P-47 海洋由来糸状菌から得られた新規ノトアミド類の構造と生合成研究(ポスター発表の部)

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We reported the structures of four prenylated indole alkaloids, notoamides A-D (1-4), which isolated from a marine-derived fungus Aspergillus sp. Although the starting substrate for 1-4 was deduced to be notoamide E (7), it was not found in the metabolites of the fungus. Then, we investigated the presence of 7 in the culture and found that it existed only in the culture incubated for five days and disappeared the next day. These results clearly indicated that 7 was produced by the fungus in the early stage and immediately converted to other metabolites. Subsequently, we carried out the feeding experiments with doubly ^<13>C-labelled 7 and obtained 3, 4, and 8-11. However, contrary to our expectation, compounds containing a bicyclo [2.2.2]diazaoctane ring such as 1 and 2 were not obtained at all. Thus, the biosynthesis of the indole alkaloids containing the bicyclo [2.2.2]diazaoctane ring is an interesting enigma, and the search for the progenitor of 1 and 2 is under investigation. Additionally, we isolated ten new alkaloids 12-21, which showed the structural diversity, and found that 21 was an opposite enantiomer of versicolamide B, which was isolated from the closely related fungus by Glores et al. They already reported the isolation of opposite enantiomers of 2 and 5. It is interesting to know the biochemical pathways involved in the selective production of three opposite enantiomers by these two fungi.
天然有機化合物討論会の論文
2008-09-01

P-47 海洋由来糸状菌から得られた新規ノトアミド類の構造と生合成研究(ポスター発表の部)

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