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The genus Claviceps (Clavicipitaceae) is noted for producing ergot alkaloids that cause ergotism. Claviceps yanagawaensis, a parasite of Zoysia japonica (family: Poaceae), has been isolated in Japan. Bioactivity screening showed that a methanol extract from a rice culture of C. yanagawaensis was cytotoxic to cancer cells. In our search for active substances, the new secalonic acid analogues (-)-5-epi-F-7 (1) and ergochrysin C (2) and a new benzoic acid analogue, dimethyl bigutol (3), were isolated along with the known compounds 3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)benzoic acid (4) and methyl veratrate (5). The structures of 1 -3 were elucidated by NMR, MS, and circular dichroism spectroscopy. MTT assays of 1 -5 using cancer cell lines (HepG2, HL60, HT29, PANC-1, and T98G) showed that 1 -4 exhibited cytotoxicity against cancer cells.