Five undescribed pentaketide derivatives, (R)-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1H-2-benzopyran-1-one (1), [(3S,4R)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1H-isochromen-3-yl]methyl acetate (2), (R)-5, 7-dimethoxy-3-((S)-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3H)-one (4b), (S)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3H)-one (5), and ap-hydroxyphenyl-2-pyridone derivative, avellaneanone (6), were isolated together with the previously reported (R)-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (3), (R)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (4a) and isosclerone (7), from the ethyl acetate extract of a culture of a marine sponge-derived fungus,Hamigera avellaneaKUFA0732. The structures of the undescribed compounds were elucidated using 1D and 2D NMR, as well as high-resolution mass spectral analyses. The absolute configurations of the stereogenic carbons in1,4b,5, and6were established by X-ray crystallographic analysis. The absolute configurations of C-3 and C-4 in2were determined by ROESY correlations and on the basis of their common biosynthetic origin with1. The crude fungal extract and the isolated compounds1,3,4b,5,6,and7were assayed for their growth inhibitory activity against various plant pathogenic fungi viz.Alternaria brassicicola,Bipolaris oryzae,Colletotrichum capsici, C. gloeosporiodes,Curvularia oryzae,Fusarium semitectum,Lasiodiplodia theobromae,Phytophthora palmivora,Pyricularia oryzae,Rhizoctonia oryzaeandSclerotium rolfsii.