Bioactive marine metabolites.: Part 104.: Miraziridine A, a novel cysteine protease inhibitor from the marine sponge Theonella aff. mirabilis
Bioactive marine metabolites.: Part 104.: Miraziridine A, a novel cysteine protease inhibitor from the marine sponge Theonella aff. mirabilis
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DOI：
10.1021/ja001859j
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发表时间：
2000-10-25
影响因子：
15
通讯作者：
Fusetani, N
中科院分区：
文献类型：
--
作者：
Nakao, Y;Fujita, M;Fusetani, N
据报道，海洋海绵Theonella mirabilis含有不寻常的缩酚肽，papuamides AD，它显示出HIV抑制和细胞毒性活性。2.在广岛大学的R/V丰潮丸号到奄美群岛和吐噶喇群岛的收集巡航中，我们遇到了一种与T. mirabilis，3具有多种生物活性，如抗真菌和蛋白酶抑制。我们已经报道了组织蛋白酶B抑制性线性肽托卡酰胺A的分离和结构测定。3进一步检测提取物得到了另一种组织蛋白酶B抑制剂，咪唑啶A（1）。4.本工作描述了米拉啶A的分离和结构鉴定（1）.在分离托卡酰胺A的过程中得到的Sephadex LH-20级分经ODS HPLC反复纯化，得到7.7 mg米拉啶A（1; 6.7× 10-5%收率，以湿重计）。通过HR-FABMS [（M+ H）+ m/z 669.3961（Δ +2.5 mmu）]和NMR数据确定，咪唑啶A（1）具有C30 H52 N8 O 9的分子式。其肽性质从1H NMR光谱中的四个酰胺质子以及13 C NMR光谱中170和175 ppm之间的六个碳信号中显而易见。
The marine sponge Theonella mirabilis was reported to contain unusual depsipeptides, papuamides AD, which showed HIV-inhibitory and cytotoxic activities. 2 During the collection cruise on R/V Toyoshio-maru of Hiroshima University to the Amami and Tokara Islands, we encountered a blue sponge closely related to T. mirabilis, 3 which exhibited a variety of bioactivities such as antifungal and protease inhibitory. We have already reported the isolation and structure determination of tokaramide A, a cathepsin B inhibitory linear peptide. 3 Further examination of the extract afforded another cathepsin B inhibitor, miraziridine A (1). 4 This work describes isolation and structure elucidation of miraziridine A (1).A Sephadex LH-20 fraction obtained during isolation of tokaramide A was repeatedly purified by ODS HPLC to furnish 7.7 mg of miraziridine A (1; 6.7× 10-5% yield based on wet weight). Miraziridine A (1) had a molecular formula of C30H52N8O9 as determined by HR-FABMS [(M+ H)+ m/z 669.3961 (Δ+ 2.5 mmu)] and NMR data. Its peptidic nature was evident from four amide protons in the 1H NMR spectrum, together with six carbon signals between 170 and 175 ppm in the 13C NMR spectrum.