A new class of conjugated strigolactone analogues with fluorescent properties: synthesis and biological activity

A new class of conjugated strigolactone analogues with fluorescent properties: synthesis and biological activity
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DOI:
10.1039/b907026e
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发表时间:
2009-01-01
影响因子:
3.2
通讯作者:
Venturello, Paolo
Venturello, Paolo
中科院分区:
化学3区
文献类型:
--
作者:
Bhattacharya, Chaitali;Bonfante, Paola;Venturello, Paolo

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合成了一类新的独脚金内酯类似物。它们与天然和合成来源的已知分子的不同之处在于两个主要特征。共轭体系从烯醇醚桥延伸到A环,B环是杂环,而C环是环状酮而不是γ-内酯。合成的关键步骤是在活化底物上的Nazarov环化。使用列当种子的生物测定表明,所有分子都强烈刺激发芽;特别是含氧类似物最活跃。有趣的是,一些新分子显示出荧光特性。
A new class of strigolactone analogues has been synthesized. They differ from known molecules, both of natural and synthetic origin, in two main features. The conjugated system extends from the enol ether bridge to the A ring, the B ring is a heterocycle while the C ring is a cyclic ketone instead of a gamma-lactone. The key step of the synthesis is a Nazarov cyclization on activated substrates. Bioassays using Orobanche seeds have revealed that all the molecules strongly stimulate germination; in particular the oxygen containing analogues are the most active. Interestingly, some of the new molecules show fluorescent properties.