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 cyclolign...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1994-12, Vol.57 (12), p.1670-1674
Main Authors: Song, Yan-Nong, Zhang, Hai-Lan, Chang, Ching-jer, Bollag, Daniel M
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
AGENTES ANTINEOPLASTICOS
Animals
ANTINEOPLASTIC AGENTS
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
AUSTROBAILIGNANS
Cattle
CHEMICAL COMPOSITION
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
CYTOTOXIC COMPOUNDS
Dioxoles
DRUG PLANTS
Drug Screening Assays, Antitumor
ESPECTROMETRIA
FEUILLE
HOJAS
Humans
KOELREUTERIN-1
Korea
LEAVES
Lignans
LIGNINAS
LIGNINE
LIGNINS
Magnetic Resonance Spectroscopy
MEDICAMENT CYTOSTATIQUE
MEDICINAL PLANTS
MOLECULAR CONFORMATION
MOLECULAR STRUCTURE
PLANTAS MEDICINALES
PLANTE MEDICINALE
Plants, Medicinal - chemistry
SAPINDACEAE
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
STEMS
SUBSTANCE TOXIQUE
SUSTANCIAS TOXICAS
TAIWAN
TALLO
TIGE
TOXIC SUBSTANCES
Tubulin - metabolism
Tumor Cells, Cultured
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Description
Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50114a008