Synthesis of strigolactones, a strategic account

Zwanenburg, B.; Zeljković, Sanja Ćavar; Pospíšil, Tomáš

doi:10.1002/ps.4105

Cited by 57 publications

(55 citation statements)

References 65 publications

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“…CYP711A isoforms in red bell pepper, red clover, and pea plants may directly convert CL into orobanchol (5) or may convert CLA into orobanchol (5) with other oxygenases such as LBO after introducing the carboxyl group to CL by CYP711. The oxidation of C-18, the methyl group in the six-membered ring of CL, is likely to be required to form the B ring, as the oxidation of C-19 is required to form the C ring 20,31) (Fig. 4).…”

Section: Discussionmentioning

confidence: 99%

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

Ueno

Nakashima

Mizutani

et al. 2018

Journal of Pesticide Science

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The bioconversion of 5-deoxystrigol (5DS) and 4-deoxyorobanchol (4DO), the simplest canonical strigolactones (SLs), into monohydroxylated SLs such as strigol, sorgomol and orobanchol was confirmed by administering of stable isotope-labeled substrates to hydroponically grown plants. Liquid chromatography-mass spectrometry analyses established that 5DS was stereoselectively converted into strigol and sorgomol by cotton (Gossypium hirsutum) and Chinese milk vetch (Astragalus sinicus), respectively. 4DO was converted into orobanchol by rice (Oryza sativa). However, the red bell pepper (Capsicum annuum), red clover (Trifolium pratense), and pea (Pisum sativum) negligibly converted 4DO into orobanchol. The red bell pepper converted ent-4DO into 2′,8-bisepi-sorgomol. These results suggest that some plants generate orobanchol without passing through 4DO.

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Section: Discussionmentioning

confidence: 99%

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

Ueno

Nakashima

Mizutani

et al. 2018

Journal of Pesticide Science

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“…Consequently, the commercially available ethyl ester auxins 14 and 15 were formylated using ethyl formate in the present of a base (NaH) in excellent yields and the resulting enols 16 and 17, respectively, were then coupled with chloro furanones 9-12 using potassium carbonate in DMF to afford hybrid-type SL analogues 18-25 in poor to very good yields (Scheme 2). In all cases, the yields of the products derived from auxin derivative 14 (18)(19)(20)(21) were higher than those of the counterparts of auxin derivative 15 (22)(23)(24)(25).…”

Section: Synthesismentioning

confidence: 83%

“…Several reviews cover the current state of affairs concerning the chemistry and bio-properties of SLs. [2][3][4][5][6][22][23][24] The availability of SLs is limited because levels of natural production are minute and their complete synthesis is quite laborious due to their complex structures. 25,26 Synthesis of simple bioactive analogues, having the same bioactiphore as natural SLs, has attracted considerable attention in recent years (Fig.…”

Section: Introductionmentioning

confidence: 99%

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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“…To overcome this issue, scientists first explored structure-activity relationship of SLs (Zwanenburg and Pospisil, 2013). These studies showed that the α/β unsaturated system and D-ring of SL analogs are indispensable for their activity, while modifications of the ABCring impacted the level of their efficiency, as shown by testing the activity of the structurally less complex analogs GR5 and GR7 (Mangnus et al, 1992b;Zwanenburg et al, 2009Zwanenburg et al, , 2016c. 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).…”

Section: Introductionmentioning

confidence: 99%

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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Synthesis of strigolactones, a strategic account

Cited by 57 publications

References 65 publications

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

Hybrid‐type strigolactone analogues derived from auxins

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

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