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Abstract

Flavonoids are micronutrients that are widely detected in foods of plant origin and have been ascribed pharmacological properties. Several biological functions of flavonoids have been thus far identified, whereas there currently exists a lack of evidence to support the relationship between the structure-activity relationship and apoptosis-inducing activity. In an attempt to determine the importance of the OH group or substitution of the 5- or 7-carbon in the diphenylpropane skeleton of flavonoids, we selected 14 different flavonoids with different structures, particularly with regard to the 5- or 7-carbon, and found that naringenin treatment caused a slight decrease in the cell viability of the human colorectal carcinoma RKO cells. Next, in order to characterize the effects of specific substitutions of the 7-carbon of naringenin on apoptosis-regulatory activities, and in an attempt to develop anti-proliferative flavonoid derivatives that would be more effective against colon cancer, we originally synthesized several modified naringenin derivatives (MNDs) including 7-O-benzyl naringenin (KUF-1) and 7-O-(m-metoxybenzyl) naringenin (KUF-2). Treatment with KUF-1 or KUF-2 resulted in significant apoptosis-inducing effects concomitant with losses in mitochondrial membrane potential, caspase activation, intracellular ROS production, and sustained ERK activation. Our data show that KUF-1 or KUF-2 regulate the apoptosis of RKO cells via intracellular ROS production coupled with the concomitant activation of the ERK signaling pathway, thereby implying that hydroxylation or substitution at C7 is critical for the apoptosis-inducing activity of flavonoids. J. Cell. Biochem. 104: 259–273, 2008. © 2007 Wiley-Liss, Inc.

  

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이 논문을 인용한 문헌 (14)

  1. 1. Kang, Kyoung-Hee, Jang, Jung-In, Baek, Seung-Bin, Ahn, Jung-Hee, Park, Yong-Sun 2011. "Diisopropyl L-Malate as a New Chiral Auxiliary for Dynamic Kinetic Resolution of α-Bromo Esters and Asymmetric Syntheses of Aminoflavones and Dihydroquinoxalinones" Bulletin of the Korean Chemical Society, 32(5): 1741~1744 
  2. 2. Kim, Jung-Hee, Kim, Hee-Jong, Bak, Ye-Sol, Kang, Jeong-Woo, Lee, Dong-Hun, Kim, Man-Sub, Park, Yun-Sun, Kim, Eun-Jin, Jung, Kang-Yeoun, Lim, Yoong-Ho, Hong, Jin-Tae, Yoon, Do-Young 2012. "Naringenin Derivative Diethyl (5,4'-dihydroxy flavanone-7-yl) Phosphate Inhibits Cell Growth and Induces Apoptosis in A549 Human Lung Cancer Cells" Journal of the Korean Society for Applied Biological Chemistry, 55(1): 75~82 
  3. 3. Oguz, Mehmet, Bhatti, Asif Ali, Dogan, Berna, Karakurt, Serdar, Durdagi, Serdar, Yilmaz, Mustafa 2020. "Formation of the inclusion complex of water soluble fluorescent calix[4]arene and naringenin: solubility, cytotoxic effect and molecular modeling studies" Journal of biomolecular structure & dynamics, 38(13): 3801~3813 
  4. 4. NavaneethaKrishnan, Saranya, Rosales, Jesusa L., Lee, Ki-Young 2019. "ROS-Mediated Cancer Cell Killing through Dietary Phytochemicals" Oxidative medicine and cellular longevity, 2019(): 1~16 
  5. 5. Murti, Yogesh, Mishra, Pradeep 2020. "Synthesis, Characterization, and Biological Evaluation of Novel Naringenin Derivatives as Anticancer Agents" Current bioactive compounds, 16(4): 442~448 
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