Induction of apoptotic cell death by synthetic naringenin derivatives in human lung epithelial carcinoma A549 cells

Eung Ryoung Lee, Yong Jin Kang, Hye Yeon Choi, Geun Ho Kang, Jung Hyun Kim, Bong Woo Kim, Ye Sun Han, Seung Yeol Nah, Hyun Dong Paik, Yong Sun Park, Ssang Goo Cho

Research output: Contribution to journalArticlepeer-review

56 Scopus citations


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 languageEnglish (US)
Pages (from-to)2394-2398
Number of pages5
JournalBiological and Pharmaceutical Bulletin
Issue number12
StatePublished - Dec 2007
Externally publishedYes


  • A549
  • Apoptosis
  • Flavonoid
  • Lung cancer
  • Reactive oxygen species
  • Synthetic naringenin derivative

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science


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