Aaptamine Derivatives with Antifungal and Anti-HIV-1 Activities from the South China Sea Sponge Aaptos aaptos

Five new alkaloids of aaptamine family, compounds (1–5) and three known derivatives (6–8), have been isolated from the South China Sea sponge Aaptos aaptos. The structures of all compounds were unambiguously elucidated by spectroscopic analyses, as well as by comparison with the literature data. Compounds 1–2 are characterized with triazapyrene lactam skeleton, whereas compounds 4–5 share an imidazole-fused aaptamine moiety. These compounds were evaluated in antifungal and anti-HIV-1 assays. Compounds 3, 7, and 8 showed antifungal activity against six fungi, with MIC values in the range of 4 to 64 μg/mL. Compounds 7–8 exhibited anti-HIV-1 activity, with inhibitory rates of 88.0% and 72.3%, respectively, at a concentration of 10 μM.

1 H NMR spectrum of compound 1 in DMSO-d6

Figure S2
13 C NMR spectrum of compound 1 in DMSO-d6

Figure S7
NOESY spectrum of compound 1 in DMSO-d6 Figure S8 IR spectrum of compound 1 Figure S9 HRESIMS of compound 1 Figure S10 UV spectrum of compound 1 Figure S11 1 H NMR spectrum of compound 2 in DMSO-d6

Figure S12
13 C NMR spectrum of compound 2 in DMSO-d6

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NOESY spectrum of compound 2 in DMSO-d6 Figure S18 IR spectrum of compound 2 Figure S19 HRESIMS of compound 2 Figure S20 UV spectrum of compound 2 Figure S21 1 H NMR spectrum of compound 3 in CDCl3

Figure S22
13 C NMR spectrum of compound 3 in CDCl3

Figure S23
DEPT135 Spectrum of compound 3 in CDCl3 Figure S24 HSQC spectrum of compound 3 in CDCl3 Figure S25 HMBC spectrum of compound 3 in CDCl3 Figure S26 1 H-1 H COSY spectrum of compound 3 in CDCl3

Figure S27
NOESY spectrum of compound 3 in CDCl3 Figure S28 IR spectrum of compound 3 Figure S29 HRESIMS of compound 3 Figure S30 UV spectrum of compound 3 Figure S31 1 H NMR spectrum of compound 4 in CDCl3

Figure S32
13 C NMR spectrum of compound 4 in CDCl3

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DEPT135 Spectrum of compound 4 in CDCl3 Figure S34 HSQC spectrum of compound 4 in CDCl3 Figure S35 HMBC spectrum of compound 4 in CDCl3 Figure S36 1 H-1 H COSY spectrum of compound 4 in CDCl3

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NOESY spectrum of compound 4 in CDCl3 Figure S38 IR spectrum of compound 4 Figure S39 HRESIMS of compound 4 Figure S40 UV spectrum of compound 4 Figure S41 1 H NMR spectrum of compound 5 in CDCl3

Figure S42
13 C NMR spectrum of compound 5 in CDCl3

Figure S43
DEPT135 Spectrum of compound 5 in CDCl3 Figure S44 HSQC spectrum of compound 5 in CDCl3 Figure S45 HMBC spectrum of compound 5 in CDCl3 Figure S46 1 H-1 H COSY spectrum of compound 5 in CDCl3

Figure S47
NOESY spectrum of compound 5 in CDCl3 Figure S48 IR spectrum of compound 5 Figure S49 HRESIMS of compound 5 Figure S50 UV spectrum of compound 5 Figure S51 1 H NMR spectrum of compound 6 in CDCl3

Figure S52
13 C NMR spectrum of compound 6 in CDCl3

Figure S53
1 H NMR spectrum of compound 7 in CDCl3

Figure S54
13 C NMR spectrum of compound 7 in CDCl3

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1 H NMR spectrum of compound 8 in CDCl3

Figure S56
13 C NMR spectrum of compound 8 in CDCl3   Table S1 NMR spectroscopic data for compounds 6-8 in CDCl3