Uncoupling effect of anacardic acids from cashew nut shell oil on oxidative phosphorylation of rat liver mitochondria.
Anacardic acids are one of natural products found in not only the cashew nut shell oil but also the nut and fruit juice. The present study was conducted to investigate the uncoupling effect of anacardic acids on oxidative phosphorylation of rat liver mitochondria using succinate (plus rotenone) as a substrate. Four anacardic acids with C15:0, C15:1, C15:2 or C15:3 as an alkyl side chain exhibited uncoupling effects similar to the classical uncoupler, 2,4-dinitrophenol on ADP/O ratio, state 4 and respiratory control ratio (RCR). Anacardic acid with C15:1 side chain was most effective for uncoupling of these compounds. Salicylic acid, which has no alkyl side chain, exhibited a very weak uncoupling effect on oxidative phosphorylation. When the carboxyl group in anacardic acids was lost converting them to the corresponding cardanols, uncoupling activity dramatically decreased regardless of the number of double bonds in the long alkyl chain. These results suggest that the C15 alkyl side chain as well as the carboxyl group may play an important role in assisting the uncoupling activity of anacardic acids in liver mitochondria of animals. This study provides the first evidence of an uncoupling effect of anacardic acids on liver mitochondria
Toyomizu
M
M
Science of Biological Function, Major of Life Science, Graduate School of Agriculture, Tohoku University, Sendai, Japan. toyomizu@bios.tohoku.ac.jp
Okamoto
K
K
Ishibashi
T
T
Chen
Z
Z
Nakatsu
T
T
D019297:2,4-Dinitrophenol / Q000494:pharmacology; D048729:Anacardic Acids; D000818:Animals; D066298:In Vitro Techniques; D008297:Male; D008930:Mitochondria, Liver / Q000187:drug effects* / Q000378:metabolism; D009754:Nuts / Q000737:chemistry*; D010085:Oxidative Phosphorylation / Q000187:drug effects*; D051381:Rats; D017207:Rats, Sprague-Dawley; D012459:Salicylates / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014475:Uncoupling Agents / Q000494:pharmacology*
D048729:Anacardic Acids; D012459:Salicylates; D014475:Uncoupling Agents; C088115:anacardic acid; D019297:2,4-Dinitrophenol