Volatiles released by a Streptomyces species isolated from the North Sea

Volatiles released by a Streptomyces species isolated from the North Sea
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DOI:
10.1002/cbdv.200590062
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发表时间:
2005-01-01
影响因子:
2.9
通讯作者:
Schulz, S
Schulz, S
中科院分区:
化学3区
文献类型:
--
作者:
Dickschat, JS;Martens, T;Schulz, S

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对北海链霉菌GWS-BW-H5菌株进行了气质联用分析(表1),分析了用闭合反萃取器(CLSA)获得的琼脂平板培养物(HE)和液体培养物(LCE)的顶空提取物。HE的挥发分主要是已知的挥发物(-)-Geosmin(4)和2-甲基异龙脑(1)。存在少量的倍半萜,它们在LCE中以更多样化的结构种类和更高的数量存在。不同的结构可以通过生物合成途径上的少量阳离子中间体来合理化。这两种培养方法之间最显著的区别是在LCE中存在Me分支的伽马内酯和三角洲内酯31-38,这是以前从自然中没有报道的。主要成分为10-甲基十二烷-5-内酯(34)、10-甲基十二烷-2-烯-4-内酯(36)和10-甲基十二烷-3-烯-4-内酯(38)。所有新内酯的结构均经合成得到确证。此外,液体培养比琼脂平板培养产生更多的挥发物。由于36株菌株对GWS-BW-H5菌株有生长抑制作用,因此对同一生境中分离到的另外12株菌株进行了生长抑制试验。观察到对其中四个菌株的拮抗活性,其阈值水平略高于对照实验中使用的青霉素G(表2)。
The North Sea Streptomyces strain GWS-BW-H5 was investigated by analyzing headspace extracts of agar-plate cultures (HE) or liquid cultures (LCE), obtained with a closed-loop stripping apparatus (CLSA), by GC/MS (Table 1). The volatile profile of the HE is dominated by the known volatiles (-)-geosmin (4) and 2-methyisoborneol (1). Small amounts of sesquiterpenes occur, which are present in a more-diverse structural variety and in higher quantities in the LCE. The different structures can be rationalized by few cationic intermediates along their biosynthetic pathway. The most-prominent difference between the two culture methods were the presence of the Me-branched gamma- and delta-lactones 31-38, not previously reported from nature, in the LCE. Major components were 10-methyldodecan-5-olide (34), 10-methyldodec-2-en-4-olide (36), and 10-methyldodec-3-en-4-olide (38). The structures of all new lactones were verified by synthesis. Furthermore, more volatiles in higher amounts were produced by the liquid culture than by to the agar plate culture. Since 36 showed inhibitory growth effects against strain GWS-BW-H5, growth inhibition against twelve other strains isolated from the same habitat was tested. Antagonistic activity against four of the strains was observed, with a slightly higher threshold level than found for penicillin G, which was used in control experiments (Table 2).