Searching for original natural products by molecular networking: detection, isolation and total synthesis of chloroaustralasines†,Organic Chemistry Frontiers

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Searching for original natural products by molecular networking: detection, isolation and total synthesis of chloroaustralasines†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-06-07 00:00:00 , DOI: 10.1039/c8qo00429c
F. Olivon _{1,

2,

3,

4,

5} , C. Apel _{1,

2,

3,

4,

5} , P. Retailleau _{1,

2,

3,

4,

5} , P. M. Allard _{6,

7,

8,

9,

10} , J. L. Wolfender _{6,

7,

8,

9,

10} , D. Touboul _{1,

2,

3,

4,

5} , F. Roussi _{1,

2,

3,

4,

5} , M. Litaudon _{1,

2,

3,

4,

5} , S. Desrat _{1,

2,

3,

4,

5}

Affiliation

With the aim of isolating structurally original natural products, a molecular networking (MN)-based prioritisation approach has been developed and applied to a collection of 292 plant extracts. It led to the selection of a sample-specific cluster of ions detected in the bark extract of Codiaeum peltatum. The MN-guided purification of the targeted compounds afforded four unprecedented chlorinated monoterpenyl quinolones named chloroaustralasines A–C and isochloroaustralasine A. Faced with inconsistent spectral data of some previously reported quinolones, the total synthesis of the corresponding dihydroxy and chlorohydrin compounds was undertaken. The desired products were obtained in three steps, allowing the structural reassignment of two erioaustralasines. The chloroperoxidase-mediated hydroxychlorination reaction developed for the synthesis of the chlorinated quinolone showed that such complex molecules could be good substrates for this enzyme and, at the same time, raised the question of the biosynthetic origin of the non-artefactual chlorohydrin moiety.

中文翻译：

通过分子网络寻找原始的天然产物：氯金丝氨酸的检测，分离和全合成†

为了分离结构上原始的天然产物，已开发了一种基于分子网络（MN）的优先排序方法，并将其应用于292种植物提取物的收集。它导致选择了在硬皮Codiaeum peltatum的树皮提取物中检测到的特定于样品的离子簇。MN指导下的目标化合物的纯化提供了四种前所未有的氯化单萜烯基喹诺酮，分别为chloroaustralasines A C和isochloroaustralasineA。面对先前报道的某些喹诺酮类化合物光谱数据不一致的情况，对相应的二羟基和氯代醇化合物进行了全合成。通过三个步骤获得了所需的产物，从而使两种麦角四氢神经氨酸的结构重新分配。为合成氯代喹诺酮而开发的由氯过氧化物酶介导的羟氯化反应表明，这种复杂分子可能是该酶的良好底物，同时提出了非人工氯醇部分的生物合成来源问题。

更新日期：2018-06-07

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