Chemodiversity of Penicillium isolated from alpine and arctic environments, including ten new species

Fig. S1. MS-FINDER annotation of asperfuran based on in silico MS2 fragmentation prediction. Experimentally obtained spectrum is in black while in silico predicted spectral scores are in red. A. Asperfuran m/z 219. 1012 M+H+. Fig. S2. GNPS annotation of asperphenamates. Experimentally obtained spectra are in black, spectra from MS2 database are coloured green. A. Asperphenamate m/z 507. 2263 M+H+. B. Asperphenamate Analog m/z 523. 2209 M+H+. Fig. S3. MS-FINDER annotation of aurantiamines based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Pre-aurantiamine m/z 235. 119 M+H+. B. Viridamine or aurantiamine m/z 303. 1815 M+H+. Fig. S4. MS-FINDER annotation of chaetoglobosins based on MS2 fragmentation prediction/analysis. Experimentally obtained spectra are in black, in silico predicted spectral scores are in red and spectra from MS2 database are coloured green. A. Chaetoglobosin A m/z 529. 2695 M+H+. B. Viomellein m/z 561. 1392 M+H+. C. Chaetoglobosin E m/z 531. 2850 M+H+. D. Cytoglobosin m/z 515. 2904 M+H+. Fig. S5. MS-FINDER annotation of chrysogenamide A based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectra are in red. A. Chrysogenamide A m/z 448. 2966 M+H+. B. Chrysogenamide A m/z 448. 2966 M+H+. Fig. S6. MS-FINDER annotation of communesins based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Communesin A m/z 457. 2587 M+H+. B. Communesin F. m/z 441. 2634 M+H+. C. Communesin G m/z 471. 2739 M+H+. D. Communesin H m/z 485. 2898 M+H+. Fig. S7. MS-FINDER annotation of fungal statins based on comparison to experimentally-derived MS2 spectra (compactin and compactin open forms) and in silico MS2 fragmentation prediction (lovastatin and pravastatin). Experimentally obtained spectra are in black, spectra from MS2 database are coloured green, and in silico predicted spectral scores are in red. A. Compactin m/z 391. 2481 M+H+. B. Compactin Open Form m/z 391. 2480 M+H-H2O+. C. Compactin Open Form m/z 391. 2482 M+H-H2O+. D. Lovastatin m/z 405. 2639 M+H+. E. Pravastatin m/z 447. 2355 M+Na+. Fig. S8. MS-FINDER annotation of additional fungal statins based on comparison to experimentally-derived MS2 spectra (ML236A) and in silico MS2 fragmentation prediction (CNP0217257, CNP0429426 and ML236A). Experimentally obtained spectra are in black, spectra from MS2 databases are coloured green while in silico predicted spectral scores are in red. A. CNP0217257 m/z 405. 2635 M+H-H2O+. B. CNP0217257 m/z 423. 2744 M+H+. C. CNP0429426 m/z 325. 2013 M+H+. D. ML236A m/z 307. 1905 M+H+. E) ML236A m/z 307. 1905 M+H+. Fig. S9. MS-FINDER annotation of cycloaspeptides based on comparison to experimentally-derived MS2 spectra (cycloaspeptide A and H) and in silico MS2 fragmentation prediction (cycloaspeptide B/C/D and E). Experimentally obtained spectra are in black, spectra from MS2 databases are coloured green, while in silico predicted spectral scores are in red. A. Cycloaspeptide A m/z 642. 3283 M+H+. B. Cycloaspeptide B/C/D m/z 628. 3127 M+H+. C. Cycloaspeptide E m/z 626. 3339 M+H+. D. “Cycloaspeptide H₁30057” m/z 672. 3394 M+H+ (see text for discussion on cycloaspeptide H annotation). Fig. S10. MS-FINDER annotation of cycloaspeptide G based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Cycloaspeptide G m/z 658. 3240 M+H+. B. Cycloaspeptide G m/z 658. 3240 M+H+. Fig. S11. MS-FINDER annotation of marcfortines based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black, spectra from MS2 database are coloured green, and in silico predicted spectral scores are in red. A. Fellutanine A m/z 373. 166 M+H+. B. Fellutanine B m/z 448. 2597 M+H+. C. Fellutanine C m/z 509. 291 M+H+. D. Amauromine m/z 509. 2914 M+H+. Fig. S12. MS-FINDER annotation of funiculosins based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Funiculosin m/z 492. 2958 M+H+. B. Funiculosin- like m/z 476. 3013 M+H+. Fig. S13. GNPS annotation of griseofulvins based on based on comparison to standard-derived MS2 spectra. Experimentally obtained spectra are in black and spectra from MS2 database are coloured green. A. Griseofulvin m/z 353. 0784 M+H+. B. Dechlorogriseofulvin m/z 319. 1176 M+H+. Fig. S14. MS-FINDER annotation of mangrovamides based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Mangrovamide F m/z 432. 2646 M+H+. B. Mangrovamide G or VM-55599 m/z 350. 2226 M+H+. Fig. S15. MS-FINDER annotation of marcfortines based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Marcfortine A m/z 478. 2704 M+H+. B. Marcfortine B m/z 464. 2546 M+H+. C. Marcfortine C m/z 448. 2597 M+H+. Fig. S16. MS-FINDER annotation of melearoride A and PF 1136B based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Melearoride A m/z 486. 3577 M+H+. B. PF 1163B m/z 462. 3219 M+H+. Fig. S17. MS-FINDER annotation of prenylated cyclodipeptides based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Penigequinolone A m/z 450. 2286 M+H-H2O+. B. Peniciherquamide m/z 494. 2647 M+H+. Fig. S18. MS-FINDER annotation of penitrems based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Penitrem B m/z 584. 3372 M+H+. B. Penitrem D m/z 568. 3423 M+H+. C. Penitrem E m/z 600. 3321 M+H+. D. Penitrem F m/z 618. 2979 M+H+. Fig. S19. MS-FINDER annotation of pseurotin A and synerazol based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Pseurotin A m/z 432. 1644 M+H+. B. Synerazol m/z 414. 1544 M+H+. Fig. S20. MS-FINDER annotation of psychrophilins based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Psychrophilin A m/z 433. 1499 M+H+. B. Psychrophilin B m/z 435. 1652 M+H+. C. Psychrophilin C m/z 407. 134 M+H+. D. Psychrophilin D m/z 449. 1820 M+H+. Fig. S21. MS-FINDER annotation of pyripyropenes based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Pyripyropene A m/z 584. 2513 M+H+. B. Pyripyropene C m/z 598. 263 M+H+. C. Pyripyropene E m/z 452. 2432 M+H+. D. dehydroxylpyripyropene A m/z 568. 2538 M+H+. E) 1-Deacetylpyripyropene A / 7-Deacetylpyripyropene A m/z 542. 2381 M+H+. Fig. S22. MS-FINDER annotation of quinolactacins based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Quinolactacin A m/z 271. 1436 M+H+. B. Quinolactacin B m/z 257. 1282 M+H+. C. Quinolactacin C m/z 287. 1388 M+H+. Fig. S23. GNPS annotation of roquefortines based on match to MS2 database spectra. Experimentally obtained spectra are in black while matched database spectra are in green. A. Roquefortine C m/z 390. 1922 M+H+. B. Roquefortine D m/z 392. 2082 M+H+. Fig. S24. MS-FINDER and GNPS annotation of quinazolinone alkaloids based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black, spectra from MS2 database are coloured green (GNPS), and in silico predicted spectra are in red (MS-FINDER). A. Sclerotigenin m/z 278. 0923 M+H+. B. Circumdatin F m/z 292. 1079 M+H+. Fig. S25. GNPS annotation of tryprostatin B based on MS2 fragmentation prediction. Experimentally obtained spectra are in black while database-matched spectra are in green. A. Tryprostatin B m/z 352. 2011 M+H+. Fig. S26. MS-FINDER annotation of unguisins based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Unguisin A m/z 759. 4212 M+H+. B. Unguisin C m/z 775. 4131 M+H+. Fig. S27. MS-FINDER annotation of viridic acid. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Viridic acid m/z 455. 2283 M+H+. Fig. S28. MS-FINDER annotation of xanthomegnins based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Xanthomegnin m/z 575. 1185 M+H+. B. Viomellein m/z 561. 1392 M+H+. C. Vioxanthin m/z 547. 1599 M+H+. D. Norlichexanthone m/z 259. 0601 M+H+. Fig. S29. GNPS annotation of yaequinolones based on match to MS2 database spectra. Experimentally obtained spectra are in black while matched database spectra are in green. A. Yaequinolone B m/z 384. 1443 M+H+. B. Yaequinolone F m/z 448. 2123 M-H2O+H+. C. Yaequinolone J1 m/z 450. 2286 M+H+. Fig. S30. MS-FINDER annotation of prenylated cyclodipeptides based on in silico MS2 fragmentation prediction. Experimentally obtained spectra are in black while in silico predicted spectral scores are in red. A. Paraherqu