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三环丁烯内酯的合成及其与已知烟碱丁烯内酯KAR1的效果比较。

Synthesis of tricyclic butenolides and comparison their effects with known smoke-butenolide, KAR1.

作者信息

Krawczyk Ewa, Koprowski Marek, Cembrowska-Lech Danuta, Wójcik Agata, Kępczyński Jan

机构信息

Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.

Department of Plant Physiology and Genetic Engineering, Faculty of Biology, University of Szczecin, Wąska 13, 71-415 Szczecin, Poland.

出版信息

J Plant Physiol. 2017 Aug;215:91-99. doi: 10.1016/j.jplph.2017.04.021. Epub 2017 Jun 1.

DOI:10.1016/j.jplph.2017.04.021
PMID:28618259
Abstract

Plant-derived smoke - butenolide, called at present karrikin 1 (KAR) is known as an important inductor of seed germination and seedling growth. In this study, tricyclic butenolides were synthesized and their effects on germination of dormant and non-dormant Avena fatua caryopses were compared, as were also their effects versus those of KAR on seedling growth. KAR was found to be most effective and to completely remove dormancy. Butenolides, rac-8 and (S)-8a, showed a low stimulatory effect on germination of dormant caryopses, visible only when applied at very high concentrations. These compounds used at concentrations 100 times those of KAR similarly increased the speed of germination and vigor of non-dormant caryopses. Likewise, growth of coleoptiles and their fresh weight were increased by KAR as well as by rac-8 and (S)-8a to a similar value. KAR and rac-8 were more effective than (S)-8a in increasing root growth. The results shown indicate that the presence of an aromatic ring in the absence of methyl group at C3 induced a much lower, or a similar, effect on germination of dormant and non-dormant Avena fatua caryopses and seedling growth compared to KAR, but only when used at much higher concentrations. The simultaneous presence of a methyl group at C3 and an aromatic ring in the compound rac-7 exerted only a slight effect on the root growth.

摘要

植物源烟雾中的丁烯内酯,目前称为卡里金1(KAR),是种子萌发和幼苗生长的重要诱导剂。在本研究中,合成了三环丁烯内酯,并比较了它们对休眠和非休眠野燕麦颖果萌发的影响,以及它们与KAR对幼苗生长的影响。发现KAR最有效且能完全解除休眠。丁烯内酯rac-8和(S)-8a对休眠颖果的萌发有低刺激作用,仅在非常高的浓度下施用时才可见。这些化合物以比KAR高100倍的浓度使用时,同样提高了非休眠颖果的萌发速度和活力。同样,KAR以及rac-8和(S)-8a使胚芽鞘的生长及其鲜重增加到相似的值。在增加根生长方面,KAR和rac-8比(S)-8a更有效。所示结果表明,与KAR相比,在C3处不存在甲基的情况下芳香环的存在对休眠和非休眠野燕麦颖果的萌发以及幼苗生长产生的影响要低得多或相似,但仅在以高得多的浓度使用时才如此。化合物rac-7中C3处甲基和芳香环的同时存在对根生长仅产生轻微影响。

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Smoke-Isolated Karrikins Stimulated Tanshinones Biosynthesis in through Endogenous Nitric Oxide and Jasmonic Acid.烟雾隔离的卡利卡丁通过内源性一氧化氮和茉莉酸刺激丹参酮的生物合成。
Molecules. 2019 Mar 29;24(7):1229. doi: 10.3390/molecules24071229.