Table 2 Identification of chemical constituents of YLTZC by UPLC-Q–TOF–MS/MS.

N1

1.85

Gallic acid*

C₇H₆O₅

169.014 1 [M − H]⁻

− 0.8

125.024 6 [M − H-CO₂]⁻

B/D

^23,24

N2

2.97

Protocatechuic acid*

C₇H₆O₄

153.018 9 [M − H]⁻

− 2.7

109.028 5 [M − H-CO₂]⁻, 91.018 9 [M − H-CO₂-H₂O]⁻

A/D

^23,24

N3

4.54

4-Hydroxycinnamic acid

C₉H₈O₃

163.040 1 [M − H]⁻

0

119.050 1 [M − H-CO₂]⁻

B/D

²⁴

N4

4.82

Vanillic acid

C₈H₈O₄

169.049 9 [M + H]⁺

2.2

151.041 4 [M + H-H₂O]⁺, 123.045 2 [M + H-H₂O-CO]⁺

B

³²

N5

5.28

Vicenin-2*

C₂₇H₃₀O₁₅

593.148 9 [M − H]⁻

− 3.9

473.105 3 [M − H-C₄H₈O₄]⁻, 383.073 8 [M − H-C₄H₈O₄-C₃H₆O₃]⁻, 353.063 4 [M − H-2C₄H₈O₄]⁻

A

²¹

N6

6.68

Kaempferol-3-O-rutinoside

C₂₇H₃₀O₁₅

595.167 1 [M + H]⁺

2.3

287.056 3 [M + H-Rha-Glc]⁺

B/C

²³

N7

6.72

Kaempferol-3-O-(2″,6″-dirhamnosyl)-glucoside

C₃₃H₄₀O₁₉

739.205 8 [M − H]⁻

− 4.5

285.039 1 [C₁₅H₁₀O₁₆]⁻, 284.032 5 [C₁₅H₁₀O₁₆-H]⁻

C

²²

N8

7.00

Quercetin

C₁₅H₁₀O₇

303.049 7 [M + H]⁺

− 0.7

257.045 5 [M + H-H₂O-CO]⁺, 213.057 1 [M + H-2CO-H₂O-O]⁺, 166.027 2 [M + H–CO-C₆H₅O₂]⁺

B/D

²⁴

N9

7.02

Rutin*

C₂₇H₃₀O₁₆

611.160 2 [M + H]⁺

− 0.8

303.048 2[M + H-Rha-Glc]⁺

B/D

²³

N10

7.41

Isoquercitrin

C₂₁H₂₀O₁₂

463.086 4 [M − H]⁻

− 3.9

301.034 8 [M − H-Glc]⁻

C/D

²⁴

N11

7.61

Ginkgolide J

C₂₀H₂₄O₁₀

425.144 7 [M + H]⁺

− 2.0

407.136 8 [M + H-H₂O]⁺, 363.144 9 [M + H-H₂O-CO₂]⁺

B

²³

N12

7.66

Neoeriocitrin

C₂₇H₃₂O₁₅

595.164 4 [M − H]⁻

− 4

459.112 3 [M − H-C₈H₈O₂]⁻, 287.055 7 [M − H-Rha-Glc]⁻, 151.003 1 [M − H-Rha-Glc-C₆H₄O₂-CO]⁻

A

²¹

N13

7.89

Ferulic acid*

C₁₀H₁₀O₄

193.050 4 [M − H]⁻

− 1.2

178.026 4 [M − H-CH₃]⁻, 134.037 4 [M − H-CH₃-CO₂]⁻

B/D

²⁴

N14

7.92

Ginkgolide C

C₂₀H₂₄O₁₁

439.123 3 [M − H]⁻

− 2.9

383.133 0 [M − H-2CO]⁻, 365.124 4 [M − H-2CO-H₂O]⁻, 321.134 2 [M − H-2CO-H₂O-CO₂]⁻, 303.123 5 [M − H-2CO-H₂O-CO₂-H₂O]⁻, 277.145 0 [M − H-2CO-H₂O-2CO₂]⁻, 259.133 8 [M − H-2CO-H₂O-2CO₂-H₂O]⁻

B

²³

N15

8.06

Quercetin-3-O-rutinoside

C₂₇H₃₀O₁₆

609.043 6 [M − H]⁻

− 4.1

300.026 5 [M − H-Rha-Glc]⁻, 271.024 2 [M − H-Rha-Glc-CO]⁻, 255.029 2 [M − H-Rha-Glc-CO-O]⁻

C

²³

N16

8.13

Kaempferol-3-O-(2″-β-D-glucopyranosyl)-α-L-rhamnoside

C₂₇H₃₀O₁₅

595.166 1 [M + H]⁺

0.6

449.107 3 [M + H-Rha]⁺, 287.055 3 [M + H-Rha-Glc]⁺

B

²³

N17

8.57

Kaempferol-4′-O-glucoside

C₂₁H₂₀O₁₁

447.092 2 [M − H]⁻

− 2.4

285.040 2[M − H-Glc]⁻

C

²²

N18

8.98

Rhoifolin

C₂₇H₃₀O₁₄

579.170 2 [M + H]⁺

− 1.1

433.113 9 [M + H-Rha]⁺, 271.058 7 [M + H-Rha-Glc]⁺

A

²¹

N19

9.01

Naringin*

C₂₇H₃₂O₁₄

581.186 0 [M + H]⁺

− 0.9

315.086 5 [M + H-Rha-C₈H₈O]⁺, 273.074 3 [M + H-Rha-Glc]⁺, 153.018 6 [M + H-Rha-Glc-C₈H₈O]⁺

A/D

²¹

N20

10.66

Meranzin

C₁₅H₁₆O₄

261.111 7 [M + H]⁺

− 1.7

189.053 7 [M + H-C₄H₈O]⁺, 159.044 5 [M + H-C₄H₈O-CH₂O]⁺, 131.048 7 [M + H-C₄H₈O-CH₂O-CO]⁺

A

³³

N21

11.22

Isorhamnetin-3-O-rutinoside

C₂₈H₃₂O₁₆

625.174 4 [M + H]⁺

− 3.1

479.118 7 [M + H-Rha]⁺, 317.064 1 [M + H-Rha-Glc]⁺

B/C

²³

N22

11.47

Ginkgolide A*

C₂₀H₂₄O₉

409.148 1 [M + H]⁺

− 3.0

391.139 9 [M + H-H₂O]⁺, 373.130 0 [M + H-2H₂O]⁺, 355.119 1 [M + H-3H₂O]⁺, 345.134 8 [M + H-2H₂O-CO]⁺, 327.124 6 [M + H-3H₂O-CO]⁺

B

²³

407.134 1 [M − H]⁻

− 1.6

351.143 6 [M − H-2CO]⁻, 333.132 1 [M − H-2CO-H₂O]⁻, 319.144 0 [M − H-2CO₂]⁻, 307.160 3 [M − H-2CO-CO₂]⁻, 289.143 3 [M − H-2CO-CO₂-H₂O]⁻, 273.148 1 [M − H-2CO₂-CO-H₂O]⁻, 245.154 0 [M − H-2CO-H₂O-2CO₂]⁻

N23

11.48

Ginkgolide B*

C₂₀H₂₄O₁₀

425.144 0 [M + H]⁺

− 0.5

407.134 3 [M + H-H₂O]⁺, 389.124 4 [M + H-2H₂O]⁺, 371.113 2 [M + H-3H₂O]⁺, 361.129 4 [M + H-2H₂O-CO]⁺, 343.119 0 [M + H-3H₂O-CO]⁺

B

²³

N24

11.92

Luteolin*

C₁₅H₁₀O₆

287.055 5 [M + H]⁺

1.8

153.019 1 [M + H-C₈H₆O₂]⁺

B

²⁴

N25

11.94

Morin

C₁₅H₁₀O₇

301.033 9 [M − H]⁻

− 4.9

273.040 1[M − H-CO]⁻, 178.998 2, 151.002 9

D

³¹

N26

12.06

Oxypeucedanin hydrate

C₁₆H₁₆O₆

305.102 2 [M + H]⁺

0.6

203.034 4 [M + H-C₅H₁₀O₂]⁺, 175.039 8 [M + H-C₅H₁₀O₂-CO]⁺, 159.045 2 [M + H-C₅H₁₀O₂-CO-O]⁺, 147.044 7 [M + H-C₅H₁₀O₂-2CO]⁺, 131.049 9 [M + H-C₅H₁₀O₂-2CO-O]⁺

A

³³

N27

12.92

Quercetin-3-methyl ether

C₁₆H₁₂O₇

315.049 6 [M − H]⁻

− 4.5

300.025 3 [M − H-CH₃]⁻, 271.023 2 [M − H-CH₃-CO]⁻

D

²⁴

N28

14.11

Naringenin*

C₁₅H₁₂O₅

273.075 6 [M + H]⁺

− 0.5

153.018 3 [M + H-C₈H₈O]⁺, 147.044 5 [M + H-C₆H₆O₃]⁺

A/D

²¹

N29

14.12

Apigenin

C₁₅H₁₀O₅

269.044 6 [M − H]⁻

− 3.6

251.036 0 [M − H-H₂O]⁻, 225.055 1 [M − H-CO₂]⁻, 151.003 5 [M − H-C₈H₆O]⁻, 117.033 9 [M − H-C₇H₄O₄]⁻

A/B/D

²⁴

N30

14.28

Pinobanksin

C₁₅H₁₂O₅

271.059 9 [M − H]⁻

− 5

253.048 8 [M − H-H₂O]⁻, 225.055 3 [M − H-H₂O-CO]⁻

D

²⁴

N31

14.42

Kaempferol

C₁₅H₁₀O₆

287.055 6 [M + H]⁺

2.1

259.061 0 [M + H–CO]⁺, 231.066 4 [M + H-2CO]⁺

A/B/D

²⁴

N32

14.88

Isorhamnetin

C₁₆H₁₂O₇

315.049 8 [M − H]⁻

− 3.9

300.025 8 [M − H-CH₃]⁻

B/D

²⁴

N33

15.38

Luteolin-methyl-ether

C₁₆H₁₂O₆

299.054 8 [M − H]⁻

− 4.4

284.030 3 [M − H-CH₃]⁻, 255.028 2

D

³⁰

N34

15.46

Kaempferide

C₁₆H₁₂O₆

301.069 3 [M + H]⁺

− 4.5

286.046 1 [M + H-CH₃]⁺, 258.052 7 [M + H-CH₃-CO]⁺

D

²⁴

N35

15.87

Quercetin-dimethyl-ether

C₁₇H₁₄O₇

329.065 4 [M − H]⁻

− 3.9

314.040 8 [M − H-CH₃]⁺, 299.018 0 [M − H-2CH₃]⁺

D

²⁴

N36

16.99

Galangin-5-methyl-ether

C₁₆H₁₂O₅

283.059 9 [M − H]⁻

− 4.6

268.036 4 [M − H-CH₃]⁺, 239.033 2 [M − H-CH₃-CO₂]⁺

D

³⁰

N37

17.10

Biochanin A

C₁₆H₁₂O₅

285.074 8 [M + H]⁺

− 3.3

270.051 0 [M + H-CH₃]⁺, 242.057 4 [M + H-CH₃-CO]⁺

D

²⁹

N38

17.32

Isomeranzin*

C₁₅H₁₆O₄

261.111 3 [M + H]⁺

− 3.2

189.053 9 [M + H-C₄H₈O]⁺, 159.044 8 [M + H-C₄H₈O-CH₂O]⁺, 131.049 1 [M + H-C₄H₈O-CH₂O-CO]⁺

A

³³

N39

18.08

Limonin*

C₂₆H₃₀O₈

469.186 3 [M − H]⁻

− 1

423.190 8 [M − H-CO₂-H₂O]⁻

A

³³

N40

18.34

Quercetin-dimethyl-ether

C₁₇H₁₄O₇

329.065 5 [M − H]⁻

− 3.7

314.039 9 [M − H-CH₃]⁺, 299.016 6 [M − H-2CH₃]⁺, 271.022 4 [M − H-2CH₃-CO]⁺

D

²⁴

N41

18.69

Gypenoside XVII

C₄₈H₈₂O₁₈

991.545 4 [M + HCOO]⁻

− 2.9

945.539 7 [M − H]⁻

C

²²

N42

19.20

Chrysin*

C₁₅H₁₀O₄

253.049 6 [M − H]⁻

− 3.9

209.059 2 [M − H-CO₂]⁻, 143.049 0 [M − H-C₃O₂-C₂H₂O]⁻

D

²⁴

255.064 3 [M + H]⁺

− 3.6

153.017 4

N43

19.58

Caffeic acid benzyl ester

C₁₆H₁₄O₄

269.081 9 [M − H]⁻

− 2.4

178.026 7 [M − H-C₇H₇]⁻, 134.037 0 [M − H-C₇H₇-CO₂]⁻

D

²⁴

N44

19.73

Pinocembrin*

C₁₅H₁₂O₄

255.065 3 [M − H]⁻

− 3.8

213.053 8 [M − H-C₂H₂O]⁻, 151.002 5

D

²⁴

257.080 7 [M + H]⁺

− 0.7

153.017 3

N45

19.78

Methoxy-chrysin

C₁₆H₁₂O₅

283.059 9 [M − H]⁻

− 4.6

268.034 9 [M-CH₃]⁻, 239.032 4 [M − H-CO₂]⁻

D

²⁴

N46

19.95

Galangin

C₁₅H₁₀O₅

269.044 3 [M − H]⁻

− 4.6

252.042 1 [M − H-H₂O]⁻, 241.049 6 [M − H –CO]⁻, 213.054 7 [M − H-2CO]⁻

D

²⁴

271.059 8 [M + H]⁺

− 1.3

153.017 7

N47

20.38

Pinobanksin-3-O-acetate

C₁₇H₁₄O₆

313.070 5 [M − H]⁻

− 4.0

253.047 6 [M-C₂H₃O-H₂O]⁻, 209.060 2 [M-C₂H₃O-H₂O-CO₂]⁻

D

²⁴

N48

20.57

3β,12β-20(S)-Trihydroxydammar-24-ene-3-O-β-D-glucopyranosyl-20-O-[β-D-6-O-acetylglucopyranosyl-(1–2)-β-D-glucopyranoside]

C₅₀H₈₄O₁₉

1033.556 0 [M + HCOO]⁻

− 2.8

987.551 5 [M − H]⁻, 945.538 6 [M − H-C₂H₂O]⁻

C

²²

N49

20.64

Phenethyl caffeate

C₁₇H₁₆O₄

283.096 6 [M − H]⁻

− 3.5

179.033 6 [M-C₈H₉]⁻, 135.043 8 [M-C₈H₉-CO₂]⁻

D

²⁴

N50

20.90

Acacetin

C₁₆H₁₂O₅

283.060 0 [M − H]⁻

− 4.1

268.034 9[M − H-CH₃]⁻, 239.032 3 [M − H-CH₃-CO]⁻, 211.037 5

D

²⁸

N51

21.38

Eupatilin

C₁₈H₁₆O₇

343.081 9 [M − H]⁻

− 1.4

328.057 0 [M − H-CH₃]⁻, 313.034 1 [M − H-2CH₃]⁻, 285.039 3 [M − H-2CH₃-CO]⁻

D

²⁸

N52

21.54

Asiatic acid

C₃₀H₄₈O₅

487.342 2 [M − H]⁻

− 1.5

423.030 2 [M − H CO₂H-H₂O-H]⁻

D

²⁷

N53

21.72

Gypenoside LXXIV

C₄₂H₇₂O₁₄

845.489 4 [M + HCOO]⁻

− 1.2

799.482 6 [M − H]⁻, 637.431 1 [M − H-Glc]⁻, 475.379 9 [M − H-2Glc]⁻

C

²²

N54

22.19

Caffeic acid cinnamyl ester

C₁₈H₁₆O₄

295.096 3 [M − H]⁻

− 4.3

178.026 2 [M − H-C₉H₉]⁻, 134.035 9 [M − H-C₉H₉-CO₂]⁻

D

²⁴

N55

22.67

Pinobanksin-3-O-propionate

C₁₈H₁₆O₆

327.085 9 [M − H]⁻

− 4.6

253.047 9 [M-C₃H₅O-H₂O]⁻, 209.060 2 [M-C₃H₅O-H₂O-CO₂]⁻, 185.060 5 [M-C₃H₅O-H₂O-C₃O₂]⁻, 181.065 8 [M-C₃H₅O-H₂O-CO₂-CO]⁻, 165.070 9 [M-C₃H₅O-H₂O-2CO₂]⁻

D

²⁴

N56

23.13

Ginsenoside-F₂

C₄₂H₇₂O₁₃

829.492 8 [M + HCOO]⁻

− 3.2

783.488 2 [M − H]⁻, 621.438 0 [M − H-Glc]⁻, 459.382 0 [M − H-2Glc]⁻

C

²²

N57

23.44

Ginsenoside Rg3

C₄₂H₇₂O₁₃

829.492 5 [M + HCOO]⁻

− 3.6

783.486 5 [M − H]⁻, 621.434 6 [M − H-Glc]⁻, 459.386 3 [M − H-2Glc]⁻

C

²⁶

N58

24.61

Pinobanksin-3-O-butyrate

C₁₉H₁₈O₆

341.101 9 [M − H]⁻

− 3.4

253.048 1 [M-C₄H₇O-H₂O]⁻, 209.060 6 [M-C₄H₇O-H₂O-CO₂]⁻, 143.050 1 [M-C₄H₇O-H₂O-C₃O₂-C₂H₂O]⁻

D

²⁴

N59

24.72

Chrysin-5-methyl-ether

C₁₆H₁₂O₄

269.079 9 [M + H]⁺

− 3.5

254.056 8 [M + H-CH₃]⁺, 226.061 2

D

²⁴

N60

24.78

Pinobanksin-3-O-pentenoate

C₂₀H₁₈O₆

353.101 4 [M − H]⁻

− 4.7

271.060 4 [M-C₅H₇O]⁻, 253.048 6 [M-C₅H₇O-H₂O]⁻

D

²⁴

N61

25.00

Damulin B

C₄₂H₇₀O₁₃

827.476 1 [M + HCOO]⁻

− 4.5

781.475 9 [M − H]⁻, 619.425 1 [M − H-Glc]⁻

C

²²

N62

26.32

Pinobanksin-3-O-pentenoateor-2-methylbutyrate

C₂₀H₂₀O₆

355.117 3 [M − H]⁻

− 4.0

253.047 8 [M-C₅H₉O-H₂O]⁻

D

²⁴

N63

26.62

Pinobanksin-3-O-hexenoate

C₂₁H₂₀O₆

367.117 0 [M − H]⁻

− 4.7

271.060 2 [M-C₆H₉O]⁻, 253.049 3 [M-C₆H₉O-H₂O]⁻

D

²⁴

N64

26.87

Pinobanksin-3-O-phenylpropionate

C₂₄H₂₀O₆

403.116 8 [M − H]⁻

− 4.7

253.049 4 [M-C₉H₉O-H₂O]⁻

D

²⁴

N65

27.84

Pinobanksin-3-O-hexanoate

C₂₁H₂₂O₆

369.132 6 [M − H]⁻

− 4.8

253.048 3 [M-C₆H₁₁O-H₂O]⁻

D

²⁴

N66

29.99

Auraptene

C₁₉H₂₂O₃

299.164 7 [M + H]⁺

1.8

163.040 0 [M + H-C₁₀H₁₆]⁺, 145.103 8 [M + H-C₁₀H₁₆-H₂O]⁺, 135.042 6 [M + H-C₁₀H₁₆-CO]⁺, 107.050 0 [M + H − C₁₀H₁₆ − 2CO]⁺

A

³³