Coumarins with an unprecedented tetracyclic skeleton and coumarin dimers from chemically engineered extracts of a marine-derived fungus |
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Authors: | Hitoshi Kamauchi Masahiro Noji Kaoru Kinoshita Toshikatsu Takanami Kiyotaka Koyama |
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Institution: | 1. Department of Pharmacognosy and Phytochemistry, Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo 204-8588, Japan;2. Department of Life and Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo 204-8588, Japan |
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Abstract: | The unprecedented tetracyclic coumarin derivatives 1 and 2 and the coumarin dimers 3–5 were isolated from chemically engineered extracts (coumarin dimerization of natural extract) of the marine-derived fungus Eurotium rubrum. The structures of these compounds were established using NMR, MS and IR methods. The absolute configuration of 1 was determined by ECD calculations. The unprecedented tetracyclic coumarin skeleton was generated by domino-Knoevenagel-Diels-Alder reactions. Compounds 1–5 showed tyrosinase inhibitory activity (IC50?=?1.7, 1.2, 4.9, 1.8 and 2.9?μM, respectively). The isolated coumarin derivatives 1–5 were not observed by HPLC analysis in crude extracts of E. rubrum, suggesting that chemically engineered extract generated these new coumarin derivatives with tyrosinase inhibitory activity. |
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Keywords: | Coumarin dimer Chemically engineered extract TDDFT calculation Tyrosinase Docking study |
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