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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)