Cancer chemopreventive in vitro activities of isoflavones isolated from Iris germanica.
Six known isoflavones were isolated from the rhizomes of Iris germanica, and were established by UV, MS and NMR techniques as irisolidone (1), irisolidone 7-O-alpha-D-glucoside (1a), irigenin (2), irilone (3), iriflogenin (4), and iriskashmirianin (5). These compounds were examined for their cancer chemopreventive potential. They were shown to be potent inhibitors of cytochrome P450 1A activity with IC 50 values in the range 0.25-4.9 microM. The isoflavones 2, 3 and 5 displayed moderate activity as inducers of NAD(P)H:quinone reductase (QR) in cultured mouse Hepa 1c1c7 cells, with CD values (concentration required to double the specific activity of QR) of 3.5-16.7 microM, whereas weak activity was observed with compounds 4 and 5 in the radical (DPPH) scavenging bioassay (IC 50 values 89.6 and 120.3 microM, respectively). With respect to anti-tumor promoting potential based on anti-inflammatory mechanisms, none of the compounds demonstrated significant activity in the concentration range tested.
Wollenweber
Eckhard
E
Institut für Botanik, Technische Universität, Darmstadt, Germany. wollenweber@bio.tu-darmstadt.de
Stevens
Jan Frederik
JF
Klimo
Karin
K
Knauft
Jutta
J
Frank
Norbert
N
Gerhäuser
Clarissa
C
D000818:Animals; D016588:Anticarcinogenic Agents / Q000302:isolation & purification / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D051545:Cyclooxygenase 1; D004354:Drug Screening Assays, Antitumor; D004790:Enzyme Induction; D004791:Enzyme Inhibitors / Q000494:pharmacology; D031323:Iris Plant / Q000737:chemistry*; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D007529:Isoflavones / Q000302:isolation & purification / Q000494:pharmacology*; D008565:Membrane Proteins; D051379:Mice; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis; D011451:Prostaglandin-Endoperoxide Synthases; D051381:Rats; D014407:Tumor Cells, Cultured
D016588:Anticarcinogenic Agents; D000972:Antineoplastic Agents, Phytogenic; D004791:Enzyme Inhibitors; D007527:Isoenzymes; D007529:Isoflavones; D008565:Membrane Proteins; D051545:Cyclooxygenase 1; D011451:Prostaglandin-Endoperoxide Synthases; C496512:Ptgs1 protein, mouse; C496513:Ptgs1 protein, rat; D016660:NAD(P)H Dehydrogenase (Quinone)