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Secalonic Acid and Benzoic Acid Analogues Exhibiting Cyto toxicity against Cancer Cells Isolated from <i>Claviceps yanagawaensis</i>
Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan
Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
Department of Environmental Science, Ishikawa Prefectural University, Nonoichi, Japan
Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
- 1 Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
- 2 Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
- 3 Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, Sakado, Japan
- 4 Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
- 5 Department of Environmental Science, Ishikawa Prefectural University, Nonoichi, Japan
- 6 Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan
Advances in Microbiology·Volume 12 (2022)·Pages 649–670·Published 15 December 2022·DOI10.4236/aim.2022.1212045
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Abstract
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.
Keywords<i>Claviceps</i>Secalonic AcidMTT Assay
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