International Journal of Analytical Chemistry

Research Article

Comprehensive Screening and Identification of Phillyrin Metabolites in Rats Based on UHPLC-Q-Exactive Mass Spectrometry Combined with Multi-Channel Data Mining

Table 1

Summary of phillyrin metabolites in rat urine, plasma, and feces.

Peak

Ionization mode

t_R/min

Formula

Theoretical Mass m/z

Experimental Mass m/z

Error (ppm)

MS/MS fragment ions

Identification

Reported/New

6.60

C₂₈H₃₅O₁₃

579.2072

579.2086

2.32

MS²(579):371(100), 356(31), 372(31), 357(20)341(19), 327(17), 113(8), 122(6), 311(6), 137(4)

Reported

6.60

C₂₇H₃₄O₁₁Na

557.1993

557.1988

−0.97

MS²(557):557(100), 373(56), 357(41), 343(37)371(26), 287(24), 359(18), 369(13), 313(10), 331(7), 179(6), 139(5)

1.61

C₁₉H₁₂ON₃

298.0962

298.0967

−2.81

MS²(298):136(100), 61(7), 137(5), 145(5), 97(4), 163(3)

−

New

2.49

C₁₇H₁₅O₆

315.0865

315.0837

−8.27

MS²(315):150(100), 193(58), 283(49), 151(42)137(29), 182(28), 225(24), 183(23), 192(13), 124(12)

−

New

3.97

C₁₈H₁₉O₇

347.1126

347.1138

3.66

MS²(347):163(100), 137(41), 165(39), 123(38)151(37), 181(28), 347(18), 193(17), 175(15), 161(10)

−

New

4.27

C₁₈H₁₉O₇

347.1126

347.1141

4.44

MS²(347):137(100), 317(26), 347(25), 209(18)139(16), 123(15), 151(13), 163(12), 191(12), 109(10)

−

New

4.58

C₁₈H₁₉O₇

347.1126

347.1140

4.18

MS²(347):123(100), 317(94), 193(52), 163(40)165(40), 137(39), 151(28), 318(20), 181(18), 299(17), 347(13), 139(12)

−

New

4.75

C₂₀H₂₅O₈

393.1543

393.1511

−8.33

MS²(393):300(100), 216(95), 240(19), 301(18)393(14), 217(12)

−

New

4.84

C₁₆H₂₅O₁₀

377.1953

377.1448

1.56

MS²(377):243(100), 377(50), 244(14), 378(12)99(9), 69(7), 359(6), 172(2), 73(2)

−

New

4.91

C₁₈H₁₉O₆

331.1177

331.1190

4.24

MS²(331):331(100), 301(86), 123(41), 333(34)332(23), 302(20), 153(18), 177(14), 275(14), 303(9), 109(6)

−

Reported

4.92

C₁₈H₂₁O₆

333.1332

333.1330

−0.71

MS²(333):123(100), 297(27), 161(19), 149(19)137(18), 175(13), 279(11), 187(11)

4.95

C₁₈H₂₁O₅

317.1384

0.16

MS²(317):123(100), 175(73), 149(31), 163(19)299(19), 137(16), 193(4), 133(3)

−

New

M10

4.96

C₁₈H₂₁O₆

333.1327

333.1348

4.52

MS²(333):333(100), 275(28), 334(22), 123(20)303(13), 285(8), 273(3)

−

Reported

M11

5.08

C₁₈H₁₉O₆

331.1177

331.1191

4.61

MS²(331):331(100), 301(42), 333(32), 123(23)332(22), 303(3), 109(3)

−

Reported

M12

5.15

C₁₈H₁₇O₇

345.0968

345.0983

4.20

MS²(345):285(100), 345(42), 286(18), 315(16)109(14), 175(14), 137(12), 346(11)

−

Reported

M13

5.30

C₁₉H₁₉O₈

375.1074

375.1088

3.70

MS²(375):329(100), 330(22), 331(2), 287(1), 137(1), 347(1)

−

New

M14

5.54

C₁₈H₁₇O₉S

409.0588

409.0601

3.28

MS²(409):329(100), 409(57), 137(30), 330(22)80(15), 410(14)

−

New

M15

5.62

C₂₀H₂₁O₅

341.1384

341.1381

−0.76

MS²(341):137(100), 291(65), 271(61), 163(45), 263(26), 187(25), 323(22), 175(19), 283(17), 153(14), 308(14), 217(14), 279(11)

−

New

M16

5.69

C₁₈H₁₇O₉S

409.0588

409.0602

3.35

MS²(409):329(100), 409(61), 137(31), 330(23), 80(17), 410(15)

−

New

M17

5.76

C₂₅H₂₇O₁₂

519.1498

519.1508

2.04

MS²(519):113(100), 343(72), 85(46), 59(26), 99(19), 75(19), 95(18), 175(17), 344(15), 71(15), 117(14), 519(13)

−

New

M18

5.92

C₁₈H₁₇O₆

329.1021

329.1031

3.33

MS²(329):137(100), 329(19), 138(8), 159(7), 109(6), 163(1)

−

New

5.74

C₁₈H₁₉O₆

331.1178

331.1177

0.29

MS²(329):149(100), 123(21), 295(13), 150(10)165(10)

M19

5.93

C₁₉H₁₉O₈

375.1074

375.1085

2.79

MS²(375):329(100), 137(63), 330(22), 189(6), 159(5), 109(4), 123(2)

−

New

M20

5.93

C₁₈H₁₅O₄

295.0964

295.0960

−1.51

MS²(295):277(100), 249(54), 295(48), 241(27)231(24), 259(19), 185(17), 213(14), 280(12), 250(11), 221(5), 186(4)

−

New

M21

5.94

C₁₈H₁₇O₅

313.1070

313.1065

−1.73

MS²(313):123(100), 277(98), 243(69), 249(48)173(44), 225(36), 295(34), 161(23), 175(16), 231(14), 283(13), 265(12), 250(12)

−

New

M22

5.96

C₂₅H₂₇O₁₂

519.1498

519.1508

2.15

MS²(301):113(100), 343(85), 85(41), 151(22), 59(21), 95(20), 344(20), 99(19), 75(17), 175(16), 71(16), 117(11), 97(10)

−

New

M23

5.98

C₂₁H₂₁O₉

417.1179

417.1195

3.67

MS²(417):113(100), 85(48), 241(40), 59(27), 99(25), 75(20), 95(19), 121(17), 117(11), 71(10), 175(9)

−

New

M24

6.14

C₂₀H₂₁O₉S

437.0901

437.0912

2.54

MS²(437):151(100), 357(71), 80(66), 437(55), 358(18), 438(16), 342(12)

−

Reported

M25

6.16

C₂₀H₂₁O₁₀S

453.0850

453.0862

2.62

MS²(453):373(100), 374(26), 453(10), 189(8), 97(6), 80(2)

−

Reported

M26

6.21

C₂₀H₂₁O₅

341.1384

341.1379

−1.29

MS²(341):137(100), 291(75), 271(54), 187(35)239(31), 263(30), 323(29), 175(22), 189(19), 283(18), 217(15), 279(14), 308(14), 311(10)

−

New

M27

6.31

C₂₀H₂₁O₆

357.1332

357.1328

−1.19

MS²(357):123(100), 151(21), 165(19), 357(11), 327(10)

−

Reported

M28

6.32

C₂₀H₂₁O₉S

437.0901

437.0913

2.75

MS²(437):357(100), 80(75), 437(62), 342(33), 151(3), 137(1)

−

Reported

M29

6.38

C₂₀H₂₁O₅

341.1384

341.1379

−1.29

MS²(341):137(100), 291(65), 271(57), 187(34)239(30), 263(24), 323(22), 283(18), 308(14), 217(14), 272(12), 231(12), 259(10)

−

New

M30

6.54

C₂₀H₂₁O₆

357.1332

357.1322

−2.90

MS²(357):151(100), 137(76), 285(66), 201(40)305(36), 254(26), 270(24), 307(23), 297(21), 322(20), 231(18), 338(18), 189(18), 291(17)

−

Reported

M31

6.55

C₂₀H₂₁O₅

341.1384

341.1379

−1.47

MS²(341):271(100), 123(96), 292(78), 151(72)201(55), 308(47), 323(44), 305(40), 161(37), 240(35), 256(31), 283(24), 311(22), 277(17)

−

New

M32

6.58

C₂₆H₂₉O₁₂

533.1652

533.1665

2.15

MS²(533):357(100), 113(84), 85(41), 358(24), 59(22), 71(19), 75(17), 95(16), 99(15), 175(12), 97(12)

−

Reported

M33

6.59

C₂₄H₃₀O₈NS

492.1687

492.1680

−1.35

MS²(492):88(100), 151(99), 355(37), 474(35), 323(34), 254(33), 189(32), 336(20), 177(17), 193(15), 369(14), 169(14), 149(13), 181(12)

−

Reported

M34

6.65

C₂₀H₂₃O₆

359.1490

359.1501

3.16

MS²(359):359(100), 360(25), 192(16), 178(14)344(12), 122(8), 284(3)

−

Reported

M35

6.69

C₁₈H₁₇O₇S

377.0689

377.0703

3.69

MS²(377):297(100), 377(54), 298(23), 378(12)107(2), 189(2), 80(1)

−

New

M36

6.76

C₂₇H₃₁O₁₂

547.1809

547.1822

2.17

MS²(547):113(100), 371(60), 85(59), 59(44), 356(38), 95(23), 117(16)87(14), 372(13), 129(13), 357(10), 175(7)

−

Reported

M37

6.77

C₁₆H₁₃O₅

285.0759

285.0754

−1.30

MS²(285):285(100), 286(20), 85(4), 270(3), 161(1)

−

New

M38

6.79

C₂₁H₂₃O₅

355.1541

355.1535

−1.41

MS²(355):137(100), 284(97), 151(74), 306(69)305(57), 201(47), 322(39), 254(37), 270(36), 337(34), 175(30), 297(24), 231(21), 189(19)

−

New

M39

6.79

C₁₉H₁₉O₆

343.1177

343.1188

3.57

MS²(343):343(100), 109(71), 137(43), 344(24)151(13), 123(4)

−

Reported

M40

6.87

C₁₆H₁₃O₇

317.0657

317.0653

−1.04

MS²(317):317(100), 318(21), 302(10), 133(2), 121(1), 109(1)

−

New

M41

6.88

C₂₀H₂₁O₉S

437.0901

437.0913

2.88

MS²(437):357(100), 437(31), 80(19), 97(6), 137(1), 151(1)

−

Reported

M42

6.92

C₂₁H₂₃O₉S

451.1057

451.1073

3.42

MS²(451):371(100), 80(81), 451(49), 356(45), 372(24), 452(14), 357(10), 97(9)

Reported

M43

6.93

C₂₁H₂₃O₆

371.1489

371.1485

−1.12

MS²(371):137(100), 151(15), 165(13), 341(9), 189(5), 353(5)

−

Reported

M44

7.05

C₁₉H₂₁N₄

305.1772

305.1779

5.95

MS²(305):205(100), 223(76), 163(44), 177(31)187(23), 121(20), 149(18), 93(16), 153(16), 206(14), 95(14), 167(14), 224(14), 107(13)

−

New

M45

7.38

C₁₅H₁₁O₅

271.0602

271.0615

5.02

MS²(271):165(100), 271(56), 272(11), 166(10)

−

New

7.36

C₁₅H₁₃O₅

273.0759

273.0756

−0.70

MS²(273):123(100), 273(58), 179(55), 255(36), 151(32), 107(29), 227(15), 274(12), 153(11)

M46

7.44

C₂₀H₂₁O₅

341.1384

341.1382

−0.41

MS²(341):123(100), 271(92), 292(78), 151(71)270(58), 323(51), 240(38), 161(37), 256(36), 311(34), 283(29), 291(28), 253(26), 277(21)

−

New

M47

7.47

C₂₀H₂₁O₆

357.1332

357.1347

3.94

MS²(357):357(100), 176(25), 358(24), 151(14)342(10), 137(9), 123(8), 177(4), 191(2)

−

New

M48

7.54

C₁₇H₁₅O₇

331.0811

−0.54

MS²(341):331(100), 332(22), 316(8), 315(6), 175(2), 122(2), 162(1), 109(1)

−

New

M49

7.61

C₁₄H₂₃O₅

271.1329

271.1553

4.68

MS²(271):227(100), 271(30), 209(25), 211(24), 228(16), 151(8), 165(5)

−

New

M50

7.63

C₁₆H₂₃O

231.1404

231.1743

−0.35

MS²(231):135(100), 69(96), 61(57)153(46), 97(41), 107(34), 95(30), 93(29), 83(27), 81(22), 111(22), 109(16), 111(13), 57(10), 136(10)

−

New

M51

7.83

C₁₈H₁₇O₃

281.1173

281.1166

−2.07

MS²(281):133(100), 263(20), 281(11), 134(10), 149(10), 245(6), 107(6), 235(2)

−

Reported

M52

8.34

C₂₁H₂₅O₆

373.1646

373.1633

−3.47

MS²(373):355(100), 159(51), 161(45), 173(28)337(24), 137(18), 95(17), 121(17), 175(16), 145(16), 149(16), 109(16), 207(15)

−

Reported

M53

8.39

C₁₈H₁₉O₅

315.1227

315.1198

−9.27

MS²(315):167(100), 189(49), 315(41), 85(38), 109(12), 168(10), 255(4)

−

Reported

M54

8.44

C₂₁H₂₃O₅

355.1541

355.1537

−0.96

MS²(355):284(100), 137(96), 151(82), 201(50)337(38), 175(37), 270(36), 297(35), 254(33), 322(32), 189(23), 179(22), 231(20), 310(19)

−

New

M55

8.49

C₁₇H₂₁O₃

273.1486

273.1487

0.80

MS²(273):273(100), 274(14), 117(11), 228(6), 137(6), 229(4), 95(2), 179(1)

−

New

M56

9.55

C₂₆H₃₅O₁₀

507.2225

507.2236

2.28

MS²(507):287(100), 331(34), 113(29), 288(22)507(21), 75(17), 463(14)

−

New

M57

9.65

C₂₀H₂₁O₇

373.1281

373.1278

−0.99

MS²(373):343(100), 373(70), 115(62), 358(42)344(21), 374(17), 325(8), 141(2), 297(2)

−

New

M58

9.90

C₁₅H₁₇O₄

261.1146

261.1132

4.15

MS²(261):261(100), 235(70), 217(59), 262(20)236(11)

−

New

M59

26.48

C₁₅H₃₁O₈

339.2035

339.2001

−3.67

MS²(339):339(100), 330(23), 341(3), 62(1)

−

New

Note: t_R: retention time; U: urine; P: plasma; F: feces; +: detected; −: undetected.