Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana

Autores
Chen, Yuchao; Kuang, Yi; Shi, Liyang; Wang, Xing; Fu, Haoyu; Yang, Shengxiang; Sampietro, Diego Alejandro; Huang, Luqi; Yuan, Yuan
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Orobanche and Striga are parasitic weeds extremely well adapted to the life cycle of their host plants. They cannot be eliminated by conventional weed control methods. Suicidal germination induced by strigolactones (SLs) analogs is an option to control these weeds. Here, we reported two new halogenated (+)-GR24 analogs, named 7-bromo-GR24 (7BrGR24) and 7-fluoro-GR24 (7FGR24), which were synthesized using commercially available materials following simple steps. Both compounds strongly promoted seed germination of Orobanche cumana. Their EC50 values of 2.3±0.28×10−8M (7BrGR24) and 0.97±0.29×10−8M (7FGR24) were 3- and 5-fold lower, respectively, than those of (+)-GR24 and rac-GR24 (EC50=5.1±1.32–5.3±1.44×10−8; p<0.05). The 7FGR24 was the strongest seed germination promoter tested, with a stimulation percentage of 62.0±9.1% at 1.0×10−8M and 90.9±3.8% at 1.0×10−6M. It showed higher binding affinity (IC50=0.189±0.012μM) for the SL receptor ShHTL7 than (+)-GR24 (IC50=0.248±0.032μM), rac-GR24 (IC50=0.319±0.032μM), and 7BrGR24 (IC50=0.521±0.087μM). Molecular docking experiments indicated that the binding affinity of both halogenated analogs to the strigolactone receptor OsD14 was similar to that of (+)-GR24. Our results indicate that 7FGR24 is a promising agent for the control of parasitic weeds.
Fil: Chen, Yuchao. Anhui University Of Chinese Medicine; China
Fil: Kuang, Yi. Zhejiang A&f University; China
Fil: Shi, Liyang. Zhejiang A&f University; China
Fil: Wang, Xing. Zhejiang A&f University; China
Fil: Fu, Haoyu. Zhejiang A&f University; China
Fil: Yang, Shengxiang. Zhejiang A&f University; China
Fil: Sampietro, Diego Alejandro. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Estudios Vegetales. Cátedra de Fitoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Huang, Luqi. Anhui University Of Chinese Medicine; China
Fil: Yuan, Yuan. China Academy Of Chinese Medical Sciences; China
Materia
GR24 ANALOGS
OROBANCHE CUMANA
PARASITIC WEEDS
STRIGOLACTONES
SUICIDAL GERMINATION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/148378
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/148378
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumanaChen, YuchaoKuang, YiShi, LiyangWang, XingFu, HaoyuYang, ShengxiangSampietro, Diego AlejandroHuang, LuqiYuan, YuanGR24 ANALOGSOROBANCHE CUMANAPARASITIC WEEDSSTRIGOLACTONESSUICIDAL GERMINATIONhttps://purl.org/becyt/ford/4.4https://purl.org/becyt/ford/4Orobanche and Striga are parasitic weeds extremely well adapted to the life cycle of their host plants. They cannot be eliminated by conventional weed control methods. Suicidal germination induced by strigolactones (SLs) analogs is an option to control these weeds. Here, we reported two new halogenated (+)-GR24 analogs, named 7-bromo-GR24 (7BrGR24) and 7-fluoro-GR24 (7FGR24), which were synthesized using commercially available materials following simple steps. Both compounds strongly promoted seed germination of Orobanche cumana. Their EC50 values of 2.3±0.28×10−8M (7BrGR24) and 0.97±0.29×10−8M (7FGR24) were 3- and 5-fold lower, respectively, than those of (+)-GR24 and rac-GR24 (EC50=5.1±1.32–5.3±1.44×10−8; p<0.05). The 7FGR24 was the strongest seed germination promoter tested, with a stimulation percentage of 62.0±9.1% at 1.0×10−8M and 90.9±3.8% at 1.0×10−6M. It showed higher binding affinity (IC50=0.189±0.012μM) for the SL receptor ShHTL7 than (+)-GR24 (IC50=0.248±0.032μM), rac-GR24 (IC50=0.319±0.032μM), and 7BrGR24 (IC50=0.521±0.087μM). Molecular docking experiments indicated that the binding affinity of both halogenated analogs to the strigolactone receptor OsD14 was similar to that of (+)-GR24. Our results indicate that 7FGR24 is a promising agent for the control of parasitic weeds.Fil: Chen, Yuchao. Anhui University Of Chinese Medicine; ChinaFil: Kuang, Yi. Zhejiang A&f University; ChinaFil: Shi, Liyang. Zhejiang A&f University; ChinaFil: Wang, Xing. Zhejiang A&f University; ChinaFil: Fu, Haoyu. Zhejiang A&f University; ChinaFil: Yang, Shengxiang. Zhejiang A&f University; ChinaFil: Sampietro, Diego Alejandro. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Estudios Vegetales. Cátedra de Fitoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Huang, Luqi. Anhui University Of Chinese Medicine; ChinaFil: Yuan, Yuan. China Academy Of Chinese Medical Sciences; ChinaFrontiers Media S.A.2021-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/148378Chen, Yuchao; Kuang, Yi; Shi, Liyang; Wang, Xing; Fu, Haoyu; et al.; Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana; Frontiers Media S.A.; Frontiers in Plant Science; 12; 9-2021; 1-91664-462XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.frontiersin.org/articles/10.3389/fpls.2021.725949/fullinfo:eu-repo/semantics/altIdentifier/doi/10.3389/fpls.2021.725949info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:53:54Zoai:ri.conicet.gov.ar:11336/148378instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:53:55.052CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
title Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
spellingShingle Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
Chen, Yuchao
GR24 ANALOGS
OROBANCHE CUMANA
PARASITIC WEEDS
STRIGOLACTONES
SUICIDAL GERMINATION
title_short Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
title_full Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
title_fullStr Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
title_full_unstemmed Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
title_sort Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana
dc.creator.none.fl_str_mv Chen, Yuchao
Kuang, Yi
Shi, Liyang
Wang, Xing
Fu, Haoyu
Yang, Shengxiang
Sampietro, Diego Alejandro
Huang, Luqi
Yuan, Yuan
author Chen, Yuchao
author_facet Chen, Yuchao
Kuang, Yi
Shi, Liyang
Wang, Xing
Fu, Haoyu
Yang, Shengxiang
Sampietro, Diego Alejandro
Huang, Luqi
Yuan, Yuan
author_role author
author2 Kuang, Yi
Shi, Liyang
Wang, Xing
Fu, Haoyu
Yang, Shengxiang
Sampietro, Diego Alejandro
Huang, Luqi
Yuan, Yuan
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv GR24 ANALOGS
OROBANCHE CUMANA
PARASITIC WEEDS
STRIGOLACTONES
SUICIDAL GERMINATION
topic GR24 ANALOGS
OROBANCHE CUMANA
PARASITIC WEEDS
STRIGOLACTONES
SUICIDAL GERMINATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/4.4
https://purl.org/becyt/ford/4
dc.description.none.fl_txt_mv Orobanche and Striga are parasitic weeds extremely well adapted to the life cycle of their host plants. They cannot be eliminated by conventional weed control methods. Suicidal germination induced by strigolactones (SLs) analogs is an option to control these weeds. Here, we reported two new halogenated (+)-GR24 analogs, named 7-bromo-GR24 (7BrGR24) and 7-fluoro-GR24 (7FGR24), which were synthesized using commercially available materials following simple steps. Both compounds strongly promoted seed germination of Orobanche cumana. Their EC50 values of 2.3±0.28×10−8M (7BrGR24) and 0.97±0.29×10−8M (7FGR24) were 3- and 5-fold lower, respectively, than those of (+)-GR24 and rac-GR24 (EC50=5.1±1.32–5.3±1.44×10−8; p<0.05). The 7FGR24 was the strongest seed germination promoter tested, with a stimulation percentage of 62.0±9.1% at 1.0×10−8M and 90.9±3.8% at 1.0×10−6M. It showed higher binding affinity (IC50=0.189±0.012μM) for the SL receptor ShHTL7 than (+)-GR24 (IC50=0.248±0.032μM), rac-GR24 (IC50=0.319±0.032μM), and 7BrGR24 (IC50=0.521±0.087μM). Molecular docking experiments indicated that the binding affinity of both halogenated analogs to the strigolactone receptor OsD14 was similar to that of (+)-GR24. Our results indicate that 7FGR24 is a promising agent for the control of parasitic weeds.
Fil: Chen, Yuchao. Anhui University Of Chinese Medicine; China
Fil: Kuang, Yi. Zhejiang A&f University; China
Fil: Shi, Liyang. Zhejiang A&f University; China
Fil: Wang, Xing. Zhejiang A&f University; China
Fil: Fu, Haoyu. Zhejiang A&f University; China
Fil: Yang, Shengxiang. Zhejiang A&f University; China
Fil: Sampietro, Diego Alejandro. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Estudios Vegetales. Cátedra de Fitoquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Huang, Luqi. Anhui University Of Chinese Medicine; China
Fil: Yuan, Yuan. China Academy Of Chinese Medical Sciences; China
description Orobanche and Striga are parasitic weeds extremely well adapted to the life cycle of their host plants. They cannot be eliminated by conventional weed control methods. Suicidal germination induced by strigolactones (SLs) analogs is an option to control these weeds. Here, we reported two new halogenated (+)-GR24 analogs, named 7-bromo-GR24 (7BrGR24) and 7-fluoro-GR24 (7FGR24), which were synthesized using commercially available materials following simple steps. Both compounds strongly promoted seed germination of Orobanche cumana. Their EC50 values of 2.3±0.28×10−8M (7BrGR24) and 0.97±0.29×10−8M (7FGR24) were 3- and 5-fold lower, respectively, than those of (+)-GR24 and rac-GR24 (EC50=5.1±1.32–5.3±1.44×10−8; p<0.05). The 7FGR24 was the strongest seed germination promoter tested, with a stimulation percentage of 62.0±9.1% at 1.0×10−8M and 90.9±3.8% at 1.0×10−6M. It showed higher binding affinity (IC50=0.189±0.012μM) for the SL receptor ShHTL7 than (+)-GR24 (IC50=0.248±0.032μM), rac-GR24 (IC50=0.319±0.032μM), and 7BrGR24 (IC50=0.521±0.087μM). Molecular docking experiments indicated that the binding affinity of both halogenated analogs to the strigolactone receptor OsD14 was similar to that of (+)-GR24. Our results indicate that 7FGR24 is a promising agent for the control of parasitic weeds.
publishDate 2021
dc.date.none.fl_str_mv 2021-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/148378
Chen, Yuchao; Kuang, Yi; Shi, Liyang; Wang, Xing; Fu, Haoyu; et al.; Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana; Frontiers Media S.A.; Frontiers in Plant Science; 12; 9-2021; 1-9
1664-462X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/148378
identifier_str_mv Chen, Yuchao; Kuang, Yi; Shi, Liyang; Wang, Xing; Fu, Haoyu; et al.; Synthesis and Evaluation of New Halogenated GR24 Analogs as Germination Promotors for Orobanche cumana; Frontiers Media S.A.; Frontiers in Plant Science; 12; 9-2021; 1-9
1664-462X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.frontiersin.org/articles/10.3389/fpls.2021.725949/full
info:eu-repo/semantics/altIdentifier/doi/10.3389/fpls.2021.725949
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Frontiers Media S.A.
publisher.none.fl_str_mv Frontiers Media S.A.
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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