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)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.
Hetzel
C E
CE
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg 24061-0212.
Gunatilaka
A A
AA
Glass
T E
TE
Kingston
D G
DG
Hoffmann
G
G
Johnson
R K
RK
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D004260:DNA Repair; D004354:Drug Screening Assays, Antitumor; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000302:isolation & purification* / Q000494:pharmacology; D010936:Plant Extracts / Q000032:analysis; D010946:Plants, Medicinal / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014709:Vero Cells; D015003:Yeasts / Q000187:drug effects / Q000235:genetics / Q000378:metabolism
D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones; D010936:Plant Extracts