{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T04:39:57Z","timestamp":1790829597483,"version":"4.1.0"},"reference-count":54,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2019,3,12]],"date-time":"2019-03-12T00:00:00Z","timestamp":1552348800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Medicines"],"abstract":"<jats:p>Background: Ocimum sanctum L. (holy basil; Tulsi in Hindi) is an important medicinal plant, traditionally used in India. Methods: The phytochemical study of the nonpolar (dichloromethane 100%) and polar (methanol:water; 7:3) extracts yielded fourteen compounds. Compounds 6, 7, 9, 11, 12, and 13, along with the methanol:water extract were evaluated for their cytotoxicity against the human cancer cell lines MCF-7, SKBR3, and HCT-116, and normal peripheral blood mononuclear cells (PBMCs). Results: Five terpenoids, namely, ursolic acid (1), oleanolic acid (2), betulinic acid (3), stigmasterol (4), and \u03b2-caryophyllene oxide (5); two lignans, i.e., (-)-rabdosiin (6) and shimobashiric acid C (7); three flavonoids, luteolin (8), its 7-O-\u03b2-D-glucuronide (9), apigenin 7-O-\u03b2-D-glucuronide (10); and four phenolics, (E)-p-coumaroyl 4-O-\u03b2-D-glucoside (11), 3-(3,4-dihydroxyphenyl) lactic acid (12), protocatechuic acid (13), and vanillic acid (14) were isolated. Compound 6 was the most cytotoxic against the human cancer lines assessed and showed very low cytotoxicity against PBMCs. Conclusions: Based on these results, the structure of compound 6 shows some promise as a selective anticancer drug scaffold.<\/jats:p>","DOI":"10.3390\/medicines6010037","type":"journal-article","created":{"date-parts":[[2019,3,13]],"date-time":"2019-03-13T04:07:37Z","timestamp":1552450057000},"page":"37","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["Antiproliferative Activity of (-)-Rabdosiin Isolated from Ocimum sanctum L."],"prefix":"10.3390","volume":"6","author":[{"given":"Alexandros","family":"Flegkas","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tanja","family":"Milosevi\u0107 Ifantis","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christina","family":"Barda","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pinelopi","family":"Samara","sequence":"additional","affiliation":[{"name":"Department of Biology, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15784 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ourania","family":"Tsitsilonis","sequence":"additional","affiliation":[{"name":"Department of Biology, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15784 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Helen","family":"Skaltsa","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,3,12]]},"reference":[{"key":"ref_1","unstructured":"Prajapati, N.D., Purohit, S.S., Sharma, A.K., and Kumar, T.A. (2003). Hand Book of Medicinal Plant, Agrobios. [1st ed.]."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"251","DOI":"10.4103\/0975-9476.146554","article-title":"Tulsi-Ocimum sanctum: A herb for all reasons","volume":"5","author":"Cohen","year":"2014","journal-title":"J. Ayurveda Integr. Med."},{"key":"ref_3","unstructured":"Pandey, B. (1990). Anita. Economic Botany, Chand and Company Ltd."},{"key":"ref_4","unstructured":"Rajeshwari, S. (1992). Ocimum sanctum: The Indian home remedy. Current Medical Scene, Cipla Ltd."},{"key":"ref_5","first-page":"765","article-title":"Validation of traditional claim of Tulsi, Ocimum sanctum Linn. as a medicinal plant","volume":"40","author":"Gupta","year":"2002","journal-title":"Indian J. Exp. Biol."},{"key":"ref_6","first-page":"279","article-title":"Tulsi: The Indian holy power plant","volume":"5","author":"Das","year":"2006","journal-title":"Nat. Prod. Radiance"},{"key":"ref_7","first-page":"291","article-title":"The Science behind sacredness of Tulsi (Ocimum sanctum L.)","volume":"53","author":"Mondal","year":"2009","journal-title":"Indian J. Physiol. Pharmacol."},{"key":"ref_8","first-page":"61","article-title":"Pharmacological activities of Ocimum sanctum (Tulsi): A review","volume":"5","author":"Pandey","year":"2010","journal-title":"JPSR"},{"key":"ref_9","first-page":"51","article-title":"Ocimum sanctum linn (TULSI)\u2014An overview","volume":"7","author":"Mohan","year":"2011","journal-title":"JPSR"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"95","DOI":"10.4103\/0973-7847.65323","article-title":"Ocimum sanctum Linn. A reservoir plant for therapeutic applications: An overview","volume":"4","author":"Pattanayak","year":"2010","journal-title":"Pharmacogn. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/S0378-8741(03)00215-0","article-title":"Antinociceptive action of Ocimum sanctum (Tulsi) in mice: Possible mechanisms involved","volume":"88","author":"Khanna","year":"2003","journal-title":"J. Ethnopharmacol."},{"key":"ref_12","first-page":"93","article-title":"In vivo studies on the effect of Ocimum sanctum L. leaf extract in mordifying the genotoxicity induced by chromium and mercury in Allium root meristems","volume":"27","author":"Babu","year":"2006","journal-title":"J. Environ. Biol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1150","DOI":"10.1111\/j.1440-1681.2006.04507.x","article-title":"Biochemical evaluation of antidiabetogenic properties of some commonly used Indian plants on streptozotocin-induced diabetes in experimental rats","volume":"33","author":"Narendhirakannan","year":"2006","journal-title":"Clin. Exp. Pharmacol. Physiol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1677\/joe.1.06615","article-title":"Ocimum sanctum leaf extracts stimulate insulin secretion from perfusd pancreas, isolated islets and clonal pancreatic beta-cells","volume":"189","author":"Hannan","year":"2006","journal-title":"J. Endocrinol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"414","DOI":"10.1111\/j.1463-1326.2005.00414.x","article-title":"Pterocarpus marsupium extract (Vijayasar) prevented the alteration in metabolic patterns induced in the normal rat by feeding an adequate diet containing fructose as sole carbohydrate","volume":"7","author":"Grovel","year":"2005","journal-title":"Diabetes Obes. Metab."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1248\/cpb.57.245","article-title":"Leishmanicidal active constituents from Nepalese medicinal plant Tulsi (Ocimum sanctum L.)","volume":"57","author":"Suzuki","year":"2009","journal-title":"Chem. Pharm. Bull."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Jamshidi, J., and Cohen, M.M. (2017). The Clinical Efficacy and Safety of Tulsi in Humans: A Systematic Review of the Literature. Evid. Based Complement. Altern. Med.","DOI":"10.1155\/2017\/9217567"},{"key":"ref_18","unstructured":"(2019, January 31). Available online: http:\/\/www.himalayawellness.com\/herbfinder\/ocimum-tenuiflorum.htm."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1076\/phbi.37.1.92.6318","article-title":"Polyphenols of \u039fcimum sanctum L. from Suriname","volume":"37","author":"Skaltsa","year":"1999","journal-title":"Pharm. Biol."},{"key":"ref_20","first-page":"286","article-title":"Phytochemical Study of the leaves of Ocimum sanctum L.","volume":"4","author":"Skaltsa","year":"1987","journal-title":"Fitoterapia"},{"key":"ref_21","first-page":"79","article-title":"Analyse de l\u2019huile essentielle d\u2019Ocimum sanctum L.","volume":"2","author":"Skaltsa","year":"1990","journal-title":"Plant. M\u00e9d. Phytoth."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Kumar, S., and Pandey, A.K. (2013). Chemistry and Biological Activities of Flavonoids: An Overview. Sci. World J.","DOI":"10.1155\/2013\/162750"},{"key":"ref_23","first-page":"13","article-title":"Saponins and their biological activities","volume":"41","author":"Desai","year":"2009","journal-title":"Pharma Times"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Bezerra, D.P., Milit\u00e3o, G.C.G., Castro de Morais, M., and Pergentino de Sousa, D. (2017). The Dual Antioxidant\/Prooxidant Effect of Eugenol and Its Action in Cancer Development and Treatment. Nutrients, 9.","DOI":"10.3390\/nu9121367"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"S327","DOI":"10.4103\/0973-1296.185738","article-title":"Purified essential oil from Ocimum sanctum Linn. triggers the apoptotic mechanism in human breast cancer cells","volume":"12","author":"Manaharan","year":"2016","journal-title":"Pharmacogn. Mag."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Mabry, T.G., Markham, K.R., and Thomas, M.B. (1970). The Systematic Identification of Flavonoids, Springer Science & Business Media.","DOI":"10.1007\/978-3-642-88458-0"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"934","DOI":"10.1021\/np50047a033","article-title":"The application of Vacuum Liquid Chromatography to the separation of terpene mixtures","volume":"49","author":"Coll","year":"1986","journal-title":"J. Nat. Prod."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1007\/BF00599857","article-title":"Chelate von Diarylbors\u00e4uren mit aliphatischen oxyalkylaminen als reagenzien f\u00fcr den nachweis von oxyphenyl-benzo-\u03b3-pyronen","volume":"44","author":"Neu","year":"1957","journal-title":"Die Naturwissenchaften"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays","volume":"65","author":"Mosman","year":"1983","journal-title":"J. Immunol. Methods"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1186\/1471-2172-14-43","article-title":"Prothymosin \u03b1 and a prothymosin \u03b1-derived peptide enhance TH1-type immune responses against defined HER-2\/neu epitopes","volume":"14","author":"Ioannou","year":"2013","journal-title":"BMC Immunol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/0378-8741(95)90032-2","article-title":"Pharmacology of oleanolic acid and ursolic acid","volume":"49","author":"Liu","year":"1995","journal-title":"J. Ethnopharmacol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"119","DOI":"10.4236\/pp.2012.32018","article-title":"Biological Activity of Betulinic Acid: A Review","volume":"3","author":"Ahmad","year":"2012","journal-title":"Pharmacol. Pharm."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"292","DOI":"10.1016\/j.metabol.2005.08.024","article-title":"Stigmasterol reduces plasma cholesterol levels and inhibits hepatic synthesis and intestinal absorption in the rat","volume":"55","author":"Batta","year":"2006","journal-title":"Metabolism"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1016\/S0014-827X(01)01092-8","article-title":"Local anaesthetic activity of \u03b2-caryophyllene","volume":"56","author":"Ghelardini","year":"2001","journal-title":"Farmaco"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2447","DOI":"10.1016\/S0031-9422(00)98002-6","article-title":"Tetrameric derivative of caffeic acid from Rabdosia japonica","volume":"28","author":"Agata","year":"1989","journal-title":"Phytochemistry"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1286","DOI":"10.1271\/bbb.60684","article-title":"High Rabdosiin and Rosmarinic acid production in Eritrichium sericeum callus cultures and the effect of the calli on Masugi-Nephritis in rats","volume":"71","author":"Inyushkina","year":"2007","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1248\/cpb.60.121","article-title":"Hyalurodinase inhibitors from Keiskea japonica","volume":"60","author":"Murata","year":"2008","journal-title":"Chem. Pharm. Bull."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"31","DOI":"10.2174\/138955709787001712","article-title":"Distribution and biological activities of the flavonoid luteolin","volume":"9","year":"2009","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/S0305-1978(01)00103-X","article-title":"Leaf flavonoid glycosides as chemosystematic characters in Ocimum","volume":"30","author":"Grayer","year":"2002","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/S0031-9422(00)89072-X","article-title":"Flavonoid variation in the liverwort Conocephalum conicum: Evidence for geographic races","volume":"15","author":"Markham","year":"1976","journal-title":"Phytochemistry"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1016\/S0031-9422(00)00309-5","article-title":"Flavonoid and phenolic glycosides from Salvia officinalis","volume":"55","author":"Lu","year":"2000","journal-title":"Phytochemistry"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Agrawal, P.K. (1989). Flavonoid glycosides. Carbon-13 NMR of Flavonoids, Elsevier.","DOI":"10.1016\/B978-0-444-87449-8.50012-2"},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Harborne, J.B. (1994). 1H NMR spectroscopy of flavonoids and their glycosides in DMSO-d6. The Flavonoids, Advances in Research Since 1986, Chapman and Hall.","DOI":"10.1007\/978-1-4899-2911-2"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1016\/S0031-9422(00)00124-2","article-title":"The phenols and prodelphinidins of white cover flowers","volume":"54","author":"Foo","year":"2000","journal-title":"Phytochemistry"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"527","DOI":"10.1248\/cpb.33.527","article-title":"Isolation and Characterization of Phenolic Compounds from Coptidis Rhizoma","volume":"33","author":"Yahara","year":"1985","journal-title":"Chem. Pharm. Bull."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"574","DOI":"10.1055\/s-2006-961558","article-title":"New constituents from Ocimum sanctum","volume":"58","author":"Norr","year":"1992","journal-title":"Planta Med."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1783","DOI":"10.1139\/v97-612","article-title":"A non-enzymatic synthesis of (S)-(-)-rosmarinic acid and a study of a biomimetic route to (+)-rabdosiin","volume":"75","author":"Charlton","year":"1997","journal-title":"Can. J. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3223","DOI":"10.1248\/cpb.36.3223","article-title":"Rabdosiin, a new rosmarinic acid dimer with a lignan skeleton, from Rabdosia japonica","volume":"36","author":"Agata","year":"1988","journal-title":"Chem. Pharm. Bull."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2645","DOI":"10.1016\/0031-9422(90)85204-S","article-title":"Two caffeic acid tetramers having enantiomeric phenyldihydronaphthalene moieties from Macrotomia euchroma","volume":"29","author":"Nishizawa","year":"1990","journal-title":"Phytochemistry"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1016\/S0031-9422(99)00623-8","article-title":"Cafeic acid oligomers in Lithospermum erythrorhizon cell suspension cultures","volume":"53","author":"Yamamoto","year":"2000","journal-title":"Phytochemistry"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1051","DOI":"10.1016\/S0968-0896(98)00063-7","article-title":"Antiallergic activities of rabdosiin and its related compounds: Chemical and biochemical evaluations","volume":"6","author":"Ito","year":"1988","journal-title":"Bioorg. Med. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"392","DOI":"10.1021\/np50117a007","article-title":"Anti-AIDS agents, 18. Sodium and potassium salts of caffeic acid tetramers from Arnebia euchromaas anti-HIV agents","volume":"58","author":"Kashiwada","year":"1995","journal-title":"J. Nat. Prod."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"776","DOI":"10.1089\/jmf.2014.0008","article-title":"Apoptosis Induction by Ocimum sanctum extract in LNCaP prostate cancer cells","volume":"18","author":"Dhandayuthapani","year":"2015","journal-title":"J. Med. Food"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1097\/CAD.0b013e328361aca1","article-title":"Ocimum sanctum Linn. (Tulsi): An ethnomedicinal plant for the prevention and treatment of cancer","volume":"24","author":"Bhattacharyya","year":"2013","journal-title":"Anticancer Drugs"}],"container-title":["Medicines"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2305-6320\/6\/1\/37\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:38:05Z","timestamp":1760186285000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2305-6320\/6\/1\/37"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,3,12]]},"references-count":54,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2019,3]]}},"alternative-id":["medicines6010037"],"URL":"https:\/\/doi.org\/10.3390\/medicines6010037","relation":{},"ISSN":["2305-6320"],"issn-type":[{"value":"2305-6320","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,3,12]]}}}