ChemInform Abstract: Synthesis of (+)‐Strigol (IV), (+)‐4′‐epi‐Strigol (V), and Their Enantiomers.

Samson, Emmanuelle; Frischmuth, Katja; Berlage, U.; Heinz, Uwe; Hobert, Kurt; Welzel, Peter

doi:10.1002/chin.199124255

Cited by 1 publication

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“…Another strigolactone, orobanchol ( 3 ), was isolated from red clover, Trifolium pretense L., an Orobanche host 15. The structures of compounds 1 to 3 have been confirmed by total synthesis;16–25 however, the spectroscopic data of the synthetic compound26, 27 with structure 4 were not in accordance with those reported for natural alectrol 12. Since then, the true structure of alectrol has remained controversial, and a bridged structure 5 for this stimulant was proposed 28.…”

Section: Naturally Occurring Germination Stimulants—the Strigolactonementioning

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

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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: Naturally Occurring Germination Stimulants—the Strigolactonementioning

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

ChemInform Abstract: Synthesis of (+)‐Strigol (IV), (+)‐4′‐epi‐Strigol (V), and Their Enantiomers.

Cited by 1 publication

References 1 publication

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

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