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Integrating carbon-halogen bond formation into medicinal plant metabolism

机译：将碳-卤素键的形成整合到药用植物代谢中

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摘要

Halogenation, which was once considered a rare occurrence in nature, has now been observed in many natural product biosynthetic pathways. However, only a small fraction of halogenated compounds have been isolated from terrestrial plants. Given the impact that halogenation can have on the biological activity of natural products1, we reasoned that the introduction of halides into medicinal plant metabolism would provide the opportunity to rationally bioengineer a broad variety of novel plant products with altered, and perhaps improved, pharmacological properties. Here we report that chlorination biosynthetic machinery from soil bacteria can be successfully introduced into the medicinal plant Catharanthus roseus (Madagascar periwinkle). These prokaryotic halogenases function within the context of the plant cell to generate chlorinated tryptophan, which is then shuttled into monoterpene indole alkaloid metabolism to yield chlorinated alkaloids. A new functional group-a halide-is thereby introduced into the complex metabolism ofrnC. roseus, and is incorporated in a predictable and regioselective manner onto the plant alkaloid products. Medicinal plants, despite their genetic and developmental complexity, therefore seem to be a viable platform for synthetic biology efforts.
机译：曾经被认为是自然界中罕见的卤代物，现在已经在许多天然产物的生物合成途径中被观察到。但是，从地面植物中仅分离出少量的卤代化合物。考虑到卤化作用可能对天然产物的生物活性产生影响，我们认为将卤化物引入药用植物代谢中将为合理地生物工程化具有改变的，甚至改善的药理特性的多种新型植物产品提供机会。在这里，我们报告说，土壤细菌的氯化生物合成机制可以成功地引入药用植物长春花（Madagascar荔枝螺）中。这些原核生物卤化酶在植物细胞内起作用，生成氯化色氨酸，然后将其穿梭入单萜吲哚生物碱代谢中，从而生成氯化生物碱。由此将新的官能团-卤化物引入到rnC的复杂代谢中。玫瑰，并以可预测和区域选择性的方式掺入植物生物碱产品中。药用植物尽管具有遗传和发育上的复杂性，但似乎是合成生物学研究的可行平台。

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  • 来源
    《Nature》 |2010年第7322期|p.461-464|共4页
  • 作者

    Weerawat Runguphan; Xudong Qu; Sarah E. OConnor;

  • 作者单位

    Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA;

    rnDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;

    rnDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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  • 正文语种 eng
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