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Journal of agricultural and food chemistry
Jan 24, 2024;72 (3): 1797-1810.

Bioprospection of Phytotoxic Plant-Derived Eudesmanolides and Guaianolides for the Control of , , and Weeds.

Jesús G Zorrilla, David M Cárdenas, Carlos Rial, José M G Molinillo, Rosa M Varela, Marco Masi, Francisco A Macías
Author Information
  1. Jesús G Zorrilla: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cinthia 4, 80126 Naples, Italy. ORCID
  2. David M Cárdenas: Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO), University of Cadiz, C/Avenida República Saharaui, 7, 11510 Puerto Real, Spain. ORCID
  3. Carlos Rial: Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO), University of Cadiz, C/Avenida República Saharaui, 7, 11510 Puerto Real, Spain. ORCID
  4. José M G Molinillo: Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO), University of Cadiz, C/Avenida República Saharaui, 7, 11510 Puerto Real, Spain. ORCID
  5. Rosa M Varela: Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO), University of Cadiz, C/Avenida República Saharaui, 7, 11510 Puerto Real, Spain. ORCID
  6. Marco Masi: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cinthia 4, 80126 Naples, Italy. ORCID
  7. Francisco A Macías: Allelopathy Group, Department of Organic Chemistry, Facultad de Ciencias, Institute of Biomolecules (INBIO), University of Cadiz, C/Avenida República Saharaui, 7, 11510 Puerto Real, Spain. ORCID
PMID: 38206382 DOI: 10.1021/acs.jafc.3c06901

Abstract

The phytotoxicities of a selection of eudesmanolides and guaianolides, including natural products and new derivatives obtained by semisynthesis from plant-isolated sesquiterpene lactones, were evaluated in bioassays against three weeds of concern in agriculture ( L., L., and L.). Both eudesmanolides and guaianolides were active against the root and shoot growth of all the species, with the eudesmanolides generally showing improved activities. The IC values obtained for the herbicide employed as positive control (on root and shoot growth, respectively, : 27.8 and 85.7 μM; : 167.5 and 288.2 μM; : 99.1 and 571.4 μM) were improved in most of the cases. Structure-activity relationships were discussed, finding that hydroxylation of the A-ring and C-13 as well as the position, number, and orientation of the hydroxyl groups and the presence of an unsaturated carbonyl group can significantly influence the level of phytotoxicity. γ-Cyclocostunolide was the most active compound in the series, followed by others such as dehydrozaluzanin C and α-cyclocostunolide (outstanding their IC values on )─natural products that can therefore be suggested as models for herbicide development if further research indicates effectiveness on a larger scale and environmental safety in ecotoxicological assessments.

Keywords

bioassays herbicide development models phytotoxicity studies sesquiterpene lactones structure−activity relationships weed control

References

J Agric Food Chem. 2017 Jun 28;65(25):5161-5172 [PMID: 28605187]
J Org Chem. 2020 Jun 5;85(11):7322-7332 [PMID: 32349482]
Pest Manag Sci. 2012 Apr;68(4):505-12 [PMID: 22190296]
Phytochemistry. 2000 Jan;53(1):45-50 [PMID: 10656406]
J Chem Ecol. 2020 Sep;46(9):871-880 [PMID: 32691372]
Eur J Med Chem. 2015 Aug 28;101:769-79 [PMID: 26222449]
Bioorg Med Chem. 2015 Sep 15;23(18):6100-10 [PMID: 26320663]
J Agric Food Chem. 2005 Jun 1;53(11):4373-80 [PMID: 15913298]
Toxins (Basel). 2023 Oct 27;15(11): [PMID: 37999495]
Plant Dis. 2016 Jan;100(1):10-24 [PMID: 30688570]
Phytochemistry. 2000 May;54(2):165-71 [PMID: 10872207]
J Fungi (Basel). 2023 Mar 03;9(3): [PMID: 36983484]
Pest Manag Sci. 2022 Feb;78(2):399-408 [PMID: 34549518]
J Agric Food Chem. 2010 Sep 22;58(18):10147-55 [PMID: 20715837]
Plants (Basel). 2021 Jun 15;10(6): [PMID: 34203650]
J Agric Food Chem. 2019 Sep 25;67(38):10764-10773 [PMID: 31487158]
Pest Manag Sci. 2016 Nov;72(11):2054-2068 [PMID: 26940902]
Pest Manag Sci. 2017 Apr;73(4):700-715 [PMID: 27739147]
Pest Manag Sci. 2022 Oct;78(10):4240-4251 [PMID: 35709310]
J Agric Food Chem. 2022 Mar 9;70(9):2806-2816 [PMID: 35225607]
J Agric Food Chem. 2020 Sep 9;68(36):9636-9645 [PMID: 32794743]
PLoS One. 2022 Feb 9;17(2):e0263798 [PMID: 35139125]
Bioorg Med Chem Lett. 2008 Jul 15;18(14):4015-7 [PMID: 18579374]
Pharmacogn Mag. 2015 Jan-Mar;11(41):180-90 [PMID: 25709231]
J Fungi (Basel). 2023 Mar 07;9(3): [PMID: 36983494]
J Agric Food Chem. 2000 Nov;48(11):5288-96 [PMID: 11087474]
Plants (Basel). 2022 Oct 26;11(21): [PMID: 36365299]
Chem Biodivers. 2009 Sep;6(9):1453-62 [PMID: 19774607]
J Fungi (Basel). 2021 Aug 16;7(8): [PMID: 34436201]
J Org Chem. 2002 Apr 19;67(8):2566-71 [PMID: 11950302]
Pest Manag Sci. 2001 Jan;57(1):3-16 [PMID: 11455629]

MeSH Term

Echinochloa
Amaranthus
Lolium
Herbicides
Plant Weeds
Sesquiterpenes

Chemicals

eudesmanolide
cyclocostunolide
Herbicides
Sesquiterpenes
Journal Article

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