The vanilloids are compounds which possess a vanillyl group. They include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid, homovanillic acid, capsaicin, etc. Isomers are the isovanilloids.
vanillyl alcohol
vanillin
vanillic acid
acetovanillon
Vanillylamine
Capsaicin
A number of vanilloids, most notably capsaicin, bind to the transient receptor potential vanilloid type 1 (TRPV1) receptor, an ion channel which naturally responds to noxious stimuli such as high temperatures and acidic pH.[1] This action is responsible for the burning sensation experienced after eating spicy peppers. Endogenously generated chemicals that trigger the TRPV1 channel of the vanilloids class are referred to as endovanilloids[2] including anandamide, 20-hydroxyeicosatetraenoic acid (20-HETE),[3] N-arachidonoyl dopamine (NADA) and N-oleoyl-dopamine (CID 5282106 from PubChem).[4]
Fatty acid amide hydrolase (FAAH), is a crucial enzyme for endovanilloid, and the N-acylethanolamines (NAEs), catabolism at TRPV1, and other cannabinoid receptors.[5]
Anandamide
Outside the food industry vanilloids such as nonivamide are used commercially in pepper spray formulations.
Other vanilloids which act at TRPV1 include resiniferatoxin and olvanil.[6]
^Pingle, SC; Matta, JA; Ahern, GP (2007). Capsaicin receptor: TRPV1 a promiscuous TRP channel. Handbook of Experimental Pharmacology. Vol. 179. pp. 155–171. doi:10.1007/978-3-540-34891-7_9. ISBN 978-3-540-34889-4. PMID 17217056.
^Van Der Stelt M, Di Marzo V (2004). "Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels". Eur J Biochem. 271 (10): 1827–34. doi:10.1111/j.1432-1033.2004.04081.x. PMID 15128293.
^Hamers A, Primus CP, Whitear C, Kumar NA, Masucci M, Montalvo Moreira SA; et al. (2022). "20-hydroxyeicosatetraenoic acid (20-HETE) is a pivotal endogenous ligand for TRPV1-mediated neurogenic inflammation in the skin". Br J Pharmacol. 179 (7): 1450–1469. doi:10.1111/bph.15726. PMID 34755897. S2CID 243939400.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^De Petrocellis L, Chu CJ, Moriello AS, Kellner JC, Walker JM, Di Marzo V (2004). "Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels". Br J Pharmacol. 143 (2): 251–6. doi:10.1038/sj.bjp.0705924. PMC 1575334. PMID 15289293.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^Silva, M.; Martins, D.; Charrua, A.; Piscitelli, F.; Tavares, I.; Morgado, C.; Di Marzo, V. (2016-08-01). "Endovanilloid control of pain modulation by the rostroventromedial medulla in an animal model of diabetic neuropathy". Neuropharmacology. 107: 49–57. doi:10.1016/j.neuropharm.2016.03.007. ISSN 0028-3908. PMID 26965218.
^Carlson, Neil R.; Birkett, Melissa A. (2017). Physiology of Behavior (12 ed.). Pearson. p. 212. ISBN 9780134320823.
The vanilloids are compounds which possess a vanillyl group. They include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid...
subfamily V member 1 (TRPV1), also known as the capsaicin receptor and the vanilloid receptor 1, is a protein that, in humans, is encoded by the TRPV1 gene...
to nerve fibers causes neuropathic pain. Capsaicin activates C fibre vanilloid receptors, giving chili peppers a hot sensation. C fibers are one class...
thermoregulatory pathways. AM404 activates vanilloid receptors causing vasodilation which is inhibited by the vanilloid receptor antagonist capsazepine. The...
times hotter than pure capsaicin. Resiniferatoxin activates transient vanilloid receptor 1 (TRPV1) in a subpopulation of primary afferent sensory neurons...
Euphorbia poissonii. It is a neurotoxin that acts via full agonism of the vanilloid receptors of sensory nerves. Tinyatoxin has a potential for pharmaceutical...
for hydrophobic interaction with vanilloids. The TM3 region is considered to be necessary for binding to vanilloids. It is surrounded by the hydrophobic...
broad groups: group 1 includes TRPC ( "C" for canonical), TRPV ("V" for vanilloid), TRPM ("M" for melastatin), TRPN and TRPA. In group 2 there are TRPP...
receptors, i.e. CB1 and CB2, beside involvement of transient receptor vanilloid type-1 (TRPV1) channels in the pain modulation, as endovanilloid signalling...
an analog of capsaicin, the primary vanilloid compound found in hot peppers. It can interact with a vanilloid receptor on primary sensory neurons mediating...
is a strong competitive antagonist of the Transient Receptor Potential Vanilloid 1 (TRPV1) receptor. I-RTX is derived from resiniferatoxin (RTX). I-RTX...
the skin. As a member of the vanilloid family, capsaicin binds to a receptor on nociceptor fibers called the vanilloid receptor subtype 1 (TRPV1). TRPV1...
Group 1 includes TRPC ( "C" for canonical), TRPV ("V" for vanilloid), TRPVL ("VL" for vanilloid-like), TRPM ("M" for melastatin), TRPS ("S" for soromelastatin)...
20062201.03. Cameron, K. M.; Dickison, W. C. (1998). "Foliar architecture of vanilloid orchids: Insights into the evolution of reticulate leaf venation in monocots"...
isomers of the vanilloids. Lee, Jeewoo; Uk Kang, Sang; Yeon Kim, Su; Eun Kim, Sung; Joon Jo, Yeong; Kim, Sunghoon (23 April 2001). "Vanilloid and isovanilloid...
the original on 12 October 2013. Retrieved 2 August 2013. Eugenol is a vanilloid contained in relatively high amounts in clove oil from Eugenia caryophyllata...
encoded by the TRPV4 gene. The TRPV4 gene encodes TRPV4, initially named "vanilloid-receptor related osmotically activated channel" (VR-OAC) and "OSM9-like...
calcium homeostasis: regulation of intestinal transient receptor potential vanilloid type 6, intestinal calcium absorption, and the 25-hydroxyvitamin D(3)...
is subdivided into 6 subfamilies based on homology: classical (TRPC), vanilloid receptors (TRPV), melastatin (TRPM), polycystins (TRPP), mucolipins (TRPML)...
anandamide, NADA is also an agonist for the vanilloid receptor subtype 1 (TRPV1), a member of the vanilloid receptor family. A fifth endocannabinoid, virodhamine...
anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist". Planta Medica. 67 (7): 628–33. doi:10.1055/s-2001-17353...
The transmembrane cation channel superfamily was defined in InterPro and Pfam as the family of tetrameric ion channels. These include the sodium, potassium...
11–12. ISBN 978-0-12-397931-5. Ross RA (November 2003). "Anandamide and vanilloid TRPV1 receptors". British Journal of Pharmacology. 140 (5): 790–801. doi:10...
Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether...
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