Comparative Study of Chemical Composition and Biological Activity of Yellow, Green, Brown, and Red Brazilian Propolis

Table 1

Propolis constituents identified by UPLC-ESI(−)-MS/MS.

M-H	Compound	Propolis origin	ESI(−)-MS/MS; (relative intensity%)	Reference
151		SP	150 (100); 147 (65); 127 (10); 121 (15)
163	p-Coumaric acid	SP, Cuba, MG, PR	163 (20); 119 (100)	a, [4, 14, 15]
179	Caffeic acid	SP, MG, PR	179 (40); 135 (100); 116 (50)	[14]
229	2,2-Dimethyl-6-carboxyethenyl-2H-1-benzopyrane	SP, MG	185 (100); 168.9 (50); 146 (20)	a, [4]
231	4-Hydroxy-3-prenylcinnamic acid	SP, MG, PR	231 (15); 187 (30); 132 (100)	a, [4, 15, 16]
233	Viscidone	SP, MG, PR	233 (25); 188 (100); 133 (50); 132 (85)	a
247	3,4-Dihydroxy-5-prenylcinnamic acid	SP, MG, PR	247 (40); 203 (60); 148 (100)	a, [16]
253	2-Hydroxy-4-; methoxychalcone	BA	253 (80); 237 (95); 209 (100); 161 (70); 136 (92)	[17]
253		SP, MG	220 (5); 162 (20), 145 (30); 118 (100)
255	Liquiritigenin	BA	255 (35); 135 (40); 119 (100)	[7, 9, 17, 18]
255		BA, Cuba	255 (45); 135 (35); 119 (100)
255		MS	254 (52); 209 (100); 191 (50); 153 (62); 123 (62); 109 (61)
285	(3S)-Vestitone	BA, MG	285 (25); 269 (33); 147 (18); 109 (100)	[18]
285	Pinobanksin-5-methyl-ether	SP, MG	285 (100); 252 (30); 163 (45); 151 (35); 136 (50)	[14]
285	Kaempferol	Cuba, BA	285 (83); 149 (100); 122 (85)	[14]
297		BA	267 (85); 205 (100)
299		BA	299 (40); 284 (100)
299	Luteolin-methyl-ether	BA	299 (40); 284 (100); 255 (25); 227 (30)	[14, 15]
299	Kaempferide	SP, Cuba, PR	299 (100); 284 (90); 200 (30); 151 (23)	[15, 16]
299	Artepillin C	SP, MG, PR	299 (90); 255 (100); 200 (97)	a, [4, 16]
301	Dihydrokaempferide	BA, SP, Cuba, MG, PR	301 (100); 283 (5); 152 (30)	a, [16]
315	(3S)-Violanone	BA	315 (20); 108 (100)	[18]
315	Quercetin-3-methyl-ether	BA	315 (80); 300 (55); 271 (50); 243 (100); 165 (48)	a, [14]
315	Isorhamnetin	SP, MG, PR	315 (100); 284 (20); 252 (30)	a, [15]
315	(3-4-Hydroxy-3-methyl-2-butenyl-4-hydroxy-5-prenyl) cinnamic acid	SP, MG	315 (100); 253 (90); 241 (88); 198 (98)	a
315	3-Hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid	SP, MG	315 (75); 271 (25); 253 (20); 244 (85); 198 (100); 146 (45)	[15]
317		BA	317 (20); 270 (23); 166 (48); 109 (100)
317		SP, MG	317 (25); 314 (50); 241 (100); 124 (73)
317		SP, MG	317 (10); 242 (40); 200 (100)
317		SP	317 (45); 273 (55); 160 (100)
317		MG	317 (40); 312 (100); 253 (50); 147 (80)
319		BA, PR	301 (100); 193 (25)
319		MS	319 (20); 223 (100);
329		BA	329 (30); 314 (55); 299 (100); 285 (35); 271 (100); 182 (60)
329	Quercetin-dimethyl-ether	SP, Cuba, MG, PR	229 (100); 314 (70); 299 (42); 270 (80); 227 (25)	[14]
329	Betuletol	SP, MG	329 (85); 314 (45); 299 (100); 270 (85); 257 (90) 198 (50); 160 (35)	a
333	Agathic acid	SP, MG, PR	333 (45); 314 (40); 257 (30); 245 (35)	a
347	Agathic acid 15-methyl ester	SP	247 (70); 259 (20); 187 (100); 163 (60); 146 (80)	a
353		Cuba, MS	353 (40); 335 (45); 151 (40); 112 (50)
361	15-Acetoxy cupressic acid	MG, SP	361 (100); 317 (70); 242 (75); 159 (45); 126 (72)	a
363	3-Prenyl-4-dihydrocinnamoyloxy cinnamic acid	SP, MG	363 (20); 187 (80); 149 (100)	a, [15]
447	(E)-3-{-4-hydroxy-3-[(E)-4-(2,3-dihydrocinnamoyl oxy)-3-methyl-2-butenyl]-5-prenylphenyl}-2-propenoic acid	SP, MG, PR	447 (10); 297 (50); 197 (15); 149 (100)	a, [16]
515	3,5-DI-O-caffeoylquinic acid	SP, MG, PR	515 (25); 353 (100); 173 (30)	a, [4, 15]

Identification based on comparison with authentic analytical standards.