{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T20:57:19Z","timestamp":1780433839543,"version":"3.54.1"},"reference-count":41,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2025,3,21]],"date-time":"2025-03-21T00:00:00Z","timestamp":1742515200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"projects MACBIOPEST","award":["MAC2\/1.1a\/289"],"award-info":[{"award-number":["MAC2\/1.1a\/289"]}]},{"name":"projects MACBIOPEST","award":["PID2022-136549OB-100"],"award-info":[{"award-number":["PID2022-136549OB-100"]}]},{"name":"program Interreg MAC 2014\u20132020 co-funded by the European Regional Development Fund (FEDER)","award":["MAC2\/1.1a\/289"],"award-info":[{"award-number":["MAC2\/1.1a\/289"]}]},{"name":"program Interreg MAC 2014\u20132020 co-funded by the European Regional Development Fund (FEDER)","award":["PID2022-136549OB-100"],"award-info":[{"award-number":["PID2022-136549OB-100"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033\/FEDER, UE","award":["MAC2\/1.1a\/289"],"award-info":[{"award-number":["MAC2\/1.1a\/289"]}]},{"name":"MCIN\/AEI\/10.13039\/501100011033\/FEDER, UE","award":["PID2022-136549OB-100"],"award-info":[{"award-number":["PID2022-136549OB-100"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Plants"],"abstract":"<jats:p>Plant-derived biopesticides are emerging as a promising and popular alternative for promoting cleaner and safer agricultural practices. The present work aims to explore Argyranthemum frutescens (Asteraceae) as a source of botanical pesticides and to validate this through a cultivation process. To this task, a bioassay-guided fractionation of the ethanolic root extracts from both wild and cultivated A. frutescens on phytopathogenic fungi of Botrytis cinerea, Fusarium oxysporum, and Alternaria alternata was conducted. This approach led to the identification of polyacetylenes with higher potency than commercial fungicides. Specifically, compounds 3 (capillin) and 5 (frutescinone) showed more than 90% growth inhibition at 0.05 mg\/mL concentration on B. cinerea, while compounds 2 (capillinol) and 3 were also more active than positive controls, Fosbel-Plus and Azoxystrobin, against F. oxysporum. The structures of the isolated polyacetylenes (1\u20136, 9, and 10) and alkamides (7, 8, and 11) were determined through spectroscopic analysis, and the absolute configuration of stereocenter C1 of compounds 1, 2, 4 and 9 was determined by NMR-spectroscopy with (R)-(-)-\u03b1-methoxy-phenylacetic as a chiral derivatizing agent, and biogenetic considerations. Overall, this study supports the potential of polyacetylenes as promising agrochemical lead compounds against phytopathogens, and validates A. frutescens cultivation as a viable source of biopesticides.<\/jats:p>","DOI":"10.3390\/plants14070985","type":"journal-article","created":{"date-parts":[[2025,3,21]],"date-time":"2025-03-21T09:09:07Z","timestamp":1742548147000},"page":"985","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Eco-Friendly Crop Protection: Argyrantemum frutescens, a Source of Biofungicides"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4306-2696","authenticated-orcid":false,"given":"Eduardo","family":"Hern\u00e1ndez-\u00c1lvarez","sequence":"first","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica Antonio Gonz\u00e1lez, Departamento de Qu\u00edmica Org\u00e1nica, Universidad de La Laguna, Avenida Astrof\u00edsico Francisco S\u00e1nchez 2, 38206 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samuel","family":"Rodr\u00edguez-Sabina","sequence":"additional","affiliation":[{"name":"Departamento de Bot\u00e1nica, Ecolog\u00eda y Fisiolog\u00eda Vegetal, Universidad de La Laguna, Avenida Astrof\u00edsico Francisco S\u00e1nchez, 38206 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-4310-0251","authenticated-orcid":false,"given":"Noelia","family":"Labrador-Garc\u00eda","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica Antonio Gonz\u00e1lez, Departamento de Qu\u00edmica Org\u00e1nica, Universidad de La Laguna, Avenida Astrof\u00edsico Francisco S\u00e1nchez 2, 38206 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Javier Hern\u00e1ndez","family":"P\u00e9rez","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica Antonio Gonz\u00e1lez, Departamento de Qu\u00edmica Org\u00e1nica, Universidad de La Laguna, Avenida Astrof\u00edsico Francisco S\u00e1nchez 2, 38206 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2117-8794","authenticated-orcid":false,"given":"Carolina P.","family":"Reyes","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica Antonio Gonz\u00e1lez, Departamento de Bioqu\u00edmica, Microbiolog\u00eda, Biolog\u00eda Celular y Gen\u00e9tica, Universidad de La Laguna, Avenida Astrof\u00edsico Francisco S\u00e1nchez 2, 38206 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda \u00c1ngeles","family":"Llar\u00eda-L\u00f3pez","sequence":"additional","affiliation":[{"name":"\u00c1rea de Gesti\u00f3n del Medio Natural y Seguridad, Cabildo Insular de Tenerife, C\/Las Macetas s\/n, Pabell\u00f3n Insular Santiago Mart\u00edn, 38108 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0641-607X","authenticated-orcid":false,"given":"Ignacio A.","family":"Jim\u00e9nez","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica Antonio Gonz\u00e1lez, Departamento de Qu\u00edmica Org\u00e1nica, Universidad de La Laguna, Avenida Astrof\u00edsico Francisco S\u00e1nchez 2, 38206 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Isabel L.","family":"Bazzocchi","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica Antonio Gonz\u00e1lez, Departamento de Qu\u00edmica Org\u00e1nica, Universidad de La Laguna, Avenida Astrof\u00edsico Francisco S\u00e1nchez 2, 38206 La Laguna, Tenerife, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,3,21]]},"reference":[{"key":"ref_1","unstructured":"Kumar, A., and Droby, S. (2021). Current status of plant diseases and food security. Food Security and Plant Disease Management, Wiley."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6482","DOI":"10.1038\/s41467-023-42142-4","article-title":"Global diversity andb of potential phytopathogenic fungi in a changing world","volume":"14","author":"Li","year":"2023","journal-title":"Nat. Commun."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"858","DOI":"10.1111\/mpp.13056","article-title":"Transcription factor control of virulence in phytopathogenic fungi","volume":"22","author":"John","year":"2021","journal-title":"Mol. Plant Pathol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1093\/femsre\/fuad061","article-title":"Mechanisms of Alternaria pathogenesis in animals and plants","volume":"47","author":"Fernandes","year":"2023","journal-title":"FEMS Microbiol. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Wang, H., Guo, Y., Luo, Z., Gao, L., Li, R., Zhang, Y., Kalaji, H.M., Qiang, S., and Chen, S. (2022). Recent advances in Alternaria phytotoxins: A review of their occurrence, structure, bioactivity, and biosynthesis. J. Fungi, 8.","DOI":"10.3390\/jof8020168"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"e13404","DOI":"10.1111\/mpp.13404","article-title":"Genetic and molecular landscapes of the generalist phytopathogen Botrytis cinerea","volume":"25","author":"Singh","year":"2024","journal-title":"Mol. Plant Pathol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.tplants.2022.08.024","article-title":"Killing Softly: A Roadmap of Botrytis cinerea pathogenicity","volume":"28","author":"Bi","year":"2023","journal-title":"Trends Plant Sci."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Seepe, H.A., Nxumalo, W., and Amoo, S.O. (2021). Natural products from medicinal plants against phytopathogenic Fusarium species: Current research endeavours, challenges and prospects. Molecules, 26.","DOI":"10.3390\/molecules26216539"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"100410","DOI":"10.1016\/j.emcon.2024.100410","article-title":"A Comprehensive review on environmental and human health impacts of chemical pesticide usage","volume":"11","author":"Zhou","year":"2025","journal-title":"Emerg. Contam."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Srivastava, P.K., Singh, V.P., Singh, A., Singh, S., Prasad, S.M., Tripathi, D.K., and Chauhan, D.K. (2020). Development of pesticide resistance in pests: A key challenge to the crop protection and environmental safety. Pesticides in Crop Production: Physiological and Biochemical Action, Wiley.","DOI":"10.1002\/9781119432241"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Harte, S.J., Bray, D.P., Nash-Woolley, V., Stevenson, P.C., and Fern\u00e1ndez-Grandon, G.M. (2024). Antagonistic and additive effect when combining biopesticides against the fall armyworm, Spodoptera frugiperda. Sci. Rep., 14.","DOI":"10.1038\/s41598-024-56599-w"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"697","DOI":"10.1007\/s10658-024-02865-6","article-title":"Back to the origins: Biopesticides as promising alternatives to conventional agrochemicals","volume":"1","author":"Aioub","year":"2024","journal-title":"Eur. J. Plant. Pathol."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Fragkouli, R., Antonopoulou, M., Asimakis, E., Spyrou, A., Kosma, C., Zotos, A., Tsiamis, G., Patakas, A., and Triantafyllidis, V. (2023). Mediterranean plants as potential source of biopesticides: An overview of current research and future trends. Metabolites, 13.","DOI":"10.20944\/preprints202308.0422.v1"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1512","DOI":"10.1002\/pan3.10511","article-title":"Cultural importance, availability and conservation status of spanish wild medicinal plants: Implications for sustainability","volume":"5","author":"Gras","year":"2023","journal-title":"People Nat."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1141","DOI":"10.1007\/s10722-008-9315-0","article-title":"Crop domestication in the Compositae: A family-wide trait assessment","volume":"55","author":"Dempewolf","year":"2008","journal-title":"Genet. Resour. Crop Evol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1111\/jse.12265","article-title":"The Compositae tree of life in the age of phylogenomics","volume":"55","author":"Mandel","year":"2017","journal-title":"J. Syst. Evol."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Rolnik, A., and Olas, B. (2021). The Plants of the Asteraceae Family as Agents in the Protection of Human Health. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22063009"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1927","DOI":"10.1042\/BST20240213","article-title":"Understanding pyrethrin biosynthesis: Toward and beyond natural pesticide overproduction","volume":"52","author":"Matsuda","year":"2024","journal-title":"Biochem. Soc. Trans."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Jaison, J.P., Balasubramanian, B., Gangwar, J., James, N., Pappuswamy, M., Anand, A.V., Al-Dhabi, N.A., Arasu, M.V., Liu, W.-C., and Sebastian, J.K. (2023). Green synthesis of bioinspired nanoparticles mediated from plant extracts of Asteraceae family for potential biological applications. Antibiotics, 12.","DOI":"10.3390\/antibiotics12030543"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Petrova, M., Miladinova-Georgieva, K., and Geneva, M. (2024). Influence of abiotic and biotic elicitors on organogenesis, biomass accumulation, and production of key secondary metabolites in Asteraceae Plants. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms25084197"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Bramwell, D., and Caujap\u00e9-Castells, J. (2011). Introduction: Islands and plants. The Biology of Island Floras, Cambridge University Press.","DOI":"10.1017\/CBO9780511844270"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1953","DOI":"10.1111\/nph.16980","article-title":"Geographical isolation, habitat shifts and hybridisation in the diversification of the Macaronesian endemic genus Argyranthemum (Asteraceae)","volume":"228","author":"White","year":"2020","journal-title":"New Phytol."},{"key":"ref_23","unstructured":"Cruz Su\u00e1rez, S.J. (2007). M\u00e1s de 100 Plantas Medicinales, Obra Social de la Caja de Canaria. [1st ed.]."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Saboti\u010d, J., Bayram, E., Ezra, D., Gaud\u00eancio, S.P., Haznedaro\u011flu, B.Z., Jane\u017e, N., Ktari, L., Luganini, A., Mandalakis, M., and Safarik, I. (2024). A guide to the use of bioassays in exploration of natural resources. Biotechnol. Adv., 71.","DOI":"10.1016\/j.biotechadv.2024.108307"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1016\/0305-1978(88)90111-1","article-title":"Distribution of acetylenes and sesquiterpene lactones in Argyranthemum from Tenerife","volume":"16","author":"Barrera","year":"1988","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"963","DOI":"10.1016\/S0031-9422(97)00063-0","article-title":"Biological activities of some Argyranthemum species","volume":"45","author":"Ravelo","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"102","DOI":"10.5943\/mycosphere\/7\/2\/2","article-title":"Fungi as endophytes in chinese Artemisia spp.: Juxtaposed elements of phylogeny, diversity and bioactivity","volume":"7","author":"Cosoveanu","year":"2016","journal-title":"Mycosphere"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"132","DOI":"10.1016\/j.indcrop.2017.02.020","article-title":"Essential oil and polyacetylenes from Artemisia ordosica and their bioactivities against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae)","volume":"100","author":"Zhang","year":"2017","journal-title":"Ind. Crops Prod."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Esmaeili, G., Fatemi, H., Avval, M.B., Azizi, M., Arouiee, H., Vaezi, J., and Fujii, Y. (2022). Diversity of chemical composition and morphological traits of eight iranian wild Salvia species during the first step of domestication. Agronomy, 12.","DOI":"10.3390\/agronomy12102455"},{"key":"ref_30","first-page":"5931","article-title":"Alkaloids and carboxylic acids from Piper nigrum","volume":"20","author":"Ee","year":"2008","journal-title":"Asian J. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1103","DOI":"10.1016\/S0031-9422(00)82618-7","article-title":"Sesquiterpenes and acetylenes from Argyranthemum adauctum ssp. jacobaeifolium","volume":"23","author":"Bohlmann","year":"1984","journal-title":"Phytochemistry"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/S0367-326X(00)00247-1","article-title":"Isolation and Complete NMR assignment of the numbing principle from Chrysanthemum morifolium","volume":"72","author":"Shahat","year":"2001","journal-title":"Fitoterapia"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4603","DOI":"10.1021\/cr2003344","article-title":"Assignment of the absolute configuration of polyfunctional compounds by NMR using chiral derivatizing agents","volume":"112","author":"Seco","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"113288","DOI":"10.1016\/j.phytochem.2022.113288","article-title":"Polyacetylenes in herbal medicine: A comprehensive review of its occurrence, pharmacology, toxicology, and pharmacokinetics (2014\u20132021)","volume":"201","author":"Xie","year":"2022","journal-title":"Phytochemistry"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1007\/s11094-014-1159-7","article-title":"Medicinal plants polyacetylene compounds of plants of the Asteraceae family (review)","volume":"48","author":"Konovalov","year":"2014","journal-title":"Pharm. Chem. J."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"e00715-21","DOI":"10.1128\/mBio.00715-21","article-title":"Discovery of the Pseudomonas polyyne protegencin by a phylogeny-guided study of polyyne biosynthetic gene cluster diversity","volume":"12","author":"Mullins","year":"2021","journal-title":"mBio"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1002\/cbdv.201400161","article-title":"Insecticidal and repellant activities of polyacetylenes and lactones derived from Atractylodes lancea rhizomes","volume":"12","author":"Chen","year":"2015","journal-title":"Chem. Biodivers."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1016\/j.phymed.2015.03.008","article-title":"Capillin, a major constituent of Artemisia capillaris Thunb. flower essential oil, induces apoptosis through the mitochondrial pathway in human leukemia HL-60 cells","volume":"22","author":"Masuda","year":"2015","journal-title":"Phytomedicine"},{"key":"ref_39","first-page":"405","article-title":"Acetylenic terrestrial anticancer agents","volume":"1","author":"Dembitsky","year":"2006","journal-title":"Nat. Prod. Commun."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1007\/s12272-016-0715-y","article-title":"Promising anti-diabetic potential of capillin and capillinol isolated from Artemisia capillaris","volume":"39","author":"Islam","year":"2016","journal-title":"Arch Pharm. Res."},{"key":"ref_41","unstructured":"(2024, May 03). One-Way ANOVA Calculator, Including Tukey HSD. Available online: https:\/\/www.socscistatistics.com\/tests\/chisquare2\/default2.aspx."}],"container-title":["Plants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2223-7747\/14\/7\/985\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T16:57:52Z","timestamp":1760029072000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2223-7747\/14\/7\/985"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3,21]]},"references-count":41,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2025,4]]}},"alternative-id":["plants14070985"],"URL":"https:\/\/doi.org\/10.3390\/plants14070985","relation":{},"ISSN":["2223-7747"],"issn-type":[{"value":"2223-7747","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,3,21]]}}}