{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,11]],"date-time":"2026-02-11T18:32:52Z","timestamp":1770834772275,"version":"3.50.1"},"reference-count":17,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2009,8,11]],"date-time":"2009-08-11T00:00:00Z","timestamp":1249948800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>Pyranoxanthones 6-8 were obtained by dehydrogenation of the respective dihydropyranoxanthones 3-5 with DDQ in dry dioxane. Two prenylated xanthones 10,11 were obtained from the reaction of 1-hydroxyxanthone (9) with prenyl bromide in alkaline medium, or by condensation of xanthone 9 with isoprene in the presence of orthophosphoric acid. The structural elucidation of the two new compounds 6,11, as well as an update of data for the already described prenylated derivatives 7,8,10 were accomplished by IR, UV, HRMS and NMR (1H, 13C, HSQC and HMBC) techniques. The effect of the prenylated xanthone derivatives on the in vitro growth of human tumor cell lines MCF-7 (breast adenocarcinoma) and NCI-H460 (non-small cell lung cancer) is also reported. Compounds 10 and 11 have been found to exhibit a moderate growth inhibitory activity against the MCF-7 cell line.<\/jats:p>","DOI":"10.3390\/ph2020033","type":"journal-article","created":{"date-parts":[[2009,8,11]],"date-time":"2009-08-11T11:07:49Z","timestamp":1249988869000},"page":"33-43","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Antitumor Activity of Some Prenylated Xanthones"],"prefix":"10.3390","volume":"2","author":[{"given":"Raquel  A.P.","family":"Castanheiro","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica Medicinal da Universidade do Porto (CEQUIMED-UP), Faculdade de Farm\u00e1cia, Universidade do Porto, Rua An\u00edbal Cunha 164, 4050-047 Porto, Portugal"}]},{"given":"Artur M.S.","family":"Silva","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica & QOPNA, Universidade de Aveiro, Campus Universit\u00e1rio de Santiago, 3810-193 Aveiro, Portugal"}]},{"given":"Na\u00efr  A.N.","family":"Campos","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Medicinal da Universidade do Porto (CEQUIMED-UP), Faculdade de Farm\u00e1cia, Universidade do Porto, Rua An\u00edbal Cunha 164, 4050-047 Porto, Portugal"}]},{"given":"Maria  S.J.","family":"Nascimento","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Medicinal da Universidade do Porto (CEQUIMED-UP), Faculdade de Farm\u00e1cia, Universidade do Porto, Rua An\u00edbal Cunha 164, 4050-047 Porto, Portugal"},{"name":"Servi\u00e7o de Microbiologia, Faculdade de Farm\u00e1cia, Universidade do Porto, Rua An\u00edbal Cunha 164, 4050-047 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4676-1409","authenticated-orcid":false,"given":"Madalena M.M.","family":"Pinto","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Medicinal da Universidade do Porto (CEQUIMED-UP), Faculdade de Farm\u00e1cia, Universidade do Porto, Rua An\u00edbal Cunha 164, 4050-047 Porto, Portugal"},{"name":"Servi\u00e7o de Qu\u00edmica Org\u00e2nica, Faculdade de Farm\u00e1cia, Universidade do Porto, Rua An\u00edbal Cunha 164, 4050-047 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2009,8,11]]},"reference":[{"key":"ref_1","unstructured":"Brahmachari, G. (2009). Natural Products: Chemistry, Biochemistry and Pharmacology, Narosa Publishing House PVT. LTD. [1st]."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2517","DOI":"10.2174\/092986705774370691","article-title":"Xanthone Derivatives: New Insights in Biological Activities","volume":"12","author":"Pinto","year":"2005","journal-title":"Curr. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"6080","DOI":"10.1016\/j.bmc.2007.06.037","article-title":"Dihydroxyxanthones Prenylated Derivatives: Synthesis, Structure Elucidation and Growth Inhibitory Activity on Human Tumor Cell Lines with Improvement of Selectivity for MCF-7","volume":"15","author":"Castanheiro","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3725","DOI":"10.1016\/S0968-0896(02)00379-6","article-title":"Xanthones as Inhibitors of Growth of Human Cancer Cell Lines and Their Effects on the Proliferation of Human Lymphocytes In Vitro","volume":"10","author":"Pedro","year":"2002","journal-title":"Bioorg. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1002\/jccs.200100014","article-title":"Synthesis of Naturally Occurring Rubilactone, Mollugin, and Dihydromollugin of Rubia cordifolia","volume":"48","author":"Ho","year":"2001","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1016\/j.ejmech.2005.10.020","article-title":"Synthesis of compounds with antiproliferative activity as analogues of prenylated natural products existing in Brazilian propolis","volume":"41","author":"Pisco","year":"2006","journal-title":"Eur. J. Med. Chem."},{"key":"ref_7","first-page":"69","article-title":"Xanthone Studies VI. Synthesis of Jacareubin, Isojacareubin and some hydroxyxanthones with allylic substituents","volume":"1","author":"Helboe","year":"1973","journal-title":"Arch. Pharm. Chemi. Sci. Ed."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Ahluwalia, V.K., Arora, K.K., and Jolly, R.S. (1982). Acid-catalysed Condensation of Isoprene with Phenols. Formation of 2,2-Dimethylchromans. J. Chem. Soc. Perkin Trans. I, 335\u2013338.","DOI":"10.1039\/p19820000335"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1002\/(SICI)1097-458X(199804)36:4<305::AID-OMR193>3.0.CO;2-N","article-title":"1H and 13C NMR Spectroscopy of Mono-, Di-, Tri-, and Tetrasubstituted Xanthones","volume":"36","author":"Fernandes","year":"1998","journal-title":"Magn. Reson. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2613","DOI":"10.1002\/hlca.19740570838","article-title":"Synthesis of New Xanthones, I","volume":"57","author":"Pinto","year":"1974","journal-title":"Helv. Chim. Acta"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Grover, P.K., Shah, G.D., and Shah, R.C. (1955). Xanthones. Part IV. A New Synthesis of Hydroxyxanthones and Hydroxybenzophenones. J. Chem. Soc., 3982\u20133985.","DOI":"10.1039\/jr9550003982"},{"key":"ref_12","first-page":"396","article-title":"Synthetic Experiments in the Benzopyrone Series: Part XLVI- Application on the Nencki Reaction in the Synthesis of Xanthones","volume":"13B","author":"Pankajamani","year":"1954","journal-title":"J. Sci. Industr. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1016\/j.ejmech.2006.10.018","article-title":"Design and synthesis of new pyranoxanthenones bearing a nitro group or an aminosubstituted side chain on the pyran ring. Evaluation of their growth inhibitory activity in breast cancer cells","volume":"42","author":"Kolokythas","year":"2007","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","first-page":"393","article-title":"Synthetic studies on morellin. Part 4: Synthesis of 2,2-dimethyl- 12-[3-methylbut-2-enyl]-2H,6H-pyrano[3,2-b]xanthen-6-one","volume":"81","author":"Raghavan","year":"2001","journal-title":"J. Indian Inst. Sci."},{"key":"ref_15","first-page":"311","article-title":"Methods for the Structural Investigation of Xanthones. Part II. Location of the Hydroxyl Groups by Ultra-Violet and Visible Spectroscopy","volume":"42","author":"Mesquita","year":"1968","journal-title":"Anal. Chim. Acta"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1093\/jnci\/83.11.757","article-title":"Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines","volume":"83","author":"Monks","year":"1991","journal-title":"J. Natl. Cancer I."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1093\/jnci\/82.13.1107","article-title":"New colorimetric cytotoxicity assay for anticancer-drug screening","volume":"82","author":"Skehan","year":"1990","journal-title":"J. Natl. Cancer I."}],"container-title":["Pharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8247\/2\/2\/33\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T22:10:55Z","timestamp":1760220655000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8247\/2\/2\/33"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,8,11]]},"references-count":17,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2009,9]]}},"alternative-id":["ph2020033"],"URL":"https:\/\/doi.org\/10.3390\/ph2020033","relation":{},"ISSN":["1424-8247"],"issn-type":[{"value":"1424-8247","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,8,11]]}}}