{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T01:30:47Z","timestamp":1760059847459,"version":"build-2065373602"},"reference-count":33,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2025,7,15]],"date-time":"2025-07-15T00:00:00Z","timestamp":1752537600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Wroc\u0142aw University of Environmental and Life Sciences"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Two new very-long-chain 5-n-alkylresorcinol (AR) homologues, that is, 5-n-nonacosylbenzene-1,3-diol and 5-n-hentriacontylbenzene-1,3-diol, were isolated from acetone extracts of Ailanthus altissima samaras. These phenolic compounds were detected in nearly equal proportions, although their total content varied considerably between samples from urban-grown trees. No correlation was observed between AR levels and the physiological state of the tree, suggesting that environmental conditions may strongly influence AR biosynthesis in A. altissima. Furthermore, the isolated AR mixture exhibited antifungal activity against soil-borne phytopathogens of the genera Fusarium and Rhizoctonia.<\/jats:p>","DOI":"10.3390\/molecules30142970","type":"journal-article","created":{"date-parts":[[2025,7,15]],"date-time":"2025-07-15T11:52:58Z","timestamp":1752580378000},"page":"2970","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Very-Long-Chain Resorcinolic Lipids of Ailanthus altissima Samaras"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5439-4795","authenticated-orcid":false,"given":"El\u017cbieta G.","family":"Magnucka","sequence":"first","affiliation":[{"name":"Laboratory of Biogeochemistry and Environmental Microbiology, Department of Plant Protection, Wroc\u0142aw University of Environmental and Life Sciences, Grunwaldzka St. 53, 50-357 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6343-1500","authenticated-orcid":false,"given":"Robert","family":"Zarnowski","sequence":"additional","affiliation":[{"name":"Department of Medicine, School of Medicine and Public Health, University of Wisconsin, 5225 Microbial Sciences Building, 1550 Linden Dr., Madison, WI 53706, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6897-6662","authenticated-orcid":false,"given":"Przemys\u0142aw","family":"B\u0105belewski","sequence":"additional","affiliation":[{"name":"Department of Horticulture, Wroc\u0142aw University of Environmental and Life Sciences, Grunwaldzki Sq. 24a, 50-363 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1009","DOI":"10.1007\/s00267-015-0546-5","article-title":"Review on invasive tree of heaven (Ailanthus altissima (Mill.) Swingle) conflicting values: Assessment of its ecosystem services and potential biological threat","volume":"56","author":"Sladonja","year":"2015","journal-title":"Environ. Manag."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Soler, J., and Izquierdo, J. (2024). The invasive Ailanthus altissima: A biology, ecology, and control review. Plants, 13.","DOI":"10.3390\/plants13070931"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"119025","DOI":"10.1016\/j.foreco.2021.119025","article-title":"The invasive tree, Ailanthus altissima, impacts understory nativity, not seedbank nativity","volume":"489","author":"Brooks","year":"2021","journal-title":"For. Ecol. Manag."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.ppees.2007.03.002","article-title":"Biological flora of Central Europe: Ailanthus altissima (Mill.) swingle","volume":"8","author":"Kowarik","year":"2007","journal-title":"Perspect. Plant Ecol. Evol. Syst."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1016\/j.jep.2021.114121","article-title":"Traditional uses, phytochemistry, and pharmacology of Ailanthus altissima (Mill.) Swingle bark: A comprehensive review","volume":"275","author":"Li","year":"2021","journal-title":"J. Ethnopharmacol."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Tan, Q.W., Ni, J.C., Shi, J.T., Zhy, J.X., and Chen, Q.J. (2020). Two novel quassinoid glycosides with antiviral activity from the samara of Ailanthus altissima. Molecules, 25.","DOI":"10.3390\/molecules25235679"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.cbi.2017.12.011","article-title":"9-Hydroxycanthin-6-one isolated from stem bark of Ailanthus altissima induces ovarian cancer cell apoptosis and inhibits the activation of tumor-associated macrophages","volume":"280","author":"Jeong","year":"2018","journal-title":"Chem. Biol. Interact."},{"key":"ref_8","first-page":"6022","article-title":"Antitumor activity of the Ailanthus altissima bark phytochemical ailanthone against breast cancer MCF-7 cells","volume":"15","author":"Wang","year":"2018","journal-title":"Oncol. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2203","DOI":"10.1002\/ptr.6681","article-title":"Anticancer properties and mechanism of action of the quassinoid ailanthone","volume":"34","author":"Bailly","year":"2020","journal-title":"Phytother. Res."},{"key":"ref_10","first-page":"121","article-title":"The pharmacological importance of Ailanthus altissima\u2014A review","volume":"5","year":"2015","journal-title":"Int. J. Pharm. Rev. Res."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Kozuharova, E., Pasdran, A., Tawaha, A.R.A., Todorova, T., Naychov, Z., and Ionkova, I. (2022). Assessment of the potential of the invasive arboreal plant Ailanthus altissima (Simaroubaceae) as an economically prospective source of natural pesticides. Diversity, 14.","DOI":"10.3390\/d14080680"},{"key":"ref_12","first-page":"1609","article-title":"Phenolic composition of leaf extracts of Ailanthus altissima (Simaroubaceae) with antibacterial and antifungal activity equivalent to standard antibiotics","volume":"12","author":"Poljuha","year":"2017","journal-title":"Nat. Prod. Commun."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Caser, M., Demasi, S., Caldera, F., Dhakar, N.K., Trotta, F., and Scariot, V. (2020). Activity of Ailanthus altissima (Mill.) Swingle extract as a potential bioherbicide for sustainable weed management in horticulture. Agronomy, 10.","DOI":"10.3390\/agronomy10070965"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Caramelo, D., Pedero, S.I., Marques, H., Simao, A.Y., Rosado, T., Barroca, C., Gominho, J., Anjos, O., and Gallardo, E. (2021). Insights into the bioactivities and chemical analysis of Ailanthus altissima (Mill.) Swingle. Appl. Sci., 11.","DOI":"10.3390\/app112311331"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"668","DOI":"10.5530\/pj.2017.5.106","article-title":"Pharmacognostic and phytochemical characteristics of Ailanthus altissima (Mill.) Swingle stem and root bark: A comparative study","volume":"9","author":"Raja","year":"2017","journal-title":"Pharmacogn. J."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Ni, J.C., Shi, J.T., Tan, Q.W., and Chen, Q.J. (2017). Phenylpropionamides, piperidine, and phenolic derivatives from the fruit of Ailanthus altissima. Molecules, 22.","DOI":"10.3390\/molecules22122107"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1080\/14786419.2018.1437434","article-title":"Two new compounds from the fruit of Ailanthus altissima","volume":"33","author":"Ni","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/cr970464o","article-title":"Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activities","volume":"99","author":"Kozubek","year":"1999","journal-title":"Chem. Rev."},{"key":"ref_19","first-page":"231","article-title":"Effect of rye 5-n-alkylresorcinols on in vitro growth of phytopathogenic Fusarium and Rhizoctonia fungi","volume":"47","author":"Zarnowski","year":"1999","journal-title":"Bull. Pol. Acad. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Magnucka, E.G., Oksi\u0144ska, M., and Pietr, S.J. (2022). The role of resorcinolic lipids of caryopsis surface in the process of cereal infection by Rhizoctonia solani and Fusarium culmorum. Appl. Sci., 12.","DOI":"10.3390\/app12157735"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4667607","DOI":"10.1155\/2022\/4667607","article-title":"An overview of alkylresorcinols biological properties and effects","volume":"2022","author":"Zabolotneva","year":"2022","journal-title":"J. Nutr. Metab."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1515\/znc-1999-1-208","article-title":"Alkylresorcinol homologs in seeds of Pisum sativum varieties","volume":"54","author":"Zarnowski","year":"1999","journal-title":"Z. Naturforsch. C"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"428","DOI":"10.1016\/j.jfca.2008.04.002","article-title":"An improved colorimetric method for the determination of alkylresorcinols in cereals and whole-grain cereal products","volume":"21","author":"Gajda","year":"2008","journal-title":"J. Food Compos. Anal."},{"key":"ref_24","first-page":"223","article-title":"Alkyl resorcinols in grains from plants from the family Gramineae","volume":"53","author":"Kubus","year":"1983","journal-title":"Acta Soc. Botan. Polon."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1002\/ps.1792","article-title":"Cycloate, an inhibitor of fatty acid elongase, modulates the metabolism of very-long-side-chain alkylresorcinols in rye seedlings","volume":"65","author":"Magnucka","year":"2009","journal-title":"Pest Manag. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"438","DOI":"10.2478\/s11658-006-0037-z","article-title":"Emulsions of oil from Adenanthera pavonina L. seeds and their protective effect","volume":"11","author":"Jaromin","year":"2006","journal-title":"Cell. Mol. Biol. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1007\/s00217-020-03627-4","article-title":"Influence of kernel thermal pre-treatments on 5-n-alkylresorcinols, polyphenols and antioxidant activity of durum and einkorn wheat","volume":"247","author":"Ciccoritti","year":"2021","journal-title":"Eur. Food Res. Technol."},{"key":"ref_28","unstructured":"Zarnowski, R., Pietr, S.J., and Hendrich, A. (2000). Sensitivity of Rhizoctonia solani to derivatives of natural resorcinols of plant origin. Third International Symposium on Rhizoctonia (ISR 2000), National Chung Hsing University."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Guimar\u00e3es, A., and Ven\u00e2ncio, A. (2022). The potential of fatty acids and their derivatives as antifungal agents: A Review. Toxins, 14.","DOI":"10.3390\/toxins14030188"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"114421","DOI":"10.1016\/j.lwt.2022.114421","article-title":"Effects of alkyl chain length on the interfacial, antibacterial, and antioxidative properties of erythorbyl fatty acid esters","volume":"174","author":"Kim","year":"2023","journal-title":"LWT"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"124631","DOI":"10.1016\/j.molliq.2024.124631","article-title":"In vitro antifungal activity, cytotoxicity and binding analysis of imidazolium based ionic liquids with fluconazole: DFT and spectroscopic study","volume":"401","author":"Kumar","year":"2024","journal-title":"J. Mol. Liq."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1515\/znc-2014-4194","article-title":"Dynamics of alkylresorcinols during rye caryopsis germination and early seedling growth","volume":"70","author":"Magnucka","year":"2015","journal-title":"Z. Naturforsch. C"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1515\/znc-2020-0085","article-title":"Monitoring of changes in 5-n-alkylresorcinols during wheat seedling development","volume":"76","author":"Magnucka","year":"2012","journal-title":"Z. Naturforsch. 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