Table 2 Metabolites identified in different organs of S. marianum extracts using UPLC-MS in negative ionization mode

1

1.36

331.25

C13H16O10

169.11, 125.11

Gallic acid hexoside

Phenolic acid glycoside

Li et al. 2003 [53]

2

1.57

327.26

C14H16O9

312.23, 192.13, 164.12

Bergenin

Phenolic acid glycoside

Li et al. 2013 [54]

3

1.69

341.29

C15H18O9

179.15, 135.15

Caffeic acid-O-hexoside

Phenolic acid glycoside

Singh et al. 2016 [55]

4

1.81

191.16

C7H12O6

147.16

Quinic acid

Phenolic acid

Haşimi et al. 2017 [56]

5

2.01

153.11

C7H6O4

109.11

Protocatechuic acid

Phenolic acid

Haşimi et al. 2017 [56]

6

2.32

167.14

C8H8O4

152.11, 123.14

Vanillic acid

Phenolic acid

Haşimi et al. 2017 [56]

7

2.48

197.17

C9H10O5

182.14, 153.17

Syringic acid

Phenolic acid

Haşimi et al. 2017 [56]

8

2.66

179.15

C9H8O4

135.15

Caffeic acid^a

Phenolic acid

Haşimi et al. 2017 [56]

9

7.91

163.15

C9H8O3

119.15

p-Coumaric acid

Phenolic acid

Haşimi et al. 2017 [56]

10

8.70

193.18

C10H10O4

178.15, 149.18

Ferulic acid

Phenolic acid

Haşimi et al. 2017 [56]

11

9.98

147.15

C9H8O2

103.15

Cinnamic acid

Unsaturated carboxylic acid

Haşimi et al. 2017 [56]

12

10.14

353.3

C16H18O9

179.15, 191.16

Chlorogenic acid

Phenolic acid

Haşimi et al. 2017 [56]

13

10.85

275.28

C15H16O5

201.25

Ursinoic acid

Terpenoid

Hines et al. 2017 [57]

14

11.01

133.08

C4H6O5

115.06

71.06

Malic acid^a

Dicarboxylic acid

Al Kadhi et al. 2017 [58]

15

11.12

115.06

C4H4O4

71.06

Fumaric acid

Dicarboxylic acid

Al Kadhi et al. 2017 [58]

16

11.74

607.49

C27H28O16

313, 295, 285.23, 151.1, 133.12

Kaempferol 3,7-dihexoside

Flavonoid

Said et al. 2017 [59]

17

12.18

609.51

C27H30O16

301.23, 272.21, 255.2, 151.1

Rutin

Flavonoid

Kumar et al. 2017 [60]

18

12.22

593.5113

C27H30O15

269.23, 151.1, 117.13

Apigenin 7-dihexoside

Flavonoid

Liu et al. 2010 [61]

19

12.31

623.54

C28H32O16

315.26, 300.22, 271.2, 151.1

Isorhamnetin-3-O-dihexoside

Flavonoid

Krasteva and Nikolov, 2008 [62]

20

12.39

579.53

C27H32O14

271.25, 151.1, 119.14, 107.09

Naringin

Flavonoid

Santoro et al. 2020 [63]

21

12.45

325.29

C15H18O8

163.15, 119.14

Coumaroyl hexoside

Phenolic acid glycoside

Li et al. 2003 [53]

22

12.51

491.38

C22H20O13

315.26, 300.22, 271.2, 151.1

Isorhamnetin-3-O-hexuronide

Flavonoid

Krasteva and Nikolov, 2008 [62]

23

12.71

447.37

C21H20O11

285.23, 151.1, 133.12

Luteolin-7-O-hexoside

Flavonoid

Santoro et al. 2020 [63]

24

12.80

477.4

C22H22O12

325, 315.26, 300.22, 271.2, 151.1

Isorhamnetin-3-O-hexoside

Flavonoid

Krasteva and Nikolov, 2008 [62]

25

12.89

431.37

C21H20O10

269.23, 151.1, 117.13

Apigenin-7-O-hexoside

Flavonoid

Liu et al. 2010 [61]

26

13.20

432.38

C21H21O10+

286.24, 151.1, 135.1

Cyanidin-3-O-deoxyhexoside

Flavonoid

Santoro et al. 2020 [63]

27

13.47

433.39

C21H22O10

271.25, 151.1, 119.14, 107.09

Naringenin 7-O- hexoside

Flavonoid

Santoro et al. 2020 [63]

28

13.53

457.36

C22H18O11

125.1, 169.11

(-)-Epigallocatechin gallate

Flavonoid gallic acid ester

Spáčil et al. 2010 [64]

29

13.91

461.40

C22H22O11

285.23, 151.1, 133.12

Rhamnocitrin-O-hexoside

Flavonoid

Said et al. 2017 [59]

30

14.21

415.37

C21H20O9

253.23, 135.1, 117.13

Daidzein-7-O-hexoside

Flavonoid

Santoro et al. 2020 [63]

31

14.44

441.37

C22H18O10

125.1, 109.1, 169.11

Catechin gallate

Flavonoid gallic acid ester

Spáčil et al. 2010 [64]

32

14.95

445.4

C22H22O10

283.26, 268.23, 224.23

Trifolirhizin

pterocarpanoid glycoside

Ye et al. 2012 [65]

33

15.10

473.41

C23H22O11

269.23, 151.1, 117.13

Apigenin 7- hexuronide, Et ester

Flavonoid

Liu et al. 2010 [61]

34

15.33

429.4

C22H22O9

267.26, 132.16, 135.1

Ononin

Flavonoid

Santoro et al. 2020 [63]

35

15.48

519.52

C26H32O11

357.38, 339.36, 221.23, 191.2

Dehydrodiconiferyl alcohol-hexoside

Neolignan

Letourneau and Volmer, 2021 [66]

36

15.54

161.13

C9H6O3

133.12

4-Hydroxycoumarin

Coumarin derivative

Ren et al. 2016 [67]

37

15.62

145.14

C9H6O2

117.13

Coumarin^a

O-hydroxycinnamic acid (Aromatic compound)

Ren et al. 2016 [67]

38

15.80

149.17

C9H10O2

131.15

p-Coumaryl alcohol^a

Monolignol

Liu et al. 2010 [61]

39

15.89

175.16

C10H8O3

147.15

4-Methylumbelliferone

Coumarin derivative

Ren et al. 2016 [67]

40

15.99

181.21

C10H14O3

163.19

2-Hydroxymethyl-5-(2-hydroxypropan-2-yl) phenol

Aromatic compound

Dictionary of Natural Products 30.2 Chemical Search

41

16.09

181.21

C10H14O3

163.19

p-Mentha-1,3,5-triene-2,7,8-triol

Aromatic compound

Dictionary of Natural Products 30.2 Chemical Search

42

16.13

217.2

C12H10O4

175.16

4-Methylumbelliferyl acetate

Coumarin derivative

Leonart et al. 2017 [68]

43

16.31

301.23

C15H10O7

272.21, 255.2, 151.1

Quercetin^a

Flavonoid

Kumar et al. 2017 [60]

44

16.43

303.24

C15H12O7

285.22, 275.23, 151.1, 125, 175

Taxifolin (Dihydroquercetin)

Flavonoid

Chen et al. 2016 [69]

45

16.56

305.26

C15H14O7

125.1

Epigallocatechin

Flavonoid

Spáčil et al. 2010 [64]

46

16.61

285.23

C15H10O6

151.1, 133.12

Kaempferol

Flavonoid

Said et al. 2017 [59]

47

16.70

287.24

C15H12O6

151.1, 135.14

Dihydrokaempferol (Aromadendrin)

Flavonoid

Said et al. 2017 [59]

48

16.77

315.26

C16H12O7

300.22, 271.2, 151.1

Isorhamnetin

Flavonoid

Krasteva and Nikolov, 2008 [62]

49

16.89

269.23

C15H10O5

151.1, 117.13

Apigenin

Flavonoid

Liu et al. 2010 [61]

50

17.10

269.23

C15H10O5

241.22, 225.23

Genistein

Flavonoid

Ye et al. 2012 [65]

51

18.38

271.25

C15H12O5

151.1, 119.14, 107.09

Naringenin

Flavonoid

Santoro et al. 2020 [63]

52

19.27

273.26

C15H14O5

151.1, 121.16

Phloretin

Chalcone derivative

Bystrom et al. 2008 [70]

53

20.13

329.28

C17H14O7

314.25, 299.22, 271.21

Tricin

Flavonoid

Kang et al. 2016 [71]

54

20.63

283.26

C16H12O5

269.23, 151.1, 117.13

Genkwanin (7-methoxyapigenin)

Flavonoid

Liu et al. 2010 [61]

55

23.55

239.25

C15H12O3

130.14, 102.13

2’,4’-Dihydroxychalcone

Chalcone derivative

Zhang et al. 2014 [72]

56

23.87

207.25

C15H12O

130.14, 102.13

Chalcone

α,β-unsaturated ketone

Motiur Rahman et al. 2013 [73]

57

24.93

497.43

C25H22O11

463, 453, 179, 125, 480, 470, 375, 355

Silyamandin

Flavonolignan

Csupor et al. 2016 [74]

58

24.99

479.41

C25H20O10

151, 451.1, 255.03, 466.09

2,3-Dehydrosilybin

Flavonolignan

Csupor et al. 2016 [74]

59

25.05

481.43

C25H22O10

463, 453, 179, 125, 433, 423, 355, 337, 325

Silychristin

Flavonolignan

Csupor et al. 2016 [74]

60

25.23

481.43

C25H22O10

463, 453, 179, 125, 409, 151, 301

Silydianin

Flavonolignan

Csupor et al. 2016 [74]

61

25.47

481.43

C25H22O10

463, 453, 179, 125, 435, 301, 283, 273, 257, 423

Silybin A

Flavonolignan

Csupor et al. 2016 [74]

62

25.69

481.43

C25H22O10

463, 453, 179, 125, 435, 301, 283, 273, 257, 423

Silybin B

Flavonolignan

Csupor et al. 2016 [74]

63

25.81

481.43

C25H22O10

463, 453, 179, 125, 435, 301, 283, 273, 257

Isosilybin A

Flavonolignan

Csupor et al. 2016 [74]

64

25.99

481.43

C25H22O10

463, 453, 179, 125, 435, 301, 283, 273, 257

Isosilybin B

Flavonolignan

Csupor et al. 2016 [74]

65

26.05

323.36

C20H20O4

201.24

Glabridin

Flavonoid

Aoki et al. 2005 [75]

66

26.15

465.43

C25H22O9

151

Silandrin

Flavonolignan

Csupor et al. 2016 [74]

67

26.28

407.48

C25H28O5

119.14, 287.33

6,8-Diprenylnaringenin

Prenyl flavonoid

Nikolic and van Breemen, 2012 [76]

68

26.35

633.88

C37H62O8

471.74, 357.55, 339.53

24-Methylenelanost-8-ene-3,25,28-triol, 3-O-hexoside

Lanostane triterpenoid

Wu et al. 2011 [77]

69

26.41

483.66

C30H44O5

465.64, 421.64

Silymin A

Ursane triterpenoid

Ahmed et al. 2007 [78]

70

26.46

469.72

C31H50O3

371.53, 353.51

3,25-Dihydroxy-24-methylenelanost-8-en-7-one

Lanostane triterpenoid

Wu et al. 2011 [77]

71

26.50

179.19

C13H8O

151.18, 137.15

12-Tridecene-4,6,8,10-tetraynal

Unsaturated fatty aldehyde

Suzuki et al. 1980 [79]

72

26.58

179.19

C13H8O

164.16, 149.13

1,3-Tridecadiene-5,7,9,11-tetrayne, 1,2-epoxide

Unsaturated fatty epoxide

Suzuki et al. 1980 [79]

73

26.63

291.41

C18H28O3

273.39, 247.4

12-oxo-phytodienoic acid

Unsaturated fatty acid

Brenna, 2013 [80]

74

26.70

277.42

C18H30O2

259.4, 233.41

Linolenic acid

Unsaturated fatty acid

Brenna, 2013 [80]

75

26.74

279.44

C18H32O2

261.42, 235.43

Linoleic acid^a

Unsaturated fatty acid

Brenna, 2013 [80]

76

26.83

281.45

C18H34O2

263.43, 237.44

Oleic acid

Unsaturated fatty acid

Brenna, 2013 [80]

77

26.88

241.35

C17H22O

223.33, 226.32

2,9,16-Heptadecatriene-4,6-diyn-8-ol

Unsaturated aliphatic alcohol

El Sayed et al. 2020 [81]

78

27.03

309.51

C20H38O2

291.49, 265.5

Gadoleic acid

Unsaturated fatty acid

Brenna, 2013 [80]

79

27.14

293.46

C19H34O2

262.43, 221.4, 81.14

Linoleic acid methyl ester

Unsaturated fatty acid methyl ester

Fagerquist et al. 1999 [82]; Härtig, 2008 [83]

80

27.18

295.48

C19H36O2

264.45, 221.4, 55.1

16-octadecenoic acid methyl ester

Unsaturated fatty acid methyl ester

Fagerquist et al. 1999 [82]; Härtig, 2008 [83]

81

27.24

227.36

C14H28O2

209.34, 183.35

Myristic acid

Saturated fatty acid

Brenna, 2013 [80]

82

27.32

255.42

C16H32O2

237.4, 211.41

Palmitic acid

Saturated fatty acid

Brenna, 2013 [80]

83

27.41

283.47

C18H36O2

265.45, 239.46

Stearic acid

Saturated fatty acid

Brenna, 2013 [80]

84

27.51

311.52

C20H40O2

293.5, 267.51

Arachidic acid

Saturated fatty acid

Brenna, 2013 [80]

85

27.66

339.58

C22H44O2

321.56, 295.57

Behenic acid

Saturated fatty acid

Brenna, 2013 [80]

86

27.88

295.52

C20H40O

277.5, 71.14

Phytol

Acyclic diterpene alcohol

El Sayed et al. 2020 [81]

87

28.30

409.63

C28H42O2

394.6, 379.57, 151.19

(R)-gamma-Tocotrienol

Fat soluble vitamin

Zhao et al. 2010 [84]