Identification and synthesis of volatiles released by the myxobacterium Chondromyces crocatus
Identification and synthesis of volatiles released by the myxobacterium Chondromyces crocatus
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DOI：
10.1016/j.tet.2004.03.005
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发表时间：
2004-04-19
期刊：
影响因子：
2.1
通讯作者：
Reichenbach, H
中科院分区：
文献类型：
--
作者：
Schulz, S;Fuhlendorff, J;Reichenbach, H
通过闭环剥离分析或固相微萃取分析琼脂平板上的粘细菌Chondromyces crocatus的培养物。气味谱主要由吡嗪类、倍半萜类和一些芳香族化合物组成，总计超过50种组分。除已知的吡嗪类化合物外，还鉴定了几个新的吡嗪类化合物：2-（1-羟基-1-甲基乙基）-3-甲氧基吡嗪（9），2-（1-羟基-1-甲基丙基）-3-甲氧基吡嗪（10），2-（1-羟基-2-甲基丙基）-3-甲氧基吡嗪（11）。在大多数样品中出现的主要吡嗪是2，5-双-（1-甲基乙基）吡嗪（3）。虽然已知的倍半萜类土臭素（1）含量较低，但在大多数样品中发现了大量的相关化合物（1（10）E，5E）-大根香叶烯-11-醇（21）。之前未报道的来自微生物的其他突出的倍半萜类化合物是（6S，10 S）-6，10-二甲基双环[4.4.0]癸-1-烯-3-酮（16），其伴随有少量的几种衍生物。这些化合物的生物合成进行了讨论，最近提出的生物合成途径1和21。(C)2004爱思唯尔有限公司保留所有权利。
Cultures of the myxobacterium Chondromyces crocatus on agar plates were analysed by closed-loop-stripping analysis or solid phase micro extraction. The odour profiles consist mainly of pyrazines, sesquiterpenoids and some aromatic compounds, summing up to more than 50 components. Several new pyrazines as 2-(1-hydroxy-1-methylethyl)-3-methoxypyrazine (9), 2-(1-hydroxy-1-methylpropyl)-3-methoxypyrazine (10), and 2-(1-hydroxy-2-methylpropyl)-3-methoxypyrazine (11) were identified besides several known pyrazines. A major pyrazine occurring in most samples was 2,5-bis-(1-methylethyl)pyrazine (3). While the well known sesquiterpenoid geosmin (1) was present in low amounts, the related compound (1(10)E,5E)-germacradien-11-ol (21) was identified in most samples in larger quantities. Other prominent sesquiterpenoids not reported before from microorganisms were (6S,10S)-6,10-dimethylbicyclo[4.4.0]dec-1-en-3-one (16), which was accompanied by smaller amounts of several derivatives. The biosynthesis of these compounds is discussed in relation to the recently proposed biosynthetic pathways to 1 and 21. (C) 2004 Elsevier Ltd. All rights reserved.