Synthesis and Seed Germination Stimulating Activity of Some Imino Analogs of Strigolactones

Kondo, Yuki; Tadokoro, Eriko; Matsuura, Mayuko; Iwasaki, K.; Sugimoto, Yukihiro; Miyake, Hideyoshi; Takikawa, Hirosato; Sasaki, Makoto

doi:10.1271/bbb.70398

Cited by 56 publications

(40 citation statements)

References 11 publications

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“…The carbon–carbon double bond of the enol ether in GR24 is replaced by a carbon–nitrogen double bond in the imino analog (Kondo et al. 2007). Among the four possible racemic stereoisomers, we isolated two stereoisomers from the reaction product mixture, possibly being a pair of epimers at C-2′ having either ( E ) or ( Z ) configuration with respect to the C–N double bond as deduced from the close similarity in their 1 H-NMR (nuclear magnetic resonance) spectra.…”

Section: Resultsmentioning

confidence: 99%

“…However, imino analogs of strigolactones, in which the carbon–carbon double bond in the enol ether is replaced by a carbon–nitrogen double bond, were recently found to show germination stimulation activity in root parasitic weeds (Kondo et al. 2007). Therefore, the essentiality of the enol ether structure in the C–D part for weed seed germination is still undetermined.…”

Section: Discussionmentioning

confidence: 99%

“…1992b) and GR24 imino analog (Kondo et al. 2007) were synthesized according to previously reported procedures. (+)-GR7 and (+)-2′- epi -GR7, and (−)- ent -GR7 and (−)- ent -2′- epi -GR7 were prepared by starting, respectively, from (1 R ,5 S )-(+)- and (1 S ,5 R )-(−)-2-oxabicyclo[3.3.0]-oct-6-en-3-one (optical purity 99%, purchased from Sigma-Aldrich, Tokyo, Japan) as reported (Mangnus and Zwanenburg 1992a).…”

Section: Methodsmentioning

confidence: 99%

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Structural Requirements of Strigolactones for Hyphal Branching in AM Fungi

Akiyama

Ogasawara

Ito

et al. 2010

Plant and Cell Physiology

308

256

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Strigolactones are a group of terpenoid lactones that act as a host-derived signal in the rhizosphere communication of plants with arbuscular mycorrhizal (AM) fungi and root parasitic weeds as well as an endogenous plant hormone regulating shoot branching in plants. Strigolactones induce hyphal branching in AM fungi at very low concentrations, suggesting a highly sensitive perception system for strigolactones present in AM fungi. However, little is known about the structural requirements of strigolactones for hyphal branching in AM fungi. Here, we tested a series of natural and synthetically modified strigolactones as well as non-strigolactone-type germination stimulants for hyphal branching-inducing activity in germinating spores of the AM fungus Gigaspora margarita. All tested compounds with a tricyclic lactone coupled to a methylbutenolide via an enol ether bond showed activity, but differed in the active concentration and in the branching pattern of hyphae. Truncation of the A- and AB-rings in the tricyclic ABC lactone of strigolactones resulted in a drastic reduction in hyphal branching activity. Although the connection of the C-ring in the tricyclic lactone to the methylbutenolide D-ring was shown to be essential for hyphal branching, the bridge structure in the C–D part was found not necessarily to be enol ether, being replaceable with either alkoxy or imino ethers. These structural requirements in AM fungi are very similar but not identical to those observed in root parasitic weeds, especially with respect to the enol ether bridge in the C–D part.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Structural Requirements of Strigolactones for Hyphal Branching in AM Fungi

Akiyama

Ogasawara

Ito

et al. 2010

Plant and Cell Physiology

308

256

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“…ST series member 22c deserves a deeper discussion. Since recent data have spurred questions about the effective role of the enol ether bridge, [35] as well as the D ring itself [9] in determining the biological activity, we decided to test 22c, a molecule lacking both functionalities. As can be deduced from the bar chart reported in Figure 5, a remarkable activity, statistically comparable to GR 24, has been observed at 10 -10 m. This result seems to confirm that, lacking specific information about the receptor active site, further structure-activity investigations are required to undoubtedly assess the role of each functional group in the molecular structure.…”

Section: Biological Activitymentioning

confidence: 99%

New Potent Fluorescent Analogues of Strigolactones: Synthesis and Biological Activity in Parasitic Weed Germination and Fungal Branching

et al. 2011

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In this work we report the synthesis of new fluorescent analogues of strigolactones, their spectroscopic properties and the evaluation of their biological activity both on seeds of Orobanche aegyptiaca and on the AM fungus Gigaspora margarita. The synthesis has been accomplished according to two different synthetic plans and allows the introduction of various substituents on the A and C rings of the framework, thus enabling access to bioactive molecules with different spectroscopic properties.

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“…As for SL-dependent germination stimulation, the D-ring is required (Akiyama et al, 2010) and the SL stereochemistry is critical (De Saint-Germain et al, 2013). Additionally, the enol-ether bridge connecting the C-D-ring is also critical for SL optimum function (Kondo et al, 2007; Akiyama et al, 2010). However, modifications of the ABC substructure (in particular the A-ring) drastically diminish bioactivity (Besserer et al, 2006; Akiyama et al, 2010; Prandi et al, 2011; Cohen et al, 2013; Boyer et al, 2014).…”

Section: From Structure To Activitymentioning

confidence: 99%

Unraveling plant hormone signaling through the use of small molecules

Rigal

Robert

2014

Front. Plant Sci.

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Plants have acquired the capacity to grow continuously and adjust their morphology in response to endogenous and external signals, leading to a high architectural plasticity. The dynamic and differential distribution of phytohormones is an essential factor in these developmental changes. Phytohormone perception is a fast but complex process modulating specific developmental reprogramming. In recent years, chemical genomics or the use of small molecules to modulate target protein function has emerged as a powerful strategy to study complex biological processes in plants such as hormone signaling. Small molecules can be applied in a conditional, dose-dependent and reversible manner, with the advantage of circumventing the limitations of lethality and functional redundancy inherent to traditional mutant screens. High-throughput screening of diverse chemical libraries has led to the identification of bioactive molecules able to induce plant hormone-related phenotypes. Characterization of the cognate targets and pathways of those molecules has allowed the identification of novel regulatory components, providing new insights into the molecular mechanisms of plant hormone signaling. An extensive structure-activity relationship (SAR) analysis of the natural phytohormones, their designed synthetic analogs and newly identified bioactive molecules has led to the determination of the structural requirements essential for their bioactivity. In this review, we will summarize the so far identified small molecules and their structural variants targeting specific phytohormone signaling pathways. We will highlight how the SAR analyses have enabled better interrogation of the molecular mechanisms of phytohormone responses. Finally, we will discuss how labeled/tagged hormone analogs can be exploited, as compelling tools to better understand hormone signaling and transport mechanisms.

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Synthesis and Seed Germination Stimulating Activity of Some Imino Analogs of Strigolactones

Cited by 56 publications

References 11 publications

Structural Requirements of Strigolactones for Hyphal Branching in AM Fungi

Structural Requirements of Strigolactones for Hyphal Branching in AM Fungi

New Potent Fluorescent Analogues of Strigolactones: Synthesis and Biological Activity in Parasitic Weed Germination and Fungal Branching

Unraveling plant hormone signaling through the use of small molecules

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