Biotransformation of the flavonoid tiliroside to 7-methylether tiliroside: bioactivity of this metabolite and of its acetylated derivative.
Incubation of kaempferol-3-O-beta-D-(6"-E-p-coumaroyl)-glucopyranoside (tiliroside) (1) with Aspergillus nidulans gives the 7-methyl ether of tiliroside (2) which is a new compound. Its structure is determined by spectroscopic methods. Cytotoxic studies of 2 and of its acetylated derivative 2a were carried out in vitro against fourteen human leukemic cell lines. Results clearly show that compound 2 is ineffective against all leukemic cell lines tested. On the contrary, compound 2a exhibited cytotoxic activity against four of the cell lines (HL60, DAUDI, HUT78 and MOLT3) and additionally, a dose- and time-dependent effect on DNA synthesis.
Demetzos
C
C
Department of Pharmacy, University of Athens, Greece.
Magiatis
P
P
Typas
M A
MA
Dimas
K
K
Sotiriadou
R
R
Perez
S
S
Kokkinopoulos
D
D
D000107:Acetylation; D001233:Aspergillus nidulans / Q000737:chemistry / Q000378:metabolism; D001578:Benzopyrans / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D001711:Biotransformation; D002455:Cell Division / Q000187:drug effects*; D004247:DNA / Q000096:biosynthesis*; D005419:Flavonoids; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019384:Nucleic Acid Synthesis Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
C108131:7-methylether tiliroside; D001578:Benzopyrans; D005419:Flavonoids; D019384:Nucleic Acid Synthesis Inhibitors; C052083:tiliroside; D004247:DNA