Crossbyanols A-D, toxic brominated polyphenyl ethers from the Hawai'ian bloom-forming Cyanobacterium Leptolyngbya crossbyana.
Crossbyanols A-D, toxic brominated polyphenyl ethers from the Hawai'ian bloom-forming Cyanobacterium Leptolyngbya crossbyana.
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DOI：
10.1021/np900661g
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发表时间：
2010-04-23
影响因子：
5.1
通讯作者：
Gerwick, William H.
中科院分区：
文献类型：
--
作者：
Choi, Hyukjae;Engene, Niclas;Smith, Jennifer E.;Preskitt, Linda B.;Gerwick, William H.
周期性地，海洋蓝细菌Leptolyngbya crossbyana在夏威夷珊瑚礁上形成广泛的水华，并导致对向珊瑚的重大损害。此外，靠近这种蓝细菌垫的珊瑚，但不是直接过度生长，已经被观察到发生漂白。因此，该蓝藻的样品进行了化学研究的生物活性次级代谢产物，可能是这种毒性现象的基础。1H NMR光谱引导的分级分离导致四种七溴化多酚醚，crossbyanols A-D（1-4）的分离。这些化合物的结构解析由于其非常低的质子碳（H/C）比而具有挑战性，但通过将标准NMR和MS数据与2 Hz优化的HMBC数据相结合来完成。crossbyanol A作为二乙酸酯的衍生化有助于其结构的归属。Crossbyanol B（2）对耐甲氧西林金黄色葡萄球菌（MRSA）的MIC值在2.0-3.9 μg/mL之间，显示出相对较强的卤虫毒性（IC 50 2.8 ppm）。
Periodically, the marine cyanobacterium Leptolyngbya crossbyana forms extensive blooms on Hawai'ian coral reefs, and results in significant damage to the subtending corals. Additionally, corals near to mats of this cyanobacterium, but not directly overgrown, have been observed to undergo bleaching. Therefore, samples of this cyanobacterium were chemically investigated for bioactive secondary metabolites that might underlie this toxicity phenomenon. 1H NMR spectroscopy-guided fractionation led to the isolation of four hepta-brominated polyphenolic ethers, crossbyanols A–D (1–4). Structure elucidation of these compounds was made challenging by their very low proton to carbon (H/C) ratio, but was completed by combining standard NMR and MS data with 2 Hz-optimized HMBC data. Derivatization of crossbyanol A as the diacetate assisted in the assignment of its structure. Crossbyanol B (2) showed antibiotic activity with an MIC value between 2.0–3.9 μg/mL against methicillin-resistant Staphylococcus aureus (MRSA) and relatively potent brine shrimp toxicity (IC50 2.8 ppm).
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