Vanilloid Explained

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.

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 .^[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]

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]

Literature

• Lee . Jeewoo . Uk Kang . Sang . Yeon Kim . Su . Eun Kim . Sung . Joon Jo . Yeong . Kim . Sunghoon . 2001 . Vanilloid and Isovanilloid Analogues as Inhibitors of Methionyl-tRNA and Isoleucyl-tRNA Synthetases . . 11 . 8 . 965–968 . 10.1016/S0960-894X(01)00096-8 . 11327601 .

Notes and References

1. Book: Pingle . SC . Matta . JA . Ahern . GP . Capsaicin receptor: TRPV1 a promiscuous TRP channel . 179 . 179 . 155–171 . 2007 . 17217056 . 10.1007/978-3-540-34891-7_9 . Handbook of Experimental Pharmacology . 978-3-540-34889-4 .
2. Van Der Stelt M, Di Marzo V. Endovanilloids. Putative endogenous ligands of transient receptor potential vanilloid 1 channels. . Eur J Biochem . 2004 . 271 . 10 . 1827–34 . 15128293 . 10.1111/j.1432-1033.2004.04081.x . free .
3. Hamers A, Primus CP, Whitear C, Kumar NA, Masucci M, Montalvo Moreira SA . etal. 20-hydroxyeicosatetraenoic acid (20-HETE) is a pivotal endogenous ligand for TRPV1-mediated neurogenic inflammation in the skin. . Br J Pharmacol . 2022 . 179 . 7 . 1450–1469 . 34755897 . 10.1111/bph.15726 . 243939400. free .
4. De Petrocellis L, Chu CJ, Moriello AS, Kellner JC, Walker JM, Di Marzo V. Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels. . Br J Pharmacol . 2004 . 143 . 2 . 251–6 . 15289293 . 10.1038/sj.bjp.0705924 . 1575334 .
5. 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 . en . 107 . 49–57 . 10.1016/j.neuropharm.2016.03.007 . 26965218 . 0028-3908.
6. Book: Carlson. Neil R.. Birkett. Melissa A.. Physiology of Behavior. 2017. Pearson. 9780134320823. 212. 12.