The role of natural products in the ligand deorphanization of TRP channels

Current Pharmaceutical Design

Volumn 14, Issue 1, 2008, Pages 2-17

  Appendino, G ^a   Minassi, A ^a   Pagani, A ^a   Ech Chahad, A ^a  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

Bisandrographolide A; Gingeroids; Indoloquinazolone Alkaloids; Melastatin; Piperine; Resiniferatoxin

Indexed keywords

4ALPHA PHORBOL DIDECANOATE; ALLYL ISOTHIOCYANATE; ANALGESIC AGENT; ANANDAMIDE; CAMPHOR; CANNABIDIOL; CAPSAICIN; CAPSAICIN DERIVATIVE; CAPSAZEPINE; CINEOLE; CINNAMALDEHYDE; EUGENOL; EVODIAMINE; GARLIC EXTRACT; GERANIOL; ISOVELLERAL; LINALOOL; MENTHOL; NATURAL PRODUCT; OLVANIL; PARACETAMOL; PIPERINE; POLYGODIAL; RESINIFERATOXIN; RICINOLEIC ACID; TERPENOID; THAPSIGARGIN; TRANSIENT RECEPTOR POTENTIAL CHANNEL; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANILLOID RECEPTOR 1 BLOCKING AGENT;

ANALGESIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; DRUG PENETRATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG RESEARCH; DRUG SENSITIVITY; DRUG STRUCTURE; DRUG TARGETING; HUMAN; HYPERALGESIA; NEUROPATHIC PAIN; NONHUMAN; OBESITY; PATHOGENESIS; POSTHERPETIC NEURALGIA; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; REVIEW; STRUCTURE ACTIVITY RELATION; TOOTH PAIN; VITILIGO;

ANIMALS; ANIMALS, GENETICALLY MODIFIED; BIOLOGICAL PRODUCTS; DISEASE MODELS, ANIMAL; DRUG DELIVERY SYSTEMS; DRUG DESIGN; GENE EXPRESSION; HUMANS; LIGANDS; TRPC CATION CHANNELS;

EID: 39449099998     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161208783330781     Document Type: Review

References (145)

1. Major reviews published in January-September 2007: A) Christensen AP, Corey DP. TRP channels in mechanosensation direct or indirect activation?. Nat Rev Neurosci 2007; 8: 510-21.
2. Prevarskaya N, Zhang L, Barrit G. TRP channels in cancer Biochim Biophys Acta Mol Bas Dis 2007: 1772: 937-4617.
3. c) Nilius B. TRP channels in disease. Biochim Biophys Acta Mol Bas Dis 2007; 1772: 805-12.
4. d) Okuhara DY, Hsia AY, Xie M. Transient receptor potential channels as drug targets. Expert Opin Ther Targets 2007: 11: 391-401.
5. e) Woodard GE, Sage SO, Rosado JA. Transient receptor potential channels and intracellular signaling. Int Rev Cytol 2007; 256: 35-67.
6. f) Nilius B, Owsianik G, Voets T, Peters, JA. Transient receptor potential cation channels in disease. Physiol Rev 2007; 87: 165-217
7. g) Flockerzi V. An introduction on TRP channels. Hand Exp Pharmacol 2007; 179: 1-19.
8. h) Story GM, Cruz, Orengo L. Feel the burn. Am Sci 2007; 95: 326-333.
9. 2+ signaling. Cell Calcium 2006; 40: 261-75
10. Minke B, Wu C, Pak WL. Induction of photoreceptor voltage noise in the dark in Drosophila mutant. Nature 1975; 258: 84-7.
11. a) Clapham DE. TRP channels as cellular sensors. Nature 2003; 426: 517-23.
12. b) Ramsay IS, Delling M, Clapham DE. An introduction to TRP channels. Annu Rev Physiol 2006; 68: 619-47.
13. Jeske NA. Patwardhan AM, Gamper N, Price TJ, Akopian AN, Hargreaves KM. Cannabinoid WIN 55,212-2 regulates TRPV1 phosphorylation in sensory neurons. J Biol Chem 2006; 281: 32879-90.
14. De Petrocellis L, Starowicz K, Moriello AS, Vivese M, Orlando P, Di Marzo V. Regulation of transient receptor potential channels of melastatin typ8 (TRPM8) effect of cAMP, cannabinoid CB(1) receptors and endovanilloids. Exp Cell Res 2007; 313; 1911-20.
15. Benedikt J, Teisinger J, Vyklicky L, Vlachova V. Ethanol inhibits cold-menthol receptor TRPM8 by modulating its interaction with membrane phosphatidylinositol 4,5-bisphosphate. J Neurochem 2007; 100: 211-24
16. Kung C. A possible unifying principle for mechanosensation. Nature 2005; 436: 647-54.
17. Suchya TM, Tape SE, Koeppe RE, Andersen OS, Sachs F, Gottlieb PA. Bilayer-dependent inhibition of mechanosensitive channels by neuroactive peptide enantiomers. Nature 2004; 430: 235-40.
18. The merging of heat, cold and touch into only one sense has long been debated in philosophy, and is known in physiology as somato-sensation. In this context, it is interesting to quote Linus Pauling "I remember reading a book on philosophy in which the author went on, page after page, on the question: If there is a leaf on a tree and you see that it is green in the springtime and red in the fall, is that the same leaf or is it a different leaf? Is the essence of leafness still in it? Words, words, words, but "chlorophyll" and "xanthophyll" - which are sensible in this connection of what has happened to that leaf - just do not appear at all." (quoted in Roesky HW, Moeckel K. Chemical Curiosities, Weinheim, Wiley-VCH, 1996; 183).
19. Cortright DN, Krause JE, Broom DC. TRP channels and pain. Biochim Biophys Acta Mol Bas Dis 2007; 1772: 978-88
20. Prevarskaya N, Zhang L, Barritt G. TRP channels in cancer. Biochim Biophys Acta Mol Bas Dis 2007; 1772: 937-46.
21. a) Chahl LA. TRP's links to schizophrenia? Biochim Biophys Acta Mol Bas Dis 2007; 1772: 968-77.
22. b) Yamamoto S, Wajima T, Hara Y, Nishida Mori Y. Transient receptor potential channels in Alzheimer disease, Biochim Biophys Acta Mol Bas Dis 2007; 1772: 958-67.
23. Calixto JB, Kassuya CA, Andre E, Ferreira J. Contribution of natural products to the discovery of the transient receptor potential (TRP) channels family and their functions. Pharmacol Ther 2005; 106: 179-208.
24. Caterina MJ, Schumacher MA, Tominaga M, Rosen TA, Levine JD, Julius D. The capsaicin receptor: A heat-activated ion channel in the pain pathway. Nature 1997; 389: 816-24.
25. For a review on the history, chemistry and biochemistry of capsaicin, see: Appedino G. In: Fattorusso E, Taglialatela-Scafati O Eds, Modern alkaloids. Structure, isolation, synthesis and biology. Weinbeim, Wiley-VCH 2007; 75-112.
26. Szolcsányi J, Jancsó-Gábor A. Sensory effects of capsaicin congeners I. Relationship between chemical structure and pain-producing potency of pungent agentg. Arzneimittelforschung 1975; 25: 1877-81.
27. Hensel H, Zotterman Y. The effect of menthol on the thermoreceptors Physiol Scand 1951; 24: 27-34.
28. Hergenhahn M, Adolf W, Hecker, E. Resiniferatoxin and other esters of novel pulyfunctional diterpenes from Euphorbia resinifera and unispina. Tetrahedron Lett 1975; 19: 1595-8.
29. Adolf W, Sorg B, Hergenhahan M, Hecker E. Structure-activity relations of polyfunctional diterpenes of the daphanane type. I. Revised structure for resiniferatoxin and structure-activity relations of resiniferonol and some of its esters. J Nat Prod 1982; 45: 347-54.
30. Szallasi A, Blumberg PM. Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper. Neuroscience 1989; 30: 515-20.
31. For a discussion see: Szallasi A, Appendino G. Vanilloid receptor TRPV1 antagonist as the next generation of painkillers. Are we putting the cart before the horse? J Med Chem 2004; 47: 2717-23.
32. Urban L, Dray A. Capsazepine, a novel capsaicin antagonist, selectively antagonizes the effects of capsaicin in the mouse spinal cord in vitro. Neurosci Lett 1991; 134: 9-11.
33. Major reviews published in the first half of 2007: A) Szallasi A, Cortright DN, Blum CA, Eid SR: The vanilloid receptor TRPV1: 10 years from channel cloning to antagonist proof-of-concept. Nat Rev Drug Discov 2007; 6: 357-72.
34. b) Westaway SM. The potential of transient receptor potential vanilloid type 1 channel modulators for the treatment of pain. J Med Chem 2007; 50: 2589-96.
35. c) Liddle RA. The role of transient receptor potential vanilloid 1 (TRPV1) channels in pancreatitis. Biochim Piophys Acta 2007; 1772: 869-78.
36. d) Ma W, Quirion R. Inflammatory mediators modulating the transiet receptor potential vanilloid 1 receptor: Therapeutic targets to treat inflammatory and neuropathic pain. Expert Opin Ther Targets 2007: 11: 307-20.
37. e) Pingle SC, Matta JA, Ahern GP. Capsaicin receptor TRPV1 a promiscuous TRP channel. Handb Exp Pharmacol 2007; 179: 155-71.
38. Zhang LL, Yan Liu D, Ma LQ, Luo ZD, Cao TB, Zhong J, et al. Activation of transient receptor potential vanilloid tyupe-1 channel prevents adipogenesis and obesity. Circ Res 2007; 100: 1063-70.
39. Dinis P, Charrua A, Avelino A, Nagy I, Quintas J, Ribau U, et al. The distribution of sensory fibers immunoreactive for the TRPV1 (capsaicin) receptor in the human prostate. Eur Urol 2005; 48: 162-7
40. Sánchez AM, Sánchez MG, Malagarie-Cazenave S, Olea N, Diaz-Laviada L. Induction of apoptosis in prostate tumor PC-3 cells and inhibition of xenograft prostate tumor growth by the vanilloid capsaicin. Apoptosis 2006; 11: 89-99.
41. Nilius B, Mahieu F, Karashima Y, Voets T. Regulation of TRP channels: A voltage-lipid connection. Biochem Soc Trans 2007; 35: 105-8.
42. Lishko PV, Procko E, Jin X, Phelps CB, Gaudet R. The ankyrin repeats of TRPV1 bind multiple ligands and modulate channel sensitivity. Neuron 2007; 54: 905-18.
43. Gilbert D, Funk K, Dekowski B, Lechler R, Keller S, Möhrlen F, et al. Caged capsaicins: New tools for the examination of TRPV1 channels in somatosensory neurons. Chembiochem 2007; 8: 89-97.
44. Appendino G, Daddario N, Minassi A, Moriello AS, De Petrocellis L, Di Marzo V. The taming of capsaicin. Reversal of vanilloid activity of N-acylvanillamines by aromatic iodimation. J Med Chem 2005; 48: 4663-9.
45. Wahl P, Foged C, Tullin S, Thomsen C. Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist. Mol Pharmacol 2001; 59: 9-15.
46. Endres-Becker J, Heppenstall PA, Mousa SA, Labuz D, Oksche A, Schäfer M, et al. Mu-opioid receptor activatian modulates transient receptor potential vanilloid 1 (TRPV1) currents in sensory neurons in a model of inflammatory pain. Mol Pharmacol 2007; 71: 12-8
47. Starowicz K, Nigam S, Di Marzo V. Biochemistry and pharmacology of endovanilloids. Pharmacol Ther 2007; 114: 13-33.
48. Di Marzo V, Bisogno T, De Petrocellis L. Endocannabinoids and related compounds: Walking back and forth between plant natural products and animal physiology. Chem Biol 2007; 14: 741-56.
49. Saghatelian A, McKinney MK, Bandell M, Patapoutian A, Cravatt BF. A FAAH-regulated class of N-acyl taurines that activates TRP ion channels. Biochemistry 2006; 45: 9007-15.
50. O'Dell DK, Rimmerman N, Pickens SR, Walker JM. Fatty acyl amides of endogenous tetrahydroisoquinolines are active at the recombinant human TRPV1 receptor. Bioorg Med Chem Lett 2007; 15: 6164-69.
51. Maione S, De Petrocellis L, de Novellis V, Moriello AS, Petrosino S, Palazzo E et al. Analgesic actions of N-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors. Br J Pharmacol 2007; 150: 766-81.
52. Högestätt ED, Jönsson BA, Ermund A, Andersson DA, Bjork H, Alexander JP, et al. Conversion of acetaminophen to the bioactive N-acylphenolamine AM404 via fatty acid amide hydrolase dependent arachidonic acid conjugation in the nervous system. J Biol Chem 2005; 280: 31405-12.
53. Kilaru A, Blancaflor EB, Venables BJ, Tripathy S, Mysore KS Chapman KD. The N-acylethanolamine-mediated regulatory pathway in plants. Chem Biodiv 2007; 4: 1933-55.
54. Chen SC, Chang TJ, Wu FS. Competitive inhibition ot the capsaicin receptor-mediated current by dehydroepiandrosterone in rat dorsal root ganglion neurong. J Pharmacol Exp Ther 2004; 311: 529-36.
55. Szallasi A, Biró T, Modarres S, Garlaschelli L, Petersen M, Klusch A, et al. Dialdehydes sesquiterpenes and other terpenoids as vanilloids. Eur J Pharmacol 1998; 356: 81-9.
56. Sterner O, Szallasi A. Novel natural vanilloid receptor agonists: New therapeutic targets for drug development. Trends Pharmacol Sci 1999; 20: 459-65.
57. André E, Campi B, Trevisani M, Ferreira J, Malheiros A, Yunes RA, et al. Pharmacological characterization of the plant sesquiterpenes polygodial and drimenal as vanilloid receptor agonists. Biochem Pharmacol 2006; 71: 1248-54.
58. Perry NB, Foster LM, Lorimer SD. Infraspecific variation of insecticidal sesquiterpene dialdehydes in Pseudowintera colorata. Phytochemistry 1996; 43: 1201-3.
59. Kobayashi Y, Nakano Y, Kizaki M, Hoshikuma K, Yokoo Y, Kamiya T, Capsaicin-like anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist. Planta Med 2001; 67: 628-33.
60. Pearce LV, Petukhov PA, Szabo T, Kedei N, Bizik F, Kozikowski AP, et al. Evodiamine functions as an agonist for the vanilloid receptor TRPV1. Org Biomol Chem 2004; 2; 2281-6.
61. Kan SF, Huang WJ, Lin LC, Wang PS. Inhibitory effects of evodiamine on the growth of human prostate cancer cell line LNCaP. In J Cancer 2004; 110: 641-51.
62. Wang C, Wang MW, Tahisro S, Onodera S, Ikejima T. Evodiamine induced human melanoma A375-S2 cell death partially through interleukin 1 mediated pathway. Biol Pharm Bull 2005; 28: 984-9.
63. Wang HP, Pu XY, Wang, XH. Distribution profiles of transient receptor potential melastatin-related and vanilloid-related channels in prostatic tissue in rat: Asian J Androl 2007; 9: 634-40.
64. Bodó E, Biró T, Telek A, Czifra G, Griger Z, Tóth BI, et al. A hot new twist to hair biology: Involvement of vanilloid receptor-1 (VR1/TRPV1) signaling in human hair growth control. Am J Pathol 2005; 166: 985-98.
65. Brand L, Berman E, Schwen R, Loomans M, Janusz J, Bolme R, et al. NE-19550: A novel, orally active anti-inflammatory analgesic. Drugs Exp Clin Res 1987; 13: 159-65.
66. Kobata K, Kobayazhi M, Kinpara S, Watanabe T. Supercritical CO2 as a reaction medium for synthesis of capsaicin analogues by lipase catalyzed transacylation of capsaicin. Biotechnol Lett 2003; 25: 1575-8.
67. Glaser ST, Abumrad NA, Fatade F, Kaczocha M, Studholme KM, Deutsch DG. Evidence against the presence of an anandamide transporter. Proc Natl Acad Sci USA 2003; 100: 4269-74.
68. Lazar J, Braun DC, Tóth A, Wang Y, Pearce LV, Pavlyukovets VA, et al. Kinetics of penetration influence the apparent potency of vanilloids on TRPV1. Mol Pharmacol 2006; 69: 1166-73.
69. Kobata K, Sutoh K, Todo T, Yazawa S, Iwai K, Watanabe T. Nordihydrocapsiate, a new capsinoid from the fruits of a nonpungetn pepper, Capsicum annum. J Nat Prod 1999; 62: 335-6.
70. Ohnuki K, Haramizu S, Oki K, Watanabe T, Yazawa S, Fushiki T. Administrition of capsiate, a non pungent capsaicin analog, promotes energy metabolism and suppresses body fat accumulation in mice. Biosci Biotechnol Biochem 2001; 65: 2735-40.
71. Macho A, Lucena C, Sancho R, Daddario N, Minassi A, Muñoz, et al. Non-pungent capsaicinoids from sweet pepper. Synthesis and evaluation of the chemopreventive and anticancer potential. Eur J Nutr 2003; 42: 2-9.
72. Appendino G, Minassi A, Daddario N, Bianchi F, Tron GC. Chemoselective esterification of phenolic acids and alcohols. Org Lett 2002; 4: 3839-41.
73. 1Fe-NTA. Free Radic Res 2005; 39: 1155-62.
74. Szallasi A. Piperine: Researchers discover new flavor in an ancient spice. Trends Pharmacol Sci 2005; 26: 437-9.
75. McNamara FN, Randall A, Gunthorpe MJ. Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1). Br J Pharmacol 2005; 144: 781-90.
76. Lin Z, Hoult JR, Bennett DC, Raman A. Stimulation of mouse mclanocyte proliferation by Piper nigrum fruit extract and its main alkaloid, piperine. Planta Med 1999; 65: 600-3.
77. Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci 2005; 25: 8924-37.
78. Moqrich A, Hwang SW, Earloey TJ, Petrus MJ, Murray AN, Spencer KS, et al. Impaired thermosensation in mice lacking TRPV3, a heat and camphor sensor in the skin. Science 2005; 307: 1468-72.
79. Yang BH, Piaqo ZG, Kim YB, Lee CH, Lee JK, Park K, et al. Activation of vanilloid receptor 1 (VR1) by eugenol. J Dent Res 2003; 82: 781-5.
80. Park CK, Li HY, Yeon KY, Jung SJ. Choi SY, Lee SJ, et al. Eugenol inhibits sodium currents in dental afferent neurons. J Dent Res 2006; 85: 900-4.
81. Xu H, Delling M, Jun JC, Clapham DE. Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels. Nat Neurosci 2006; 9: 628-35.
82. Chrubasik S, Pittler MH, Roufogalis BD. Zingiberis rhizoma: A comprehensive review on the ginger effect and efficacy profiles. Phytomedicine 2005; 12: 684-701.
83. Iwasaki Y, Morita A, Iwasawa T, Kobata K, Sekiwa Y, Morimitsu Y, et al. A nonpungent component of steamed ginger -[10] shogaol- increases adrenalina secretion via the activation of TRPV1. Nutr Neurosci 2066; 9: 169-78.
84. Siemens J, Zhou S, Piskorowski R, Nikai T, Lumpkin EA, Basbaum AI, et al. Spider toxin activate the capsaicin receptor to produce inflammatory pain. Nature 2006; 444: 208-12.
85. Kitaguchi T, Swartz KJ. An inhibitor of TRPV1 channels isolated from funnel Web spider venom. Biochemistry 2005; 44:155544-9.
86. Block E, Deorazio R. Chemistry in a salad bowl: Comparative organosultur chemistry of garlic, onion and shiitake. Pure Appl Chem 1994; 66; 2205-6.
87. Jacobs C. A scent of therapy: Pharmacological implications of natural products containing redox-active sulfur atoms. Nat Prod Rep 2006; 23: 851-63.
88. Hinman A, Chuang H, Bautista DM, Julius D. TRP channel activation by reversibile covalent modification. Proc Natl Acad Sci USA 2006; 103: 19564-8.
89. a) Jordt SE, Bautista, DM, Chuang HH, McKemy DD, Zygmunt PM, Högestatt ED, et al. Mustard oils and cannabinoids excite sensory nerve fibres through the TRP channel ANKTM1 Nature 2004; 427: 260-5.
90. b) Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TF, et al. ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell 2003: 112: 816-29.
91. Yasumoto T. The chemistry and biological function of natural marine toxins. Chem Rec 2001; 1: 228-42.
92. E, Yanagihara A, Rianier JD, Tytgat J. TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning. Biochem Biophys Res Commun 2007; 361: 214-7.
93. Cuypers E, Yanagihara A, Karlsson E, Tytgart J. Jellyfish and other enidarian envenomations cause pain by affecting TRPV1 channels. FEBS Lett 2006; 580: 5728-32.
94. Bisogno T, Hanus L, De Petrocellis L, Teltilibon S. Ponde DE, Brandi I, et al. Molecular targets for cannabidiol and its synthetic analogues: Effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis anandamide. Br J Pharmacol 2001; 134: 845-52
95. Pertwee R.G. The diverse CB(1) and CB(2) receptor pharmacology of three plant cannabinoids. Delta(9)-tetrahydrocannabinol, cannabidiol and Delta(9)-tetrahydrocannabivarin. Bri J Pharmacol 2007; (in press).
96. Toth A, Kedei N, Szabo T, Wang Y, Blumberg PM, Thapsigargin binds to and inhibits cloned vanilloid receptor-1. Biochem Biophys Res Conmmun 2002; 293: 777-82.
97. Vieira C, Evangelista S, Cirillo R, Terracciano, R, Lippi A, Maggi CA, et al. Antinociceptive activity of ricinoleic acid, a capsaicin like compound devoid of pungent properties. Eur J Pharmacol 2000; 407: 109-16.
98. Appendino G, De Petrocellis L, Trevisani M, Minassi A, Daddario N, Moriello AS, et al. Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential. J Pharm Exp Ther 2005; 312; 561-70.
99. Szallasi A, Biró T, Szabó T, Modarres S, Petersen M, Klusch A, et al. A non-pungent triprenyl phenol of fungal origin, scutgeral stimulates rat dorsal root ganglion neurons via interaction at vanilloid receptor. Br J Pharmacol 1999; 126: 1351-8
100. Vogt-Eisele AK, Weber K, Sherkheli MA, Vielhavebr G, Panten J, Gisselmann G, et al. Monoterpenoid igonists of TRPV3. Br J Pharmacol 2007; 151: 530-40.
101. Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Pgapoutian A, Story GM. More than cool: Promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci 2006; 32: 335-43.
102. Plant TD, Strotmann R. TRPV4. Handb Exp Pharmacol 2007; 179: 189-205.
103. Watanabe H, Vriens J, Prenen J, Droogmans G, Voets T, Nilius B. Anandamide and arachidonic acid use epoxyeicosatrienoic acids to activated TRPV4 channels. Nature 2003; 424: 434-8.
104. Watanabe H, Davis JB, Smart D, Jerman JC, Smith GD, Hayes P, et al. Activation of TRPV4 channels (hVRL-2/mTRP12) by phorbol derivatives. J Biol Chem 2002; 277: 13569-77.
105. Appendino G, Bertolino A, Minassi A, Annunziata R, Szallasi A, De Petrocellis L, et al. Synthesis and biological evaluation of phorbol-resiniferatoxin (RTX) hybrids. Eur J Org Chem 2004; 3413-21.
106. Vriens J, Owsianik G, Janssens A, Voets T, Nilius B. Determinants of 4alfa-phorbol sensitivity in transmembrane domains 3 and 4 of the cation channel TRPV4. J Biol Chem 2007; 282: 12796-803.
107. Samy PP, Thwin MM, Gopalakrishnakone P. Phytochemistry, pharmacology and clinical use of Andrographys paniculata. Nat Prod Commun 2007; 2: 607-18.
108. Smith PL, Maloney KN, Pothen RG, Clardy J, Clapham DE. Bisandrographolic from Andrographys paniculata activates TRPV4 channels. J Biol Chem 2006; 281: 29897-904.
109. a) Peier AM Moqrich A, Hergarden AC, Reeve AJ, Andersson DA, Story GM, et al. A TRP charmel that senses cold stimuli and menthol. Cell 2002; 108: 705-15.
110. b) McKemy DD, Neuhausser WM, Julius D. Identification of a cold receptor reveals a general role for TRP channels in thermosensation. Nature 2002; 416: 52-8.
111. Tsavaler. L, Shapero MH, Morkowski S, Laus R. Trp-p8, a novel prostate-specific gene, is up-replated in prostate cancer and other malignancies and shares high homology with transient receptor potential calcium channel proteins. Cancer Res 2001; 61: 3760-69.
112. Zhang L, Barritt GJ. Evidence that TRPM8 is an androgen-dependent Ca2+ channel required for the survival of prostate cancer cells. Cancer Res 2004; 64: 8365-73.
113. Velazco MI, Wuensche L, Deladoey P. Use of cubebol as a flavoring ingredient. United States Patent 6, 214788, April 10, 2001.
114. Hopp R, Menthol: Its origins, chemistry, physiology and toxicological properties. Rec Adv Tobacco Science 1993; 19: 3-46.
115. Watson HR, Hems R, Rowsell DG, Spring DJ. New compounds with menthol cooling effect. J Soc Cosmet Chem 1978; 29: 185-200.
116. Beck B, Bidaux G, Bavencoffe A, Lemonnier L, Thebault S, Shuba Y, et al Prospects for prostate cancer imaging and therapy using high-affinity TRPM8 activators. Cell-Calcium 2007; 41: 285-94.
117. Karashima Y, Damann N, Prenen J, Talavera K, Segal A, Voets T, et al, Bimodal action of menthol on the transient receptor potential channel TRPA1 J Neurosci 2007; 27: 9874-84.
118. Beherndt HJ, Germann T, Gillen C, Hatt H, Jostock R. Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging Plate reader (FLIP) assay. Br J Pharmacol 2004; 141: 737-45.
119. Sawada Y, Hosokawa H, Hori A, Matsumura K, Kobayashi S. Cold sensitivity of recombinant TRPA1 channels. Brain Res 2007; 1160: 39-46.
120. Cuaijungco MP, Grimm C, Heller S. TRP Channels as candidate for hearing and balance abnormalities in vertebrates. Biochim Biophys Acta 2007; 1772: 1022-7.
121. Corey DP. What is the hair cell transduction channel? J Physiol 2006; 576: 23-8
122. Bautista DM, Jordt SE, Nikai T, Tsuruda PR, Read AJ, Poblete J, et al. TRPA1 mediates the inflammatory actions of environmental irritants and proalgesic agents. Cell 2006; 124: 1123-5.
123. McNamara CR, Mandel-Brehm J, Bautista DM, Siemens J, Deranian KL, Zhao M, et al. TRPA1 mediates formalin-induced pain. Proc Natl Acad Sci USA 2007; 404:13525-30.
124. Trevisani M, Siuernens J, Materazzi S, Bautista DM, Nassini R, Campi B, et al. 4-Hydroxynonenal, and endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1. Proc Natl Acad Sci USA 2007; 104: 13519-24.
125. Macpherson LJ, Dubin AE, EvnasMJ, Marr F, Schultz PG, Cravatt BF, et al. Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines. Nature 2007, 445: 541-5.
126. Ohita T, Imagawa T, Ito S. Novel agonistic action of mustard oil on recombinant and endogenous porcine transient receptor potential VI (pTRPV1) channels. Biochem Pharmacol 2007; 73: 1646-56.
127. Halkier Barn Gershenzon J. Biology and biochemistry of glucosinolates. Annu Rev Plant Biol 2006; 57: 303-33
128. It is interesting to remark that the composition of cinnamon oil depends on the plant organ under consideration. Cinnamaldehyde is the major consituents of the bark oil, while eugenol prevails in the leaves oil, and camphor in the root-bark oil. (Wijesekera RO. Historical overview of the cinnamon industry. CRC Crit Rev Food Sci Nutr 1978; 10: 1-30). These primary constituents are all TRP ligands, and so cinnamon qualifies as the archetypal TRP-plant!
129. Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, et al. Noxious cold ion channel TRPAI is activated by pungetn compounds and bradykinin. Neuron 2004; 41: 849-57.
130. Kaske S, Krasteva G, Koenig P, Kummer W, Hofmman T, Gudermann T, Chubanov V, et al. TRPM5, a taste-signalling transient receptor potential ion-channel, is a ubiquitous signaling component in chemosensory cells. BMC Neurosci 2007; 8: 49.
131. Rozin P, Shenker J. Liking oral cold and hot irritant sensations: specificity to type of irritant and locus of stimulation. Chem Senses 1989; 14: 771-9.
132. Lyall V, Heck GL, Vinnikova AK, Ghosh S, Phan TH, Alam RI, et al. The mammalian amiloride - insensitive non-specific slat taste receptor is a vanilloid receptor-1 variant. J Physiol 2004; 558: 147-159.
133. Riera CE, Vogel H, Simon SA, le Coutre J. Artificial sweeteners and salts peroducing a metallic taste sensation activate TRPVI receptors. Am J Physiol Regul Integr Comp Physiol 2007; 293: R626-34.
134. Kuhn C, Bufe B, Winning M, Hofmann T, Frank O, Behrens M, et al. Bitter taste receptors for saccharin and acesulfame K. J Neurosci 2004; 24: 10260-5.
135. Trevisani M, Smart D, Gunthorpe MJ, Tognetto M, Barbieri M, Campi B, et al. Ethanol elicits and potentiates nociceptor responses via the vanilloid receptor-1. Nat Neurosci 2002; 5: 546-51.
136. Geppetti P, Materazzi S, Nicoletti P. The transient receptor potential vanilloid-1. Role in airway inflammation and disease. Eur J Pharmacol 2006; 533: 207-14.
137. Talavera K, Yasumatsu K, Voets T, Droogmans G, Shigemura N, Ninomiya Y, et al. Heat activation of TRPM5 underlies sensitivity of sweet taste. Nature 2005; 438: 1022-25.
138. Fonfria E, Murdock PR, Cusdin FS, Benham CD, Kelsell RE, McNulty S. Tissue distribution profiles of the human TRPM cation channel family. J Recept Signal Transduct Res 2006; 26: 159-78.
139. Jang HJ, Kokrashvili Z, Theodorakis MJ, Carlson OD, Kim BJ, Zhou J, et al. Gut-expressed gustducin and taste receptors regulate secretion of glucagon-like peptide-1. Proc Natl Acad Sci USA 2007; 104: 15069-74.
140. In this context, it is interesting to note that the apoptotic properties of capsaicin, traditionally attributed to a direct interaction with mitochandrial membranes, have now been suggested to be mediated by interaction with a specific TRPs TRPV6 (Chow J, Nomg M, Zhang J, Chai J. TRPV6 mediates capsaicin-induced apoptosis in gastric cancer cells. Mechanisms behind a possible new "hot" cancer treatment. Biochem Biophys Acta 2007; 1773: 565-76).
141. Culshaw AJ, Bevan S, Christianserf M, Copp P, Davis A, Davis C, et al. Identification and biological characterisation of 6-aryl-7-isoprpylquinazolinones as novel TRPV1 antagonists that are effective in models of chronic pain. J Med Chem 2006; 49: 471-4.
142. Newman DJ, Cragg GM. Natural products as sources of new drugs over the last 25 years. J Nat Prod 2007; 70; 461-77, and references therein.
143. Abbott GW. Molecular mechanisms of cardiac voltage-gated potassium channelopathies. Curr Pharm Des 1006; 12(28): 3631-44.
144. Panaghie G, Abbott GW. The impact of ancillary subunits on small-molecule interactions with voltage-gated potassium channels. Curr Pharm Des 2006; 12(18): 2285-302.
145. Roger S, Potier M, Vandier C, Besson P, Le Guennec JY. Voltagegated sodium channels: New targets in cancer therapy? Curr Pharm Des 2006; 12(28): 3681-95.