ChemInform Abstract: THE PREPARATION OF SYNTHETIC ANALOGS OF STRIGOL

Johnson, A. W.; GOWDA, G.; Hassanali, Ahmed; Knox, John R.; Monaco, Sam; Razavi, Zia; Rosebery, Gerald

doi:10.1002/chin.198136361

Cited by 14 publications

(30 citation statements)

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“…13). As already described (Johnson et al, 1981), GR5 analogs (Table VII) were less active than their corresponding GR24 analogs (about 10-to 1,000-fold). Interestingly, analog 23 presented moderate activity in comparison with GR5 or GR24 (about 100 and 10,000 times less active, respectively; Supplemental Fig.…”

supporting

confidence: 71%

“…4). The D analog of GR5 (30) was furnished from g-butyrolactone, and the 3,4-dimethylbutenolide D-ring precursor 15 was easily obtained in bulk quantities (Canevet and Graff, 1978;Johnson et al, 1981). The influence of the replacement of the enol ether linkage by a thioenol ether and an enamine was also examined.…”

Section: Synthesis Of Sl Analogsmentioning

confidence: 99%

“…(+)-and (2)-Solanacol and solanacyl acetate were prepared by the procedure described previously in our laboratory (Chen et al, 2010). GR5 was synthesized by known procedures (Johnson et al, 1981), natural SLs (orobanchol, orobanchyl acetate, fabacyl acetate) were generously supplied by Prof. K. Yoneyama, and SLs (strigol, strigyl acetate, 5-deoxystrigol, sorgolactone) were derived by organic synthesis using known procedures or supplied by Bayer CropScience.…”

Section: General Remarksmentioning

confidence: 99%

“…3). These compounds and GR24 analogs have also been found to be light sensitive (Johnson et al, 1981). Activities of SLs could be detected at concentrations as low as 10 213 M on AM fungi (Akiyama and Hayashi, 2006), 10 212 M on seeds of parasitic weeds , and 10 28 M for GR24 on lateral buds (Gomez-Roldan et al, 2008).…”

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confidence: 99%

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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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supporting

confidence: 71%

Section: Synthesis Of Sl Analogsmentioning

confidence: 99%

Section: General Remarksmentioning

confidence: 99%

mentioning

confidence: 99%

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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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“…Strigolactones are carotenoid-derived terpenoid lactones previously shown to stimulate mycorrhizal hyphal branching and seed germination of the plant parasitic weeds Striga and Orobanche (Cook et al, 1972;Akiyama et al, 2005;Humphrey and Beale, 2006). ccd7 and ccd8 mutants of rice and pea are deficient in strigolactones, and the strigolactone analog, GR24 (Johnson et al, 1981), can restore branching inhibition in these mutants as well as in max1, max3, and max4 (Gomez-Roldan et al, 2008;Umehara et al, 2008). In the shoot, strigolactone signal transduction probably involves the F-box Leu-rich repeat protein, MAX2 (Stirnberg et al, 2002(Stirnberg et al, , 2007Booker et al, 2005).…”

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confidence: 99%

Interactions between Auxin and Strigolactone in Shoot Branching Control

et al. 2009

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In Arabidopsis (Arabidopsis thaliana), the carotenoid cleavage dioxygenases MORE AXILLARY GROWTH3 (MAX3) and MAX4 act together with MAX1 to produce a strigolactone signaling molecule required for the inhibition of axillary bud outgrowth. We show that both MAX3 and MAX4 transcripts are positively auxin regulated in a manner similar to the orthologous genes from pea (Pisum sativum) and rice (Oryza sativa), supporting evolutionary conservation of this regulation in plants. This regulation is important for branching control because large auxin-related reductions in these transcripts are associated with increased axillary branching. Both transcripts are up-regulated in max mutants, and consistent with max mutants having increased auxin in the polar auxin transport stream, this feedback regulation involves auxin signaling. We suggest that both auxin and strigolactone have the capacity to modulate each other's levels and distribution in a dynamic feedback loop required for the coordinated control of axillary branching.

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A standardized bioassay for evaluation of potential germination stimulants for seeds of parasitic weeds

Mangnus

Stommen

Zwanenburg

1992

J Plant Growth Regul

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Abstract.A standard bioassay for the evaluation of the biological activity of potential germination stimulants for seeds of parasitic weeds has been designed by carefully reconsidering all steps of a literature procedure. Addition of a surfactant to the solution for sterilization of the seeds gave a considerable reduction of contamination during the conditioning and stimulation process. Furthermore, it was shown that the water/seed ratio during conditioning affects the germination results. For the seed conditioning and stimulation process, the "sandwich" technique was introduced, whereby the seeds were placed between two layers of glass fiber filter paper discs. The standardized bioassay has been used for the evaluation of the stimulatory activity of numerous (new) synthetic analogues of strigol (the natural germination stimulan0. It is essential to include a reference compound--GR24, an analogue of strigol, is recommended--in every test series, because it was observed that, although a standard bioassay was used, germination percentages obtained with GR24 solutions vary from test to test. For seeds of Striga hermonthica, seasonal effects were found in the germination percentages obtained with GR24 as stimulant. Test results with strigol analogues having modifications in ring D reveal that structural variations in this part of the molecule have dramatic effects on the biological activity of strigol analogues.Parasitic weeds of the genera Striga and Orobanche cause severe damage to graminaceous and leguminous crops, respectively, in tropical and semitropical areas. The lives of more than 400 million people in Africa, India, and the middle East are affected by severe reductions of food crop yields through heavy infestations of these parasitic weeds (Musselman 1987, Parker 1986, Ramaiah 1987.

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ChemInform Abstract: THE PREPARATION OF SYNTHETIC ANALOGS OF STRIGOL

Abstract: Strigol (I) ist ein Stimulans für das Wachstum von parasitären Unkräutern der Gattung Striga und Orobanche (d. h. wirksam für deren Wachstum im Boden, bevor ein parasitäres Wachstum erfolgen kann, wodurch die Wirtspflanzen geschädigt werden).

Cited by 14 publications

References 1 publication

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

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

Interactions between Auxin and Strigolactone in Shoot Branching Control

A standardized bioassay for evaluation of potential germination stimulants for seeds of parasitic weeds

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