title: Cytotoxic cyclolignans from Koelreuteria henryi.
abstract: Chemical investigation of the cytotoxic fraction of Koelreuteria henryi resulted in the isolation of three cyclolignans. A new cyclolignan, named koelreuterin-1 was elucidated as furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(8H)-one,5-(7-methoxy-1, 3- benzodioxol-5-yl)[1]. Two known cyclolignans were characterized as austrobailignan-1 [2] and austrobailignan-2 [3]. The structure elucidation of 1 was based on extensive 1H- and 13C-nmr spectral analyses. Further chemical conversion of 2 to 3 and oxidative transformation of 2 to 1 unambiguously confirmed the structure of 1. The cytotoxicity and tubulin polymerization inhibitory activity of 1-3 are discussed.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
authors.forename: Y N
authors.initials: YN
authors.lastname: Song
authors.forename: H L
authors.initials: HL
authors.lastname: Zhang
authors.forename: C J
authors.initials: CJ
authors.lastname: Chang
authors.forename: D M
authors.initials: DM
authors.lastname: Bollag
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D002417:Cattle; D004149:Dioxoles; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007723:Korea; D017705:Lignans; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*; D014404:Tubulin / Q000378:metabolism; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004149:Dioxoles; D017705:Lignans; D014404:Tubulin; C093025:koelreuterin 1; C093024:austrobailignan 2; C093023:austrobailignan 1; D015107:4-Butyrolactone