Cytotoxic prenylated flavanones from Monotes engleri.
From the leaves of Monotes engleri, five prenylated flavanones were isolated as constituents that displayed cytotoxic activity against several human cancer cell lines. There of these substances are novel, namely, 6-(1,1-dimethylallyl)naringenin, 6-(1,1-dimethylallyl)eriodictyol and 3'-O-methyl-6-(1,1-dimethylallyl)-eriodictyol, with the other two active substances being the known flavanones, 6,8-diprenyleriodictyol and hiravanone. Additionally, two novel, but non-cytotoxic, biogenetically related flavanones were isolated, 6-[(2RS)-hydroxy-3-methyl-3-butenyl]-8-prenyleriodictyol and 5,4'-dihydroxy-4",4"-dimethyl-5"-methyl-5"H-dihydrofurano[2",3": 6,7]flavanone. The structures of the new compounds were determined by spectral analysis 1D- and 2D-NMR experiments.
Seo
E K
EK
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.
Silva
G L
GL
Chai
H B
HB
Chagwedera
T E
TE
Farnsworth
N R
NR
Cordell
G A
GA
Pezzuto
J M
JM
Kinghorn
A D
AD
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000633:toxicity*; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000302:isolation & purification* / Q000633:toxicity*; D005910:Glioma / Q000188:drug therapy; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000302:isolation & purification* / Q000633:toxicity*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000972:Antineoplastic Agents, Phytogenic; D005419:Flavonoids; D010936:Plant Extracts