Literature DB >> 22082666

Strigolactone analogues and mimics derived from phthalimide, saccharine, p-tolylmalondialdehyde, benzoic and salicylic acid as scaffolds.

Binne Zwanenburg1, Alinanuswe S Mwakaboko.   

Abstract

A series of new strigolactone (SL) analogues is derived from simple and cheap starting materials. These SL analogues are designed using a working model. The first analogue is a modified Nijmegen-1, the second contains saccharin as substituent (bio-isosteric replacement of a carbonyl in Nijmegen-1 by a sulfonyl group) and the third one is derived from p-tolylmalondialdehyde. These new SL analogues are appreciably to highly active as germination stimulants of seeds of Striga hermonthica and Orobanche cernua. The SL analogue derived from saccharin is the most active one. A serendipitous and most rewarding finding is that the compound obtained by a direct coupling of saccharin with the chlorobutenolide exhibits a high germination activity especially towards O. cernua seeds. Two other SL mimics are obtained from benzoic and salicylic aid by a direct coupling reaction with chlorobutenolide, both of them are very active germinating agents. These SL mimics represent a new type of germination stimulants. A tentative molecular mechanism for the mode of action of these SL mimics has been proposed.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 22082666     DOI: 10.1016/j.bmc.2011.10.057

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  7 in total

1.  Structure-activity relationship studies of strigolactone-related molecules for branching inhibition in garden pea: molecule design for shoot branching.

Authors:  François-Didier Boyer; Alexandre de Saint Germain; Jean-Paul Pillot; Jean-Bernard Pouvreau; Victor Xiao Chen; Suzanne Ramos; Arnaud Stévenin; Philippe Simier; Philippe Delavault; Jean-Marie Beau; Catherine Rameau
Journal:  Plant Physiol       Date:  2012-06-21       Impact factor: 8.340

2.  Karrikins force a rethink of strigolactone mode of action.

Authors:  Mark T Waters; Adrian Scaffidi; Gavin R Flematti; Steven M Smith
Journal:  Plant Signal Behav       Date:  2012-07-25

Review 3.  Molecular basis of strigolactone perception in root-parasitic plants: aiming to control its germination with strigolactone agonists/antagonists.

Authors:  Takuya Miyakawa; Yuqun Xu; Masaru Tanokura
Journal:  Cell Mol Life Sci       Date:  2019-10-05       Impact factor: 9.261

4.  Strigolactone and karrikin signal perception: receptors, enzymes, or both?

Authors:  Bart J Janssen; Kimberley C Snowden
Journal:  Front Plant Sci       Date:  2012-12-28       Impact factor: 5.753

5.  New Strigolactone Mimics as Exogenous Signals for Rhizosphere Organisms.

Authors:  Florin Oancea; Emilian Georgescu; Radoslava Matusova; Florentina Georgescu; Alina Nicolescu; Iuliana Raut; Maria-Luiza Jecu; Marius-Constantin Vladulescu; Lucian Vladulescu; Calin Deleanu
Journal:  Molecules       Date:  2017-06-09       Impact factor: 4.411

6.  Hybrid-type strigolactone analogues derived from auxins.

Authors:  Daniel Blanco-Ania; Jurgen J Mateman; Adéla Hýlová; Lukáš Spíchal; Luc M Debie; Binne Zwanenburg
Journal:  Pest Manag Sci       Date:  2019-08-23       Impact factor: 4.845

Review 7.  Strigolactones: new plant hormones in action.

Authors:  Binne Zwanenburg; Tomáš Pospíšil; Sanja Ćavar Zeljković
Journal:  Planta       Date:  2016-02-02       Impact factor: 4.116

  7 in total

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