. 2022 Jun 30;9:941487. doi: 10.3389/fnut.2022.941487

Table 5.

Phenolic profile of nine Norwegian apple samples from the NIBIO Ullensvang area (sample no. 15 “Furuholm,” “Fuhr,” no. 30 “Kaupanger,” no. 44 “Prins,” no. 47 “Raud Gravenstein,” no. 66 “Tormodseple,” no. 68 “Tveiteple,” no. 69 “Ulgenes,” no. 71 “Vanleg Torstein,” and no. 72 “Vinterrosenstips”).

t _R , min	Compound name	Molecular formula, [M–H]⁻	Calculated mass, [M–H]⁻	Exact mass, [M–H]⁻	Δ ppm	MS² fragments, (% base peak)	MS³ fragments, (% base peak)	MS⁴ fragments, (% base peak)	15	30	44	47	66	68	69	71	72	References
4.10	Protocatechiuic acid O-hexoside	C₁₃H₁₅O $O_{9}^{-}$	315.07216	315.07178	1.18	108 (9), 109 (12), 151 (8), 152 (49), 153 (100), 163 (9), 165 (13)	108 (22), 109 (100)	81 (63), 123 (100)	+	+	+	+	–	+	+	+	+	(47)
4.22	Gallic acid ^a	C₇H₅ $O_{5}^{-}$	169.01425	169.01398	1.60	125 (100)	107 (100)	NR	+	+	+	+	+	+	+	+	+
4.56	Protocatechiuic acid ^a	C₇H₅ $O_{4}^{-}$	153.01933	153.01893	2.65	109 (100), 110 (5)	65 (100), 81 (71)	NR	+	+	+	+	+	+	+	+	+
4.80	3- O -Caffeoylquinic acid ^a	C₁₆H₁₇ $O_{9}^{-}$	353.08781	353.08727	1.51	135 (7), 179 (32), 191 (100), 192 (4)	85 (92), 109 (21), 111 (47), 127 (100), 171 (26), 173 (72)	81 (16), 85 (100), 95 (16), 99 (15), 109 (12)	+	–	+	+	+	+	–	–	+
4.96	Caffeic acid hexoside	C₁₅H₁₇ $O_{9}^{-}$	341.08781	341.08768	0.36	135 (9), 147 (10), 161 (42), 179 (100), 180 (6), 203 (8), 281 (4)	135 (100)	91 (12), 107 (100), 117 (30)	+	+	+	+	+	+	+	+	+	(48)
5.07	5- O -Caffeoylquinic acid ^a	C₁₆H₁₇ $O_{9}^{-}$	353.08781	353.08754	0.74	179 (6), 191 (100), 192 (5), 305 (5), 315 (3)	85 (100), 93 (49), 111 (25), 127 (69), 171 (29), 173 (62)	NR	+	+	–	+	+	+	–	–	+
5.10	B type proanthocyanidin isomer 1	C₃₀H₂₅ $O_{12}^{-}$	577.13515	577.13293	3.85	287 (8), 289 (24), 407 (53), 425 (100), 426 (8), 451 (26), 559 (8)	273 (7), 381 (6), 407 (100)	281 (94), 283 (37), 285 (100), 297 (36), 389 (35)	–	+	–	–	–	–	+	+	–	(49)
5.44	5- O -Caffeoylquinic acid isomer	C₁₆H₁₇ $O_{9}^{-}$	353.08781	353.08751	0.84	179 (3), 191 (100)	85 (94), 93 (58), 111 (36), 127 (100), 171 (26), 173 (72)	81 (5), 83 (20), 85 (100), 99 (33), 109 (24)	+	+	+	+	+	+	+	+	+	(50, 51)
5.49	Catechin ^a	C₁₅H₁₃ $O_{6}^{-}$	289.07176	289.07106	2.44	179 (10), 203 (8), 205 (33), 231 (6), 245 (100), 246 (7), 247 (5)	161 (19), 175 (11), 187 (23), 188 (15), 203 (100), 227 (28)	157 (13), 161 (29), 175 (100), 185 (18), 188 (58)	+	+	–	+	–	–	+	+	+
5.54	p -Coumaric acid hexoside	C₁₅H₁₇ $O_{8}^{-}$	325.09289	325.09283	0.19	119 (9), 145 (100), 163 (76), 187 (43), 205 (8), 265 (15), 289 (48)	117 (100)	NR	+	+	+	+	+	+	+	+	+	(48)
5.57	3- O - p -Coumaroylshikimic acid	C₁₆H₁₅ $O_{7}^{-}$	319.08233	319.08224	0.26	119 (10), 137 (9), 139 (6), 145 (100), 146 (8), 257 (5), 275 (6)	117 (100)	NR	+	–	+	+	+	+	–	+	+	(52)
5.68	B type proanthocyanidin isomer 2	C₃₀H₂₅ $O_{12}^{-}$	577.13515	577.13373	2.45	287 (6), 289 (17), 407 (46), 425 (100), 426 (7), 451 (19), 559 (5)	273 (7), 381 (5), 407 (100)	281 (73), 283 (37), 285 (100), 297 (31), 389 (27)	+	+	+	+	+	+	+	+	+	(49)
5.83	Ferulic acid hexoside	C₁₆H₁₉ $O_{9}^{-}$	355.10346	355.10282	1.80	134 (4), 160 (4), 175 (33), 193 (100), 217 (39), 235 (6), 295 (4)	134 (100), 149 (31), 178 (17)	106 (100)	+	+	+	+	+	+	+	+	+	(48)
5.96	Caffeic acid ^a	C₉H₇ $O_{4}^{-}$	179.03498	179.03485	0.76	89 (16), 113 (5), 119 (6), 135 (100), 136 (6), 143 (13), 161 (9)	91 (100), 93 (22), 107 (99), 117 (6)	NR	+	+	+	+	+	+	+	+	+
6.00	Epicatechin ^a	C₁₅H₁₃ $O_{6}^{-}$	289.07176	289.07127	1.69	179 (9), 203 (8), 205 (31), 231 (4), 245 (100), 246 (7), 247 (4)	161 (18), 175 (10), 187 (22), 188 (13), 203 (100), 227 (25)	161 (38), 174 (24), 175 (100), 185 (25), 188 (80)	+	+	+	+	+	+	+	+	+
6.06	4- O - p -Coumaroylquinic acid	C₁₆H₁₇ $O_{8}^{-}$	337.09289	337.09266	0.68	163 (6), 173 (100)	71 (19), 93 (100), 109 (8), 111 (54), 155 (14)	NR	+	+	+	+	+	+	+	+	+	(53, 54)
6.07	p -Coumaric acid ^a	C₉H₇ $O_{3}^{-}$	163.04007	163.03986	1.28	101 (33), 113 (15), 119 (100), 120 (13), 131 (48), 133 (32), 143 (21)	78 (15), 91 (100)	NR	+	+	+	+	+	+	+	+	+
6.12	3- O -Caffeoylshikimic acid	C₁₆H₁₅ $O_{8}^{-}$	335.07724	335.07721	0.09	135 (25), 161 (3), 179 (100), 180 (7)	135 (100)	79 (100), 107 (16), 108 (35), 117 (6)	+	–	–	–	+	–	–	+	+	(55)
6.15	p -Hydroxybenzoic acid ^a	C₇H₅ $O_{3}^{-}$	137.02442	137.02436	0.44	109 (8), 93 (100)	93 (100)	NR	+	+	+	+	+	+	+	+	+
6.34	p -Hydroxyphenylacetic acid ^a	C₈H₇ $O_{3}^{-}$	151.04007	151.03998	0.60	121 (14), 107 (100), 95 (70), 79 (16), 59 (23)	123 (10), 95 (32), 79 (100), 69 (10), 51 (18)	108 (100)	–	+	+	–	–	–	–	–	+
6.35	Methyl 3- O -caffeoylquinate	C₁₇H₁₉ $O_{9}^{-}$	367.10346	367.10297	1.31	133 (6), 135 (22), 161 (100), 162 (7), 179 (3), 193 (3), 335 (3)	133 (100)	105 (100)	+	+	+	+	+	+	+	+	+	(56, 57)
6.46	Aesculetin ^a	C₉H₅ $O_{4}^{-}$	177.01933	177.01923	0.56	149 (8), 133 (100), 105 (12), 89 (4)	89 (100)	NR	–	–	–	–	–	–	–	–	–
6.58	Methyl 5- O -caffeoylquinate	C₁₇H₁₉ $O_{9}^{-}$	37.10346	367.10313	0.88	134 (3), 135 (44), 136 (4), 161 (11), 179 (100), 180 (9), 191 (20)	135 (100)	79 (57), 91 (19), 106 (57), 107 (100), 117 (10)	+	+	+	+	–	+	+	+	+
6.65	Syringic acid ^a	C₉H₉ $O_{5}^{-}$	197.04555	197.04550	0.25	183 (100), 153 (41), 138 (10)	167 (100), 138 (9), 123 (5)	NR	–	+	+	+	–	–	–	+	–
6.67	3-Hydroxyphloretin 2'- O -pentosyl-(1–6)-hexoside	C₂₆H₃₁ $O_{15}^{-}$	583.16684	583.16461	3.83	167 (3), 271 (5), 289 (100)	123 (3), 125 (40), 167 (100), 245 (17), 271 (71)	123 (100), 125 (14)	+	+	+	+	+	+	+	+	+	(49)
6.78	Quercetin 3- O -glucoside ^a	C₂₁H₁₉ $O_{12}^{-}$	463.08820	463.08597	4.82	300 (37), 301 (100), 302 (10)	151 (75), 179 (100), 255 (31), 257 (12), 271 (46), 272 (18)	151 (100)	+	+	+	+	+	+	+	+	+
6.91	Methyl 3- O - p -coumaroylquinate	C₁₇H₁₉ $O_{8}^{-}$	351.10854	351.10794	1.71	117 (5), 119 (9), 145 (100), 146 (6), 163 (3)	117 (100)	NR	+	+	+	+	+	+	+	+	+	(5)
6.93	Rutin ^a	C₂₇H₂₉ $O_{16}^{-}$	609.14611	609.14592	0.31	301 (100)	179 (100), 151 (78), 107 (4)	151 (100), 107 (2)	+	+	+	+	+	+	+	+	+
7.04	Quercetin 3- O -pentoside isomer 1	C₂₀H₁₇ $O_{11}^{-}$	433.07764	433.07641	2.83	300 (15), 301 (100), 302 (10)	151 (79), 179 (100), 255 (18), 271 (18), 273 (19), 283 (16)	151 (100)	+	+	+	+	+	+	+	+	+	(49)
7.14	Phloretin 2'- O -pentosyl-(1–6)-hexoside	C₂₆H₃₁ $O_{14}^{-}$	567.17193	567.16998	3.44	167 (5), 273 (100), 274 (10)	123 (4), 125 (3), 167 (100)	123 (100), 125 (13), 151 (3)	+	+	+	+	+	+	+	+	+	(49)
7.16	3-Hydroxyphloretin	C₁₅H₁₃ $O_{6}^{-}$	289.07176	289.07147	1.00	125 (39), 167 (100), 245 (19), 271 (74)	123 (100), 125 (14), 151 (3)	NR	+	+	–	+	+	+	+	+	+	(58)
7.22	Quercetin 3- O -pentoside isomer 2	C₂₀H₁₇ $O_{11}^{-}$	433.07764	433.07756	0.18	300 (11), 301 (100), 302 (11)	151 (78), 179 (100), 255 (12), 271 (9), 273 (18), 283 (14)	151 (100)	+	+	–	+	+	+	+	+	+	(49)
7.32	Quercetin 3- O -rhamnoside ^a	C₂₁H₁₉ $O_{11}^{-}$	447.09329	447.09319	0.21	300 (20), 301 (100), 302 (8)	151 (77), 179 (100), 255 (29), 271 (41), 273 (20), 283 (21)	151 (100)	+	+	+	+	+	+	+	+	+
7.37	Isorhamnetin 3- O -rutinoside ^a	C₂₈H₃₁ $O_{16}^{-}$	623.16176	623.16173	0.05	315 (100), 300 (20), 271 (9), 255 (6)	300 (100), 287 (5), 272 (4)	271 (100), 255 (50), 151 (4)	+	+	+	+	+	+	+	+	+
7.43	Vanillic acid ^a	C₈H₇ $O_{4}^{-}$	167.03498	167.03492	0.36	153 (10), 152 (79), 124 (11), 123 (100), 108 (222)	108 (100)	123 (29), 80 (35), 78 (100)	+	+	+	+	+	+	+	+	+
7.50	Naringin ^a	C₂₇H₃₁ $O_{14}^{-}$	579.17193	579.17145	0.83	459 (100), 357 (5), 313 (26), 271 (44), 235 (12)	441 (30), 357 (100), 339 (31), 271 (54), 235 (87)	339 (100), 169 (22), 151 (50), 125 (21)	+	–	+	+	+	+	–	–	+
7.56	Sinapic acid ^a	C₁₁H₁₁ $O_{5}^{-}$	223.06120	223.06118	0.09	208 (100), 179 (31), 164 (20)	193 (10), 164 (100), 149 (14), 135 (3)	149 (100), 135 (33)	+	–	+	–	–	+	–	–	+
7.65	Isorhamnetin 3- O -glucoside ^a	C₂₂H₂₁ $O_{12}^{-}$	477.10385	477.10208	3.71	357 (21), 315 (48), 314 (100), 300 (5), 285 (10), 271 (11)	300 (30), 285 (100), 271 (73), 257 (8), 243 (24)	270 (100)	+	+	+	+	+	+	+	+	+
7.65	Kaempferol 7- O -glucoside ^a	C₂₁H₁₉ $O_{11}^{-}$	447.09329	447.09192	3.06	327 (18), 285 (80), 284 (100), 255 (9)	255 (100), 227 (9)	227 (100), 211 (61)	+	+	+	+	+	+	+	+	+
7.67	Phloretin 2′-O-glucoside (Phloridzin) ^a	C₂₁H₂₃ $O_{10}^{-}$	435.12967	435.12909	1.34	273 (100), 274 (7)	123 (4), 125 (3), 167 (100)	123 (100), 125 (13), 151 (3)	+	+	+	+	+	+	+	+	+
7.67	Phloretin ^a	C₁₅H₁₃ $O_{5}^{-}$	273.07685	273.07674	0.39	123 (3), 125 (3), 167 (100), 168 (6)	123 (100), 125 (12), 151 (3)	81 (100), 95 (64), 97 (4), 105 (3), 108 (5)	+	+	+	+	+	+	+	+	+
7.58	Ferulic acid ^a	C₁₀H₉ $O_{4}^{-}$	193.05063	193.05062	0.05	178 (72), 149 (100), 134 (39)	134 (100)	NR	+	+	+	+	+	+	+	+	+
8.90	Quercetin ^a	C₁₅H₉ $O_{7}^{-}$	301.03538	301.03479	1.94	151 (46), 179 (100), 180 (4), 193 (3), 257 (6), 271 (5), 273 (8)	151 (100)	63 (5), 65 (3), 83 (13), 107 (100)	+	+	+	+	+	+	+	+	+
9.05	Eriodictyol ^a	C₁₅O₁₁ $O_{6}^{-}$	287.05611	287.05533	2.72	151 (100), 107 (8)	107 (100)	65 (100)	+	+	+	+	+	+	+	+	+
9.93	Naringenin ^a	C₁₅H₁₁ $O_{5}^{-}$	271.06120	271.05989	4.83	225 (5), 177 (11), 151 (100)	107 (100)	65 (100)	+	+	+	+	+	+	+	+	+
10.11	Kaempferol ^a	C₁₅H₉ $O_{6}^{-}$	285.04046	285.03979	2.35	255 (100), 227 (10)	211 (100), 195 (4), 167 (16)	211 (41), 137 (100)	+	+	+	+	+	+	+	+	+
12.21	Acacetin ^a	C₁₆H₁₁ $O_{5}^{-}$	283.06119	283.06033	3.04	268 (100)	268 (100), 240 (29)	239 (13), 223 (18), 211 (100), 196 (74), 172 (62)	+	–	+	+	+	+	–	–	+

^aConfirmed using standards, while the other compounds were identified by evaluation of its HRMS and MSⁿ data (see references in the table).

“NR,” not recorder; “+,” present compound; “–,” not present compound. The bold values refer to the most intense ions.