Supplementary Materials

16S rRNA Gene Sequence

CGAAGGGTCACCTTAGAAAAATAAAGTTGGGTGTCGGCTGGCGCCGGCCGGGCCTACAGAGCAGGTGACAAAGCCCCAT ACGCTCGAGGACCGGACGCGGTGCCGCCGCTGCCTTTCGGGCCCGTCCCCCGGGAGAGGGGGACGGGGGCCCAACACAC AAGCCGTGCTTGAGGGCAGCAATGACGCTCGGACAGGCATGCCCCCCGGAATACCAGGGGGCGCAATGTGCGTTCAAAG ACTCGATGATTCACTGAATTCTGCAATTCACATTACTTATCGCATTTCGCTGCGTTCTTCATCGATGCCGGAACCAAGAGA TCCGTTGTTGAAAGTTTTAACTGATTACGATAATCAACTCAGACTGCATACTTTCAGAACAGCGTTCATGTTGGGGTCTTC GGCGGGCGCGGGCCCGGGGGCGCAAGGCCTCCCCGGCGGCCGTCGAAACGGCGGGCCCGCCGAAGCAACAAGGTACGAT AGACACGGGTGGGAGGTTGGACCCAGAGGGCCCTCACTCGGTAATGATCCTTCCGCAGGTTCACCCTACGGAAG LOCUS KJ175457 550 bp DNA linear PLN 03-FEB-2014 DEFINITION Aspergillus fumigatus isolate M1103.2732 18S ribosomal RNA gene, partial sequence; internal transcribed spacer 1, 5.8S ribosomal RNA gene, and internal transcribed spacer 2, complete sequence; and 28S ribosomal RNA gene, partial sequence. ACCESSION KJ175457

VERSION KJ175457.1 GI:576867471 KEYWORDS SOURCE Aspergillus fumigatus ORGANISM Aspergillus fumigatus Eukaryota; Fungi; Dikarya; Ascomycota; Pezizomycotina; Eurotiomycetes; Eurotiomycetidae; Eurotiales; Aspergillaceae; Aspergillus. REFERENCE 1 (bases 1 to 550) AUTHORS De Respinis,S., Weissenhorn,S., Bosshard,P.P., Petrini,L.E., Tonolla,M. and Petrini,O. TITLE Identification of Aspergillus species in the Flavi and Fumigati Sections by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry JOURNAL Unpublished REFERENCE 2 (bases 1 to 550) AUTHORS De Respinis,S., Weissenhorn,S., Bosshard,P.P., Petrini,L.E., Tonolla,M. and Petrini,O. TITLE Direct Submission JOURNAL Submitted (23-JAN-2014) Laboratory of Applied Microbiology, University of Applied Sciences of Southern Switzerland (SUPSI), Via Mirasole 22A, Bellinzona, Ticino 6501, Switzerland

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All Compounds Structures

OCH3 OCH3 H3C OH

OH O H3C CH3 OCH3 O O O O N N CH CH CH3 3 3 N N OAc H3CO N H3CO N H H O O O O CH3 CH3 H3C H3C CH3 OAc

Compound 1 Compound 2 Compound 3

OH O O O OH O OH OH OH N N N N N N H3CO N H3CO N H3CO N H O O O CH3 O O CH 3 O O CH3 H3C CH3 CH3 H3C H3C CH3 CH 3

Compound 4 Compound 5 Compound 6

H C H C 3 CH3 HOOC 3 O CH 3 CH3 CH3 H3C OCH3 CH3 H3C CH3 CH 3 OAc

CH3 OCH3 O OH HO O O O

O CH3 OAc Compound 9 Compound 7 Compound 8

H CO 3 O O OCH3 OCH3 OCH3 O H3C OH H3C OH O OH O H3C OH O COOCH3 OH O OH H3CO Compound 11 Compound 12 Compound 10 CH O 3 O N NH O CH3 O CH3 N CH3 O CH HN O 3 O HN H N N N CH 3 CH3 H3C N CH3 CH3 Compound 14 O Compound 13 OH O Compound 15 O O NH OH H3C OCH3 O OH Compound 16 Chart 1. Structure of Compounds 1–16.

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OCH3 OCH3 H3C OH

OH O O O OCH3 O

N N H3CO N H H O CH3

H3C

1 Figure S1. H-NMR (400 MHz, CDCl3) spectrum of compound 1.

OCH3 OCH3 H3C OH

OH O O O OCH3 O

N N H3CO N H H O CH3

H3C

13 Figure S2. C-NMR (100 MHz, CDCl3) spectrum of compound 1.

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OCH3 OCH3 H3C OH

OH O O O OCH3 O

N N H3CO N H H O CH3

H3C

Figure S3. HSQC spectrum of compound 1.

OCH3 OCH3 H3C OH

OH O O O OCH3 O

N N H3CO N H H O CH3

H3C

Figure S4. Expanded HSQC spectrum of compound 1.

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OCH3 OCH3 H3C OH

OH O O O OCH3 O

N N H3CO N H H O CH3

H3C

Figure S5. HMBC spectrum of compound 1.

Figure S6. Expanded HMBC spectrum of compound 1.

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OCH3 OCH3 H3C OH

H OH O O OCH3 O O H N N H3CO N H H H O CH3

H3C

Figure S7. Key correlation signal of HMBC Spectrum of compound 1.

OCH3 OCH3 H3C OH

OH O O O OCH3 O

N N H3CO N H H O CH3

H3C

Figure S8. NOESY spectrum of compound 1.

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Figure S9. Expanded NOESY spectrum of compound 1.

OCH3 OCH3 H3C OH

H OH O O OCH3 O O H N N H3CO N H H H O CH3

H3C

Figure S10. Key NOESY spectrum of compound 1.

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OCH3 OCH3 H H3C OH

H OH O O OCH3 O O H N N H3CO N H H H O CH3

H3C

Figure S11. Key NOESY spectrum of compound 1.

Figure S12. HR-ESIMS of compound 1.

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100 S 95

90

85

80

75

70 587.57 946.67 631.67 739.66 865.14

65 557.52 717.30 528.81 643.81 891.49 60 764.50 971.68

55 780.62 %T 2846.93 918.96 50 834.34 3132.03 1129.40 998.69

45 2951.87 1014.92 3431.79

40 818.09 1409.34 1155.30 35 1107.95 1436.95

30 1464.47 1291.45 1369.04 25 1318.64 1723.72 1241.01 20 1631.99 1062.87

15 1585.95 1218.47 3000 2000 1000 Wavenumbers (cm-1)

Figure S13. IR spectrum of compound 1.

H3C CH3

CH 3 CH3 CH3 OAc H O O H CH3 OAc

1 Figure S14. H-NMR (400 MHz, DMSO-d6) spectrum of compound 2.

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1 Figure S15. Expanded H-NMR (400 MHz, DMSO-d6) spectrum of compound 2.

H3C CH3

CH3 CH3 CH3 OAc H O O H CH3 OAc

13 Figure S16. C-NMR (100 MHz, DMSO-d6) Spectrum of compound 2.

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H3C CH3

CH3 CH3 CH3 OAc H O O H CH3 OAc

13 Figure S17. Expanded C-NMR (100 MHz, DMSO-d6) Spectrum of compound 2.

Figure S18. DEPT135 Spectrum (100 MHz, DMSO-d6) of compound 2.

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H3C CH3

CH 3 CH3 CH3 OAc H O O H CH3 OAc

Figure S19. Expanded DEPT135 Spectrum (100 MHz, DMSO-d6) of compound 2.

H3C CH3

CH CH3 CH3 3 OAc H O O H CH3 OAc

Figure S20. HSQC Spectrum of compound 2.

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H3C CH3

CH 3 CH3 CH3 OAc H O O H CH3 OAc

Figure S21. Expanded HSQC Spectrum of compound 2.

H3C CH3

CH 3 CH3 CH3 OAc H O O H CH3 OAc

Figure S22. HMBC Spectrum of compound 2.

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Figure S23. Expanded HMBC Spectrum of compound 2.

H3C CH3

CH 3 CH3 CH3 OAc H O O H CH3 OAc

Figure S24. COSY Spectrum of compound 2.

S15

CH3

H CH3

CH3 CH3 OAc H CH3 O O H CH3 OAc

Figure S25. NOESY Spectrum of compound 2.

Figure S26. HR-ESIMS of compound 2.