Contalactone, a contaminant formed during chemical synthesis of the strigolactone reference GR24 is also a strigolactone mimic.
Arabidopsis thaliana
Medicago truncatula
Pisum sativum
Plant hormone
Rhizophagus irregularis
Root parasitic plants
Strigolactone mimics
Structural determination
α/β-hydrolase
Journal
Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434
Informations de publication
Date de publication:
Dec 2019
Dec 2019
Historique:
received:
12
06
2019
revised:
28
08
2019
accepted:
28
08
2019
pubmed:
10
9
2019
medline:
18
12
2019
entrez:
10
9
2019
Statut:
ppublish
Résumé
Strigolactone (SL) plant hormones control plant architecture and are key players in both symbiotic and parasitic interactions. GR24, a synthetic SL analog, is the worldwide reference compound used in all bioassays for investigating the role of SLs in plant development and in rhizospheric interactions. In 2012, the first characterization of the SL receptor reported the detection of an unknown compound after incubation of GR24 samples with the SL receptor. We reveal here the origin of this compound (P270), which comes from a by-product formed during GR24 chemical synthesis. We present the identification of this by-product, named contalactone. A proposed chemical pathway for its formation is provided as well as an evaluation of its bioactivity on pea, Arabidopsis, root parasitic plant seeds and AM fungi, characterizing it as a SL mimic. Quality of GR24 samples can be easily checked by carrying out microscale hydrolysis in a basic aqueous medium to easily detect P270 as indicator of the presence of the contalactone impurity. In all cases, before being used for bioassays, GR24 must be careful purified by preparative HPLC.
Identifiants
pubmed: 31499274
pii: S0031-9422(19)30548-5
doi: 10.1016/j.phytochem.2019.112112
pii:
doi:
Substances chimiques
GR24 strigolactone
0
Heterocyclic Compounds, 3-Ring
0
Lactones
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
112112Informations de copyright
Copyright © 2019 Elsevier Ltd. All rights reserved.