52(P-9) Haliclona属海綿より得られたlembehyne Aの神経分化誘導活性と合成研究(ポスター発表の部)
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概要
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Lembehyne A (1), a novel long chain polyacetylene was isolated from an Indonesian marine sponge of Haliclona sp. The total chemical structure of 1 was determined by spectroscopic study, chemical degradation, and modified Mosher's method. Lembehyne A (1) induced bipolar neuritogenesis of Neuro 2A cells at 1μg/ml concentration. Acetylcholinesterase activity of Neuro 2A was also increased by the treatment of 1. Furthermore, the cell cycle of Neuro 2A cells was found to be specifically blocked by 1 at G1 phase. The first total synthesis of 1 was achieved by utilizing alkyne formation with dimethyl-1-diazo-2-oxopropylphosphonate and asymmetric reduction with Alpine-borane as the key reactions. Segment C_1-C_<10> (6) and segment C_<11-36> (10) were synthesized apart and connected in the final step. In order to reveal important functional groups for the biological activity in 1, the structure-activity relationship study was performed by synthesizing several analogues (13-17). The structural modification of the 1-yn-3-ol moiety in 1 led to complete or partial loss of biological activity. The analogue V (17) lacking C_<11>-C_<36> unsaturated long alkyl chain was also inactive. These results indicate that the 1-yn-3-ol group including 3R configuration and the unsaturated long alkyl chain part in 1 were important for the neuronal differentiation inducing activity of 1.
- 天然有機化合物討論会の論文
- 2001-09-01
著者
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村上 啓寿
阪大院薬
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MURAKAMI Nobutoshi
Kyoto Pharmaceutical University
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村上 啓寿
阪大院薬:presto
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村上 啓寿
Jst‐presto
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Matsumura N
Res. Foundation Itsuu Lab. Tokyo Jpn
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青木 俊二
兵庫医療大薬
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小林 資正
阪大院薬
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青木 俊二
阪大院薬
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松井 耕平
阪大院薬
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中島 辰雄
阪大院薬
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