Strigolactone Analogs Derived from Ketones Using a Working Model for Germination Stimulants as a Blueprint
Strigolactone Analogs Derived from Ketones Using a Working Model for Germination Stimulants as a Blueprint
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DOI：
10.1093/pcp/pcr031
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发表时间：
2011-04-01
影响因子：
4.9
通讯作者：
Zwanenburg, Binne
中科院分区：
文献类型：
--
作者：
Mwakaboko, Alinanuswe S.;Zwanenburg, Binne
独脚金内酯是植物界重要的信号化合物。在这里，我们重点关注它们对寄生杂草独脚金和列当属种子的发芽刺激作用。更具体地说，是关于从简单环酮衍生的新型活性独脚金内酯类似物的设计和合成。由 1-茚满酮、1-四氢萘酮、环戊酮、环己酮和一系列取代的环己酮（包括香芹酮和胡薄荷酮）衍生的新类似物是通过用甲酸乙酯对酮进行甲酰化，然后与卤代丁烯内酯偶联来制备的。衍生自 1-四氢萘酮的类似物的两种对映体均已通过使用纯手性合成子进行偶联反应来制备。对于其他三种独脚金内酯类似物，已通过手性柱色谱法获得对映体。所有类似物对独脚金(Striga hermomonthica)和列当(Orobanche crenata)和O. cernua的种子都具有明显的发芽活性。在 D 环上具有与天然存在的三棱醇相同的构型的立体异构体比相应的对映体具有更高的刺激作用。从1-茚满酮和1-四氢萘酮获得的类似物具有与众所周知的兴奋剂GR 24相当的活性。从2-苯基环己酮、香芹酮和胡薄荷酮衍生的类似物也具有良好的发芽反应。结果表明，该工作模型适用于设计新型生物活性独脚金内酯。
Strigolactones are important signaling compounds in the plant kingdom. Here we focus on their germination stimulatory effect on seeds of the parasitic weeds Striga and Orobanche spp. and more particularly on the design and synthesis of new active strigolactone analogs derived from simple cyclic ketones. New analogs derived from 1-indanone, 1-tetralone, cyclopentanone, cyclohexanone and a series of substituted cyclohexanones (including carvone and pulegone) are prepared by formylation of the ketones with ethyl formate followed by coupling with a halo butenolide. Both enantiomers of the analog derived from 1-tetralone have been prepared by employing a homochiral synthon for the coupling reaction. For three other strigolactone analogs the antipodes have been obtained by chromatography on a chiral column. All analogs have an appreciable germinating activity towards seeds of Striga hermomonthica and Orobanche crenata and O. cernua. Stereoisomers having the same configuration at the D-ring as in naturally occurring strigol have a higher stimulatory effect than the corresponding antipodes. The analogs obtained from 1-indanone and 1-tetralone have an activity comparable with that of the well known stimulant GR 24. Analogs derived from 2-phenyl-cylohexanone, carvone and pulegone also have a good germinating response. The results show that the working model for designing new bioactive strigolactones is applicable.