Toxins and biologically active secondary metabolites of Microcystis sp isolated from Lake Kinneret

Toxins and biologically active secondary metabolites of Microcystis sp isolated from Lake Kinneret
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DOI:
10.1560/fe24-vyuf-ctbd-hb7x
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发表时间:
2006-01-01
影响因子:
3.2
通讯作者:
Carmeli, Shmuel
Carmeli, Shmuel
中科院分区:
化学3区
文献类型:
--
作者:
Beresovsky, Dina;Hadas, Ora;Carmeli, Shmuel

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多年来,蓝藻被认为是Kinneret湖(加利利海,以色列)浮游植物种群的次要,可忽略不计的组成部分。然而,在过去的十年中,一些新的物种入侵了湖泊,其他更常见的物种出现得更频繁,浓度也更高。最近,我们从Kinneret湖分离到两株微囊藻。两者都产生了一系列肝毒性微囊藻毒素。在一项生物测定指导的研究中,我们在其中一种微囊藻菌株(MB-K)的分泌物中发现,化感活性归因于一种新的代谢物,微碳素A(1)。随后,基于其蛋白酶抑制活性,从培养的(MB-K)菌株的亲水性提取物中分离出另外两种新的代谢产物,微肽素KT 946(2)和鱼腥肽素KT 864(3)。均相和异相2D-NMR技术以及HRMS确定了三种化合物的总体结构。从光谱数据和Marveland的HPLC方法的组合推导出2和3的相对和绝对立体化学。
For many years cyanobacteria were considered a minor, negligible component of the phytoplankton population in Lake Kinneret (Sea of Galilee, Israel). However, during the last decade several new species invaded the lake and other, more common species were present more frequently and in higher concentrations. Recently, we isolated two Microcystis sp. strains from Lake Kinneret. Both produced an array of hepatotoxic microcystins. In a bioassay-guided study we identified in exudates of one of the Microcystis strains (MB-K) that allelopathic activity was attributed to a novel metabolite, microcarbonin A (1). Subsequently, two other novel metabolites, micropeptin KT946 (2) and anabaenopeptin KT864 (3), were isolated from the hydrophilic extract of the cultured (MB-K) strain, based on their protease inhibition activity. Homo- and heteronuclear-2D-NMR techniques, as well as HRMS, determined the gross structure of the three compounds. The relative and absolute stereochemistry of 2 and 3 was deduced from a combination of spectral data and Marfey's method for HPLC.