Ethanolic Extract of Polish Propolis: Chemical Composition and TRAIL-R2 Death Receptor Targeting Apoptotic Activity against Prostate Cancer Cells
Table 1
The content (mg/g) and characterization of phenolic compounds of the ethanol extract of Polish propolis determined using their spectral characteristic in negative ions in LC-ESI/MS.
Peak
Retention time (min)
(M−H)−
MS/MS fragments
Compound name*
Quantity (mg/g of propolis)**
1
2.26
179.0349
161.0241/135.0440
Caffeic acida
3.90
2
2.53
121.0288
121.0288
Benzoic acidbc
0.86d
3
2.69
237.0772
163.0406/145.0284/117.0342
Ni
Tr
4
2.79
163.0406
119.0488
-Coumaric acida
28.65
5
2.88
267.0899
160.0154/133.0276
Ni
Tr
6
3.01
193.0492
178.0258/149.0613/134.0375
Ferulic acida
22.01
7
3.18
357.0989
279.0655/147.0441
Ferulic acid derivativec
0.59e
8
3.31
295.0815
161.0241/133.0299
Ferulic acid derivativec
Tr
9
3.57
359.1129
163.0380/145.0284/119.0510
Coumaric acid derivativec
0.16g
10
3.72
389.1221
193.0492/134.0375/175.0399/160.0154
Ferulic acid derivativec
0.75e
11
3.88
279.086
145.0284/117.0342
Ni
Tr
12
4.15
415.1065
253.0730/179.0349/161.0241/135.0440
Caffeic acid derivativec
0.11f
13
4.27
355.1176
179.0349/163.0380/135.0440/119.0488
Caffeic and coumaric acids derivativec
Tr
14
4.61
399.1051
253.0697/179.0349/163.0380/119.0488
Coumaric and caffeic acids derivativec
1.83g
15
4.70
429.1214
253.0697/193.0492/161.0241/134.0375
Ferulic acid derivativec
2.12e
16
4.86
269.0469
151.0042/117.0342
Apigenina
1.98
17
4.96
383.1137
Coumaric acid derivativec
3.97g
18
5.05
271.0616
253.0502/197.0596/161.0605/125.0241/107.0134
Pinobanksina
12.78
19
5.10
383.1137
163.0406/119.0510
Coumaric acid derivativec
22.87g
20
5.20
413.1240
193.0492/163.0380/134.0375/119.0488
Coumaric and ferulic acids derivative (metoxy-)c
13.44e
21
5.27
443.1320
193.0492/163.0380/134.0375/119.0488
Coumaric and ferulic acids derivative (dimetoxy-)c
3.98e
22
5.44
259.1917
193.0492/163.0380/134.0375/119.0489
Ferulic acid derivativec
2.02e
23
5.63
283.0594
193.0492/134.0375
Ferulic acid derivativec
0.3e
24
5.73
441.1179
179.0349/163.0406/135.0440/119.0388
Caffeic and coumaric acids derivativec
Tr
25
5.79
315.0512
121.0288
Rhamnetina
0.49
26
5.86
471.1305
297.1136/193.0492
Ni
Tr
27
6.25
425.1242
163.0406/119.0510
Coumaric acid derivativec
5.00
28
6.32
247.0982
179.0349/163.0380/135.0440
Coumaric and caffeic acids derivativec
0.31f
29
6.35
253.0502
143.0510
Chrysina
6.56
30
6.41
269.0804
178.0258/163.0380/134.0375/119.0488
Ni
—
31
6.56
269.0435
171.0446/151.0042/117.0342
Galangina
0.47
32
6.56
299.0572
Kaempferideg
Tr
33
6.66
313.0745
253.0502
Pinobanksin-3-O-acetateb
Tr
34
6.94
249.1131
161.0241/133.0299
Ni
—
35
7.13
253.0860
162.0308/151.0394/145.0284/117.0342
Methoxyflavanonebc
20.50h
36
7.25
283.0973
163.0380/145.0653/119.0488
Coumaric acid derivativec
10.49g
37
8.80
449.2537
361.2026/253.0502/121.0288
Benzoic acid derivativec
5.20d
Ni: not identified. Tr: traces.
*a: confirmed by standard; b: confirmed by reference [41, 42]; c: confirmed by MS fragmentation.
**d: expressed as cinnamic acid; e: expressed as ferulic acid; f: expressed as caffeic acid; g: expressed as -coumaric acid; h: expressed as apigenin.