Table 2 Characterization of secondary metabolites from “A. Unguis isolate SP51-EGY” fungal extract by Q-TOF LC-HRMS analysis (A = positive, B = negative ionization mode)
Proposed Compounds [A] | RT (min) | Molecular Formula | Molecular Weight (m/z) | Fragment ions | Mass Error (ppm) | Ionization ESI (+) | Reference | |
|---|---|---|---|---|---|---|---|---|
Peptides | ||||||||
1 | Isoleucyl-Alanine | 23.528 | C9 H18 N2 O3 | 202.1323 | 185.1284, 156.9625, 86.0971 | -0.57 | [M-H2O + H]+ | [48] |
2 | L-isoleucyl-L-proline | 27.265 | C11 H20 N2 O3 | 228.1483 | 211.1450, 183.0928 | -0.9 | [M-H2O + H]+ | HMDB0011174 |
3 | L-phenylalanyl-L-proline | 31.723 | C14 H18 N2 O3 | 262.1327 | 245.1293, 217.1071 | -0.92 | [M-H2O + H]+ | HMDB0011177 |
4 | L-prolyl-L-phenylalanine | 33.901 | C14 H18 N2 O3 | 262.1329 | 245.1295, 217.1013, 70.0663, 60.0840 | -1.12 | [M-H2O + H]+ | HMDB0011179 |
5 | Angiotensin IV [H-Val-Tyr-Ile-His-Pro-Phe-OH] | 53.456 | C40 H54 N8 O8 | 774.4077 | 775.4149, 676.3474, 497.2835, 399.2646, 265.1774, 236.1617, 72.0820 | -1.58 | [M + H]+ | [48] |
6 | Histidinyl-Cysteine | 100.8 | C9 H14 N4 O3 S | 258.0784 | 241.0754, 223.0647 | 0.99 | [M-H2O + H]+ | [48] |
7 | Cysteinyl-Histidine | 101.92 | C9 H14 N4 O3 S | 258.0785 | 241.0754,223.0647 | 0.47 | [M-H2O + H]+ | HMDB0028777 [48] |
Fatty acids | ||||||||
8 | (2E,4E)-2,7-Dimethyl-2,4-octadienedioic acid | 44.577 | C10 H14 O4 | 198.0896 | 181.0863, 156.1209, 129.0530, 115.9653, 95.9737, | -1.93, | [M-H2O + H]+ | [48] |
9 | Methyl 18,18-dibromo-9E,17 -octadecadien-5,7-diynoate | 88.605 | C19 H24 Br2 O2 | 442.0157 | 443.0238, 425.2169, 352.3414, | -3.22 | [M + H]+ | (CFM-ID) |
10 | 8,12-octadecadienoic acid | 89.069 | C18 H32 O2 | 280.2422 | 280.2654, 263.2383, 95.0864 | -6.97 | [M-H2O + NH4]+ | [49] |
11 | Butyl butyrate | 93.044 | C8 H16 O2 | 144.1161 | 145.1229, 127.1128 | -7.1 | [M-H2O + H]+ | [48] |
12 | Valproic acid | 94.929 | C8 H16 O2 | 144.1161 | 127.1129, | -1.1 | [M-H2O + H]+ | [50] |
Amides | ||||||||
13 | Palmitic amide | 92.832 | C16 H33 N O | 255.2579 | 256.2615, 124.0879 | -6.11 | [M + H]+ | [48] |
14 | Oleamide | 94.533 | C18 H35 NO | 281.2736 | 282.2808, 127.1128 | -1.75 | [M + H]+ | [49] |
15 | N-oleoyl alanine | 95.485 | C21 H39 N O3 | 353.2946 | 352.3416, 336.2913, 282.2807, 127.1128 | -4.53 | [M-H2O + H]+ | [49] |
16 | Sphingosine | 95.547 | C18 H37 N O2 | 299.2837 | 282.2807, 124.0879 | -4.34 | [M-H2O + H]+ | MassBank of Japan (https://www.mssj.jp/), HMDB0000252 |
17 | D-erythro-Sphingosine C-20 | 100.6 | C20 H41 N O2 | 327.3154 | 352.3413, 310.3121, 309.3143, 284.2964, | -5.16 | [M-H2O + H]+ | (CFM-ID) |
18 | Stearamide | 100.9 | C18 H37 N O | 283.2891 | 284.2965, 223.0648, 124.0877, 116.1076 | -5.73 | [M + H]+ | [48] |
19 | Anandamide (20:l, n-9) | 101.57 | C22 H43 NO2 | 353.3311 | 336.3268, 317.3032, 223.0646,100.0765 | -4.87 | [M-H2O + H]+ | HMDB0031678 [48] |
20 | Stearoylethanolamide | 101.61 | C20 H41 N O2 | 327.315 | 310.3121, 284.2964, 124.0878 | -3.85 | [M-H2O + H]+ | [48] |
Triglycerides | ||||||||
21 | MG(16:0/0:0/0:0) | 95.338 | C19 H38 O4 | 330.2785 | 353.2683, 331.2892, 313.2755 | -4.49 | [2 M + Na]+ | HMDB0011533 (CFM-ID) |
22 | 2-(14,15-Epoxyeicosat-rienoyl) Glycerol | 102.5 | C23 H38 O5 | 394.2735 | 352.3412, 285.0956, 223.0674 | -3.87 | [M-H2O + H]+ | [48] |
23 | Triricinolein (triglyceride) | 137.45 | C57 H104 O9 | 932.7694 | 951.7786, 933.7768, 657.5075, 519.1396, 321.2411, 285.0956 | -1.44 | [M + NH4]+ | [48] |
Others | ||||||||
24 | Lyciumoside IV [acyclic diterpene glycoside] | 55.225 | C38 H64 O16 | 776.4243 | 759.4209, 380.2147, 315.1830 | -6.29 | [M-H2O + H]+ | HMDB0033499 [48] |
25 | Hydroxy ibuprofen | 62.635 | C13 H18 O3 | 222.1267 | 227.1053, 205.1232, 187.1127, 157.0480 | -4.8 | [M-H2O + Na]+ | [48] |
26 | trans-Resveratrol | 68.579 | C14 H12 O3 | 228.0797 | 233.0583, 211.0765, 197.9894, 185.0427 | -4.63 | [M-H2O + Na]+ | [48] |
27 | Eszopiclone | 80.271 | C17 H17 Cl N6 O3 | 388.1059 | 411.0957, 389.1132, 371.1047, 352.3411, 129.0533 | -2.27 | [M + Na]+ | [48] |
28 | Zopiclone | 82.176 | C17 H17 Cl N6 O3 | 388.1058 | 411.0954, 389.1133, 371.1094, 352.3410, 129.0532 | -1.8 | [M + Na]+ | [48] |
29 | Methenolone | 89.075 | C20 H30 O2 | 302.2237 | 302.2472, 167.0564 | 0.87 | [M-H2O + NH4]+ | HMDB0041928 [48] |
30 | 2,4,6-Triethyl-1,3,5-trithiane | 101.92 | C9 H18 S3 | 222.0574 | 223.0647, 124.0877 | -0.36 | [M + H]+ | [48] |
31 | Rifamycin O | 125.81 | C39 H47 N O14 | 753.2991 | 772.2763, 667.1737, 519.1405, 223.0647 | 0.78 | [M-H2O + K]+ | (CFM-ID) |
32 | Uroporphyrin I | 139.85 | C40 H38 N4 O16 | 830.2347 | 848.2731, 832.2411, 758,2226 | -7.73 | [M + NH4]+ | [48] |
33 | Vitisifuran A | 150.31 | C56 H40 O12 | 904.252 | 124.0877 | 0.02 | [M + NH4]+ | HMDB0034785 [48] |
Proposed Compounds [B] | RT (min) | Molecular Formula | Molecular Weight (m/z) | Fragment ions | Mass Error (ppm) | Ionization ESI (-) | Reference | |
Peptides | ||||||||
1 | 5-Methoxy-DL-tryptophan | 33.421 | C12 H14 N2 O3 | 234.1019 | 215.0841, 112.9868 | -6.04 | [M-H2O-H]− | [48] |
2 | Angiotensin IV | 53.428 | C40 H54 N8 O8 | 774.4093 | 433.256, 221.129, 114.056 | -3.67 | [M + HCOO]− | Manually confirmed |
3 | Se- Adenosylseleno-homo- cysteine | 84.53 | C14 H20 N6 O5 Se | 426.0666 | 407.0482 ,248.9631 | 5.41 | [M-H2O-H]− | HMDB0011117 [48] |
Fatty acids | ||||||||
4 | Isopropyl 3-(3,4-dihydroxy phenyl)-2-hydroxypropanoate | 43.097 | C12 H16 O5 | 240.1013 | 221.0835, 112.9868 | -6.51 | [M-H2O-H]− | [48] |
5 | 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid | 44.172 | C12 H16 O5 | 240.1014 | 238.9334, 221.0836 | -6.86 | [M-H2O-H]− | HMDB0061112 [48] |
6 | (2E,4E)-2,7-Dimethyl-2,4-octadienedioic acid | 44.529 | C10 H14 O4 | 198.0907 | 198.0907,179.0728 | -7.66 | [M-H2O-H]− | HMDB0034099 [48] |
7 | 18,18-dibromo-9E,17-octadecadien-5,7-diynoic acid | 77.759 | C18 H24 Br2 O2 | 428 | 426.9936, 248.9628 | -3.18 | [M-H]− | (CFM-ID) |
8 | 9R,10 S-dihydroxy-stearic acid | 95.305 | C18 H36 O4 | 316.2636 | 316.2636, 112.9869 | -2.2 | [M + CH3COO]- | HMDB0302281 [49] |
Triglyceride | ||||||||
9 | MG(0:0/18:0/0:0) [monoglyceride] | 101.66 | C21 H42 O4 | 358.3105 | 403.3084,358.3105 | -5.98 | [M + HCOO]− | [48] HMDB0011535 |
10 | Triricinolein (triglyceride) | 137.32 | C57 H104 O9 | 932.772 | ,297.2455, | -4.24 | [M + HCOO]− | HMDB0038061 [48] |
Halogenated, phenolic compounds and glycosides | ||||||||
11 | 5-Hydroxythalidomide | 60.829 | C13 H10 N2 O5 | 274.0607 | 255.0447, | -1.71 | [M-H2O-H]− | HMDB0013871 [48] |
12 | Granisetron | 63.003 | C18 H24 N4 O | 312.1955 | 293.1776 | -1.69 | [M-H2O-H]− | [48] |
13 | Sulfasalazine | 67.065 | C18 H14 N4 O5 S | 398.0692 | 398.0692,371.1158 | -0.71 | [M + HCOO -H2O]− | HMDB0014933 [49] |
14 | Fenofibric acid | 68.719 | C17 H15 Cl O4 | 318.0679 | 359.0714, | -6.4 | [M + CH3COO - H2O]− | HMDB0252207 MassBank of Japan (https://www.mssj.jp/) |
15 | Umbelliprenin [coumarin] | 72.239 | C24 H30 O3 | 366.2186 | 383.1782, 347.2017, 248.9632, 112.9868 | 2.49 | [M + Cl -H2O]− | [48] |
16 | Alpha-CEHC (alpha-Carboxyethylhydroxy-chroman) | 74.282 | C16 H22 O4 | 278.1537 | 277.1464, 248.6929 | -6.31 | [M-H]− | [48] |
17 | 4-Dodecylbenzenesulfonic acid | 82.422 | C18 H30 O3 S | 326.1936 | 325.1863, 293.1811, | -6.24 | [M-H]− | [49] |
18 | Nafcillin | 82.982 | C21 H22 N2 O5 S | 414.1253 | 459.1240, 415.0301, 325.1864, | -0.36 | [M + HCOO]− | [48] |
19 | Persicachrome | 95.311 | C25 H36 O3 | 384.2641 | 384.2641,365.2487 | 2.31 | [M-H2O-H]− | HMDB0036425 [48] |
20 | Lyciumoside IV, [acyclic diterpene glycoside] | 55.207 | C38 H64 O16 | 776.4251 | 803.4128,776.4251 | -7.3 | [M + HCOO-H2O]− | HMDB0033499 [49] |
21 | Piceid (Resveratrol glycoside) | 66.684 | C20 H22 O8 | 390.1336 | 390.1336, 371.1158 | -5.53 | [M-H2O-H]− | HMDB0031422 [48] |