From Wikipedia, the free encyclopedia
Chemical compounds containing a vanillyl group
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 (
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]
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]
References
-
^ 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.
Literature