Stability of strigolactone analog GR24 toward nucleophiles

Halouzka, Rostislav; Tarkowski, Petr; Zwanenburg, B.; Zeljković, Sanja Ćavar

doi:10.1002/ps.4782

Cited by 27 publications

(27 citation statements)

References 40 publications

(71 reference statements)

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“…In addition, the lack of stability of these compounds limits their application. Degradation reactions occur preferentially in basic media and the slowest reaction occurs in the presence of sulfur‐containing nucleophiles with a half‐life of ≤ 19 h . As a consequence, strigolactone mimics are preferred over natural strigolactones.…”

Section: Chemical Signal Hunters: Parasitic Plantsmentioning

confidence: 99%

“…212,216 In addition, the lack of stability of these compounds limits their application. Degradation reactions occur preferentially in basic media and the slowest reaction occurs in the presence of sulfur-containing nucleophiles with a half-life of ≤ 19 h. 217 As a consequence, strigolactone mimics are preferred over natural strigolactones. Strigolactams and phthalimide derivatives are examples of mimics that strongly stimulate O. cumana, O. minor, P. ramosa and P. aegyptiaca germination.…”

Section: Chemical Signal Hunters: Parasitic Plantsmentioning

confidence: 99%

See 1 more Smart Citation

Recent advances in allelopathy for weed control: from knowledge to applications

Macías

Mejías

Molinillo

2019

Pest Management Science

183

131

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Allelopathy is the biological phenomenon of chemical interactions between living organisms in the ecosystem, and must be taken into account in addressing pest and weed problems in future sustainable agriculture. Allelopathy is a multidisciplinary science, but in some cases, aspects of its chemistry are overlooked, despite the need for a deep knowledge of the chemical structural characteristics of allelochemicals to facilitate the design of new herbicides. This review is focused on the most important advances in allelopathy, paying particular attention to the design and development of phenolic compounds, terpenoids and alkaloids as herbicides. The isolation of allelochemicals is mainly addressed, but other aspects such as the analysis and activities of derivatives or analogs are also covered. Furthermore, the use of allelopathy in the fight against parasitic plants is included. The past 12 years have been a prolific period for publications on allelopathy. This critical review discusses future research areas in this field and the state of the art is analyzed from the chemist's perspective. © 2019 Society of Chemical Industry

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Section: Chemical Signal Hunters: Parasitic Plantsmentioning

confidence: 99%

Section: Chemical Signal Hunters: Parasitic Plantsmentioning

confidence: 99%

Recent advances in allelopathy for weed control: from knowledge to applications

Macías

Mejías

Molinillo

2019

Pest Management Science

183

131

View full text Add to dashboard Cite

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“…40) It should be noted that, in most cases, SL degradation experiments have been conducted at relatively high concentrations (>mM) far above the water solubility of SLs, and SL degradation is often monitored by a high performance liquid chromatograph equipped with UV-visible or photodiode array detector by which detection of SLs at concentrations lower than µM is rather difficult. 41) In contrast, biologically active concentrations of SLs in the rhizosphere would be lower than µM; therefore, it is im- portant to conduct SL degradation experiments at these biological concentrations. For example, typical concentrations of SLs in the culture media of plants grown hydroponically under phosphate deficiency are at nM levels and no significant degradation of SLs in the media was detected when the growth media was left at room temperature overnight after removal of the plants (K. Yoneyama, unpublished).…”

Section: Stability Of Slsmentioning

confidence: 99%

Recent progress in the chemistry and biochemistry of strigolactones

Yoneyama

2020

J. Pestic. Sci.

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Strigolactones (SLs) are plant secondary metabolites derived from carotenoids. SLs play important roles in the regulation of plant growth and development in planta and coordinate interactions between plants and other organisms including root parasitic plants, and symbiotic and pathogenic microbes in the rhizosphere. In the 50 years since the discovery of the first SL, strigol, our knowledge about the chemistry and biochemistry of SLs has advanced explosively, especially over the last two decades. In this review, recent advances in the chemistry and biology of SLs are summarized and possible future outcomes are discussed.

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“…The use of natural SLs for this purpose is not a realistic alternative because chemical synthesis of these compounds is very laborious. In addition, plants produce and release SLs in very low amounts, even under phosphate starvation that triggers both processes (Halouzka, Tarkowski, Zwanenburg, & Ćavar, 2018;Matusova, 2005;Stewart & Press, 1990;Sugimoto, Wigchert, Thuring, & Zwanenburg, 1998;Wigchert et al, 1999;Xie, Yoneyama, & Yoneyama, 2010). Although significant success has been achieved in the development of a wide array of SL analogs (Jia et al, 2016;Kondo et al, 2007;Mwakaboko & Zwanenburg, 2011a, 2011bZwanenburg & Pospíšil, 2013), the practicability of the SLbased suicidal germination strategy has been rarely explored in field trials (Zwanenburg et al, 2016(Zwanenburg et al, , 2009.…”

Section: Introductionmentioning

confidence: 99%

Suicidal germination as a control strategy for Striga hermonthica (Benth.) in smallholder farms of sub‐Saharan Africa

Kountche

Jamil

Yonli

et al. 2019

Plants People Planet

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Societal Impact Statement Infestation by the parasitic plant Striga hermonthica is a severe threat to food security in sub‐Saharan Africa, impacting the production of the major staple crops pearl millet and sorghum, equating to 7–10 billion $ losses. Using Striga seed dependency on host‐released germination stimulants, we have developed and validated a method for addressing the problem of accumulated parasite seedbanks—the major obstacle in combating Striga infestation in African rain‐fed fields. Application of our method promises to alleviate the problem posed by this pernicious weed by increasing crop production for smallholder farmers. Summary The root parasitic plant Striga hermonthica is a major threat to global food security, causing enormous losses in yields of the main staple crops in sub‐Saharan Africa, which include pearl millet, sorghum, maize and rice. Sustainable Striga control should ideally lead to the depletion of the vast, long‐lived Striga seedbank, and this can be achieved by inducing suicidal seed germination through application of strigolactone (SL) analogs in the absence of host plants. However, this “suicidal germination” strategy has not been evaluated under the natural rain‐fed conditions that prevail in Striga‐prone regions. We have developed and validated a protocol for suicidal germination in laboratory and natural conditions in Striga‐infested rain‐fed African fields. Three SL analogs were tested and these resulted to between 65% and 55% reduction in Striga emergence in pearl millet and sorghum fields, respectively. We conclude that suicidal germination is an effective method for reducing the Striga seedbank. Moreover, the minimal demands of our protocol, in terms of water consumption and amount of selected SL analogs, make it affordable and applicable at a large scale in African rain‐fed agriculture, holding promise for sustainable cleaning of heavily Striga‐infested fields in sub‐Saharan Africa.

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Stability of strigolactone analog GR24 toward nucleophiles

Abstract: This study provides valuable information on the chemical stability of GR24 in different plant growth media and buffers. Such information is valuable for scientists using GR24 treatments to study SL-regulated processes in plants. © 2017 Society of Chemical Industry.

Cited by 27 publications

References 40 publications

Recent advances in allelopathy for weed control: from knowledge to applications

Recent advances in allelopathy for weed control: from knowledge to applications

Recent progress in the chemistry and biochemistry of strigolactones

Suicidal germination as a control strategy for Striga hermonthica (Benth.) in smallholder farms of sub‐Saharan Africa

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