic acid N/A O   Phenols, caffeic acid derivatives
3 16.75 263.128 C15H18O4 0.236 4.13 Artemisin N/A O   Sesquiterpene lactone (drug for malaria)
4 15.48 315.087 C17H14O6 1.098 11.64 Rosinidin N/A O   Anthocyanidins
5 12.89 317.066 C16H12O7 0.091 4.79 Rhamnetin N/A O   Flavonoids (anti-inflammatory activity)
6 16.90 329.102 C18H16O6 0.352 4.62 Ophiopogonanone A N/A O   Homoisoflavonoids (antioxidant activity) (Wang et al. 2017)
7 10.83 338.139 C20H19NO4 0.053 4.02 Columbamine N/A O   Alkaloids (antidiabetic agent)
8 14.45 343.118 C19H18O6 0.691 5.27 Tetramethoxyflavone N/A O   Flavonoid (anticancer activity)
9 15.49 285.112 C17H16O4 0.039 5.03 CAPE 7.8    Phenols, caffeic acid derivatives
10 12.48 285.075 C16H12O5 0.025 7.18 Genkwanin 7.3    Flavonoids (anti-inflammatory activity)
11 18.43 295.227 C18H30O3 0.698 11.48 Kamlolenic acid 4.9    Fatty acids, Kamala oil's glyceride
12 14.43 255.065 C15H10O4 0.020 17.12 Chrysin 4.6    Flavonoids
13 17.98 357.133 C20H20O6 0.319 6.89 (2S)-5,7,3′,4′-tetrahydroxy-6-(1,1-dimethylallyl)flavanone 4.2    Flavonoids (anticancer activity)
14 10.66 269.081 C16H12O4 0.033 4.11 Strobochrysin 3.9    Flavonoids (anticancer activity)
15 17.69 269.081 C16H12O4 0.331 5.89 Tectochrysin 3.7    Flavonoids (antibacterial activity)
16 9.99 317.066 C16H12O7 0.003 4.83 Quercetin 3-methyl ether 3.7    Flavonoids (antioxidant activity)
17 10.90 273.076 C15H12O5 -0.029 4.70 Butein 2.8    Chalconoids (anti-inflammatory activity)
18 14.83 257.081 C15H12O4 0.144 10.44 Pinocembrin 1.1    Flavonoids (anticancer activity)
19 19.30 268.264 C17H33NO 0.276 4.52 (5-heptyl-6-methyloctahydroindolizin-8-yl)methanol -1.7    Semiochemicals
20 20.27 310.310 C20H39NO 0.045 5.89 N-Hexadecanoylpyrrolidine -2.0    Alkaloids
21 15.25 301.071 C16H12O6 0.086 8.27 Kaempferide -3.4    Flavonoids (antibacterial activity)
22 15.75 331.081 C17H14O7 0.103 7.87 Quercetin 3,7′-dimethyl ether -3.5    Flavonoids (vasorelaxant activity)
23 18.26 215.107 C14H14O2 0.558 4.60 Dihydropinosylvin N/A   O Phenols (antifungal activity)
24 16.24 231.102 C14H14O3 0.169 4.25 Aucuparin N/A   O Benzenoid (phytoalexin)
25 13.18 233.117 C14H16O3 0.133 7.79 Pterosin E N/A   O Indanones (anti-inflammatory activity)
26 12.39 249.112 C14H16O4 0.072 4.08 Prenyl caffeate N/A   O Caffeic acid derivatives (flavoring agent)
27 16.96 271.097 C16H14O4 0.181 4.68 Haginin B N/A   O Flavonoids
28 18.78 273.258 C20H32 0.285 9.26 Casbene N/A   O Diterpenoids (antifungal activity) (Sitton and West 1975)
29 17.59 301.180 C19H24O3 0.000 17.75 Artepillin C N/A   O Cinnamic acid derivatives (anti-inflammatory activity)
30 12.48 311.128 C19H18O4 0.077 5.04 Moracin N N/A   O Flavonoids
31 17.81 321.243 C20H32O3 0.386 4.27 Hydroxyeicosatetraenoic acid (HETE) N/A   O Unsaturated fatty acids
32 9.86 363.180 C20H26O6 0.080 4.51 Gibberellin A36 N/A   O Diterpenoids (plant hormones) (Stowe and Yamaki 1959)
33 15.13 391.212 C22H30O6 0.427 6.68 Neoquassin N/A   O Quassinoids (insecticidal activity) (Dou et al. 2008)
34 7.21 517.134 C25H24O12 0.184 5.04 Apigenin 7-(2′′,3′′-diacetylglucoside) N/A   O Flavonoids (anti-cancer effect)
35 19.74 527.337 C32H46O6 0.759 4.27 (24E)-3alpha-acetoxy-15alpha-hydroxy-23oxo-7,9(11),24-lanostatrien-26-oic acid N/A   O Triterpenes
  1. No. 1 to 18: key compounds with a fold change of ≥ 2 and no. 19 to 35: key compounds with a fold change of ≤ − 2
  2. Numbers in italic represent the compounds observed only in each sample