Methyl phenlactonoates are efficient strigolactone analogs with simple structure

Jamil, Muhammad; Kountche, Boubacar Amadou; Haider, Imran; Guo, Xiujie; Ntui, Valentine Otang; Jia, Kun; Ali, Shawkat; Hameed, Umar F. Shahul; Nakamura, Hidemitsu; Lyu, Y.; Jiang, Kai; Hirabayashi, Kei; Tanokura, Masaru; Arold, Stefan T.; Asami, Tadao; Al‐Babili, Salim

doi:10.1093/jxb/erx438

Cited by 58 publications

(65 citation statements)

References 73 publications

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“…The presence of non-canonical SLs as a separate family of SLs was further supported by the identification of heliolactone (Ueno et al, 2014), zealactone, zeapyranolactone (Charnikhova et al, 2017(Charnikhova et al, , 2018, and avenaol (Yasui et al, 2017). Recently, we have developed MPs as analogs of non-canonical SLs, which are characterized by a simple structure and showed reasonable activity in different bioassays (Jamil et al, 2018). These encouraging results prompted us to develop a new series of MPs, with the aim of generating high-active and simple SL analogs.…”

Section: Discussionmentioning

confidence: 90%

“…Three selected MPs (MP16, MP18, MP21) and rac-GR24 were tested for their chemical stability at 21 ± 1 • C in aqueous solution with a pH of 5.5-6.0, as described previously (Jamil et al, 2018). Compound solution (1 mg ml −1 ) was prepared with 175 µl ethanol and 750 µl Mili-Q water.…”

Section: Stability Measurementmentioning

confidence: 99%

“…Purification of ShHTL7/OsD14 was carried out by adopting the procedure explained previously (Jamil et al, 2018). In vitro YLG hydrolysis assays were conducted as described before .…”

Section: In Vitro Ylg (Yoshimulactone Green) Assaysmentioning

confidence: 99%

“…Other simple analogs were developed by isosteric replacement leading to imino SL analogs (Kondo et al, 2007), CISA-1 (Rasmussen et al, 2013) and strigolactams (Lachia et al, 2015). We recently reported the synthesis of Nitro-Phenlactones (Jia et al, 2016) and a series of Methyl-Phenlactonoates (MPs) (Jamil et al, 2018, which were designed based on the structure of carlactone and carlactonoic acid, respectively. In this paper, we further proposed a new series of carlactonoic acid-based SL analogs.…”

Section: Introductionmentioning

confidence: 99%

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A New Series of Carlactonoic Acid Based Strigolactone Analogs for Fundamental and Applied Research

et al. 2020

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Strigolactones (SLs) are a group of carotenoid derived plant hormones that play a key role in establishing plant architecture and adapting it to environmental changes, and are involved in plants response to biotic and abiotic stress. SLs are also released into the soil to serve as a chemical signal attracting beneficial mycorrhizal fungi. However, this signal also induces seed germination in root parasitic weeds that represent a major global threat for agriculture. This wide spectrum of biological functions has made SL research one of the most important current topics in fundamental and applied plant science. The availability of SLs is crucial for investigating SL biology as well as for agricultural application. However, natural SLs are produced in very low amounts, and their organic synthesis is quite difficult, which creates a need for efficient and easyto-synthesize analogs and mimics. Recently, we have generated a set of SL analogs, Methyl Phenlactonoates (MPs), which resemble the non-canonical SL carlactonoic acid. In this paper, we describe the development and characterization of a new series of easyto-synthesize MPs. The new analogs were assessed with respect to regulation of shoot branching, impact on leaf senescence, and induction of seed germination in different root parasitic plants species. Some of the new analogs showed higher efficiency in inhibiting shoot branching as well as in triggering parasitic seed germination, compared to the commonly used GR24. MP16 was the most outstanding analog showing high activity in different SL biological functions. In summary, our new analogs series contains very promising candidates for different applications, which include the usage in studies for understanding different aspects of SL biology as well as large scale field application for combating root parasitic weeds, such as Striga hermonthica that devastates cereal yields in sub-Saharan Africa.

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Section: Discussionmentioning

confidence: 90%

Section: Stability Measurementmentioning

confidence: 99%

“…Purification of ShHTL7/OsD14 was carried out by adopting the procedure explained previously (Jamil et al, 2018). In vitro YLG hydrolysis assays were conducted as described before .…”

Section: In Vitro Ylg (Yoshimulactone Green) Assaysmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A New Series of Carlactonoic Acid Based Strigolactone Analogs for Fundamental and Applied Research

et al. 2020

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“…Jamil et al published a remarkable result, where the half maximal concentration of a methyl phenlactonoate (MP1) was 1 nM towards S. hermonthica and the activity on P. ramosa was similar to control. 47 Saccharin and cyclic keto-enol analogues were moderately active towards S. hermonthica and comparable with 18 and 22. 31,48 Fluorescent analogues are worth mentioning, although tested on a different parasitic weed (Orobanche aegyptiaca), which showed bioactivity at picomolar levels.…”

Section: Bioassaysmentioning

confidence: 87%

Hybrid‐type strigolactone analogues derived from auxins

Blanco‐Ania

Mateman

Hýlová

et al. 2019

Pest Management Science

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BACKGROUND: Strigolactones (SLs) have a vast number of ecological implications because of the broad spectrum of their biological activities. Unfortunately, the limited availability of SLs restricts their applicability for the benefit of humanity and renders synthesis the only option for their production. However, the structural complexity of SLs impedes their economical synthesis, which is unfeasible on a large scale. Synthesis of SL analogues and mimics with a simpler structure, but with retention of bioactivity, is the solution to this problem. RESULTS: Here, we present eight new hybrid-type SL analogues derived from auxin, synthesized via coupling of auxin ester [ethyl 2-(1H-indol-3-yl)acetate] and of ethyl 2-phenylacetate with four D-rings (mono-, two di-and trimethylated). The new hybrid-type SL analogues were bioassayed to assess the germination activity of seeds of the parasitic weeds Striga hermonthica,Orobanche minor and Phelipanche ramosa using the classical method of counting germinated seeds and a colorimetric method. The bioassays revealed that analogues with a natural monomethylated D-ring had appreciable to good activity towards the three species and were the most active derivatives. By contrast, derivatives with the trimethylated D-ring showed no activity. The dimethylated derivatives (2,4-dimethyl and 3,4-dimethyl) were slightly active, especially towards P. ramosa. CONCLUSIONS: New hybrid-type analogues derived from auxins have been prepared. These analogues may be attractive as potential suicidal germination agents for parasitic weed control because of their ease of preparation and relevant bioactivity.

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Chemistry of Strigolactones, Key Players in Plant Communication

Daignan‐Fornier,

Keita,

Boyer

2024

ChemBioChem

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Today, the use of artificial pesticides is questionable and the adaptation to global warming is a necessity. The promotion of favorable natural interactions in the rhizosphere offers interesting perspectives for changing the type of agriculture. Strigolactones (SLs), the latest class of phytohormones to be discovered, are also chemical mediators in the rhizosphere. We present in this review the diversity of natural SLs, their analogs, mimics, and probes essential for the biological studies of this class of compounds. Their biosynthesis and access by organic synthesis are highlighted especially concerning noncanonical SLs, the more recently discovered natural SLs. Organic synthesis of analogs, stable isotope‐labeled standards, mimics, and probes are also reviewed here. In the last part, the knowledge about the SL perception is described as well as the different inhibitors of SL receptors that have been developed.

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Methyl phenlactonoates are efficient strigolactone analogs with simple structure

Abstract: We developed easy to synthesize and efficient strigolactone analogs with great application potential. Biological activities and receptor binding assays demonstrate the effect of structural modification on the efficacy and specificity of strigolactones.

Cited by 58 publications

References 73 publications

A New Series of Carlactonoic Acid Based Strigolactone Analogs for Fundamental and Applied Research

A New Series of Carlactonoic Acid Based Strigolactone Analogs for Fundamental and Applied Research

Hybrid‐type strigolactone analogues derived from auxins

Chemistry of Strigolactones, Key Players in Plant Communication

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