{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T21:12:51Z","timestamp":1789161171267,"version":"build-2803163510"},"reference-count":49,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2025,7,25]],"date-time":"2025-07-25T00:00:00Z","timestamp":1753401600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100007088","name":"Faculty of Pharmacy, Jagiellonian University Medical College, Cracow, Poland","doi-asserted-by":"publisher","award":["N42\/DBS\/000422"],"award-info":[{"award-number":["N42\/DBS\/000422"]}],"id":[{"id":"10.13039\/501100007088","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Priority Research Area qLIFE under the Strategic Programme Excellence Initiative at the Jagiellonian University","award":["N42\/DBS\/000422"],"award-info":[{"award-number":["N42\/DBS\/000422"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Two triterpene saponins, hederagenin glucosides, including a novel monodesmoside: 3-O-\u03b2-D-glucopyranosyl(1\u21923)-\u03b2-D-glucopyranosyl] hederagenin (compound 1), were isolated from the fruits of Oxybasis rubra (L.) S.Fuentes, Uotila &amp; Borsh (Amaranthaceae). These compounds, together with hederagenin itself (compound 4) and a commercially available 28-O-\u03b2-D-glucopyranosyl hederagenin ester (compound 3), were evaluated for cytotoxicity and selectivity across a wide panel of human cancer cell lines (skin, prostate, gastrointestinal, thyroid, and lung). All four compounds exhibited dose- and time-dependent effects, with varying potency depending on the specific cancer type. The isolated bidesmosidic saponin (3-O-\u03b2-D-glucopyranosyl(1\u21923)-\u03b2-D-glucopyranosyl] hederagenin 28-O-\u03b2-D-glucopyranosyl ester\u2014compound 2) showed the strongest activity and selectivity, with an IC50 = 6.52 \u03bcg\/mL after 48 h incubation against WM793 melanoma, and almost no effect on normal HaCaT skin cells (IC50 = 39.94 \u03bcg\/mL). Multivariate analysis of the obtained data using principal component analysis (PCA) and hierarchical cluster analysis (HCA) supported the assumption that cytotoxicity is influenced by the type of compound, its concentration, and the intrinsic sensitivity of the cell line. Structure-activity observations between closely related hederagenin derivatives are also briefly presented.<\/jats:p>","DOI":"10.3390\/molecules30153126","type":"journal-article","created":{"date-parts":[[2025,7,25]],"date-time":"2025-07-25T12:56:43Z","timestamp":1753448203000},"page":"3126","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Saponins from Oxybasis rubra (L.) S.Fuentes, Uotila &amp; Borsh: Comparative Assessment of Cytotoxic Potential Against a Wide Panel of Cancer Cell Lines"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1426-2218","authenticated-orcid":false,"given":"Karolina","family":"Grabowska","sequence":"first","affiliation":[{"name":"Chair of Pharmacognosy, Jagiellonian University Medical College, 9 Medyczna Str., 30-688 Cracow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9403-1307","authenticated-orcid":false,"given":"Adam","family":"Mynarski","sequence":"additional","affiliation":[{"name":"Chair of Pharmacognosy, Jagiellonian University Medical College, 9 Medyczna Str., 30-688 Cracow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5636-8646","authenticated-orcid":false,"given":"Agnieszka","family":"Galanty","sequence":"additional","affiliation":[{"name":"Chair of Pharmacognosy, Jagiellonian University Medical College, 9 Medyczna Str., 30-688 Cracow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9780-7924","authenticated-orcid":false,"given":"Dagmara","family":"Wr\u00f3bel-Biedrawa","sequence":"additional","affiliation":[{"name":"Chair of Pharmacognosy, Jagiellonian University Medical College, 9 Medyczna Str., 30-688 Cracow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3594-1241","authenticated-orcid":false,"given":"Pawe\u0142","family":"\u017bmudzki","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry, Jagiellonian University Medical College, 9 Medyczna Str., 30-688 Cracow, Poland"},{"name":"Center for the Development of Therapies for Civilization and Age-Related Diseases, Jagiellonian University Medical College, Skawi\u0144ska 8, 31-066 Krakow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1251-7192","authenticated-orcid":false,"given":"Irma","family":"Podolak","sequence":"additional","affiliation":[{"name":"Chair of Pharmacognosy, Jagiellonian University Medical College, 9 Medyczna Str., 30-688 Cracow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.15171\/jhp.2018.01","article-title":"Medicinal plants: Past history and future perspective","volume":"7","author":"Lorigooini","year":"2018","journal-title":"J. Herbmed Pharmacol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"770","DOI":"10.1021\/acs.jnatprod.9b01285","article-title":"Natural products as sources of new drugs over the nearly four decades from 01\/1981 to 09\/2019","volume":"83","author":"Newman","year":"2020","journal-title":"J. Nat. Prod."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5","DOI":"10.3372\/wi.42.42101","article-title":"A novel phylogeny-based generic classification for Chenopodium sensu lato, and a tribal rearrangement of Chenopodioideae (Chenopodiaceae)","volume":"42","author":"Uotila","year":"2012","journal-title":"Willdenowia"},{"key":"ref_4","first-page":"103","article-title":"Plants used against cancer. A survey 967\u20131971","volume":"34","author":"Hartwell","year":"1971","journal-title":"Lloydia"},{"key":"ref_5","unstructured":"Chamberlin, R.V. (1911). The Ethno-Botany of the Gosiute Indians of Utah, New Era Printing Company. Available online: https:\/\/books.google.pl\/books?id=5LQUAAAAYAAJ."},{"key":"ref_6","first-page":"280","article-title":"The genus Chenopodium: Phytochemistry, ethnopharmacology and pharmacology","volume":"3","author":"Nedialkov","year":"2009","journal-title":"Pharmacol. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"e0003","DOI":"10.3989\/collectbot.2024.v43.0003","article-title":"On the occurrence of Oxybasis rubra (Amaranthaceae) in Sardinia, with notes on Chenopodium blitoides and C. humile","volume":"43","author":"Iamonico","year":"2024","journal-title":"Collect. Bot."},{"key":"ref_8","unstructured":"(2025, May 12). Plants of the World Online. Available online: https:\/\/powo.science.kew.org."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"831","DOI":"10.2307\/2258503","article-title":"Chenopodium rubrum L.","volume":"57","author":"Williams","year":"1969","journal-title":"J. Ecol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1016\/j.aquabot.2016.09.008","article-title":"Effects of temperature, moisture and soil type on seedling emergence and mortality of riparian plant species","volume":"136","author":"Veen","year":"2017","journal-title":"Aquat. Bot."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1007\/BF00197956","article-title":"Accumulation of phenolic acid conjugates and betacyanins, and changes in the activities of enzymes involved in feruloylglucose metabolism in cell-suspension cultures of Chenopodium rubrum L.","volume":"184","author":"Bokern","year":"1991","journal-title":"Planta"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1016\/S0031-9422(96)00568-7","article-title":"Melatonin: Occurrence and daily rhythm in Chenopodium rubrum","volume":"44","author":"Eder","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1016\/S0031-9422(96)00818-7","article-title":"Oxidized phytosterols increase by ageing in photoautotrophic cell cultures of Chenopodium rubrum","volume":"45","author":"Meyer","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"209","DOI":"10.5507\/bp.2008.032","article-title":"Ascaridole and related peroxides from the genus Chenopodium","volume":"152","author":"Dembitsky","year":"2008","journal-title":"Biomed. Pap. Med. Fac. Univ. Palacky. Olomouc Czech Repub."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/j.sjbs.2015.01.017","article-title":"Antioxidative and cytotoxic potential of some Chenopodium L. species growing in Poland","volume":"23","author":"Nowak","year":"2016","journal-title":"Saudi J. Biol. Sci."},{"key":"ref_16","first-page":"855","article-title":"Phenolic acid LC\/MS profile of Chenopodium rubrum and evaluation of cytotoxic activity","volume":"13","author":"Mynarski","year":"2018","journal-title":"Nat. Prod. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Grabowska, K., \u017bmudzki, P., Galanty, A., and Podolak, I. (2025). Simultaneous Quantification of Bioactive Triterpene Saponins Calenduloside E and Chikusetsusaponin IVa in Different Plant Parts of Ten Amaranthaceae Species by UPLC-ESI-MS\/MS Method. Molecules, 30.","DOI":"10.3390\/molecules30051088"},{"key":"ref_18","first-page":"27","article-title":"In vitro cytotoxic activity of Indian medicinal plants used traditionally to treat cancer","volume":"4","author":"Sundaram","year":"2011","journal-title":"Asian J. Pharm. Clin. Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"577","DOI":"10.1007\/s11101-015-9394-4","article-title":"Phytochemistry and bioactivity of triterpene saponins from Amaranthaceae family","volume":"14","author":"Mroczek","year":"2015","journal-title":"Phytochem. Rev."},{"key":"ref_20","first-page":"159","article-title":"Characterization of triterpene saponin composition of white, yellow and red beetroot (Beta vulgaris L.)","volume":"72","author":"Tekieli","year":"2022","journal-title":"Pol. J. Food Nutr. Sci."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1919","DOI":"10.1016\/j.phytochem.2008.03.001","article-title":"Triterpene saponins from Chenopodium quinoa Willd","volume":"69","author":"Kuljanabhagavad","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_22","first-page":"1419","article-title":"30-normedicagenic acid glycosides from Chenopodium foliosum","volume":"7","author":"Nedialkov","year":"2012","journal-title":"Nat. Prod. Commun."},{"key":"ref_23","first-page":"10","article-title":"Phytochemistry, Traditional uses, pharmacology of Indian medicinal plant Chenopodium album (Linn)","volume":"4","author":"Kumar","year":"2015","journal-title":"World J. Pharm. Pharm. Sci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2024","DOI":"10.1080\/14786419.2018.1483928","article-title":"Saponins from the roots of Chenopodium bonus\u2014henricus L.","volume":"33","author":"Nedialkov","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"El Hazzam, K., Hafsa, J., Sobeh, M., Mhada, M., Taourirte, M., El Kacimi, K., and Yasri, A. (2020). An Insight into Saponins from Quinoa (Chenopodium quinoa Willd): A Review. Molecules, 25.","DOI":"10.3390\/molecules25051059"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Grabowska, K., Pecio, \u0141., Galanty, A., \u017bmudzki, P., Oleszek, W., and Podolak, I. (2021). Serjanic acid glycosides from Chenopodium hybridum L. with good cytotoxicity and selectivity profile against several panels of human cancer cell lines. Molecules, 26.","DOI":"10.3390\/molecules26164915"},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Grabowska, K., Galanty, A., Pecio, \u0141., Stojakowska, A., Malarz, J., \u017bmudzki, P., Zagrodzki, P., and Podolak, I. (2024). Selectivity screening and structure\u2014Cytotoxic activity observations of selected oleanolic acid (OA)-type saponins from the Amaranthaceae family on a wide panel of human cancer cell lines. Molecules, 29.","DOI":"10.3390\/molecules29163794"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"105858","DOI":"10.1016\/j.fitote.2024.105858","article-title":"An outlook on the versatility of plant saponins: A review","volume":"174","author":"Jolly","year":"2024","journal-title":"Fitoterapia"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2141","DOI":"10.1002\/ptr.6371","article-title":"Saponins as chemosensitizing substances that improve effectiveness and selectivity of anticancer drug\u2014Minireview of in vitro studies","volume":"33","author":"Koczurkiewicz","year":"2019","journal-title":"Phytother. Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"100191","DOI":"10.1016\/j.focha.2023.100191","article-title":"Saponins: A concise review on food related aspects, applications and health implications","volume":"2","author":"Sharma","year":"2023","journal-title":"Food Chem. Adv."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"115226","DOI":"10.1016\/j.foodres.2024.115226","article-title":"Sources, metabolism, health benefits and future development of saponins from plants","volume":"197","author":"Wang","year":"2024","journal-title":"Food Res. Int."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1007\/s11101-022-09830-3","article-title":"Saponins as cytotoxic agents: An update (2010\u20132021). Part II\u2014Triterpene saponins","volume":"22","author":"Podolak","year":"2023","journal-title":"Phytochem. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Korda, A., R\u00e1rov\u00e1, L., Pakulski, Z., Strnad, M., Okle\u0161\u0165kov\u00e1, J., Kuczynska, K., Cmoch, P., Gwardiak, K., and Karczewski, R. (2020). New lupane bidesmosides exhibiting strong cytotoxic activities in vitro. Bioorg. Chem., 100.","DOI":"10.1016\/j.bioorg.2020.103868"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Liu, Y., Jiang, P., Zhang, M.L., Pan, J., Guan, W., Li, X.M., Yang, B.Y., and Kuang, H.X. (2022). Triterpenoid saponins from the fruit of Acanthopanax senticosus (rupr. & Maxim.) harms. Front. Chem., 10.","DOI":"10.3389\/fchem.2022.825763"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1373","DOI":"10.1002\/cbdv.201100234","article-title":"Studies on the chemical constituents and biological activities of Ixeris","volume":"10","author":"Zhang","year":"2013","journal-title":"Chem. Biodiv."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"190002","DOI":"10.21127\/yaoyimr20190002","article-title":"Phytochemical and Biological Progress of Ixeris sonchifoia (Bge.) Hance","volume":"3","author":"Wen","year":"2019","journal-title":"Med. Res."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Li, K.W., Liang, Y.Y., Xie, S.M., Niu, F.J., Guo, L.Y., Liu, Z.H., Zhou, C.Z., and Wang, L.Z. (2020). Ixeris sonchifolia: A review of its traditional uses, chemical constituents, pharmacology and modern applications. Biomed. Pharmacother., 125.","DOI":"10.1016\/j.biopha.2020.109869"},{"key":"ref_38","unstructured":"Feng, X.Z. (2001). Studies on the Constituents and Biological Activities of Mixers Sonchifolia. [Ph.D. Thesis, Shenyang Pharmaceutical University]."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1036","DOI":"10.1055\/s-2003-45152","article-title":"Three new triterpenoid saponins from Ixeris sonchifolia and their cytotoxic activity","volume":"69","author":"Feng","year":"2003","journal-title":"Planta Med."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2327","DOI":"10.1002\/cbdv.200800070","article-title":"Naturally occurring triterpenoid saponins","volume":"7","author":"Dinda","year":"2010","journal-title":"Chem. Biodivers."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1418","DOI":"10.1016\/j.bbagen.2006.05.004","article-title":"Structure\u2014Activity relationships of some hederagenin diglycosides: Haemolysis, cytotoxicity and apoptosis induction","volume":"1760","author":"Chwalek","year":"2006","journal-title":"Biochim. Biophys. Acta Gen. Subj."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.sajb.2023.04.018","article-title":"In vitro antiproliferative activity of triterpenoid saponins from leaves of Hedera helix L. grown in Romania","volume":"158","author":"Tatia","year":"2023","journal-title":"S. Afr. J. Bot."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1016\/j.phytol.2023.05.002","article-title":"LC-MS guided isolation of cytotoxic saponins from the flower buds of Lonicera macranthoides","volume":"55","author":"Wang","year":"2023","journal-title":"Phytochem. Let."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"24188","DOI":"10.1039\/C8RA03666G","article-title":"Current knowledge and development of hederagenin as a promising medicinal agent: A comprehensive review","volume":"8","author":"Zeng","year":"2018","journal-title":"RSC Adv."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Dycha, N., Michalak-Tomczyk, M., Jachu\u0142a, J., Oko\u0144, E., Jarz\u0105b, A., Tokarczyk, J., Koch, W., Gawe\u0142-B\u0119ben, K., Kuku\u0142a-Koch, W., and Wawruszak, A. (2025). Chemopreventive and anticancer activity of selected triterpenoids in melanoma. Cancers, 17.","DOI":"10.3390\/cancers17101625"},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Wang, W., Jin, Y., Liu, M.K., Zhang, S.Y., Chen, H., and Song, J. (2025). Current progress of hederagenin and its derivatives for disease therapy (2017\u2013Present). Molecules, 30.","DOI":"10.3390\/molecules30061275"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"116619","DOI":"10.1016\/j.ejmech.2024.116619","article-title":"Recent advances in the chemistry and biology of oleanolic acid and its derivatives","volume":"276","author":"Verma","year":"2024","journal-title":"Eur. J. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3885","DOI":"10.1016\/0031-9422(90)85352-G","article-title":"A triterpenoid glycoside from Menyanthes trofoliata","volume":"29","author":"Janeczko","year":"1990","journal-title":"Phytochemistry"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.indcrop.2016.11.022","article-title":"Two new triterpenoid saponins from the leaves of Impatiens parviflora DC. and their cytotoxic activity","volume":"96","author":"Grabowska","year":"2017","journal-title":"Ind. Crops Prod."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/15\/3126\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T18:16:05Z","timestamp":1760033765000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/15\/3126"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,25]]},"references-count":49,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2025,8]]}},"alternative-id":["molecules30153126"],"URL":"https:\/\/doi.org\/10.3390\/molecules30153126","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,25]]}}}