AMPK-associated signaling to bridge the gap between fuel metabolism and hepatocyte viability

Figure 3 Chemical structures of adenosine monophosphate-activated protein kinase activators. A: Dithiolethione derivatives: Oltipraz [4-methyl-5-(2-pyrazinyl)-1,2-dithiol-3-thione], CJ11764 (5-pyrazinyl-1,2-dithiole-3-thione), CJ12064 [5-(6-methoxypyrzinyl)-4-methyl-1,2-dithiole-3-thione], CJ11842 (4-methyl-5-phenyl-1,2-dithiole-3-thione), CJ11840 (5-benzo[b]thiophene-3-yl-1,2-dithiole-3-thione), CJ11792 (4,5,6,7-tetrahydrobenzo-1,2-dithiole-3-thione), CJ11788 (5,6-dihydro-4H-cyclopenta-1,2-dithiole-3-thione), CJ11766 (4-ethyl-5-pyrazin-2-yl-1,2-dithiole-3-thione), CJ12073 [5-(6-Ethoxypyrazin-2-yl)-4-methyl-1,2-dithiole-3-thione], CJ11780 (5-methyl-1,2-dithiole-3-thione); B: Metabolites of oltipraz: First, oxidative desulfuration of the thione among approximately 1% of oltipraz to yield M1 [4-methyl-5-(2-pyrazinyl)-1,2-dithiol-3-one], which is not metabolized further; and secondly, desulfuration, methylation, and molecular rearrangement among a large amount of oltipraz to yield M2 [7-methyl-6,8-bis(methylthio)H-pyrrolo(1,2-a)-pyrazine], which is metabolized to other oxidized forms; C: Phytochemicals: Resveratrol (flavonoid found in the skin of red grapes and red wine), isoLQ (a flavonoid aglycone of isoliquiritin from licorice), LQ (a flavonoid aglycone of liquiritin from licorice), sauchinone (a lignan in Saururus chinensis), baicalin (the major flavonoid compound in Scutellaria baicalensis).