The vasorelaxant effects of 1-nitro-2-phenylethane involve stimulation of the soluble guanylate cyclase-cGMP pathway

Gottlieb, 1959, Occurrence of 1-nitro-2-phenylethane in Ocotea pretiosa and Aniba canelilla, J Org Chem, 24, 2070, 10.1021/jo01094a050 Gottlieb, 1972, Chemosystematics on the Lauraceae, Phytochemistry, 5, 1537, 10.1016/0031-9422(72)85001-5 Matsuo, 1972, 1-Nitro-2-phenylethane: a possible intermediate in the biosynthesis of benzyl glucosinolate, Phytochemistry, 11, 697, 10.1016/0031-9422(72)80034-7 Du, 1996, Isolation of a microsomal enzyme system involved in glucosinolate biosynthesis from seedlings of Tropaeolum majus L, Plant Physiol, 111, 831, 10.1104/pp.111.3.831 Wittstock, 2000, Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate, J Biol Chem, 275, 14659, 10.1074/jbc.275.19.14659 Tieman, 2006, Tomato aromatic amino acid decarboxylases participate in synthesis of the flavor volatiles 2-phenylethanol and 2-phenylacetaldehyde, Proc Natl Acad Sci USA, 103, 8287, 10.1073/pnas.0602469103 de Siqueira, 2010, 1-Nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, elicits a vago-vagal bradycardiac and depressor reflex in normotensive rats, Eur J. Pharmacol, 638, 90, 10.1016/j.ejphar.2010.03.060 Interaminense, 2011, Cardiovascular effects of 1-nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, in spontaneously hypertensive rats, Fundam Clin Pharmacol, 25, 661, 10.1111/j.1472-8206.2010.00891.x Donnerer, 1982, Analysis of the effects of intravenously injected capsaicin in the rat, Naunyn Schmiedebergs Arch Pharmacol, 320, 54, 10.1007/BF00499072 Oger, 1994, Aniba canelilla (H.B.K.) Mez essential oil: analysis of chemical constituents and fugistatic properties, J Essent Oil Res, 6, 493, 10.1080/10412905.1994.9698432 Lahlou, 2005, Cardiovascular effects of the essential oil of Aniba canelilla bark in normotensive rats, J Cardiovasc Pharmacol, 46, 412, 10.1097/01.fjc.0000175876.25296.f4 da Silva, 2007, Antioxidant capacity and cytotoxicity of essential oil and methanol extract of Aniba canelilla (H.B.K.) Mez, J Agric Food Chem, 55, 9422, 10.1021/jf071928e Morris, 1998, Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function, J Comput Chem, 19, 1639, 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B Ma, 2007, NO and CO differentially activate soluble guanylyl cyclase via a heme pivot-bend mechanism, EMBO J, 26, 578, 10.1038/sj.emboj.7601521 Sanner, 1999, Integrating computation and visualization for biomolecular analysis: an example using python and AVS, Pac Symp Biocomput, 4, 392 Noguera, 1992, Different and common intracellular calcium-stores mobilized by noradrenaline and caffeine in vascular smooth muscle, Naunyn Schmiedebergs Arch Pharmacol, 345, 333, 10.1007/BF00168695 Christensen, 2001, Location of resistance arteries, J Vasc Res, 38, 1, 10.1159/000051024 Niedel, 1983, Phorbol diester receptor copurifies with protein kinase C, Proc Natl Acad Sci USA, 80, 36, 10.1073/pnas.80.1.36 Leuner, 2010, Simple 2,4-diacylphloroglucinols as classic transient receptor potential-6 activators: identification of a novel pharmacophore, Mol Pharmacol, 77, 368, 10.1124/mol.109.057513 Levine, 1972, Prostaglandin production by mouse fibrosarcoma cells in culture: inhibition by indomethacin and aspirin, Biochem Biophys Res Commun, 47, 888, 10.1016/0006-291X(72)90576-1 Lippe, 1991, Actions of vasopressin and isoprenaline on the ionic transport across the isolated frog skin in the presence and the absence of adenyl cyclase inhibitors MDL12330A and SQ22536, Comp Biochem Physiol, 99, 209 Kase, 1987, K-252 compounds, novel and potent inhibitors of protein kinase C and cyclic nucleotide-dependent protein kinases, Biochem Biophys Res Commun, 142, 436, 10.1016/0006-291X(87)90293-2 Garthwaite, 1995, Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one, Mol Pharmacol, 48, 184 Gruetter, 1981, Relationship between cyclic guanosine 3′:5′-monophosphate formation and relaxation of coronary arterial smooth muscle by glyceryl trinitrate, nitroprusside, nitrite and nitric oxide: effects of methylene blue and methemoglobin, J Pharmacol Exp Ther, 219, 181 McDaniel, 2001, Capacitative Ca2+ entry in agonist-induced pulmonary vasoconstriction, Am J Physiol Lung Cell Mol Physiol, 280, L870, 10.1152/ajplung.2001.280.5.L870 Langlands, 1990, The effect of phenylephrine on inositol 1,4,5-trisphosphate levels in vascular smooth muscle measured using a protein binding assay system, Biochem Biophys Res Commun, 173, 1258, 10.1016/S0006-291X(05)80922-2 Vallot, 2001, Functional coupling between the caffeine/ryanodine-sensitive Ca2+ store and mitochondria in rat aortic smooth muscle cells, Biochem J, 357, 363, 10.1042/0264-6021:3570363 Ji, 1998, Nitric oxide selectively inhibits intracellular Ca++ release elicited by inositol trisphosphate but not caffeine in rat vascular smooth muscle, J Pharmacol Exp Ther, 285, 16 Itoh, 1981, Effects of vasodilator agents on smooth muscle cells of the coronary artery of the pig, Br J Pharmacol, 74, 455, 10.1111/j.1476-5381.1981.tb09991.x Pauvert, 2000, NO-induced modulation of calcium-oscillations in pulmonary vascular smooth muscle, Cell Calcium, 27, 329, 10.1054/ceca.2000.0123 Ju, 2010, Nitroaromatic compounds, from synthesis to biodegradation, Microbiol Mol Biol Rev, 74, 250, 10.1128/MMBR.00006-10 Artz, 1998, NO release from NO donors and nitrovasodilators: comparisons between oxyhemoglobin and potentiometric assays, Chem Res Toxicol, 11, 1393, 10.1021/tx980205+ Martin, 2012, Mechanism of binding of NO to soluble guanylyl cyclase: implication for the second NO binding to the heme proximal site, Biochemistry, 51, 2737, 10.1021/bi300105s Minamiyama, 2002, Organic nitrate tolerance is induced by degradation of some cytochrome P450 isoforms, Redox Rep, 7, 339, 10.1179/135100002125000947 Evgenov, 2006, NO-independent stimulators and activators of soluble guanylate cyclase: discovery and therapeutic potential, Nat Rev Drug Discov, 5, 755, 10.1038/nrd2038 Wohlfart, 1999, Release of nitric oxide from endothelial cells stimulated by YC-1, an activator of soluble guanylyl cyclase, Br J Pharmacol, 128, 1316, 10.1038/sj.bjp.0702921 Priviero, 2005, Mechanisms underlying relaxation of rabbit aorta by BAY 41-2272, a nitric oxide-independent soluble guanylate cyclase activator, Clin Exp Pharmacol Physiol, 32, 728, 10.1111/j.1440-1681.2005.04262.x Teixeira, 2006, J Pharmacol Exp Ther, 317, 258, 10.1124/jpet.105.095752 Selwood, 2001, Synthesis and biological evaluation of novel pyrazoles and indazoles as activators of the nitric oxide receptor, soluble guanylate cyclase, J Med Chem, 44, 78, 10.1021/jm001034k Takagi, 2001, Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum, Eur J Pharmacol, 411, 161, 10.1016/S0014-2999(00)00907-9 Salom, 2006, Relaxant effect of sildenafil in the rabbit basilar artery, Vascul Pharmacol, 44, 10, 10.1016/j.vph.2005.07.010 Tsai, 2010, Is Nostoc H-NOX a NO sensor or redox switch, Biochemistry, 49, 6587, 10.1021/bi1002234 Lamothe, 2004, Functional characterization of nitric oxide and YC-1 activation of soluble guanylyl cyclase: structural implication for the YC-1 binding site, Biochemistry, 43, 3039, 10.1021/bi0360051 Stasch, 2001, NO-independent regulatory site on soluble guanylate cyclase, Nature, 410, 212, 10.1038/35065611 Koglin, 2003, A functional domain of the α1 subunit of soluble guanylyl cyclase is necessary for activation of the enzyme by nitric oxide and YC-1 but is not involved in heme binding, J Biol Chem, 278, 12590, 10.1074/jbc.M212740200 Francis, 2010, cGMP-dependent protein kinases and cGMP phosphodiesterases in nitric oxide and cGMP action, Pharmacol Rev, 62, 525, 10.1124/pr.110.002907 Morgado, 2012, Cyclic nucleotide-dependent relaxation pathways in vascular smooth muscle, Cell Mol Life Sci, 69, 247, 10.1007/s00018-011-0815-2