52(P-23) 蛍光ラベル化したHippospongic Acid A類縁体の合成とその生理活性(ポスター発表の部)

概要

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Hippospongic acid A (1) is a triterpene isolated from marine sponge, Hippospongia sp. This natural product is a very interesting compound because it specifically inhibits gastrulation of the starfish embryos, a fundamental process that occurs during embryonic development of multicellular animals. In order to obtain the information about the binding site for hippospongic acid A in cellular level, fluorescence-labeled hippospongic acid A analogue 16 has been synthesized. Our synthetic strategy towards 16 consists of coupling a hydropyran ring unit (segment A) and geranyl unit (segment B) followed by attachment of fluorophore through suitable linkers as illustrated in Scheme 1. According to the previously reported procedures, the terpenoid part 3 has been synthesized. Dansyl and AMCA groups were selected as fluorophore. They were connected through C_6 or C_<12> methylene linkers to complete the synthesis of 16. The dancyl-labeled compound 16a showed the inhibitory activity at the concentration of 4.68μM. But the inhibitory activity was not specific for gastrulation and in higher concentration 16a was found to inhibit the cleavage step. 16b did not show inhibitory activity, probably due to its high hydrophobicity. On the other hand, AMCA-labeled compound 16c showed the specific gastrulation inhibitory activity at the concentration of 3.13μM.
2004-10-01