Table 1 UPLC/MS/MS chemical profiling of M. koenigii seeds (MKS) and pericarps (MKP) total methanolic extracts analyzed in positive ionization mode

1

Arginine

C₆H₁₄N₄O₂

7,642,201.43

977,949.1231

157, 142

a. a

PubChem

2

Choline

C₅H₁₄NO

76,350,000

24,250,000

104

a. a

Mass bank

3

L-Proline

C₅H₉NO₂

210,000,000

134,000,000

116

a. a

Mass bank

4

Sucrose

C₁₂H₂₂O₁₁

184,000,000

51,200,000

103, 147, 217, 129.0

s

PubChem

5

N-Methyl proline

C₆H₁₁NO₂

1,170,000,000

741,000,000

130

a. a

PubChem

6

Pipecolic acid

C₆H₁₁NO₂

301,569.2959

0

130

a. a

PubChem

7

Methyltyramine

C₉H₁₃NO

58,658.0631

63,021.9247

152

a. a

PubChem

8

Tyrosine

C₉H₁₁NO₃

80,303,487.6

2,655,587.393

165

a. a

Mass bank

9

L-Phenylalanine

C₉H₁₁NO₂

13,500,000

2,944,520.029

166

a. a

Mass bank

10

trans-Caffeic acid

C₉H₈O₄

2,399,231.1

2,287,464.008

137, 145, 161

ph. a

[53]

11

Vanillin

C₈H₈O₃

6085.8

35,193.795

151

or. a

Mass bank

12

Sinapine

C₁₆H₂₄NO₅

27,450,000

618,316.7549

311, 251, 207, 154, 134, 175, 147

al

[54]

13

Ferulic acid

C₁₀H₁₀O₄

543,150.3

406,270.7775

116, 134, 151, 179, 163

ph. a

[53]

14

Sinapic acid

C₁₁H₁₂O₅

0

274,217.6905

181, 133

ph. a

[55]

15

Ferulic acid

C₁₀H₁₀O₄

487,415.2455

1,315,427.147

151

ph. a

[53]

16

Myricetin-O-galactoside

C₂₁H₂₀O₁₃

3,668,754.278

6,818,027.776

317, 272, 181, 152

fl

[56]

17

Quercetin-O-robinobioside

C₂₇H₃₀O₁₆

0

6283.2525

303, 257, 229, 153

fl

[53]

18

Quercetin-O-pentoside

C₂₀H₁₈O₁₁

5413.8

306,761.175

303, 257, 153

fl

[53]

19

Quercetin-3-O-arabinoglucoside

C₂₆H₂₈O₁₆

0

830,138.1678

303, 257, 153

fl

[53]

20

Quercitrin

C₂₁H₂₀O₁₁

54,517.05

44,918.4225

303, 257, 153

fl

[53]

21

Isoquercetrin

C₂₁H₂₀O₁₂

0

2,656,850.99

303, 257, 153

fl

[53]

22

Quercetin

C₁₅H₁₀O₇

0

2,656,850.99

153, 137

fl

[57]

23

3-Cyanocoumarin

C₁₀H₅NO₂

276,376.2057

160,704.7273

143, 127

c

Pub Chem

24

Quercetin 3-[6''-(3-hydroxy-3-methylglutaryl)galactoside]

C₂₇H₂₈O₁₆

0

1,884,947.526

303

Fl

[58]

25

1,4-Cyclohexanedicarboxylic acid

C₈H₁₂O₄

4,673,649.844

7,212,019.694

173, 109

or. a

Pub Chem

26

Caffeic acid

C₉H₈O₄

9,272,176.45

9,700,346.324

145, 135, 119, 108

Ph.a

[59]

27

6-Quinolinol

C₉H₇NO

9,550,000

2,684,161.91

146

q. d

-

28

Toddalenone

C₁₅H₁₄O₅

0

246,958.313

259, 243, 231, 216, 188, 173, 160, 145

c

[60]

29

8-[3-oxo-2-[(E)-pent-2-enyl]cyclopenten-1-yl]octanoic acid

C₁₈H₂₈O₃

117,714.6141

210,026.6953

279, 189

or. a

-

30

5-Demethylnobiletin

C₂₀H₂₀O₈

11,469.15

1,957,974.795

359, 341, 328, 285, 215

fl

[61, 62]

31

Meranzin hydrate

C₁₅H₁₈O₅

0

5,879,825.79

260, 220, 219, 218, 217, 202,

190, 189

c

[63]

32

9-hydroxy-10,12-octadecadienoic acid

C₁₈H₃₂O₃

900,991.0101

0

231, 155, 143

f. a

-

33

Isosinensetin

C₂₀H₂₀O₇

0

9740.5875

358, 343, 329, 297

meth. fl

[62]

34

8-[3-oxo-2-[(E)-pent-2-enyl]cyclopenten-1-yl]octanoic acid

C₁₈H₂₈O₃

117,714.6141

210,026.6953

279, 189

or. a

-

35

Murralonginol isovalerate

C₂₀H₂₄O₅

6,652,025.661

6,822,046.414

231 227 199 189 149

131, 115

c

[64]

36

Mukoenine A/ Girinimbilol

C₁₈H₁₉NO

3,867,078.249

3,902,050.4

265, 209

al. car

[65]

37

Sinensetin

C₂₀H₂₀O₇

32,761.05

15,288.6825

358, 343, 329, 297

meth. fl

[62]

38

Panitin D

C₂₁H₂₄O₇

9,663,560.23

9,981,945.935

359, 289

c

[66]

39

Norrangiformic acid

C₂₀H₃₆O₆

9,663,560.23

9,981,945.935

219, 189, 131

or. a

-

40

Isomurralonginol isovalerate

C₂₀H₂₄O₅

0

21,750,000

231 227 199 189 149

131, 115

c

[64]

41

Lauryldiethanolamine, 2-[dodecyl(2-hydroxyethyl)amino]ethanol

C₁₆H₃₅NO₂

12,100,000

12,850,000

227, 189, 131

ph. l

-

42

Phytosphingosine

C₁₈H₃₉NO₃

623,500,000

645,000,000

281, 189, 131

ph. l

-

43

5,7-dimethoxy-8-(3-methyl-2-keto-butyl) coumarin

C₁₆H₁₈O₅

5,885,914.12

5,888,624.311

217, 163

c

[67]

44

1-Formyl –3 methoxy- 6-methyl carbazole

C₁₅H₁₃NO₂

928,179.825

1,067,860.417

209, 189

al. car

[68]

45

Mukoeic acid

C₁₄H₁₁NO₃

22,250,000

23,450,000

227, 213, 199, 196, 153

al. car

[69]

46

6-(2′,3′-dihydroxy-3-methylbutyl)-8-prenylumbelliferone

C₁₉H₂₄O₅

453,491.6069

4,248,155.097

314, 299, 281, 241, 227, 213

c

[70]

47

Scopolin

C₁₆H₁₈O₉

3,536,652.666

0

311, 193, 163

c

[71]

48

Mukonine

C₁₅H₁₃NO₃

5,802,146.81

0

237, 207, 189

al. car

[72]

49

Toddalosin

C₃₂H₃₄O₉

95,265.02805

76,083.57335

281, 189

di. c

[73]

50

5-Methoxymurrayatin

C₂₁H₂₈O₇

0

5,024,939.153

291, 275, 249, 219, 161

c

[74]

51

10-Methoxy-7-methyl-2H-benzo[g]chromen-2-one

C₁₅H₁₂O₃

16,550,000

8,828,620.29

235, 213, 211, 147, 145

c

[75]

52

Isogirinimbine

C₁₈H₁₇NO

11,031,096.4

15,400,000

249, 236, 220

al. car

[53]

53

7-Geranyloxy-6-methoxycoumarin

C₂₀H₂₄O₄

40,400,000

44,950,000

192, 177, 164, 149

c

[75]

54

Koenine

C₁₈H₁₇NO₂

37,600,000

68,600,000

279, 264, 251, 248

al. car

[53]

55

Iso-Koenigine

C₁₉H₁₉NO₃

27,350,000

19,850,000

294, 278, 263, 227

al. car

[76]

56

Lauryl diethanolamide, N,N-bis(2-hydroxyethyl)dodecanamide

C₁₆H₃₃NO₃

47,900,000

46,550,000

275, 253

ph. l

-

57

Murrayanone

C₁₇H₂₀O₆

54,000,000

50,450,000

321, 250, 249,

235, 234, 206, 204, 163, 121

c

[77]

58

Tocopherol

C₂₉H₅₀O₂

25,750,000

22,300,000

431, 165

v

-

59

Murrafoline C

C₃₆H₃₄N₂O₂

13,350,000

14,600,000

511, 469, 263, 256, 248, 227

al. car

[78]

60

Murrangatin acetate

C₁₇H₁₈O₆

5,977,754.904

6,277,441.261

261, 243

c

[79]

61

Murrafoline B

C₃₂H₃₀N₂O₂

8,106,287.259

16,750,000

419, 278, 263, 248, 237, 211

al. car

[78]

62

6, 7-Dimethoxy- 1-hydroxy- 3-methyl-carbazole

C₁₅H₁₅NO₃

10,850,000

11,400,000

243, 238, 208, 204, 189

al. car

[80]

63

FA 18:3 + 1O

C₁₈H₃₀O₃

0

4,471,821.225

255, 144

f. a

-

64

Koenigine

C₁₉H₁₉NO₃

0

251,000,000

294, 278, 263, 227

al. car

[76]

65

Koenimbine

C₁₉H₁₉NO₂

703,757.8632

14,000,000

279, 264, 251, 248

al. car

[53]

66

Murrayone/ murralongin

C₁₅H₁₄O₄

5,401,031.872

6,206,718.388

259, 147, 131

c

[81]

67

Mahanimbidine

C₂₃H₂₅NO

12,150,000

9,753,928.303

316, 289, 263, 249, 205

al. car

[82]

68

Dehydroosthol

C₁₅H₁₄O₃

6,686,703.306

5,400,000

228, 212, 187, 183, 155, 131, 115

c

[83]

69

Koenidine/ Koenigicine

C₂₀H₂₁NO₃

58,450,000

441,500,000

323.3,

308, 282

al. car

[84]

70

Linolenic acid

C₁₈H₃₀O₂

8,446,326.588

5,211,895.507

255, 143

f. a

-

71

Sorbitane Monostearate

C₂₄H₄₆O₆

2,905,584.903

5,112,299.484

279, 210

ph. l

-

72

Mukoline

C₁₄H₁₃NO₂

1,764,592.179

0

212, 210, 198, 183, 167,

154

al. car

[85]

73

Isomahanine

C₂₃H₂₅NO₂

58,000,000

0

292, 266, 251, 238, 226

al. car

[53]

74

Bismurrayafoline A

C₂₈H₂₄N₂O₂

0

14,700,000

211, 181

al. car

[86]

75

Murrastinine C/ murrayacine

C₁₈H₁₅NO₂

196,500,000

237,500,000

262, 235

al. car

[87, 88]

76

Koenimbine

C₁₉H₁₉NO₂

995,500,000

1,590,000,000

279, 264, 251, 248

al. car

[53]

77

Murrayacinine/ Murrastinine A

C₂₃H₂₃NO₂

0

83,550,000

345, 263

al. car

[89]

78

Murrayamine B

C₂₄H₂₇NO₂

5,489,804.386

4,573,318.02

292, 266, 251, 238, 226

al. car

[53]

79

8, 8″- bis koenigine

C₃₈H₃₆N₂O₆

7,068,983.514

3,038,558.311

601, 585, 561, 308

al. car

[76]

80

Murrafoline A

C₄₁H₄₂N₂O₂

8,726,698.764

5,107,492.778

579, 538, 511

al. car

[90]

81

Murrayamine A

C₁₈H₁₇NO₂

32,400,000

15,400,000

263,235

al. car

[91]

82

Girinimbine

C₁₈H₁₇NO

0

44,400,000

249, 236, 220

al. car

[53]

83

Bis-pyrayafoline

C₄₆H₄₈N₂O₄

4,475,024.414

22,750,000

609, 347, 263

al. car

[92]

84

Mahanimbilol

C₂₃H₂₇NO

3,960,307.007

9,418,516.407

264,

250, 249, 248, 210, 209, 180

al. car

[93]

85

9-Formyl-3-methyl carbazole

C₁₄H₁₁NO

832,925.0605

4,664,774.08

209, 183, 181

al. car

[94]

86

Murrastinine B

C₁₈H₁₇NO₂

22,250,000

4,938,563.829

264, 251, 248

al. car

[87]

87

3,6,9,12-Tetraoxatetracosan-1-ol

C₂₀H₄₂O₅

18,800,000

20,100,000

270, 227

ph. l

-

88

Pyrayafoline B/ Koenine

C₁₈H₁₇NO₂

37,500,000

51,000,000

279, 264, 251, 248

al. car

[53]

89

8,8'-Bismurrayamine A, dimethyl ether

C₃₈H₃₆N₂O₄

0

14,000,000

571, 555, 527

al. car

Pub Chem

90

Mukonine isomer

C₁₅H₁₃NO₃

37,500,000

20,700,000

237, 207, 189

al. car

[72]

91

Paniculatin

C₂₀H₂₄O₆

18,050,000

89,550,000

289, 232, 205, 175, 149, 145

c

[95]

92

Oleamide

C₁₈H₃₅NO

163,000,000

26,200,000

255

f. am

-

93

N-Methylaniline

C₇H₉N

246,500,000

105,500,000

108

a. a

94

Mexoticin

C₁₆H₂₀O₆

0

14,800,000

292, 266, 251, 238, 226

c

[53]

95

Rutin

C₂₇H₃₀O₁₆

109,600,000

78,350,000

465, 303

fl

[96]

96

Koenoline

C14H13NO2

876,148.0045

1,194,907.637

227, 212, 210, 198, 183, 167, 154, 139 127

al. car

[97]

97

Mukolinidine

C₁₄H₁₁NO₂

92,400,000

101,400,000

211, 183, 155, 139, 129, 127

al. car

[98]

98

Murrayamine C

C₂₄H₂₇NO₂

11,800,000

11,800,000

292, 266, 251, 238, 226

al. car

[53]

99

3-Formylcarbazole

C₁₃H₉NO

43,250,000

65,950,000

179, 154

al. car

[99]

100

Euchrestine A

C₁₈H₁₉NO₂

37,200,000

52,350,000

225

al. car

[100]

101

Murrayanine

C₁₄H₁₁NO₂

110,900,000

123,500,000

211, 183, 155, 139, 129, 127

al. car

[98]

102

Murrastanine A

C₁₃H₁₁NO₂

4,480,991.944

5,036,686.238

199

al. car

[101]