Cytotoxic cyclolignans from Koelreuteria henryi.
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.
Song
Y N
YN
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
Zhang
H L
HL
Chang
C J
CJ
Bollag
D M
DM
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
D000972:Antineoplastic Agents, Phytogenic; D004149:Dioxoles; D017705:Lignans; D014404:Tubulin; C093025:koelreuterin 1; C093024:austrobailignan 2; C093023:austrobailignan 1; D015107:4-Butyrolactone