N-hydroxycinnamide derivatives of osthole ameliorate hyperglycemia through activation of AMPK and p38 MAPK

Molecules

Volumn 20, Issue 3, 2015, Pages 4516-4529

  Lee, Wei Hwa ^a   Wu, Hsueh Hsia ^b   Huang, Wei Jan ^b   Li, Yi Ning ^b   Lin, Ren Jye ^c,d   Lin, Shyr Yi ^c,d   Liang, Yu Chih ^b,c  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^b TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^c TAIPEI MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

^d TAIPEI MEDICAL UNIVERSITY   (Taiwan)

Author keywords

AMP activated protein kinase (AMPK); Glucose uptake; N hydroxycinnamide; Osthole; p38 MAPK; Skeletal muscle; Streptozotocin

Indexed keywords

ANTIDIABETIC AGENT; COUMARIC ACID; COUMARIN DERIVATIVE; GLUCOSE TRANSPORTER 4; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE KINASE; MITOGEN ACTIVATED PROTEIN KINASE P38; OHC-2M COMPOUND; OHC-4P COMPOUND; OSTHOLE; STREPTOZOCIN;

ANIMAL; CHEMISTRY; CYTOLOGY; DIABETES MELLITUS, EXPERIMENTAL; DRUG EFFECTS; ENZYMOLOGY; METABOLISM; RAT; SKELETAL MUSCLE; SYNTHESIS;

AMP-ACTIVATED PROTEIN KINASES; ANIMALS; COUMARIC ACIDS; COUMARINS; DIABETES MELLITUS, EXPERIMENTAL; GLUCOSE TRANSPORTER TYPE 4; HYPOGLYCEMIC AGENTS; MUSCLE, SKELETAL; P38 MITOGEN-ACTIVATED PROTEIN KINASES; RATS; STREPTOZOCIN;

EID: 84928809968     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules20034516     Document Type: Article

References (29)

1. Towler, M.C.; Hardie, D.G. AMP-activated protein kinase in metabolic control and insulin signaling. Circ. Res. 2007, 100, 328-341.
2. Richter, E.A.; Hargreaves, M. Exercise, GLUT4, and skeletal muscle glucose uptake. Physiol. Rev. 2013, 93, 993-1017.
3. Govers, R. Cellular regulation of glucose uptake by glucose transporter GLUT4. Adv. Clin. Chem. 2014, 66, 173-240.
4. Sakamoto, K.; Holman, G.D. Emerging role for AS160/TBC1D4 and TBC1D1 in the regulation of GLUT4 traffic. Am. J. Physiol. Endocrinol. Metab. 2008, 295, E29-E37.
5. Zou, M.H.; Kirkpatrick, S.S.; Davis, B.J.; Nelson, J.S.; Wiles, W.G., IV; Schlattner, U.; Neumann, D.; Brownlee, M.; Freeman, M.B.; Goldman, M.H. Activation of the AMP-activated protein kinase by the anti-diabetic drug metformin in vivo role of mitochondrial reactive nitrogen species. J. Biol. Chem. 2004, 279, 43940-43951.
6. Konrad, D.; Rudich, A.; Bilan, P.J.; Patel, N.; Richardson, C.; Witters, L.A.; Klip, A. Troglitazone causes acute mitochondrial membrane depolarisation and an AMPK-mediated increase in glucose phosphorylation in muscle cells. Diabetologia 2005, 48, 954-966.
7. Merrill, G.F.; Kurth, E.J.; Hardie, D.G.; Winder, W.W. AICA riboside increases AMP-activated protein kinase, fatty acid oxidation, and glucose uptake in rat muscle. Am. J. Physiol. 1997, 273, E1107-E1112.
8. Park, C.E.; Kim, M.J.; Lee, J.H.; Min, B.I.; Bae, H.; Choe, W.; Kim, S.S.; Ha, J. Resveratrol stimulates glucose transport in C2C12 myotubes by activating AMP-activated protein kinase. Exp. Mol. Med. 2007, 39, 222-229.
9. Kim, J.H.; Park, J.M.; Kim, E.K.; Lee, J.O.; Lee, S.K.; Jung, J.H.; You, G.Y.; Park, S.H.; Suh, P.G.; Kim, H.S. Curcumin stimulates glucose uptake through AMPK-p38 MAPK pathways in L6 myotube cells. J. Cell Physiol. 2010, 223, 771-778.
10. Cai, E.P.; Lin, J.K. Epigallocatechin gallate (EGCG) and rutin suppress the glucotoxicity through activating IRS2 and AMPK signaling in rat pancreatic beta cells. J. Agric. Food Chem. 2009, 57, 9817-9827.
11. Cao, W.H.; Xiong, Y.; Collins, Q.F.; Liu, H.Y. p38 mitogen-activated protein kinase plays a critical role in the control of energy metabolism and development of cardiovascular diseases. Zhong Nan Da Xue Xue Bao Yi Xue Ban 2007, 32, 1-14. (In Chinese)
12. Somwar, R.; Perreault, M.; Kapur, S.; Taha, C.; Sweeney, G.; Ramlal, T.; Kim, D.Y.; Keen, J.; Cote, C.H.; Klip, A.; et al. Activation of p38 mitogen-activated protein kinase alpha and beta by insulin and contraction in rat skeletal muscle: potential role in the stimulation of glucose transport. Diabetes 2000, 49, 1794-1800.
13. Goel, A.; Nag, P.; Rahuja, N.; Srivastava, R.; Chaurasia, S.; Gautam, S.; Chandra, S.; Siddiqi, MI.; Srivastava, A.K. Discovery of biaryl-4-carbonitriles as antihyperglycemic agents that may act through AMPK-p38 MAPK pathway. Mol. Cell Endocrinol. 2014, 394, 1-12.
14. Kim, S.H.; Hwang, J.T.; Park, H.S.; Kwon, D.Y.; Kim, M.S. Capsaicin stimulates glucose uptake in C2C12 muscle cells via the reactive oxygen species (ROS)/AMPK/p38 MAPK pathway. Biochem. Biophys. Res. Commun. 2013, 439, 66-70.
15. Xu, X.; Zhang, Y.; Qu, D.; Jiang, T.; Li, S. Osthole induces G2/M arrest and apoptosis in lung cancer A549 cells by modulating PI3K/Akt pathway. J. Exp. Clin. Cancer Res. 2011, 30, 33.
16. Liao, P.C.; Chien, S.C.; Ho, C.L.; Wang, E.I.; Lee, S.C.; Kuo, Y.H.; Jeyashoke, N.; Chen, J.; Dong, W.C.; Chao, L.K.; et al. Osthole regulates inflammatory mediator expression through modulating NF-κB, mitogen-activated protein kinases, protein kinase C, and reactive oxygen species. J. Agric. Food Chem. 2010, 58, 10445-10451.
17. Li, X.X.; Hara, I.; Matsumiya, T. Effects of osthole on postmenopausal osteoporosis using ovariectomized rats, comparison to the effects of estradiol. Biol. Pharm. Bull 2002, 25, 738-742.
18. Liang, H.J.; Suk, F.M.; Wang, C.K.; Hung, L.F.; Liu, D.Z.; Chen, N.Q.; Chen, Y.C.; Chang, C.C.; Liang, Y.C. Osthole, a potential antidiabetic agent, alleviates hyperglycemia in db/db mice. Chem. Biol. Interact. 2009, 181, 309-315.
19. Zhang, Y.; Xie, M.; Xue, J.; Gu, Z. Osthole improves fat milk-induced fatty liver in rats: Modulation of hepatic PPAR-alpha/gamma-mediated lipogenic gene expression. Planta Med. 2007, 73, 718-724.
20. Lee, W.H.; Lin, R.J.; Lin, S.Y.; Chen, Y.C.; Lin, H.M.; Liang, Y.C. Osthole Enhances Glucose Uptake through Activation of AMP-Activated Protein Kinase in Skeletal Muscle Cells. J. Agric. Food Chem. 2011, 59, 12874-12881.
21. Wagh, R.D.; Mahajan, H.S.; Kaskhedikar, S.G. Synthesis and antioxidant activity of substituted phenylalkene hydroxamic acids. Asian J. Chem. 2007, 19, 4188-4192.
22. Huang, W.J.; Chen, C.C.; Chao, S.W.; Lee, S.S.; Hsu, F.L.; Lu, Y.L.; Hung, M.F.; Chang, C.I. Synthesis of N-hydroxycinnamides capped with a naturally occurring moiety as inhibitors of histone deacetylase. ChemMedChem 2010, 5, 598-607.
23. Huang, W.J.; Chen, C.C.; Chao, S.W.; Yu, C.C.; Yang, C.Y.; Guh, J.H.; Lin, Y.C.; Kuo, C.I.; Yang, P.; Chang, C.I. Synthesis and evaluation of aliphatic-chain hydroxamates capped with osthole derivatives as histone deacetylase inhibitors. Eur. J. Med. Chem. 2011, 46, 4042-4049.
24. Summers, J.B.; Kim, K.H.; Mazdiyasni, H.; Holms, J.H.; Ratajczyk, J.D.; Stewart, A.O.; Dyer, R.D.; Carter, G.W. Hydroxamic acid inhibitors of 5-lipoxygenase: Quantitative structure-activity relationships. J. Med. Chem. 1990, 33, 992-998.
25. McGee, S.L.; Sparling, D.; Olson, A.L.; Hargreaves, M. Exercise increases MEF2- and GEF DNA-binding activity in human skeletal muscle. FASEB J. 2006, 20, 348-349.
26. McGee, S.L.; Hargreaves, M. Exercise and skeletal muscle glucose transporter 4 expression: molecular mechanisms. Clin. Exp. Pharmacol. Physiol. 2006, 33, 395-399.
27. Xi, X.; Han, J.; Zhang, J.Z. Stimulation of glucose transport by AMP-activated protein kinase via activation of p38 mitogen-activated protein kinase. J. Biol. Chem. 2001, 276, 41029-41034.
28. Somwar, R.; Koterski, S.; Sweeney, G.; Sciotti, R.; Djuric, S.; Berg, C.; Trevillyan, J.; Scherer, P.E.; Rondinone, C.M.; Klip, A. A dominant-negative p38 MAPK mutant and novel selective inhibitors of p38 MAPK reduce insulin-stimulated glucose uptake in 3T3-L1 adipocytes without affecting GLUT4 translocation. J. Biol. Chem. 2002, 277, 50386-50395.
29. Liu, L.Y.; Huang, W.J.; Lin, R.J.; Lin, S.Y.; Liang, Y.C. N-Hydroxycinnamide derivatives of osthole presenting genotoxicity and cytotoxicity against human colon adenocarcinoma cells in vitro and in vivo. Chem. Res. Toxicol. 2013, 26, 1683-1691.