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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

From: A local Talaromyces atroroseus TRP-NRC isolate: isolation, genetic improvement, and biotechnological approach combined with LC/HRESI-MS characterization, skin safety, and wool fabric dyeing ability of the produced red pigment mixture

Peak ID Rt, min Found monoisotopic mass MW, amu = Da MF Chemical name
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
  1. Rt retention time, MW molecular weight, MF molecular formula, amu/Da atomic mass unit/Dalton. Underlined bold numbers (160) refer to a serial numeration of the metabolites identified