Bioactive Furanonaphthoquinones from Crescentia cujete

Bioassay-directed fractionation of the MeCOEt extract of Crescentia cujete (Bignonaceae) resulted in the isolation of (2S,3S)-3-hydroxy-5,6-dimethoxydehydroiso-alpha-lapachone [1], (2R)-5,6-dimethoxydehydroiso-alpha-lapachone [2], (2R)-5-methoxydehydroiso-alpha-lapachone [3], 2-(1-hydroxyethyl)napht...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1993-09, Vol.56 (9), p.1500-1505
Main Authors: Heltzel, Carl E, Gunatilaka, A. A. Leslie, Glass, Thomas E, Kingston, David G. I, Hoffmann, Glenn, Johnson, Randall K
Format: Article
Language:English
Subjects:
AGENTES ANTINEOPLASTICOS
Animals
ANTINEOPLASTIC AGENTS
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
BIOASSAYS
CHEMISTRY
CHIMIE
Chromatography, Thin Layer
CRESCENTIA CUJETE
DNA Repair
DOSAGE BIOLOGIQUE
Drug Screening Assays, Antitumor
ENSAYO BIOLOGICO
EXTRACTOS VEGETALES
EXTRAIT D'ORIGINE VEGETALE
FRACCIONAMIENTO
FRACTIONATION
FRACTIONNEMENT
ISOLATION
Magnetic Resonance Spectroscopy
MEDICAMENT CYTOSTATIQUE
Molecular Conformation
MOLECULAR STRUCTURE
Naphthoquinones - isolation & purification
Naphthoquinones - pharmacology
PANAMA
PLANT EXTRACTS
Plant Extracts - analysis
Plants, Medicinal - chemistry
QUIMICA
QUINONAS
QUINONE
QUINONES
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
STEREOCHEMISTRY
Stereoisomerism
STRUCTURE
Vero Cells
Yeasts - drug effects
Yeasts - genetics
Yeasts - metabolism
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Description
Summary:Bioassay-directed fractionation of the MeCOEt extract of Crescentia cujete (Bignonaceae) resulted in the isolation of (2S,3S)-3-hydroxy-5,6-dimethoxydehydroiso-alpha-lapachone [1], (2R)-5,6-dimethoxydehydroiso-alpha-lapachone [2], (2R)-5-methoxydehydroiso-alpha-lapachone [3], 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [4], 5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [5], 2-isopropenylnaphtho[2,3-b]furan-4,9-dione [6], and 5-hydroxydehydroiso-alpha-lapachone [7]. Compounds 1-3 are new, and all compounds are bioactive, showing selective activity towards DNA-repair-deficient yeast mutants. The isolation, structure elucidation, and biological activities of these compounds are reported.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50099a008