38 子のう菌Talaromyces luteus、T. helicusより得られた新azaphilone代謝産物(口頭発表の部)
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概要
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In our screening program on biologically active fungal metabolites, two new azaphilones having monoamine oxidase inhibitory (MAOI) activity, TL-1 (1) and -2 (2), were isolated from an Ascomycete, Talaromyces luteus In our successive work to search related compounds to 1 and 2 from Talaromyces fungi, three new azaphilones named TL-3 (3),-4 (4) and -5 (5) from T. luteus, and four new ones named TH-1 (8),-2 (9),-3 (10) and -4 (11) from T. helicus have been isolated. Physico-chemical and spectral data of 3 and 4 suggested that 3 is similar to 1 and is constructed with the partial structures 3A and 3B, and 4 is an isomer of 3. The ^1H- and ^<13>C-NMR data of 3, 4 and their tetrahydro derivative (6) showed that structures of TL-3 and -4 were deduced to be 3 and 4 which is the 11Z isomer of 3, respectively. Structure of TL-5 was estimated to be 5 in comparison of the NMR data of 5 with those of chaetoviridin A (7). Physico-chemical and spectral data of 8-11 suggested that 8-11 are isomeric each other and 8 is similar in part to 7-epi-sclerotiorin (12). The NMR data of 8 indicated that 8 is constructed with the partial structures 8A and 8B_1 or 8B_2. The fact that 8 gives 13 on alkaline degradation and 14 on methylation suggested the structure 8 for TH-1 which contains 8A and 8B_1. Comparison of the NMR data of 9-11 with those of 8 indicated that structures of TH-2, -3 and -4 are deduced to be 9, 10 and 11, respectively. From the comparison of MAOI activity of these azaphilones, it is suggested that the OH at position 8 and the conjugated unsaturated system from position 3 to 11 are indispensable to exhibit the MAOI activity. The OH at position 8 seemed to be also important to exhibit suppressive activity against lymphocyte proliferation.
- 天然有機化合物討論会の論文
- 1993-09-10
著者
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吉田 栄治
Faculty Of Pharmaceutical Sciences Chiba University
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藤本 治宏
千葉大院薬
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山崎 幹夫
千葉大学薬学部医薬品素材学講座
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山崎 幹夫
千葉大・薬
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藤本 治宏
千葉大・薬
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吉田 栄治
千葉大・薬
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馬場 美由紀
千葉大・薬
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馬場 美由紀
Faculty Of Pharmaceutical Sciences Chiba University
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