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Aromatic compounds were isolated from an extract of Eurotium herbariorum NU-2, which is used in the process of manufacturing karebushi (a katsuobushi). The seventeen compounds were identified as anthraquinone derivatives (A1-A6), eurotinone derivatives (B1, B2), indole-containing diketopiperazine derivatives (C1-C6), and benzaldehyde derivatives (D1-D3). 2-Methyleurotinone (B1), isoechinulin A (C6), tetrahydroauroglaucin (D1), isodihydroauroglaucin (D2), and flavoglaucin (D3) exhibited significantly higher DPPH (1, 1-diphenyl-2picrylhydrazyl) scavenging activity compared to α-tocopherol, a standard radical scavenger (P < 0.05). Asperflavin (A4), isoechinulin B (C1), neoechinulin B (C2), and variecolorin O (C4) had similar activity to α-tocopherol. The extract of E. herbariorum NU-2 exhibited high radical scavenging activity compared to other filamentous fungi from katsuobushi, and also contained higher levels of isoechinulin B (C1), echinulin (C5), tetrahydroauroglaucin (D1), and flavoglaucin (D3). The concentration of tetrahydroauroglaucin (D1) in the filamentous fungus extract was highly correlated with the radical scavenging activity.

Isolation of Aromatic Compounds Produced by Eurotium herbariorum NU-2 from Karebushi, a Katsuobushi, and their DPPH-Radical Scavenging Activities