title: First Occurrence of a Furano-glycyrrhetinoate and Its Cytotoxicity.
abstract: (18α)-Glycyrrhetinic acid (4) was prepared from (18β)-glycyrrhetinic acid (1), and the cytotoxicity of some derivatives was investigated by photometric SRB assays employing several human tumor cell lines. In summary, (18β)-1 is slightly more cytotoxic than its (18α) epimer 4, but its cytotoxicity is negligible. Higher cytotoxicity was observed for the esters 2 and 5 and for the 3-O-acetylated esters 3 and 6. Cytotoxicity was improved dramatically when the hydroxyl group at position C-3 was replaced by an amino moiety. SeO2 oxidations gave access to a novel furano-glycyrrhetinoate 15. Interestingly, its seleno analog 16 is approximately five to six times less cytotoxic for the tumor cell lines tested, and tumor/non-tumor selectivity is lost upon replacement of the oxygen by a selenium substituent.
authors.affiliation: Department of Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Lucie
authors.initials: L
authors.lastname: Heller
authors.affiliation: Department of Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Sven
authors.initials: S
authors.lastname: Sommerwerk
authors.affiliation: Department of Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Felix
authors.initials: F
authors.lastname: Tzschöckell
authors.affiliation: Department of Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Jana
authors.initials: J
authors.lastname: Wiemann
authors.affiliation: Department of Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Schwarz
authors.affiliation: Department of Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: Bianka
authors.initials: B
authors.lastname: Siewert
authors.affiliation: Chair of Oman's Medicinal Plants and Marine Natural Products, University of Nizwa, Birkat Al-Mauz, Nizwa, Sultanate of Oman.
authors.forename: Ahmed
authors.initials: A
authors.lastname: Al-Harrasi
authors.affiliation: Department of Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany.
authors.forename: René
authors.initials: R
authors.lastname: Csuk
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D015195:Drug Design; D005347:Fibroblasts / Q000187:drug effects / Q000473:pathology; D006034:Glycyrrhetinic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D015394:Molecular Structure; D041681:NIH 3T3 Cells; D009369:Neoplasms / Q000188:drug therapy* / Q000473:pathology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D006034:Glycyrrhetinic Acid
keywords: Cytotoxicity; Furano-glycyrrhetinoate; Glycyrrhetinic acid; SeO2 oxidation; Selenophene