Synthesis and biological evaluation of potential substrates for the isolation of the strigol receptor

Thuring, Jan Willem; Keltjens, Rolf; Nefkens, G. H. L.; Zwanenburg, B.

doi:10.1039/a604685a

Cited by 14 publications

(23 citation statements)

References 18 publications

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“…Various labels can be introduced by reaction with the amino group, for instance the rather bulky fluorescent dansyl group. The bioactivity of this dansylamino‐GR 24 is in the same range as that of GR 24 itself 75. The synthesis of biotin‐labelled GR 24 ( 29 ) having a PEG spacer and having the required natural stereochemistry was accomplished (Fig.…”

Section: Search For the Receptor Proteinmentioning

confidence: 99%

“…The stereochemistry of labelled GR 24 should be the same as that of natural strigolactones in order to achieve optimal binding to the receptor. The synthetic elaboration of GR 24 reveals that amino‐GR 24 ( 28 ) can be prepared by nitration and subsequent reduction 75. Various labels can be introduced by reaction with the amino group, for instance the rather bulky fluorescent dansyl group.…”

Section: Search For the Receptor Proteinmentioning

confidence: 99%

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Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Zwanenburg

Mwakaboko

Reizelman

et al. 2009

Pest Management Science

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220

192

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The structures of naturally occurring germination stimulants for seeds of the parasitic weeds Striga spp. and Orobanche spp. are described. The bioactiphore in this strigolactone family of stimulants is deduced from a structure-activity relationship and shown to reside in the CD part of the stimulant molecule. A molecular mechanism for the initial stages of seed germination is proposed. The influence of stereochemistry on the stimulant activity is significant. Combining this molecular information leads to a model for the design of synthetic strigolactones. Nijmegen-1 is a typical example of a highly active, newly designed synthetic stimulant. The occurrence of natural stimulants not belonging to the strigolactone family, such as cotylenin and parthenolide, is briefly described. The biosynthesis of natural strigolactones from beta-carotene is analysed in terms of isolated and predicted stimulants. This scheme will be helpful in the search for new strigolactones from root exudates. Protein fishing experiments to isolate and characterise the receptor protein using biotin-labelled GR 24 are described. A receptor protein of 60 kD was identified by this method. Nijmegen-1 has been tested as a suicidal germination agent in field trials on tobacco infested by Orobanche ramosa L. The preliminary results are highly rewarding. Finally, some future challenges in synthesis are described. These include synthesising new natural and synthetic stimulants and establishing the molecular connection between strigolactones as germination stimulants, as the branching factor for arbuscular mycorrhizal fungi and as an inhibitor of shoot branching.

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Section: Search For the Receptor Proteinmentioning

confidence: 99%

Section: Search For the Receptor Proteinmentioning

confidence: 99%

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Zwanenburg

Mwakaboko

Reizelman

et al. 2009

Pest Management Science

Self Cite

220

192

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“…GR24, 29-epi-GR24, and derivatives 1, 29-epi-1, 2, 29-epi-2, 4, and 5 (Fig. 2) were prepared according to the procedures described Thuring et al, 1997;Reizelman et al, 2003); compound 3 was prepared according to the procedure described by Fell and Harbridge (1990) and d'orenone according to the procedure of Schachtschabel and Boland (2007). (+)-and (2)-Solanacol and solanacyl acetate were prepared by the procedure described previously in our laboratory (Chen et al, 2010).…”

Section: General Remarksmentioning

confidence: 99%

Structure-Activity Relationship Studies of Strigolactone-Related Molecules for Branching Inhibition in Garden Pea: Molecule Design for Shoot Branching

et al. 2012

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Initially known for their role in the rhizosphere in stimulating the seed germination of parasitic weeds such as the Striga and Orobanche species, and later as host recognition signals for arbuscular mycorrhizal fungi, strigolactones (SLs) were recently rediscovered as a new class of plant hormones involved in the control of shoot branching in plants. Herein, we report the synthesis of new SL analogs and, to our knowledge, the first study of SL structure-activity relationships for their hormonal activity in garden pea (Pisum sativum). Comparisons with their action for the germination of broomrape (Phelipanche ramosa) are also presented. The pea rms1 SL-deficient mutant was used in a SL bioassay based on axillary bud length after direct SL application on the bud. This assay was compared with an assay where SLs were fed via the roots using hydroponics and with a molecular assay in which transcript levels of BRANCHED1, the pea homolog of the maize TEOSINTE BRANCHED1 gene were quantified in axillary buds only 6 h after application of SLs. We have demonstrated that the presence of a Michael acceptor and a methylbutenolide or dimethylbutenolide motif in the same molecule is essential. It was established that the more active analog 23 with a dimethylbutenolide as the D-ring could be used to control the plant architecture without strongly favoring the germination of P. ramosa seeds. Bold numerals refer to numbers of compounds.

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“…At the end of the 90s', the preparation of biologically active, labelled strigol analogues was proposed as a strategy to identify the strigol receptor in the seeds of parasitic plants (Thuring et al, 1997). For this purpose, amino-GR24 was prepared and functionalized with affinity tags or photoaffinity labels, among others, biotin and the fluorescent dansyl and rhodamine groups, which were introduced on the A-ring because of its remote position with respect to the supposed bioactiphore ( Figure 16) (Reizelman et al, 2003).…”

Section: From Functional Sls Analogues To Functionalized Sls Analoguesmentioning

confidence: 99%

Shaping Small Bioactive Molecules to Untangle Their Biological Function: A Focus on Fluorescent Plant Hormones

Lace

Prandi

2016

Molecular Plant

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Modern biology overlaps with chemistry in explaining the structure and function of all cellular processes at the molecular level. Plant hormone research is perfectly located at the interface between these two disciplines, taking advantage of synthetic and computational chemistry as a tool to decipher the complex biological mechanisms regulating the action of plant hormones. These small signaling molecules regulate a wide range of developmental processes, adapting plant growth to ever changing environmental conditions. The synthesis of small bioactive molecules mimicking the activity of endogenous hormones allows us to unveil many molecular features of their functioning, giving rise to a new field, plant chemical biology. In this framework, fluorescence labeling of plant hormones is emerging as a successful strategy to track the fate of these challenging molecules inside living organisms. Thanks to the increasing availability of new fluorescent probes as well as advanced and innovative imaging technologies, we are now in a position to investigate many of the dynamic mechanisms through which plant hormones exert their action. Such a deep and detailed comprehension is mandatory for the development of new green technologies for practical applications. In this review, we summarize the results obtained so far concerning the fluorescent labeling of plant hormones, highlighting the basic steps leading to the design and synthesis of these compelling molecular tools and their applications.

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Synthesis and biological evaluation of potential substrates for the isolation of the strigol receptor

Cited by 14 publications

References 18 publications

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Structure-Activity Relationship Studies of Strigolactone-Related Molecules for Branching Inhibition in Garden Pea: Molecule Design for Shoot Branching

Shaping Small Bioactive Molecules to Untangle Their Biological Function: A Focus on Fluorescent Plant Hormones

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