Table 3 Chemical structures and exact masses of the metabolites identified in the pigment water extract of T. atroroseus TRP NRC by UHPLC/HRESI-MS

2

0.68

272.9545 [M−H]⁻

274.0590

C13H10N2O5

(E)-3-oxo-3-((1-(4-oxo-4H-Benzo[e][1,3]oxazin-2-yl)ethylidene)amino)propanoic acid, 1

2

387.0887 [M−H]⁻

388.1522

C21H24O7

Xanthomonasin-A, 2

3

0.74

438.1913 [M−H]⁻

439.1267

C23H21NO8

Mitorubrinolamine acetate, 3

440.2273 [M+H]⁺

4

0.98

440.2050 [M+H]⁺

462.1462 [M+Na]⁺

438.2209 [M−H]⁻

4

357.1845 [M+H]⁺

356.1624

C21H24O5

Dihydrorubropunctatin, 4 or Monasfluore-A, 5

4

190.9803 [M−H]⁻

192.0899

C10H12N2O2

Dihydrochrysogine, 6

4

412.1799 [M−H]⁻

413.1838

C23H27NO6

Dehydroglycylrubropunctatin, 7

4

510.2267 [M−H]⁻

511.2206

C28H33NO8

N-Glutarylmonascorubramine, 8

6

1.17

488.1899 [M+H]⁺

487.3086

C32H41NO3

Talaroconvolutin-A, 9

486.2599 [M−H]⁻

6

119.9371 [M+H]⁺

119.0219

C3H5NO4,

β-Nitropropanoic acid, 10

7

1.28

488.2377 [M+H]⁺

487.3086

C32H41NO3

Talaroconvolutin-A, 9

486.2180 [M−H]⁻

7

539.3469 [M+H]⁺

538.0900

C30H18O10

Skyrin, 11

8

1.47

424.3120 [M−H]⁻

425.2202

C25H31NO5

PP-R; 7-(2-Hydroxyethyl)monascorubramine, 12

426.2246 [M+H]⁺

8

428.3271 [M−H]⁻

429.2515

C25H35NO5

Tetrahydro-PP-R, 13

430.1977 [M+H]⁺

9

2.75

227.0675 [M+H]⁺

226.1205

C12H18O4

2,4-Dihydroxypentyl)-2-methylbenzene-1,3diol, 14

11

6.13

470.4424 [M−H]⁻

471.2773

C31H37NO3

Deoxytalaroconvolutin-A, 15

12

6.80

352.1925 [M−H]⁻

353.1627

C21H23NO4

Rubropunctamine, 16

14

7.84

697.4280 [M+H]⁺

696.2692

C40H44N2O5S2

Hydrooxy-present pigment, 17

695.4290 [M−H]⁻

14

349.3371 [M+H]⁺

348.1209

C18H20O7

Glauconic acid, 18

15

8.32

502.1199 [M−H]⁻

503.3036

C32H41NO4

Dehydrotalaroconvolutin-B

Dehydro ZG-1494a, 19

16

9.38

390.1997 [M+H]⁺

389.2202

C22H31NO5

Dehydro-Purpuride, 20

16

430.2012 [M+H]⁺

429.2515

C25H35NO5

Tetrahydro-PP-R, 21

16

452.2859 [M−H]⁻

453.1788

C25H27NO7

Dehydro-N-threoninerubropunctamine, 22

17

10.24

221.2123 [M−H]⁻

222.0892

C12H14O4

1-(3,5-Dihydroxy-4-methylphenyl)pentane-2,4-dione, 23

17

401.1828 [M−H]−

402.1315

C21H22O8

Pinophilin-B, 24

17

472.3087 [M−H]⁻

473.2930

C31H39NO3

Demethyltalaroconvolutin-A, 25

17

494.3125 [M−H]⁻

495.1893

C27H29NO8

Dehydroazaphilone pigment, 26

17

562.2547 [M−H]⁻

563.3611

C35H49NO5

Talaroconvolutin-D, 27

18

11.26

476.2532 [M+H]⁺

475.3086

C31H41NO3

Demethyl-dihydrotalaroconvolutin-A, 28

18

474.2838 [M−H]⁻

18

498.2573 [M+H]⁺

497.2050

C27H31NO8

Azaphilone pigment, 29

496.3168 [M−H]⁻

19

11.55

539.2065 [M−H]⁻

540.2108

C28H32N2O9

N-glutamylmonascorubraminic acid, 30

19

392.1892 [M+H]⁺

391.2359

C22H33NO5

Purpuride, 31

414.2019 [M+Na]⁺

20

11.66

436.2874⁻ [M+HCO₂]⁻

20

233.1178 [M+H]⁺

232.0199

C14H16O3

Sorbicillin, 32

19

293.1682 [M−H]⁻

294.1256

C19H18O3

3-Hydroxy-1,8,8,9-tetramethyl-8,9-dihydro-4H-phenaleno[1,2-b]furan-4-one

(Atrovenetin derivative, 33)

20

293.1252 [M−H]⁻

294.0852

C13H14N2O6

2-(2-(2-Carboxyacetamido)propanamido)-benzoic acid,(Atrovenetin metabolite, 34)

20

385.1713 [M−H]⁻

386.2093

C23H30O5

Ankaflavin, 35

21

11.78

274.2042 [M+H]⁺

273.0750

C13H11N3O4

The oxidized form of (E)-3-oxo-3-((1-(4-oxo-1,4-dihydroquinazolin-2-yl)ethylidene)-amino)-propanoic acid (Atrovenetin metabolite, 36)

296.2686 [M+Na]⁺

22

11.90

412.2079 [M+H]⁺

411.1682

C23H25NO6

PP-V pigment, 37 or purpactin C

22

318.3012 [M+H]⁺

317.0648

C14H11N3O6

(E)-2-((1-(4-oxo-1,4-Dihydroquinazolin-2-yl)ethylidene)carbamoyl)malonic acid, 38

340.3239 [M+Na]⁺

22

230.1811 [M+H]⁺

229.0851

C12H11N3O2

(E)-N-(1-(4-oxo-1,4-Dihydroquinazolin-2-yl)ethylidene)acetamide, 39

23

12.33

475.4114 [M−H]⁻

476.2563

C30H36O5

Sophoraisoflavanone-C, 40

24

12.87

415.1910 [M+H]⁺

414.1679

C23H26O7

Dihydro PP-O

437.1733 [M+Na]⁺

Or Purpactin-A & B, 41

453.1935 [M+K]⁺

24

617.3195 [M+H]⁺

616.4128

C40H54O5

Dihydro-4-ketonostoxanthin, 42

25

13.33

395.2523 [M−H]⁻

396.0845

C21H16O8

Mitorubrinal, 43

25

327.1714 [M−H]⁻

328.0947

C18H16O6

(R)-3,7-Dihydroxy-1,8,8,9-tetramethyl-8,9-dihydro-4H,6H-benzo[de]furo[2,3g]isochromene-4,6-dione, 44

26

16.62

399.2009 [M+H]⁺

398.1002

C21H18O8

Mitorubrinol, 45

26

383.1822 [M+H]⁺

382.1780

C23H26O5

PP-Y; Monascorubrin, 46

26

301.0924 [M+H]⁺

300.0270

C15H8O7

Emodic acid, 47

27

17.91

506.3542 [M+H]⁺

505.3192

C32H43NO4

Talaroconvolutin-B, 48

528.3842 [M+Na]⁺

(ZG-1494a)

Two stereoisomers at C-5 or 26

28

20.36

339.2800 [M−H]⁻

340.1311

C20H20O5

Dehydroatrovenetin, 49

29

20.84

359.2497 [M+H]⁺

358.1780

C21H26O5

Monascin, 50

29

239.1775 [M+H]⁺

238.1722

C18H22

2,3,9,10-Tetramethyl-1,2,3,4-tetrahydroanthracene, 51

30

22.79

589.1694 [M−H]⁻

590.1061

C30H22O13

Deoxyxanthoepoein, 52

30

385.0434 [M−H]⁻

386.1366

C21H22O7

Azaphilone, 53

32

23.40

613.1418 [M−H]⁻

614.1636

C30H30O14

Octahydroxanthoepoein, 54

34

23.64

403.3223 [M−H]⁻

404.2199

C23H32O6

Hydrolytic product of Ankaflavin, 55

39

25.19

283.2244 [M−H]⁻

284.0685

C16H12O5

Erythroglaucin, 56

40

25.28

283.1718 [M−H]⁻

284.0685

C16H12O5

Physcion, 57

41

25.35

384.1975 [M−H]⁻

385.2253

C23H31NO4

Tetrahydromonascorubramine, 58

42

25.41

391.2597 [M+H]⁺

390.1234

C21H23ClO5

Sclerotiorin, 59

(Orange azaphilone pigment)

413.2316 [M+Na]⁺

52

26.65

357.0226 [M−H]⁻

358.1053

C19H18O7

Norherqueinone, 60