Synthesis, structural characterization, and biological evaluation of all four enantiomers of strigol analog GR7

Mangnus, E. M.; Zwanenburg, B.

doi:10.1021/jf00016a035

Cited by 39 publications

(28 citation statements)

References 9 publications

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“…The difference in activity between the diastereoismers is less pronounced at higher concentrations 20. The same trends have been observed for other sets of strigolactone diastereoisomers: GR 7,45, 46 strigol18 and demethylsorgolactone ( 13 ) (Fig. 6).…”

Section: Stereochemistrysupporting

confidence: 80%

“…Setting up such a library of reference compounds is a real challenge. The present authors have developed some methodologies that can be helpful in controlling the stereochemistry in a synthesis sequence 19, 20, 43, 45, 47. An example is an elegant method for installing the desired stereochemistry during coupling with the D‐ring by a palladium‐mediated asymmetric synthesis using the Trost ligand 84.…”

Section: Future Challenges In Synthesismentioning

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

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: Stereochemistrysupporting

confidence: 80%

Section: Future Challenges In Synthesismentioning

confidence: 99%

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

Zwanenburg

Mwakaboko

Reizelman

et al. 2009

Pest Management Science

220

192

View full text Add to dashboard Cite

show abstract

“…The use of 100% methanol resulted in a 70-80% loss already in 3 h and orobanchol and solanacol were degraded for over 92% within 12 h. The effect of water, 5% methanol/water and 100% methanol on compound recovery after 3 h can also be deduced from the comparison of peak intensities in representative chromatograms (Additional file 1: Figure S1). These SL stability issues in methanol were already previously discussed [16,19,37,40]. Surprisingly, a recently developed UHPLC-MS/MS based method for direct determination of tomato SLs in minute amount of root tissue routinely includes 100% methanol as solubilizing solvent for standard stocks and samples [39].…”

Section: Strigolactone Stability In Solventsmentioning

confidence: 94%

“…One of the first and most critical steps in quantitative analysis of compounds with limited stability is the selection of appropriate solvents. With respect to their chemical nature, all SLs are in general adequately soluble in water, aqueous organic solvent mixtures as well as in polar aprotic solvents, like ethyl acetate or DMSO [16,21,40]. Employment of water-miscible organic solvents meets compatibility conditions with reversed phase-based (RP) SPE purification prior to final UHPLC-MS/MS analysis.…”

Section: Strigolactone Stability In Solventsmentioning

confidence: 99%

An improved strategy to analyse strigolactones in complex sample matrices using UHPLC–MS/MS

et al. 2020

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Background Strigolactones represent the most recently described group of plant hormones involved in many aspects of plant growth regulation. Simultaneously, root exuded strigolactones mediate rhizosphere signaling towards beneficial arbuscular mycorrhizal fungi, but also attract parasitic plants. The seed germination of parasitic plants induced by host strigolactones leads to serious agricultural problems worldwide. More insight in these signaling molecules is hampered by their extremely low concentrations in complex soil and plant tissue matrices, as well as their instability. So far, the combination of tailored isolation—that would replace current unspecific, time-consuming and labour-intensive processing of large samples—and a highly sensitive method for the simultaneous profiling of a broad spectrum of strigolactones has not been reported. Results Depending on the sample matrix, two different strategies for the rapid extraction of the seven structurally similar strigolactones and highly efficient single-step pre-concentration on polymeric RP SPE sorbent were developed and validated. Compared to conventional methods, controlled temperature during the extraction and the addition of an organic modifier (acetonitrile, acetone) to the extraction solvent helped to tailor strigolactone isolation from low initial amounts of root tissue (150 mg fresh weight, FW) and root exudate (20 ml), which improved both strigolactone stability and sample purity. We have designed an efficient UHPLC separation with sensitive MS/MS detection for simultaneous analysis of seven natural strigolactones including their biosynthetic precursors—carlactone and carlactonoic acid. In combination with the optimized UHPLC–MS/MS method, attomolar detection limits were achieved. The new method allowed successful profiling of seven strigolactones in small exudate and root tissue samples of four different agriculturally important plant species—sorghum, rice, pea and tomato. Conclusion The established method provides efficient strigolactone extraction with aqueous mixtures of less nucleophilic organic solvents from small root tissue and root exudate samples, in combination with rapid single-step pre-concentration. This method improves strigolactone stability and eliminates the co-extraction and signal of matrix-associated contaminants during the final UHPLC–MS/MS analysis with an electrospray interface, which dramatically increases the overall sensitivity of the analysis. We show that the method can be applied to a variety of plant species.

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“…Characterization of the Striga seed's receptor site for germination signals might clarify structure-activity relationships between these molecules which are active as germination stimulants. There have been many efforts to develop synthetic germination stimulants based on simple analogs of strigol (34)(35)(36)(37)(38). The lactone rings, the linkage between them and the substituents on them, seem to be of crucial importance for germination stimulant activity.…”

Section: Host Control Of Striga Development By Means Of Chemical Signalsmentioning

confidence: 99%

Chemical Communication Between the Parasitic Weed Striga and Its Crop Host

Butler

1994

ACS Symposium Series

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Adaptation of Striga to parasitism includes not only dependence upon a host plant for metabolic inputs such as water, minerals, and energy, but also for developmental signals. In this way parasite and host development are highly integrated. The early host-derived chemical signals Striga requires, for seed germination and for initiation of the haustorium by which it attaches to host roots, are exuded from host roots into the soil. After Striga penetrates the host root, subsequent developmental signals are apparently exchanged directly, through vascular tissue. Germination stimulants for most Striga hosts have been identified as strigol-type compounds (strigolactones). Sorghum genotypes which produce extremely low amounts of stimulant are resistant to Striga. The gene for this trait has been mapped and incorporated into improved sorghums being released for production. Subsequent host-derived signals required by Striga are being characterized for possible independent mechanisms of resistance.Plants that have surrendered their independence and adopted a parasitic lifestyle generally obtain their water, minerals, and/or energy (in the form of photosynthate) from their host plant. But successful parasitism involves much more than dependence upon a host for metabolic inputs. In addition to these essentials, the parasite's growth, morphological development and even its manner of reproduction must be compatible with that of the host. In effect, the entire life cycle of the parasite must, to a significant extent, be integrated with that of the host. This integration is necessarily more intimate, more molecular, than the integration of plants which depend upon other organisms for pollination or seed dispersal with the lifestyles and characteristics of the organisms which provide these services.Because their requirements are so specific and complex, parasitic plants would seem to be more vulnerable than independent, non-parasitic plants. Successful plant parasitism involves a series of stringent conditions and interactions, all of which 0097-6156/95/0582-0158$08.00/0

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Synthesis, structural characterization, and biological evaluation of all four enantiomers of strigol analog GR7

Cited by 39 publications

References 9 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

An improved strategy to analyse strigolactones in complex sample matrices using UHPLC–MS/MS

Chemical Communication Between the Parasitic Weed Striga and Its Crop Host

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