Online citations, reference lists, and bibliographies.
← Back to Search

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

Save to my Library
Download PDF
Analyze on Scholarcy Visualize in Litmaps
Share
Reduce the time it takes to create your bibliography by a factor of 10 by using the world’s favourite reference manager
Time to take this seriously.
Get Citationsy
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
10.1126/science.154.3753.1189
Germination of Witchweed (Striga lutea Lour.): Isolation and Properties of a Potent Stimulant
C. E. Cook (1966)
10.1021/JA00772A048
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)
10.1039/P19760000410
Synthesis of the germination stimulant (±)-strigol
G. A. Macalpine (1976)
10.1139/V76-299
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
Macalpine (1976)
Synthesis of germination stimulant (+/2)-strigol
G A Macalpine (1976)
10.1126/science.197.4305.789
Identification of the Female Japanese Beetle Sex Pheromone: Inhibition of Male Response by an Enantiomer
J. Tumlinson (1977)
10.1016/0040-4020(78)80100-8
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)
10.1002/chin.198136361
THE PREPARATION OF SYNTHETIC ANALOGS OF STRIGOL
A. Johnson (1981)
10.1039/P19810001734
The preparation of synthetic analogues of strigol
A. Johnson (1981)
10.1016/0008-6215(84)85008-9
Protection of the amino group of amino sugars by the acylvinyl group: Part I, glycoside formation by the fischer reaction
A. Gómez-Sánchez (1984)
10.1139/B87-049
Positional differences in size, morphology, and in vitro performance of pea axillary buds
K. Gould (1987)
10.1055/S-1988-27700
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
(1988)
10.1016/S0040-4020(01)85124-3
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)
10.1016/S0040-4039(00)97588-9
2,5-dimethoxy-2,5-dihydrofuran: A convenient synthon for a novel mono-protected glyoxal; synthesis of 4-hydroxybutenolides
S. Fell (1990)
10.1002/CHIN.199150130
A Convenient Preparation of Acetone Solutions of Dimethyldioxirane.
W. Adam (1991)
10.1002/CBER.19911241036
Kurzmitteilung / Short Communication A Convenient Preparation of Acetone Solutions of Dimethyldioxirane
W. Adam (1991)
10.1021/JF00018A032
Tentative molecular mechanism for germination stimulation of Striga and Orobanche seeds by strigol and its synthetic analogues
E. Mangnus (1992)
10.1021/JF00019A031
Improved synthesis of strigol analog GR24 and evaluation of the biological activity of its diastereomers
E. Mangnus (1992)
10.1038/363067A0
Origin and diversification of endomycorrhizal fungi and coincidence with vascular land plants
L. Simon (1993)
10.1016/0008-6215(95)00124-C
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)
10.1039/a604685a
Synthesis and biological evaluation of potential substrates for the isolation of the strigol receptor
J. Thuring (1997)
10.1104/pp.115.3.1251
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)
10.1093/NAR/29.9.E45
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)
10.1046/J.1365-313X.2002.01419.X
Micrografting techniques for testing long-distance signalling in Arabidopsis.
C. Turnbull (2002)
10.1016/S0040-4039(02)02744-2
Convenient synthesis of 3-aminomethylenedihydrofuran-2-ones
N. Zanatta (2003)
10.1094/PHYTO.2003.93.4.451
Defense Gene Expression Analysis of Arabidopsis thaliana Parasitized by Orobanche ramosa.
C. D. Dos Santos (2003)
10.1039/B210678G
Synthesis and bioactivity of labelled germination stimulants for the isolation and identification of the strigolactone receptor.
Anat Reizelman (2003)
10.1101/GAD.256603
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)
10.18637/JSS.V014.I09
GETTING STARTED WITH THE R COMMANDER: A BASIC-STATISTICS GRAPHICAL USER INTERFACE TO R
J. Fox (2004)
10.1023/A:1010718020095
Long-distance signalling and a mutational analysis of branching in pea
C. Beveridge (2004)
10.1016/j.cub.2004.06.061
MAX3/CCD7 Is a Carotenoid Cleavage Dioxygenase Required for the Synthesis of a Novel Plant Signaling Molecule
Jonathan Booker (2004)
10.1104/pp.105.061382
The Strigolactone Germination Stimulants of the Plant-Parasitic Striga and Orobanche spp. Are Derived from the Carotenoid Pathway1
R. Matúšová (2005)
10.1038/nature03608
Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi
K. Akiyama (2005)
10.1271/bbb.69.98
Confirmation and Quantification of Strigolactones, Germination Stimulants for Root Parasitic Plants Striga and Orobanche, Produced by Cotton
D. Sato (2005)
10.1093/AOB/MCL063
Strigolactones: chemical signals for fungal symbionts and parasitic weeds in plant roots.
K. Akiyama (2006)
10.1104/pp.106.087676
Branching Genes Are Conserved across Species. Genes Controlling a Novel Signal in Pea Are Coregulated by Other Long-Distance Signals1
X. Johnson (2006)
10.1371/journal.pbio.0040226
Strigolactones Stimulate Arbuscular Mycorrhizal Fungi by Activating Mitochondria
A. Besserer (2006)
10.1007/s00425-007-0600-5
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)
10.1021/JF0715121
2'-epi-orobanchol and solanacol, two unique strigolactones, germination stimulants for root parasitic weeds, produced by tobacco.
Xiaonan Xie (2007)
10.1021/JO062236C
Efficient generation of a trisporoid library by combination of synthesis and biotransformation.
Doreen Schachtschabel (2007)
10.1016/J.TPLANTS.2007.03.009
Rhizosphere communication of plants, parasitic plants and AM fungi.
H. Bouwmeester (2007)
10.1016/J.PHYTOCHEM.2007.07.017
Isolation and identification of alectrol as (+)-orobanchyl acetate, a germination stimulant for root parasitic plants.
Xiaonan Xie (2008)
10.1038/nature07271
Strigolactone inhibition of shoot branching
V. Gómez-Roldán (2008)
10.1039/b717689a
Facile preparation of metallic triflates and triflimidates by oxidative dissolution of metal powders.
S. Antoniotti (2008)
10.1038/nature07272
Inhibition of shoot branching by new terpenoid plant hormones
Mikihisa Umehara (2008)
10.1016/j.plaphy.2008.04.012
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)
10.1038/nrmicro1987
Arbuscular mycorrhiza: the mother of plant root endosymbioses
M. Parniske (2008)
10.1016/j.phytochem.2008.12.013
Fabacyl acetate, a germination stimulant for root parasitic plants from Pisum sativum.
Xiaonan Xie (2009)
10.1002/ps.1726
Strigolactones: structures and biological activities.
K. Yoneyama (2009)
10.1002/ps.1706
Structure and function of natural and synthetic signalling molecules in parasitic weed germination.
B. Zwanenburg (2009)
10.1093/pcp/pcp091
d14, a strigolactone-insensitive mutant of rice, shows an accelerated outgrowth of tillers.
Tomotsugu Arite (2009)
10.1104/pp.108.134783
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)
10.1146/annurev-phyto-073009-114453
The strigolactone story.
Xiaonan Xie (2010)
10.1002/chem.201002817
Stereochemistry, total synthesis, and biological evaluation of the new plant hormone solanacol.
V. X. Chen (2010)
10.1104/pp.110.166645
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)
10.1007/s00425-010-1310-y
Strigolactones affect lateral root formation and root-hair elongation in Arabidopsis
Y. Kapulnik (2010)
10.1021/jo1010476
Short synthesis of the seed germination inhibitor 3,4,5-trimethyl-2(5H)-furanone.
Riccardo Surmont (2010)
10.1584/JPESTICS.G10-17
Structure–activity relationship of naturally occurring strigolactones in Orobanche minor seed germination stimulation
H. I. Kim (2010)
10.1242/dev.051987
Strigolactones enhance competition between shoot branches by dampening auxin transport
S. Crawford (2010)
10.1016/J.TET.2010.06.072
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)
10.1016/j.pbi.2009.10.003
New genes in the strigolactone-related shoot branching pathway.
C. Beveridge (2010)
10.1093/pcp/pcq055
Strigolactones as Germination Stimulants for Root Parasitic Plants
K. Yoneyama (2010)
10.1016/J.SOILBIO.2009.11.007
First indications for the involvement of strigolactones on nodule formation in alfalfa (Medicago sativa)
M. Soto (2010)
10.1093/pcp/pcq058
Structural Requirements of Strigolactones for Hyphal Branching in AM Fungi
K. Akiyama (2010)
10.1002/EJOC.201100616
New Potent Fluorescent Analogues of Strigolactones: Synthesis and Biological Activity in Parasitic Weed Germination and Fungal Branching
C. Prandi (2011)
10.1021/cr100109t
Quorum sensing in Gram-negative bacteria: small-molecule modulation of AHL and AI-2 quorum sensing pathways.
W. R. Galloway (2011)
10.1038/nrm3088
Signal integration in the control of shoot branching
M. Domagalska (2011)
10.1104/pp.111.186783
Antagonistic Action of Strigolactone and Cytokinin in Bud Outgrowth Control1[W]
E. Dun (2011)
10.1104/pp.111.182725
The Pea TCP Transcription Factor PsBRC1 Acts Downstream of Strigolactones to Control Shoot Branching1[W]
Nils Braun (2011)
10.1016/j.bmcl.2011.06.019
New branching inhibitors and their potential as strigolactone mimics in rice.
Kosuke Fukui (2011)
10.1007/s00425-011-1568-8
How do nitrogen and phosphorus deficiencies affect strigolactone production and exudation?
K. Yoneyama (2011)
10.1039/c0ob00735h
Aromatic A-ring analogues of orobanchol, new germination stimulants for seeds of parasitic weeds.
H. Malik (2011)
10.1021/jf2024193
Ent-2'-epi-Orobanchol and its acetate, as germination stimulants for Striga gesnerioides seeds isolated from cowpea and red clover.
K. Ueno (2011)
10.1242/dev.058495
Strigolactones regulate protonema branching and act as a quorum sensing-like signal in the moss Physcomitrella patens
Hélène Proust (2011)
10.1016/j.bmc.2011.10.057
Strigolactone analogues and mimics derived from phthalimide, saccharine, p-tolylmalondialdehyde, benzoic and salicylic acid as scaffolds.
B. Zwanenburg (2011)
10.1021/jf202418a
Structural requirements of strigolactones for germination induction of Striga gesnerioides seeds.
K. Ueno (2011)
10.1073/pnas.1111902108
Strigolactone signaling is required for auxin-dependent stimulation of secondary growth in plants
J. Agustí (2011)
10.1007/s00425-011-1516-7
Strigolactones promote nodulation in pea
E. Foo (2011)
10.1002/ps.3257
Strigolactones--intriguing biologically active compounds: perspectives for deciphering their biological role and for proposing practical application.
M. Vurro (2012)
10.1039/c1mb05195d
Strigolactones as small molecule communicators.
Y. Tsuchiya (2012)
10.1016/j.bmcl.2012.04.016
Exploring the molecular mechanism of karrikins and strigolactones.
A. Scaffidi (2012)
10.1126/science.1218094
The Path from β-Carotene to Carlactone, a Strigolactone-Like Plant Hormone
Adrian Alder (2012)
10.1002/EJOC.201200062
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
S Yamaguchi
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)
Hz
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
N MaxIr
4S*)-4-Methyl-5-oxotetrahydrofuran-2-yl)oxy)methyl)-3,3a,4,8b-tetrahydro-2H-indeno
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
H Malik
)-4-Methyl-5-oxo-2,5-dihydrofuran-2-yl)thio)methylene)-3,3a,4,8b-tetrahydro-2H-indeno
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)
RS*)-3,4-Dimethyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)methylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one
CH), 142.84 (C), 142.81 (C), 139.0 (C)



This paper is referenced by
10.1007/S11104-021-04943-8
Efficiency and bioavailability of new synthetic strigolactone mimics with potential for sustainable agronomical applications
L. Borghi (2021)
10.1002/EJOC.202100204
Strigolactones: Phytohormones with Promising Biomedical Applications
C. Prandi (2021)
10.1016/j.plantsci.2021.110880
Signaling network regulating plant branching: Recent advances and new challenges.
A. Kotov (2021)
10.1016/j.envpol.2021.116486
Strigolactone GR24 improves cadmium tolerance by regulating cadmium uptake, nitric oxide signaling and antioxidant metabolism in barley (Hordeum vulgare L.).
Chengwei Qiu (2021)
10.1007/978-1-0716-1429-7_17
Synthesis of Profluorescent Strigolactone Probes for Biochemical Studies.
Alexandre de Saint Germain (2021)
10.1111/tpj.15415
Integration of the SMXL/D53 strigolactone signalling repressors in the model of shoot branching regulation in Pisum sativum.
Stephanie C. Kerr (2021)
10.1016/J.XPLC.2021.100166
A Phelipanche ramosa KAI2 protein perceives strigolactones and isothiocyanates enzymatically
Alexandre de Saint Germain (2021)
10.1007/978-1-0716-1429-7_10
Methods for Phenotyping Shoot Branching and Testing Strigolactone Bioactivity for Shoot Branching in Arabidopsis and Pea.
Aitor Muñoz (2021)
10.1002/9781119552154.ch16
Strigolactones in Overcoming Environmental Stresses
Megha D. Bhatt (2020)
10.1186/s13007-020-00669-3
An improved strategy to analyse strigolactones in complex sample matrices using UHPLC–MS/MS
Kristýna Floková (2020)
10.1111/tpj.15059
Strigolactone biosynthesis, transport and perception.
Kiyoshi Mashiguchi (2020)
10.3389/fpls.2020.00018
The Full-Size ABCG Transporter of Medicago truncatula Is Involved in Strigolactone Secretion, Affecting Arbuscular Mycorrhiza
J. Banasiak (2020)
10.1016/j.sajb.2020.02.009
Plant-endophytic fungi interactions: A strigolactone perspective
L. O. Omoarelojie (2020)
10.1007/s42994-020-00031-0
On improving strigolactone mimics for induction of suicidal germination of the root parasitic plant Striga hermonthica
I. Takahashi (2020)
10.1016/j.phytochem.2020.112349
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)
10.1101/2020.08.12.248138
Diverse roles of MAX1 homologues in rice
M. Marzec (2020)
10.3389/fpls.2020.00216
Karrikin Improves Osmotic and Salt Stress Tolerance via the Regulation of the Redox Homeostasis in the Oil Plant Sapium sebiferum
F. Shah (2020)
10.1101/2020.06.09.136473
A Phelipanche ramosa KAI2 Protein Perceives enzymatically Strigolactones and Isothiocyanates
Alexandre de Saint Germain (2020)
10.1074/jbc.RA119.011509
Flexibility of the petunia strigolactone receptor DAD2 promotes its interaction with signaling partners
H. Lee (2020)
10.1007/s00572-020-00965-9
Initiation of arbuscular mycorrhizal symbiosis involves a novel pathway independent from hyphal branching
Quentin Taulera (2020)
10.1101/2020.11.24.395954
The Physcomitrium (Physcomitrella) patens PpKAI2L receptors for strigolactones and related compounds highlight MAX2 dependent and independent pathways
Mauricio Lopez-Obando (2020)
10.3390/genes11111348
Diverse Roles of MAX1 Homologues in Rice
M. Marzec (2020)
10.1111/nph.16489
Science and application of strigolactones
Ernest B. Aliche (2020)
10.1016/j.nbt.2018.08.001
New hybrid type strigolactone mimics derived from plant growth regulator auxin.
A. Hýlová (2019)
10.1093/pcp/pcz108
The Control Of Zealactone Biosynthesis And Exudation Is Involved In The Response To Nitrogen In Maize Root.
Laura Ravazzolo (2019)
10.1002/ANGE.201901626
Strigolactone: Pflanzenhormone mit vielversprechenden Eigenschaften
H. Bouwmeester (2019)
10.1002/ps.5553
Hybrid‐type strigolactone analogues derived from auxins
Daniel Blanco-Ania (2019)
10.1007/978-3-030-12153-2_6
The Chemistry of Strigolactones
C. Prandi (2019)
10.1002/anie.201901626
Strigolactones. A New Plant Hormone with Promising Features.
H. Bouwmeester (2019)
10.1101/cshperspect.a034686
How Do Strigolactones Ameliorate Nutrient Deficiencies in Plants?
K. Yoneyama (2019)
10.1016/j.bmcl.2019.07.018
Synthetic agonist of HTL/KAI2 shows potent stimulating activity for Arabidopsis seed germination.
K. Fukui (2019)
10.1007/978-3-030-12153-2_4
The role of strigolactones in plant-microbe interactions
S. Rochange (2019)
See more
Semantic Scholar Logo Some data provided by SemanticScholar