Absolute structure, biosynthesis, and anti-microtubule activity of phomopsidin, isolated from a marine-derived fungus Phomopsis sp. |
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| Authors: | Hisayoshi Kobayashi Shiori MeguroTakeshi Yoshimoto Michio Namikoshi |
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| Institution: | a Institute of Molecular and Cellular Biosciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0032, Japan
b Department of Ocean Sciences, Tokyo University of Fisheries, Minato-ku, Tokyo 108-8477, Japan |
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| Abstract: | The absolute configuration of phomopsidin, a marine-derived fungal metabolite from Phomopsis sp. isolated at Pohnpei, was determined by the exciton chirality method as 6S, 7S, 8S, 11S, 12R, and 15R. The biosynthetic study using 13C-labeled precursors revealed the origin of all carbon atoms in phomopsidin, which was built by nine acetates and three methyl groups from l-methionine. Inhibitory activities of phomopsidin and its Me ester derivative against microtubule assembly were examined together with the structurally related compounds MK8383, solanapyrones, and tanzawaic acids. Phomopsidin and its (16Z)-isomer (MK8383) showed anti-microtubule activity at IC50 of 5.7 and 8.0 μM, respectively, while the Me ester and other compounds were not active at 100 μM. |
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| Keywords: | phomopsidin marine-derived fungus absolute stereochemistry biosynthesis anti-microtubule activity |
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