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. 2016 Nov 19;21(11):1576. doi: 10.3390/molecules21111576

Table 1.

(Poly)phenolic compounds in rosemary extract identified by ultra-high performance liquid chromatography-mass spectrometry (UHPLC-MSn) in negative ionization mode under different mass spectrometry (MS) conditions.

ID. Compounds RT (min) [M − H] (m/z) MS2 ion Fragments (m/z) a MS3 ion Fragments (m/z) a Exp. 1 c Exp. 2 c Ident. d
1 Caffeic acid 6.82 179 135 x x Std
2 Medioresinol 7.18 387 207 b, 163, 369 163 x x [4,12]
3 p-Coumaric acid 7.93 163 119 119 x x [4]
4 Luteolin-rutinoside 8.78 593 285 285, 241, 175, 199, 217 x - [4,22]
5 Luteolin-hexoside 8.98 447 285, 378 285, 241, 267, 199, 175 x x [4]
6 Isorhamnetin-3-O-hexoside 9.28 477 315, 300, 357, 462 300 x x [4]
7 4-hydroxybenzoic acid 9.47 137 93, 137 x x [4]
8 Apigenin-7-O-glucoside 9.82 431 269 225, 149, 201, 183, 281 x x [23]
9 Hesperidin (Hesperetin-7-O-rutinoside) 9.87 609 301 286, 242, 257, 283, 125 x x Std
10 Homoplantaginin (Hispidulin 7-glucoside) 10.04 461 299, 446, 284, 341 284, 255, 179 x x [3]
11 Rosmarinic acid 10.11 359 161, 179, 197, 223 161, 133 x x Std
12 Luteolin-7-O-glucuronide 10.28 461 285 241, 217, 175, 199 x x [4]
13 Dihydroxy-dimethoxyflavone derivative 10.33 387 313, 343 298 x - [4,24]
14 Dihydroxy-dimethoxyflavone 10.71 313 298 269, 283, 297, 280 x - [4,24]
15 Medioresinol derivative 11.22 593 387, 561, 519 207, 163, 369 x x [12]
16 Dihydroxy-dimethoxyflavone 11.24 313 298 283, 297, 269, 150 x - [4,24]
17 Luteolin-3′-acetyl-O-glucuronide 11.25 503 285, 399, 443 241, 243, 217, 199, 175 x x [13,23]
18 Medioresinol-glucuronide 11.37 563 387, 531, 489 207, 163, 369 x x [12]
19 Eriodictyol 11.46 287 151 107 x x [25]
20 Isorhamnetin-rutinoside 11.51 623 315, 300 300 x x [4,22]
21 Luteolin 11.75 285 285, 241, 199, 217, 257, 151, 179, 213 x x [4,22,26]
22 Isorhamnetin 11.91 315 300, 301, 287 300, 216, 228, 256, 272 x x [4,22]
23 Trihydroxy-methoxyflavone 11.98 299 284 283, 227, 256, 212, 200 x x [3,27]
24 Methyl rosmarinate 12.36 373 179, 135, 305 135 x x [26]
25 Apigenin-7-O-rutinoside 12.58 577 269, 307 269, 225, 201, 181, 149 x x [4,22]
26 Apigenin 13.02 269 269, 225, 149, 201, 183 181, 197, 169, 224 x x [4,22]
27 Hispidulin-rutinoside 13.21 607 299, 284, 269, 323 284 x - [3,27]
28 Hesperetin 13.41 301 286, 242, 257, 283, 125 258, 242, 199, 174, 215 x x [28]
29 5,6,7,10-tetrahydro-7-hydroxy rosmariquinone derivative 14.88 345 301 301, 258, 283, 273, 217 x x [14]
30 Cirsimaritin 14.98 313 298 283, 297, 269 x x [4,12]
31 Carnosol methyl ether isomer 15.35 343 328, 299 313, 299, 285 x x [14]
32 Rosmanol 15.46 345 283, 301, 327 268, 240, 227, 265, 239 x x Std
33 Rosmadial isomer or rosmanol quinone 15.97 343 299, 315 284, 243, 213, 256, 281 x x [3,4,13]
34 Rosmanol isomer (epirosmanol) 16.22 345 283, 301, 327 268, 227, 240, 239, 265 x x [3]
35 Carnosol quinone 16.27 327 299, 258 284, 271 x x [29]
36 Isosakuranetin 16.44 285 270, 229, 214, 201, 242 x x [25]
37 Genkwanin 16.45 283 268 268 x x [3,4]
38 Carnosic acid hexoside 16.76 493 331, 373, 313, 179 287, 244 x x Std
39 Rosmanol isomer (epiisorosmanol) 17.18 345 301 301, 286 x x [12]
40 5,6,7,10-tetrahydro-7-hydroxy rosmariquinone derivative 17.41 345 301 301, 258, 283, 273, 217 x x [14]
41 Carnosol methyl ether isomer 17.78 343 299, 328, 285, 343, 315 284, 243, 281, 299, 256 x x [14]
42 Carnosol methyl ether isomer 17.99 343 328, 313, 343, 299, 285 313, 300, 285, 257 x x [14]
43 Carnosic acid derivative 18.15 455 331, 287 287, 244 x x Std
44 Rosmanol methyl ether 18.59 359 283, 329, 300 268, 240, 227, 265, 239 x - [14]
45 Rosmadial or rosmanol quinone 18.62 343 299 243, 216, 284 x x [14]
46 Epiisorosmanol methyl ether 18.79 359 315 300 x - [14]
47 Rosmanol methyl ether isomer 18.96 359 283, 329, 300 268, 240, 227, 265, 239 x x [14]
48 Carnosol 19.07 329 285 270, 285, 269, 201, 214 x x Std
49 Carnosic acid quinone 19.51 329 285 270, 285, 201, 227 x x [30]
50 4′-Methoxytectochrysin 19.76 297 282, 269, 297, 254 267, 281, 238 x x [20]
51 Rosmadial 19.87 343 315, 299 287, 269, 297 x x [3,4,13]
52 Rosmaridiphenol 20.09 315 285, 179, 135 285, 214, 201, 270 x x [3,31]
53 5,6,7,10-tetrahydro-7-hydroxy rosmariquinone 20.37 301 258, 283, 273, 217, 233 243, 257, 188, 215, 162 x x [14]
54 Carnosic acid 20.85 331 287 287, 244, 272, 217 x x Std
55 12-O-Methylcarnosic acid 21.87 345 301, 286 286 x x Std
56 Carnosol isomer 21.88 329 329, 314, 299, 285 x x [31]
57 Betulinic acid 23.71 455.5 327, 317, 353, 409, 437 x x Std

a Fragment ions are listed in order of relative abundance; b MS2 ions in bold were those subjected to MS3 fragmentation; c Exp. 1, detected under experimental condition 1 (carnosol), Exp. 2, experimental condition 2 (rosmarinic acid); d Ident., identification mode: [Reference] or Std (standard, compound identified by comparison of its retention time and MS data with that of a reference compound). Some compounds were defined as “derivatives” since parts of their spectra match those of their corresponding parent compounds but they cannot be fully elucidated.