Abstract
Although flavonoids, which are both qualitatively and quantitatively one of the largest groups of natural products, exhibit a variety of beneficial health effects, the exact molecular mechanism of the cellular activities is still not fully explained and there currently exists a lack of evidence for any relationship between the structure-activity relationship and apoptosis-inducing activity. In order to determine the importance of the OH group or substitution of the 5 or carbon-7 in the diphenylpropane skeleton of flavonoids, we originally synthesized several modified naringenin derivatives, including 7-O-benzyl naringenin (KUF-1) and 7-O-(MeO-L-Leu-D-Pro-carbonylmethyl) naringenin (KUF-7). Treatment with KUF-1 or KUF-7 resulted in significant apoptosis-inducing effects concomitant with chromatin condensation, caspase activation, and intracellular ROS production. Our data indicate that originally synthesized naringenin derivatives, KUF-1 and KUF-7 differentially regulate the apoptosis of A549 cells via intracellular ROS production coupled with the concomitant activation of the caspase cascade signaling pathway, thereby implying that hydroxylation or substitution at Carbon-7 is critical for the apoptosis-inducing activity of flavonoids.
Original language | English (US) |
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Pages (from-to) | 2394-2398 |
Number of pages | 5 |
Journal | Biological and Pharmaceutical Bulletin |
Volume | 30 |
Issue number | 12 |
DOIs | |
State | Published - Dec 2007 |
Externally published | Yes |
Keywords
- A549
- Apoptosis
- Flavonoid
- Lung cancer
- Reactive oxygen species
- Synthetic naringenin derivative
ASJC Scopus subject areas
- Pharmacology
- Pharmaceutical Science