(−)-Ternatin inhibits adipogenesis and lipid metabolism in 3T3-L1 cells

Barak, 1999, PPAR gamma is required for placental, cardiac, and adipose tissue development, Mol Cell, 4, 585, 10.1016/S1097-2765(00)80209-9 Cao, 1991, Regulated expression of three C/EBP isoforms during adipose conversion of 3T3-L1 cells, Genes Dev, 5, 1538, 10.1101/gad.5.9.1538 Cornelius, 1994, Regulation of adipocyte development, Annu Rev Nutr, 14, 99, 10.1146/annurev.nu.14.070194.000531 Darlington, 1998, The role of C/EBP genes in adipocyte differentiation, J Biol Chem, 273, 30057, 10.1074/jbc.273.46.30057 Duvnjak, 2007, Pathogenesis and management issues for non-alcoholic fatty liver disease, World J Gastroenterol, 13, 4539, 10.3748/wjg.v13.i34.4539 Farmer, 2006, Transcriptional control of adipocyte formation, Cell Metab, 4, 263, 10.1016/j.cmet.2006.07.001 Farrell, 2006, Nonalcoholic fatty liver disease: from steatosis to cirrhosis, Hepatology, 43, S99, 10.1002/hep.20973 Franssen, 2008, Obesity and dyslipidemia, Endocrinol Metab Clin North Am, 37, 10.1016/j.ecl.2008.06.003 Fruhbeck, 2001, The adipocyte: a model for integration of endocrine and metabolic signaling in energy metabolism regulation, Am J Physiol-Endocrinol Metab, 280, E827, 10.1152/ajpendo.2001.280.6.E827 Fruhbeck, 2008, Overview of adipose tissue and its role in obesity and metabolic disorders, Methods Mol Biol, 456, 1, 10.1007/978-1-59745-245-8_1 Fujimori, 2007, A novel pathway to enhance adipocyte differentiation of 3T3-L1 cells by up-regulation of lipocalin-type prostaglandin D synthase mediated by liver X receptor-activated sterol regulatory element-binding protein-1c, J Biol Chem, 282, 18458, 10.1074/jbc.M701141200 Harada, 2007, Hepatic de novo lipogenesis is present in liver-specific ACC1-deficient mice, Mol Cell Biol, 27, 1881, 10.1128/MCB.01122-06 Harmon, 2001, Differential effects of flavonoids on 3T3-L1 adipogenesis and lipolysis, Am J Physiol-Cell Physiol, 280, C807, 10.1152/ajpcell.2001.280.4.C807 Im, 2006, Regulation of GLUT4 gene expression by SREBP-1c in adipocytes, Biochem J, 399, 131, 10.1042/BJ20060696 Ito, 2003, Characterization of MCH-mediated obesity in mice, Am J Physiol-Endocrinol Metab, 284, E940, 10.1152/ajpendo.00529.2002 Juvet, 2003, On the role of liver X receptors in lipid accumulation in adipocytes, Mol Endocrinol, 17, 172, 10.1210/me.2001-0210 Kaluzny, 1985, Rapid separation of lipid classes in high-yield and purity using bonded phase columns, J Lipid Res, 26, 135, 10.1016/S0022-2275(20)34412-6 Kasturi, 1983, Increased synthesis and accumulation of phospholipids during differentiation of 3T3-L1-cells into adipocytes, J Biol Chem, 258, 3559, 10.1016/S0021-9258(18)32698-X Kim, 2007, Hibiscus sabdariffia L. water extract inhibits the adipocyte differentiation through the P13-K and MAPK pathway, J Ethnopharmacol, 114, 260, 10.1016/j.jep.2007.08.028 Kim, 2008, Green tea seed oil reduces weight gain in C57BL/6J mice and influences adipocyte differentiation by suppressing peroxisome proliferator-activated receptor-γ, Pflugers Arch: Eur J Physiol, 457, 293, 10.1007/s00424-008-0537-y Kobilka, 1992, Adrenergic-receptors as models for G protein-coupled receptors, Annu Rev Neurosci, 15, 87, 10.1146/annurev.ne.15.030192.000511 Koutnikova, 2003, Compensation by the muscle limits the metabolic consequences of lipodystrophy in PPAR gamma hypomorphic mice, Proc Natl Acad Sci USA, 100, 14457, 10.1073/pnas.2336090100 Langhans, 2003, Role of the liver in the control of glucose-lipid utilization and body weight, Curr Opin Clin Nutr Metabolic Care, 6, 449, 10.1097/01.mco.0000078993.96795.16 Macdougald, 1995, Transcriptional regulation of gene-expression during adipocyte differentiation, Annu Rev Biochem, 64, 345, 10.1146/annurev.bi.64.070195.002021 Madsen, 2003, Adipocyte differentiation of 3T3-L1 preadipocytes is dependent on lipoxygenase activity during the initial stages of the differentiation process, Biochem J, 375, 539, 10.1042/bj20030503 Mann, 2005, Public health. Provocative study says obesity may reduce U.S. life expectancy, Science, 307, 1716, 10.1126/science.307.5716.1716 Maxwell, 2003, Novel putative SREBP and LXR target genes identified by microarray analysis in liver of cholesterol-fed mice, J Lipid Res, 44, 2109, 10.1194/jlr.M300203-JLR200 Mcgowan, 1983, A peroxidase-coupled method for the colorimetric determination of serum triglycerides, Clin Chem, 29, 538, 10.1093/clinchem/29.3.538 Miyamoto, 2008, Suppressive effects of nobiletin on hyperleptinemia and colitis-related colon carcinogenesis in male ICR mice, Carcinogenesis, 29, 1057, 10.1093/carcin/bgn080 Mizuarai, 2005, Identification of dicarboxylate carrier Slc25a10 as malate transporter in de novo fatty acid synthesis, J Biol Chem, 280, 32434, 10.1074/jbc.M503152200 Ogden, 2007, The epidemiology of obesity, Gastroenterology, 132, 2087, 10.1053/j.gastro.2007.03.052 Parekh, 2007, Abnormal lipid and glucose metabolism in obesity: Implications for nonalcoholic fatty liver disease, Gastroenterology, 132, 2191, 10.1053/j.gastro.2007.03.055 Postic, 2004, Role of the liver in the control of carbohydrate and lipid homeostasis, Diabetes Metab, 30, 398, 10.1016/S1262-3636(07)70133-7 Rangwala, 2000, Transcriptional control of adipogenesis, Annu Rev Nutr, 20, 535, 10.1146/annurev.nutr.20.1.535 Reaven, 2004, Obesity, insulin resistance, and cardiovascular disease, Rec Progr Hormone Res, 59, 207, 10.1210/rp.59.1.207 Repa, 2000, Regulation of mouse sterol regulatory element-binding protein-1c gene (SREBP-1c) by oxysterol receptors, LXRα and LXRβ, Genes Dev, 14, 2819, 10.1101/gad.844900 Rosen, 2000, Molecular regulation of adipogenesis, Annu Rev Cell Dev Biol, 16, 145, 10.1146/annurev.cellbio.16.1.145 Rosen, 2000, Transcriptional regulation of adipogenesis, Genes Dev, 14, 1293, 10.1101/gad.14.11.1293 Saito, 2007, Nobiletin enhances differentiation and lipolysis of 3T3-L1 adipocytes, Biochem Biophys Res Commun, 357, 371, 10.1016/j.bbrc.2007.03.169 Shimokawa, 2008, Whole structure-activity relationships of the fat-accumulation inhibitor (−)-ternatin: recognition of the importance of each amino acid residue, J Med Chem, 51, 5912, 10.1021/jm800741n Shimokawa, 2008, Synthesis and inhibitory effect on fat accumulation of (−)-ternatin derivatives modified in the beta-OH-d-Leu(7) moiety, Org Biomol Chem, 6, 58, 10.1039/B714710D Shimokawa, 2008, Biological activity, structural features, and synthetic studies of (−)-ternatin, a potent fat-accumulation inhibitor of 3T3-L1 adipocytes, Chem: Asian J, 3, 438, 10.1002/asia.200700243 Shimokawa, 2006, (−)-Ternatin, a highly N-methylated cyclic heptapeptide that inhibits fat accumulation: structure and synthesis, Tetrahedron Lett, 47, 4445, 10.1016/j.tetlet.2006.04.073 Shimokawa, 2007, Convergent synthesis and in vivo inhibitory effect on fat accumulation of (−)-ternatin, a highly N-methylated cyclic peptide, Bioorg Med Chem Lett, 17, 4447, 10.1016/j.bmcl.2007.06.015 Spiegelman, 1996, Obesity: rounding out the big picture, Cell, 87, 377, 10.1016/S0092-8674(00)81359-8 Sugimoto, 2007, A novel acetyl-CoA carboxylase inhibitor reduces de novo fatty acid synthesis in HepG2 cells and rat primary hepatocytes, Arch Biochem Biophys, 468, 44, 10.1016/j.abb.2007.09.012 Tamura, 2007, Intracellular lipid accumulation and insulin resistance in skeletal muscle and liver, Jpn J Phys Fitness Sports Med, 56, 34, 10.7600/jspfsm.56.34 Trayhurn, 2001, Physiological role of adipose tissue: white adipose tissue as an endocrine and secretory organ, Proc Nutr Soc, 60, 329, 10.1079/PNS200194 Unger, 1995, Lipotoxicity in the pathogenesis of obesity-dependent Niddm – genetic and clinical implications, Diabetes, 44, 863, 10.2337/diabetes.44.8.863 Wu, 1999, Cross-regulation of C/EBP alpha and PPAR gamma controls the transcriptional pathway of adipogenesis and insulin sensitivity, Mol Cell, 3, 151, 10.1016/S1097-2765(00)80306-8 Yamamoto, 2007, Protein kinase A suppresses sterol regulatory element-binding protein-1C expression via phosphorylation of liver X receptor in the liver, J Biol Chem, 282, 11687, 10.1074/jbc.M611911200 Yasufumi, 1990, Effect of simvastatin (MK-733) on the regulation of cholesterol synthesis in Hep G2 cells, Biochem Pharmacol, 40, 843, 10.1016/0006-2952(90)90325-F Yeh, 1995, Cascade regulation of terminal adipocyte differentiation by three members of the C/EBP family of leucine zipper proteins, Genes Dev, 9, 168, 10.1101/gad.9.2.168 Yoshikawa, 2001, Identification of liver X receptor-retinoid X receptor as an activator of the sterol regulatory element-binding protein 1c gene promoter, Mol Cell Biol, 21, 2991, 10.1128/MCB.21.9.2991-3000.2001