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Structure-Activity Relationship Studies Of Strigolactone-Related Molecules For Branching Inhibition In Garden Pea: Molecule Design For Shoot Branching1[W]
F. Boyer, Alexandre de Saint Germain, J. Pillot, Jean-Bernard Pouvreau, V. X. Chen, S. Ramos, Arnaud Stévenin, P. Simier, P. Delavault, J. Beau, C. Rameau
Published 2012 · Biology, Medicine
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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.
This paper references
Germination of Witchweed (Striga lutea Lour.): Isolation and Properties of a Potent Stimulant
C. E. Cook (1966)
Germination stimulants. II. Structure of strigol, a potent seed germination stimulant for witchweed (Striga lutea)
C. E. Cook (1972)
Germination stimulants. 2. Structure of strigol-potent seed germination stimulant for witchweed (Striga lutea Lour.)
C E Cook (1972)
Synthesis of the germination stimulant (±)-strigol
G. A. Macalpine (1976)
REACTIONS OF OXYGEN AND SULFUR ANIONS WITH OXAZOLIDINE AND THIAZOLIDINE DERIVATIVES OF 2-MESYLOXYMETHYLGLYCERALDEHYDE ACETONIDE
G. Just (1976)
Furanone 16 was obtained by bromation of 2-benzoyloxy-2-buten-4-olide (Limberg and Thiem, 1995) by the same procedure as for 5-bromo-3-methyl-2(5H)-furanone
Synthesis of germination stimulant (+/2)-strigol
G A Macalpine (1976)
Identification of the Female Japanese Beetle Sex Pheromone: Inhibition of Male Response by an Enantiomer
J. Tumlinson (1977)
Réactions de friedel-crafts de dérivés aromatiques sur des composés dicarbonylés-1,4éthyléniques-2,3.ii alkylations par quelques hydroxy-5 ou chloro-5 dihydro-2,5 furannones-2. nouvelle méthode de synthèse des acides 1h-indènecarboxyliques-1
J. Canevet (1978)
THE PREPARATION OF SYNTHETIC ANALOGS OF STRIGOL
A. Johnson (1981)
The preparation of synthetic analogues of strigol
A. Johnson (1981)
Protection of the amino group of amino sugars by the acylvinyl group: Part I, glycoside formation by the fischer reaction
A. Gómez-Sánchez (1984)
Positional differences in size, morphology, and in vitro performance of pea axillary buds
K. Gould (1987)
Aflatoxins Revisited: Convergent Synthesis of the ABC-Moiety
S. Wolff (1988)
the same procedure as for 19 to give the desired products 22/29-epi-22 (1:1, unseparable mixture; 38 mg, 66%) as a colorless oil
Preparation of 5-bromotetronates [4-alkoxy-5-bromo-2(5H)-furanones] and a new concept for the synthesis of aflatoxins and related structure types. Tributyltin hydride versus palladium-promoted intramolecular hydroarylation.
H. Martin (1989)
2,5-dimethoxy-2,5-dihydrofuran: A convenient synthon for a novel mono-protected glyoxal; synthesis of 4-hydroxybutenolides
S. Fell (1990)
A Convenient Preparation of Acetone Solutions of Dimethyldioxirane.
W. Adam (1991)
Kurzmitteilung / Short Communication A Convenient Preparation of Acetone Solutions of Dimethyldioxirane
W. Adam (1991)
Tentative molecular mechanism for germination stimulation of Striga and Orobanche seeds by strigol and its synthetic analogues
E. Mangnus (1992)
Improved synthesis of strigol analog GR24 and evaluation of the biological activity of its diastereomers
E. Mangnus (1992)
Origin and diversification of endomycorrhizal fungi and coincidence with vascular land plants
L. Simon (1993)
β-elimination of protected aldono-1,4-lactones as a general approach to the synthesis of 2-keto-3-deoxyaldonic acids containing four to six carbon atoms
G. Limberg (1995)
New ramosus mutants at loci Rms1, Rms3 and Rms4 resulting from the mutation breeding program at Versailles
C. Rameau (1997)
Synthesis and biological evaluation of potential substrates for the isolation of the strigol receptor
J. Thuring (1997)
The rms1 Mutant of Pea Has Elevated Indole-3-Acetic Acid Levels and Reduced Root-Sap Zeatin Riboside Content but Increased Branching Controlled by Graft-Transmissible Signal(s)
C. Beveridge (1997)
A new mathematical model for relative quantification in real-time RT-PCR.
M. Pfaffl (2001)
A new mathematical model for relative quanti fi cation in real - time RT - PCR
C Prandi (2001)
Micrografting techniques for testing long-distance signalling in Arabidopsis.
C. Turnbull (2002)
Convenient synthesis of 3-aminomethylenedihydrofuran-2-ones
N. Zanatta (2003)
Defense Gene Expression Analysis of Arabidopsis thaliana Parasitized by Orobanche ramosa.
C. D. Dos Santos (2003)
Synthesis and bioactivity of labelled germination stimulants for the isolation and identification of the strigolactone receptor.
Anat Reizelman (2003)
MAX4 and RMS1 are orthologous dioxygenase-like genes that regulate shoot branching in Arabidopsis and pea.
Karim Sorefan (2003)
Synthesis and bioactivity of labelled germination stimulants for the isolation and identi fi cation of the strigolactone receptor
C Ruyter-Spira (2003)
GETTING STARTED WITH THE R COMMANDER: A BASIC-STATISTICS GRAPHICAL USER INTERFACE TO R
J. Fox (2004)
Long-distance signalling and a mutational analysis of branching in pea
C. Beveridge (2004)
MAX3/CCD7 Is a Carotenoid Cleavage Dioxygenase Required for the Synthesis of a Novel Plant Signaling Molecule
Jonathan Booker (2004)
The Strigolactone Germination Stimulants of the Plant-Parasitic Striga and Orobanche spp. Are Derived from the Carotenoid Pathway1
R. Matúšová (2005)
Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi
K. Akiyama (2005)
Confirmation and Quantification of Strigolactones, Germination Stimulants for Root Parasitic Plants Striga and Orobanche, Produced by Cotton
D. Sato (2005)
Strigolactones: chemical signals for fungal symbionts and parasitic weeds in plant roots.
K. Akiyama (2006)
Branching Genes Are Conserved across Species. Genes Controlling a Novel Signal in Pea Are Coregulated by Other Long-Distance Signals1
X. Johnson (2006)
Strigolactones Stimulate Arbuscular Mycorrhizal Fungi by Activating Mitochondria
A. Besserer (2006)
Nitrogen deficiency as well as phosphorus deficiency in sorghum promotes the production and exudation of 5-deoxystrigol, the host recognition signal for arbuscular mycorrhizal fungi and root parasites
K. Yoneyama (2007)
2'-epi-orobanchol and solanacol, two unique strigolactones, germination stimulants for root parasitic weeds, produced by tobacco.
Xiaonan Xie (2007)
Efficient generation of a trisporoid library by combination of synthesis and biotransformation.
Doreen Schachtschabel (2007)
Rhizosphere communication of plants, parasitic plants and AM fungi.
H. Bouwmeester (2007)
Isolation and identification of alectrol as (+)-orobanchyl acetate, a germination stimulant for root parasitic plants.
Xiaonan Xie (2008)
Strigolactone inhibition of shoot branching
V. Gómez-Roldán (2008)
Facile preparation of metallic triflates and triflimidates by oxidative dissolution of metal powders.
S. Antoniotti (2008)
Inhibition of shoot branching by new terpenoid plant hormones
Mikihisa Umehara (2008)
Biosynthetic considerations could assist the structure elucidation of host plant produced rhizosphere signalling compounds (strigolactones) for arbuscular mycorrhizal fungi and parasitic plants.
K. Rani (2008)
Arbuscular mycorrhiza: the mother of plant root endosymbioses
M. Parniske (2008)
Fabacyl acetate, a germination stimulant for root parasitic plants from Pisum sativum.
Xiaonan Xie (2009)
Strigolactones: structures and biological activities.
K. Yoneyama (2009)
Structure and function of natural and synthetic signalling molecules in parasitic weed germination.
B. Zwanenburg (2009)
d14, a strigolactone-insensitive mutant of rice, shows an accelerated outgrowth of tillers.
Tomotsugu Arite (2009)
Strigolactone Acts Downstream of Auxin to Regulate Bud Outgrowth in Pea and Arabidopsis1[C][OA]
P. Brewer (2009)
Stri - golactone acts downstream of auxin to regulate bud outgrowth in pea and Arabidopsis
PB Brewer (2009)
The strigolactone story.
Xiaonan Xie (2010)
Stereochemistry, total synthesis, and biological evaluation of the new plant hormone solanacol.
V. X. Chen (2010)
Physiological Effects of the Synthetic Strigolactone Analog GR24 on Root System Architecture in Arabidopsis: Another Belowground Role for Strigolactones?1[C][W][OA]
C. Ruyter-Spira (2010)
Strigolactones affect lateral root formation and root-hair elongation in Arabidopsis
Y. Kapulnik (2010)
Short synthesis of the seed germination inhibitor 3,4,5-trimethyl-2(5H)-furanone.
Riccardo Surmont (2010)
Structure–activity relationship of naturally occurring strigolactones in Orobanche minor seed germination stimulation
H. I. Kim (2010)
Strigolactones enhance competition between shoot branches by dampening auxin transport
S. Crawford (2010)
A new efficient synthesis of GR24 and dimethyl A-ring analogues, germinating agents for seeds of the parasitic weeds Striga and Orobanche spp.
H. Malik (2010)
New genes in the strigolactone-related shoot branching pathway.
C. Beveridge (2010)
Strigolactones as Germination Stimulants for Root Parasitic Plants
K. Yoneyama (2010)
First indications for the involvement of strigolactones on nodule formation in alfalfa (Medicago sativa)
M. Soto (2010)
Structural Requirements of Strigolactones for Hyphal Branching in AM Fungi
K. Akiyama (2010)
New Potent Fluorescent Analogues of Strigolactones: Synthesis and Biological Activity in Parasitic Weed Germination and Fungal Branching
C. Prandi (2011)
Quorum sensing in Gram-negative bacteria: small-molecule modulation of AHL and AI-2 quorum sensing pathways.
W. R. Galloway (2011)
Signal integration in the control of shoot branching
M. Domagalska (2011)
Antagonistic Action of Strigolactone and Cytokinin in Bud Outgrowth Control1[W]
E. Dun (2011)
The Pea TCP Transcription Factor PsBRC1 Acts Downstream of Strigolactones to Control Shoot Branching1[W]
Nils Braun (2011)
New branching inhibitors and their potential as strigolactone mimics in rice.
Kosuke Fukui (2011)
How do nitrogen and phosphorus deficiencies affect strigolactone production and exudation?
K. Yoneyama (2011)
Aromatic A-ring analogues of orobanchol, new germination stimulants for seeds of parasitic weeds.
H. Malik (2011)
Ent-2'-epi-Orobanchol and its acetate, as germination stimulants for Striga gesnerioides seeds isolated from cowpea and red clover.
K. Ueno (2011)
Strigolactones regulate protonema branching and act as a quorum sensing-like signal in the moss Physcomitrella patens
Hélène Proust (2011)
Strigolactone analogues and mimics derived from phthalimide, saccharine, p-tolylmalondialdehyde, benzoic and salicylic acid as scaffolds.
B. Zwanenburg (2011)
Structural requirements of strigolactones for germination induction of Striga gesnerioides seeds.
K. Ueno (2011)
Strigolactone signaling is required for auxin-dependent stimulation of secondary growth in plants
J. Agustí (2011)
Strigolactones promote nodulation in pea
E. Foo (2011)
Strigolactones--intriguing biologically active compounds: perspectives for deciphering their biological role and for proposing practical application.
M. Vurro (2012)
Strigolactones as small molecule communicators.
Y. Tsuchiya (2012)
Exploring the molecular mechanism of karrikins and strigolactones.
A. Scaffidi (2012)
The Path from β-Carotene to Carlactone, a Strigolactone-Like Plant Hormone
Adrian Alder (2012)
Highly Selective Formation of β-Glycosides of N-Acetylglucosamine Using Catalytic Iron(III) Triflate
Arnaud Stévenin (2012)
Antago - nistic action of strigolactone and cytokinin in bud outgrowth control
EA Dun (2012)
Plant branching inhibitor, method for producing same, and plant branching inhibitory composition
CH), 128.2 (C), 126.2 (C)
CDCl 3 ) d 171.41 (C), 171.37 (C), 171.02 (C), 170.98 (C), 156.43 (C), 156.28 (C), 151.4 (CH)
CDCl 3 ) major isomer d 175.0 (2 C), 144.2 (C), 143.4 (CH)
HRMS (ESI) m/z calculated for C 17 H 14 O 6 Na
78 (s, 6 H). 13 C-NMR (125 MHz
HRMS (ESI) m/z calculated for C 17 H 20 NO 6
CDCl 3 ) d 178.5 (C), 176.2 (C), 141.8 (C), 139.0 (C)
C), 150.0 (CH), 128.5 (C
) m/z calculated for C 18 H 16 O 5 Na
Supplemental Figure S4. Stimulatory activity of GR24, GR5, 23, and 30 toward P. ramosa seed germination
Synthesis of germination stimulant ( + / 2 ) - strigol
Canevet and Graff, 1978) by the same procedure as for 19 to give the desired product 31 (361 mg, 51%) as a white solid. Melting point, 74.5°C to 76
CDCl 3 ) d 178.5 (C), 176.2 (C), 141.8 (C), 139.0 (C), 130.1 (CH)
90 (s, 1 H), 5.89 (d
35 (CH), 114.8 (C), 114.6 (C)
Mangnus and Zwanenburg, 1992) by the same procedure as for 35 to give the desired product 38 (5 mg, 50%) as a colorless oil. 1 H-NMR (500 MHz
CDCl 3 ) d 171.0 (C), 162.1 (C)
CH), 142.84 (C), 142.81 (C), 139.0 (C)
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L. Borghi (2021)
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C. Prandi (2021)
Signaling network regulating plant branching: Recent advances and new challenges.
A. Kotov (2021)
Strigolactone GR24 improves cadmium tolerance by regulating cadmium uptake, nitric oxide signaling and antioxidant metabolism in barley (Hordeum vulgare L.).
Chengwei Qiu (2021)
Synthesis of Profluorescent Strigolactone Probes for Biochemical Studies.
Alexandre de Saint Germain (2021)
Integration of the SMXL/D53 strigolactone signalling repressors in the model of shoot branching regulation in Pisum sativum.
Stephanie C. Kerr (2021)
A Phelipanche ramosa KAI2 protein perceives strigolactones and isothiocyanates enzymatically
Alexandre de Saint Germain (2021)
Methods for Phenotyping Shoot Branching and Testing Strigolactone Bioactivity for Shoot Branching in Arabidopsis and Pea.
Aitor Muñoz (2021)
Strigolactones in Overcoming Environmental Stresses
Megha D. Bhatt (2020)
An improved strategy to analyse strigolactones in complex sample matrices using UHPLC–MS/MS
Kristýna Floková (2020)
Strigolactone biosynthesis, transport and perception.
Kiyoshi Mashiguchi (2020)
The Full-Size ABCG Transporter of Medicago truncatula Is Involved in Strigolactone Secretion, Affecting Arbuscular Mycorrhiza
J. Banasiak (2020)
Plant-endophytic fungi interactions: A strigolactone perspective
L. O. Omoarelojie (2020)
On improving strigolactone mimics for induction of suicidal germination of the root parasitic plant Striga hermonthica
I. Takahashi (2020)
Chemical identification of 18-hydroxycarlactonoic acid as an LjMAX1 product and in planta conversion of its methyl ester to canonical and non-canonical strigolactones in Lotus japonicus.
Narumi Mori (2020)
Diverse roles of MAX1 homologues in rice
M. Marzec (2020)
Karrikin Improves Osmotic and Salt Stress Tolerance via the Regulation of the Redox Homeostasis in the Oil Plant Sapium sebiferum
F. Shah (2020)
A Phelipanche ramosa KAI2 Protein Perceives enzymatically Strigolactones and Isothiocyanates
Alexandre de Saint Germain (2020)
Flexibility of the petunia strigolactone receptor DAD2 promotes its interaction with signaling partners
H. Lee (2020)
Initiation of arbuscular mycorrhizal symbiosis involves a novel pathway independent from hyphal branching
Quentin Taulera (2020)
The Physcomitrium (Physcomitrella) patens PpKAI2L receptors for strigolactones and related compounds highlight MAX2 dependent and independent pathways
Mauricio Lopez-Obando (2020)
Diverse Roles of MAX1 Homologues in Rice
M. Marzec (2020)
Science and application of strigolactones
Ernest B. Aliche (2020)
New hybrid type strigolactone mimics derived from plant growth regulator auxin.
A. Hýlová (2019)
The Control Of Zealactone Biosynthesis And Exudation Is Involved In The Response To Nitrogen In Maize Root.
Laura Ravazzolo (2019)
Strigolactone: Pflanzenhormone mit vielversprechenden Eigenschaften
H. Bouwmeester (2019)
Hybrid‐type strigolactone analogues derived from auxins
Daniel Blanco-Ania (2019)
The Chemistry of Strigolactones
C. Prandi (2019)
Strigolactones. A New Plant Hormone with Promising Features.
H. Bouwmeester (2019)
How Do Strigolactones Ameliorate Nutrient Deficiencies in Plants?
K. Yoneyama (2019)
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