{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,6]],"date-time":"2026-03-06T18:11:41Z","timestamp":1772820701992,"version":"3.50.1"},"reference-count":55,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2024,12,16]],"date-time":"2024-12-16T00:00:00Z","timestamp":1734307200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Romanian Ministry of Research, Innovation and Digitization (MCID)","award":["2PFE\/2021"],"award-info":[{"award-number":["2PFE\/2021"]}]},{"name":"Romanian Ministry of Research, Innovation and Digitization (MCID)","award":["7 N\/2022-23020101(SIA-PRO)"],"award-info":[{"award-number":["7 N\/2022-23020101(SIA-PRO)"]}]},{"name":"National Research, Development and Innovation Plan 2022\u20132027","award":["2PFE\/2021"],"award-info":[{"award-number":["2PFE\/2021"]}]},{"name":"National Research, Development and Innovation Plan 2022\u20132027","award":["7 N\/2022-23020101(SIA-PRO)"],"award-info":[{"award-number":["7 N\/2022-23020101(SIA-PRO)"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Twelve compounds (1\u201312), kaempferol (1), luteolin (2), luteolin 4\u2032-O-\u03b2-xyloside (3), luteolin 4\u2032-O-\u03b2-glucoside (4), quercetin 4\u2032-O-\u03b2-xyloside (5), kaempferol-3-O-[6\u2033-O-(E)-p-coumaroyl]-\u03b2-D-glucoside (trans-tiliroside) (6), protocatechuic acid (7), gallic acid (8), methyl gallate (9), ethyl gallate (10), shikimic acid-3-O-gallate (11), and 3,3\u2032,4\u2032-tri-O-methyl-ellagic acid 4-sulfate (12), were isolated and identified from the aerial parts of Helianthemum cinereum (Cav.) Pers (synonym: Helianthemum rubellum C. Presl. All compounds were isolated by applying different chromatographic procedures, such as silica gel, RP-18 and Sephadex LH-20 columns. The structures were elucidated by extensive spectroscopic methods, mainly nuclear magnetic resonance NMR 1D and 2D, and mass spectrometry, as well as by comparison with the reported spectroscopic data. The two organic extracts, ethyl acetate (EtOAc) and butanol (BuOH), were evaluated for their potent phenolic and flavonoid contents using the Folin\u2013Ciocalteu and aluminum chloride colorimetric methods. Furthermore, the antioxidant activity of the two extracts was determined using the DPPH, FRAP, and ABTS methods. Pure trans-tiliroside (6), the main isolated compound, and luteolin 4\u2032-O-\u03b2-xyloside (3) were evaluated for their antitumor activity against the lung cancer (A549), melanoma (A375) and pancreatic cancer (Mia PaCa-2 and Panc-1) cell lines by MTT assay.<\/jats:p>","DOI":"10.3390\/molecules29245935","type":"journal-article","created":{"date-parts":[[2024,12,16]],"date-time":"2024-12-16T12:09:28Z","timestamp":1734350968000},"page":"5935","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Phytochemical Study and In Vitro Antioxidant Activity of Helianthemum cinereum Along with Antitumor Activity of the Isolated trans-Tiliroside and Luteolin 4\u2032-O-\u03b2-Xyloside"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4718-0099","authenticated-orcid":false,"given":"Anis","family":"Bertella","sequence":"first","affiliation":[{"name":"Department of Molecular and Cellular Biology, Faculty of Life and Nature Sciences, Abbes Laghrour University Khenchela, BP 1252 Road of Batna, Khenchela 40004, Algeria"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6380-4378","authenticated-orcid":false,"given":"Abla","family":"Smadi","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry and Environmental Chemistry (LCCE), Department of Chemistry, Faculty of Matter Sciences, University of Batna 1, Batna 05000, Algeria"}]},{"given":"Hakim","family":"Benhabrou","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry and Environmental Chemistry (LCCE), Department of Chemistry, Faculty of Matter Sciences, University of Batna 1, Batna 05000, Algeria"}]},{"given":"Diana","family":"Salvador","sequence":"additional","affiliation":[{"name":"Department of Biology & CESAM, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2052-3012","authenticated-orcid":false,"given":"Magdalena","family":"Wrona","sequence":"additional","affiliation":[{"name":"Institute of Bio- and Geosciences 2, Forschungszentrum J\u00fclich GmbH, 52428 J\u00fclich, Germany"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4673-0696","authenticated-orcid":false,"given":"Helena","family":"Oliveira","sequence":"additional","affiliation":[{"name":"Department of Biology & CESAM, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4975-9347","authenticated-orcid":false,"given":"Abouamama","family":"Sidaoui","sequence":"additional","affiliation":[{"name":"Department of Biology, Faculty of Sciences and Technology, Amine Elokkal El Hadj Moussa Egakhamouk University of Tamanghasset, Tamanghasset 11000, Algeria"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8208-2251","authenticated-orcid":false,"given":"Georgiana","family":"Gavril-Luminita","sequence":"additional","affiliation":[{"name":"Department of Bioinformatics, National Institute of Research and Development for Biological Sciences, 296 Splaiul Independentei, Sector 6, 060031 Bucharest, Romania"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4249-7089","authenticated-orcid":false,"given":"Diana C. G. A.","family":"Pinto","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Department of Chemistry, Campus Universit\u00e1rio de Santiago, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8407-0078","authenticated-orcid":false,"given":"Ewa","family":"Olewnik-Kruszkowska","sequence":"additional","affiliation":[{"name":"Physical Chemistry and Physicochemistry of Polymers, Faculty of Chemistry, Nicolaus Copernicus University in Tor\u00fan, Gagarin 7 Street, 87-100 Tor\u00fan, Poland"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2685-5739","authenticated-orcid":false,"given":"Cristina","family":"Ner\u00edn","sequence":"additional","affiliation":[{"name":"Departmento de Qu\u00edmica Anal\u00edtica, Instituto de Investigaci\u00f3n en Ingenier\u00eda de Arag\u00f3n (I3A), Escuela de Ingenier\u00eda y Arquitectura (EINA), Universidad de Zaragoza, Mar\u00eda de Luna 3 (Edificio Torres Quevedo), 50018 Zaragoza, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur M. S.","family":"Silva","sequence":"additional","affiliation":[{"name":"LAQV\/REQUIMTE, Department of Chemistry, Campus Universit\u00e1rio de Santiago, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2641-3271","authenticated-orcid":false,"given":"Fatma","family":"Bitam","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry and Environmental Chemistry (LCCE), Department of Chemistry, Faculty of Matter Sciences, University of Batna 1, Batna 05000, Algeria"},{"name":"Department of Pharmacy, Faculty of Medicine, University of Batna 2, Batna 05000, Algeria"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Kubitzki, K., and Bayer, C. (2003). Cistaceae. 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