Table 1.
List of the significantly discriminant metabolites selected using the PLS-DA model (VIP > 0.7 and p < 0.05) based on the UHPLC–LTQ–Orbitrap–MS datasets for A. flavus extracts following the VOC treatments.
| No. | RT (min) | Tentative metabolites | [M + H]+ | [M − H]‒ | M.W | Elemental composition | Error (ppm)a | MSn fragment pattern | p value | References |
|---|---|---|---|---|---|---|---|---|---|---|
| Alkaloid | ||||||||||
| 1 | 5.63 | Aspergilline C | 441.2026 | 439.1951 | 440 | C24H29N2O6 (+) | 1.353 | (+) 441 > 291, 265 > 177 | 5.00E−06 | Uka et al.50 |
| Xanthone | ||||||||||
| 2 | 5.86 | 5-Methoxysterigmatocystin | 355.0819 | 353.0728 | 354 | C19H15O7 (+) | 1.917 | (−) 353 > 338 > 323, 310 > 295, 279 | 1.23E−03 | Carvajal-Campos et al.51 |
| Coumarin | ||||||||||
| 3 | 6.12 | Aflatoxin B1 | 313.0710 | 311.0619 | 312 | C17H13O6 (+) | 1.007 | (+) 313 > 285 > 270, 257 > 253, 242 | 2.39E−02 | Carvajal-Campos et al.51 |
| Anthraquinones/ quinones | ||||||||||
| 4 | 6.55 | Asparasone A | 381.0583 | 357.0673 | 358 | C18H14O8Na (+) | 0.686 | 357 > 339, 299 | 3.00E−05 | Carvajal-Campos et al.51 and Malysheva et al.52 |
| 5 | 6.72 | Anthraquinone derivative 1 | 269.0804 | 267.0796 | 268 | C16H13O4 (+) | − 1.804 | 267 > 252 > 223, 208 > 195 | 3.90E−05 | Fouillaud et al.53 |
| 6 | 7.10 | Anthraquinone derivative 2 | ‒ | 315.0555 | 316 | C16H11O7 (‒) | 5.409 | 315 > 297 > 269, 253 > 241, 225 | 0.00E+00 | Fouillaud et al.53 and Carvajal-Campos et al.51 |
| 7 | 5.56 | Chrysophanol | 255.0657 | 253.0551 | 254 | C15H11O4 (+) | 1.743 | (+) 255 > 237, 227, 199 > 181, 171 > 153 (−) 253 > 253, 224, 209, 185 | 1.00E−06 | Tripathi et al.54 |
| 8 | 7.26 | Versicolorin B | 341.0656 | 339.0558 | 340 | C18H13O7 (+) | 0.178 | 339 > 321, 311, 297 > 295, 269, 253 | 0.00E+00 | Carvajal-Campos et al.51 |
| 9 | 7.94 | Versicolorin A | 339.0504 | 337.0410 | 338 | C18H11O7 (+) | 1.330 | 337 > 309 > 281, 265 > 252 | 1.71E−02 | Carvajal-Campos et al.51 |
| Indole/ Indole terpenes | ||||||||||
| 10 | 7.61 | Sulpinine C | 536.3008 | 534.2937 | 536 | C32H42NO6 (+) | − 1.258 | 534 > 476 > 416 > 400, 358 | 6.50E−05 | Laakso and Gloer55 |
| 11 | 8.13 | α-Cyclopiazonic acid (CPA) | 337.1545 | 335.1450 | 336 | C20H21N2O3 (+) | − 1.095 | 335 > 180, 154, 140 | 1.10E−03 | Uka et al.50 |
| 12 | 8.72 | Paxilline | 436.2480 | 434.2399 | 435 | C27H34NO4 (+) | − 0.080 | 434 > 415, 346 > 331, 316, 302 | 2.70E−05 | Carvajal-Campos et al.51 |
| Fatty acid derivatives/ oxylipins | ||||||||||
| 13 | 6.44 | 9,12,13-TriHOME | 353.2305 | 329.2383 | 330 | C18H34O5Na (+) | 1.938 | (−) 329 > 311 > 293, 229, 211, 199, 171 | 8.60E−05 | Singh and Lee13 and Son et al.56 |
| 14 | 7.04 | Fatty acid derivative | 295.2262 | 293.2164 | 294 | C18H31O3 (+) | − 1.834 | (−) 293 > 275, 235 > 231, 177 | 1.05E−02 | CHCD |
| 15 | 7.51 | 5,8-DiHODE | 335.2192 | 311.2270 | 312 | C18H32O4Na (+) | − 3.483 | (−) 311 > 293, 275, 173 > 249, 231 | 1.79E−03 | Singh and Lee13 |
| 16 | 7.84 | 12,13-DiHOME(9) | 337.2350 | 313.2433 | 314 | C18H34O4Na (+) | − 2.899 | (−) 313 > 295 > 277, 259, 251, 233 | 0.00E+00 | Singh and Lee13; Standard compound |
| 17 | 8.00 | Dihydroxy-octadecadienoic acid (DiHODE) | 335.2191 | 311.2274 | 312 | C18H32O4Na | − 0.479 | (−) 311 > 293, 275, 211, 187, 171, 157 | 4.10E−05 | Son et al.56; CHCD |
| 18 | 9.41 | Fatty acid derivative | 297.2422 | 295.2322 | 296 | C18H33O3 (+) | − 0.678 | (−) 295 > 277, 251 > 233, 179, 165, 139 | 0.00E+00 | CHCD |
| Miscellaneous | ||||||||||
| 19 | 7.75 | Aspergilone A | 387.1931 | 431.1896 | 386 | C26H27O3 (+) | − 6.176 | (+)387 > 331 > 275, 231, 175 | 0.00E+00 | Shao et al.57 |
| 20 | 7.84 | Aszonapyrone A | 457.2947 | 455.2870 | 456 | C28H41O5 (+) | − 0.242 | 455 > 437, 411, 393 > 375, 325, 287, 269 | 2.23E−04 | Kimura et al.58 |
| 21 | 9.16 | Averufin | 391.1653 | 367.0869 | 368 | C20H15O7 (‒) | 4.696 | 367 > 349, 323, 267 > 223 | 2.00E−06 | KNApSAcK core system |
| Non-identified | ||||||||||
| 22 | 5.14 | N.I. 1 | 445.2339 | 443.2264 | 444 | C24H33N2O6 (+) | 0.464 | 445 > 267, 250 > 179, 137 | 2.00E−06 | ‒ |
| 23 | 5.20 | N.I. 2 | 246.1129 | 244.1025 | 245 | C14H16NO3 (+) | 1.748 | 246 > 228 > 200 > 183, 133 | 4.00E−06 | ‒ |
| 24 | 6.47 | N.I. 3 | 525.2715 | 523.2636 | 524 | C27H41O10 (+) | 4.048 | 523 > 417 > 311 > 267 | 0.00E+00 | ‒ |
| 25 | 7.17 | N.I. 4 | 548.2863 | 546.2801 | 547 | C29H42NO9 (+) | 1.663 | 546 > 417, 311 | 2.36E−04 | ‒ |
| 26 | 7.77 | N.I. 5 | ‒ | 339.0558 | ‒ | C11H15O12 (‒) | − 3.183 | ‒ | 2.78E−04 | ‒ |
| 27 | 7.98 | N.I. 6 | 532.2917 | 530.2847 | 531 | C25H42N2O10 (+) | − 0.365 | 530 > 401 > 383, 357, 285 > 203, 179 | 1.04E−04 | ‒ |
| 28 | 9.25 | N.I. 7 | 581.2431 | 579.2350 | 580 | C23H42O15Na (+) | − 0.238 | 579 > 523, 417 > 347, 149 | 0.00E+00 | ‒ |
| 29 | 9.45 | N.I. 8 | 540.4253 | 538.4178 | 539 | C31H58NO6 | − 1.841 | 538 > 519, 494, 450, 408, 337, 355 | 4.16E−04 | ‒ |
| 30 | 10.40 | N.I. 9 | 669.3312 | 667.3269 | 668 | C41H47O8 (‒) | − 0.377 | 667 > 637 > 619, 431, 369 > 351, 267, 225 | 2.05E−03 | ‒ |
| 31 | 10.59 | N.I. 10 | 637.3049 | 681.3083 | 636 | C27H47N3O14 (+) | − 0.415 | 681 > 653 > 447 > 285 > 267 | 2.24E−03 | ‒ |
| 32 | 11.25 | N.I. 11 | 637.3063 | 635.2993 | 636 | C27H47N3O14 (+) | − 0.415 | 635 > 367 > 337, 267, 149 | 0.00E+00 | ‒ |
RT: Retention time for chromatographic elution. CHCD: Combined Chemical Dictionary, Chapman and Hall, London, UK, 1992.
aMass tolerance from elemental composition analysis.