Skip to main content
SpringerLink
Log in

Allelochemicals from Thapsia garganica leaves for Lolium perenne L. control: the magic of mixtures

  • Original Article
  • Published:
Chemoecology Aims and scope Submit manuscript

Abstract

Luteolin 7-O-glucoside (1), 10β-acetoxy-8α-butyryloxy-11α-hydroxy-2β-((2-methylbutanoyl)oxy)-1βH,6αH,7αH,11βH-guaian-3-en-12,6-olide (2) and thapsigargin (3) herbicidal activities’ were evaluated in comparison with their binary and tertiary mixtures, against Lolium perenne. These allelochemicals were isolated from Thapsia garganica leaves methanolic extract. Experiments were carried out by irrigation and spray in pot trials. Each compound was tested at the concentration that inhibits 50% of L. perenne root growth (IC50). Mixtures were prepared at the total concentration determined to inhibit 50% of weed root growth based upon the IC50 value for each compound (1000 µM, 154 µM and 300 µM for 1, 2 and 3, respectively). The greatest herbicidal effect was observed in tertiary mixtures, followed by binary ones, and single compounds showed the lowest phytotoxicity. Moreover, spray treatment was more effective at inhibiting growth of L. perenne, compared with irrigation. For sprayed binary mixtures, the 2 and 3 mixture showed the best inhibitions in shoot (75.79%) and root (91.02%) growth, and fresh weight (89.28%). These values significantly improved those of the most active single compound, 1 (48.01%, 58.62% and 57.14%, respectively, following spray). On the other hand, compound 3, whose structure is related to guaianolide sesquiterpene lactones, was a common constituent of the most active mixtures, suggesting that it plays a more relevant role in the improvement of the phytotoxicity of mixtures. Results obtained for the spray treatment of the tertiary mixture of 1 (333.33 µM), 2 (51.33 µM) and 3 (100 µM) were even more prominent, since weed growth was completely inhibited. After irrigation with a tertiary mixture, the greatest inhibitions in shoot and root growth and fresh weight did not exceed 88.16%, 94% and 90.47%, respectively. The results reported highlight a synergistic behavior of the test allelochemicals which could be applied in the development of bio-herbicides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Data availability

All data generated or analyzed during this study are included in this published article.

Abbreviations

IC50 :

Concentration determined to inhibit 50% of weed root growth

References

  • Akhtar Y, Isman MB (2012) Plant natural products for pest management: the magic of mixtures. Advanced technologies for managing insect pests. Springer, Dordrecht, pp 231–247

    Google Scholar 

  • Cala A, Zorrilla JG, Rial C, Molinillo JM, Varela RM, Macías FA (2019) Easy access to alkoxy, amino, carbamoyl, hydroxy, and thiol derivatives of sesquiterpene lactones and evaluation of their bioactivity on parasitic weeds. J Agric Food Chem 67(38):10764–10773

    Article  CAS  Google Scholar 

  • Castellano D, Macías FA, Castellano M, Cambronero R (2001) FITOMED (Automated system for the measurement of variable lengths). Spain Patent No. P9901565

  • Chibani S, Al-Dabbas M, Abuhamdah S, Aburjai T, Bencheraiet R, Kabouche A, Jay M, Kabouche Z (2014) Flavonoids and antioxidant activity of Thapsia garganica from Algeria. Chem Nat Compd 50(2):357–359

    Article  CAS  Google Scholar 

  • Chotsaeng N, Laosinwattana C, Charoenying P (2017) Herbicidal activities of some allelochemicals and their synergistic behaviors toward Amaranthus tricolor L. Molecules 22(11):1841

    Article  Google Scholar 

  • Chotsaeng N, Laosinwattana C, Charoenying P (2021) Enantioselective and synergistic herbicidal activities of common amino acids against Amaranthus tricolor and Echinochloa crus-galli. Molecules 26(7):2071

    Article  CAS  Google Scholar 

  • Cogo J, de Oliveira Caleare A, Ueda-Nakamura T, Dias Filho BP, Ferreira ICP, Nakamura CV (2012) Trypanocidal activity of guaianolide obtained from Tanacetum parthenium (L.) Schultz-Bip. and its combinational effect with benznidazole. Phytomedicine 20(1):59–66

    Article  CAS  Google Scholar 

  • Goulding LV, Yang J, Jiang Z, Zhang H, Lea D, Emes RD et al (2020) Thapsigargin at non-cytotoxic levels induces a potent host antiviral response that blocks influenza A virus replication. Viruses 12(10):1093

    Article  CAS  Google Scholar 

  • Hozayn M, El-Shahawy TA, Abd El-Monem AA, El-Saady AA, Darwish MA (2015) Allelopathic effect of Casuarina equisetifolia L. on wheat, associated weeds and nutrient content in the soil. Afr J Agric Res 10(14):1675–1683

    Article  Google Scholar 

  • Jabran K (2017) Manipulation of allelopathic crops for weed control. Springer, Dordrecht

    Book  Google Scholar 

  • Jmii G, Molinillo JMG, Zorrilla JG, Haouala R (2020a) Allelopathic activity of Thapsia garganica L. leaves on lettuce and weeds, and identification of the active principles. S Afr J Bot 131:188–194. https://doi.org/10.1016/j.sajb.2020.02.027

    Article  CAS  Google Scholar 

  • Jmii G, Khadhri A, Haouala R (2020b) Thapsia garganica allelopathic potentialities explored for lettuce growth enhancement and associated weed control. Sci Hortic 262:109068

    Article  CAS  Google Scholar 

  • Joel DM, Chaudhuri SK, Plakhine D, Ziadna H, Steffens JC (2011) Dehydrocostus lactone is exuded from sunflower roots and stimulates germination of the root parasite Orobanche cumana. Phytochemistry 72(7):624–634

    Article  CAS  Google Scholar 

  • Koul O, Walia S (2009) Comparing impacts of plant extracts and pure allelochemicals and implications for pest control. CAB Rev: Perspec Agric Vet Sci Nutr Nat Resour 4(049):1–30

    Google Scholar 

  • Lambert M, Wolfender JL, Stærk D, Christensen SB, Hostettmann K, Jaroszewski JW (2007) Identification of natural products using HPLC-SPE combined with CAPNMR. Anal Chem 79(2):727–735

    Article  CAS  Google Scholar 

  • Macías FA, Castellano D, Molinillo JMG (2000) Search for a standard phytotoxic bioassay for allelochemicals. Selection of standard target species. J Agric Food Chem 48:2512–2521

    Article  Google Scholar 

  • Macías FA, Santana A, Durán AG, Cala A, Galindo JC, Galindo JL, Molinillo JM (2013) Guaianolides for multipurpose molecular design. In: Pest management with natural products. American Chemical Society, pp 167–188

  • Michellon R (1987) Etude des effets allélopathiques d’une couverture de Kikuyu (Pennisetum clandestinum) sur geranium, cultures vivrières et certaines plantes adventices. Mémoire de Fin d’Etudes, Centre de coopération internationale en recherche agronomique pour le développement, 174 p

  • Nebo I, Varela RM, Molinillo JMG, Sampaio OM, Severino VGP, Cazal CM, daSilva MFGF, Fernandes JB, Macias FA (2014) Phytotoxicity of alkaloids, coumarins and flavonoids isolated from 11 species belonging to the Rutaceae and Meliaceae families. Phytochem Lett 8:226–232

    Article  CAS  Google Scholar 

  • Rial C, Novaes P, Varela RM, Molinillo JMG, Macias FA (2014) Phytotoxicity of Cardoon (Cynara cardunculus) Allelochemicals on standard target species and weeds. J Agric Food Chem 62:6699–6706

    Article  CAS  Google Scholar 

  • Scott IM, Puniani E, Durst T, Phelps D, Merali S, Assabgui RA, Sanchez-Vindas P, Poveda L, Philogène BJR, Arnason JT (2002) Insecticidal activity of Piper tuberculatum Jacq. extracts: synergistic interaction of piperamides. Agric for Entomol 4(2):137–144

    Article  Google Scholar 

  • Smitt UW, Moldt P, Christensen SB (1986) Structure of a pro-1,4-dimethylazulene guainolide from Thapsia garganica L. Acta Chemica Scandinavia Series B-Organic Chemistry and Biochemistry 40:711–714

    Article  Google Scholar 

  • Trezzi MM, Vidal RA, Junior AAB, Bittencourt HVH, da Silva Souza Filho AP (2016) Allelopathy: driving mechanisms governing its activity in agriculture. J Plant Interact 11(1):1–20

    Article  Google Scholar 

  • Tuyen P, Xuan T, Tu Anh T, Van Mai T, Ahmad A, Elzaawely A, Khanh T (2018) Weed suppressing potential and isolation of potent plant growth inhibitors from Castanea crenata Sieb. et Zucc. Molecules 23(2):345

    Article  Google Scholar 

  • Yin J, Si CL, Wang MH (2008) Antioxidant activity of flavonoids and their glucosides from Sonchus oleraceus L. J Appl Biol Chem 51(2):57–60

    Article  CAS  Google Scholar 

  • Zorrilla JG, Cala A, Rial C, Mejías FJR, Molinillo JM, Varela RM, Macías FA (2020) Synthesis of Active Strigolactone Analogues Based on Eudesmane-and Guaiane-Type Sesquiterpene Lactones. J Agric Food Chem 68(36):9636–9645

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We would like to thank the Higher Institute of Agronomy of Chott Meriem for its financial support.

Funding

The authors have not disclosed any funding.

Author information

Authors and Affiliations

  1. Faculty of Sciences Tunis, University of Tunis El Manar, 2092, Tunis, Tunisia

    Ghofrane Jmii

  2. Research Laboratory Agro-Biodiversity and Ecotoxicology LR21AGRO2, Higher Agronomic Institute of Chott-Mariem, University of Sousse, 4042, Sousse, Tunisia

    Ghofrane Jmii & Rabiaa Haouala

  3. Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), School of Science, University of Cadiz, C/Republica Saharaui, 7, 11510, Puerto Real, Spain

    Jesús G. Zorrilla

Authors
  1. Ghofrane Jmii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jesús G. Zorrilla
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rabiaa Haouala
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

HR conceived and designed tables. JG wrote the manuscript. GZJ reviewed the manuscript and designed figures. The authors read and approved the manuscript.

Corresponding author

Correspondence to Ghofrane Jmii.

Ethics declarations

Conflict of interest

The authors have not disclosed any competing interests.

Additional information

Communicated by Günther Raspotnig.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jmii, G., Zorrilla, J.G. & Haouala, R. Allelochemicals from Thapsia garganica leaves for Lolium perenne L. control: the magic of mixtures. Chemoecology 32, 81–87 (2022). https://doi.org/10.1007/s00049-022-00369-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00049-022-00369-5

Keywords

Search

Navigation