Two new isocoumarin derivatives, including a new 5-hydroxy-8-methyl-2
H, 6
H-pyrano[3,4-
g]chromen-2,6-dione (
1) and 6,8-dihydroxy-3,7-dimethylisocoumarin (
2b), a new chevalone derivative, named chevalone E (
3), and a new natural product pyripyropene S (
6)
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Two new isocoumarin derivatives, including a new 5-hydroxy-8-methyl-2
H, 6
H-pyrano[3,4-
g]chromen-2,6-dione (
1) and 6,8-dihydroxy-3,7-dimethylisocoumarin (
2b), a new chevalone derivative, named chevalone E (
3), and a new natural product pyripyropene S (
6) were isolated together with 6, 8-dihydroxy-3-methylisocoumarin (
2a), reticulol (
2c),
p-hydroxybenzaldehyde, chevalone B, chevalone C, S14-95 (
4), and pyripyropene E (
5) from the ethyl acetate extract of the undescribed marine sponge-associated fungus
Aspergillus similanensis KUFA 0013. The structures of the new compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound
3, X-ray analysis was used to confirm its structure and the absolute configuration of its stereogenic carbons. Compounds
1,
2a–
c and
3–
6 were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria,
Candida albicans ATCC 10231, and multidrug-resistant isolates from the environment. Chevalone E (
3) was found to show synergism with the antibiotic oxacillin against methicillin-resistant
Staphylococcus aureus (MRSA).
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