Hydroxy-''alpha''-sanshool is a molecule found in plants from the genus ''

Zanthoxylum ''Zanthoxylum'' is a genus of about 250 species of deciduous and evergreen trees, shrubs and climbers in the family Rutaceae that are native to warm temperate and subtropical areas worldwide. It is the type genus of the tribe Zanthoxyleae in ...

''. It is believed to be responsible for the numbing and tingling sensation caused by eating food cooked with Sichuan peppercorns and

Uzazi The term Uzazi refers to the dried fruit of the West African deciduous shrub ''Zanthoxylum gilletii'', syn. ''Fagara tessmannii'', a member of the 'prickly ash' ''Zanthoxylum ''Zanthoxylum'' is a genus of about 250 species of deciduous ...

. The term ''sanshool'' in the compound's name is derived from the

Japanese Japanese may refer to: * Something from or related to Japan, an island country in East Asia * Japanese language, spoken mainly in Japan * Japanese people, the ethnic group that identifies with Japan through ancestry or culture ** Japanese diaspor ...

term for the Japanese pepper, (literally, mountain pepper), to which was appended the suffix ''-ol'', indicating an

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

Mechanism

The chemical structure of hydroxy-''alpha''-sanshool is similar to that of

capsaicin Capsaicin (8-methyl-''N''-vanillyl-6-nonenamide) ( or ) is an active component of chili peppers, which are plants belonging to the genus ''Capsicum''. It is a chemical irritant for mammals, including humans, and produces a sensation of burning ...

, but the

mechanism of action In pharmacology, the term mechanism of action (MOA) refers to the specific biochemical interaction through which a drug substance produces its pharmacological effect. A mechanism of action usually includes mention of the specific molecular targe ...

by which it induces nerve sensations has been a matter of debate. Although the compound is an agonist at the pain integration channels

TRPV1 The transient receptor potential cation channel 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. It was the first isolated member of th ...

and

TRPA1 Transient receptor potential cation channel, subfamily A, member 1, also known as transient receptor potential ankyrin 1, TRPA1, or The Wasabi Receptor, is a protein that in humans is encoded by the ''TRPA1'' (and in mice and rats by the ''Trpa1' ...

like capsaicin, newer evidence suggests that the

tandem pore domain potassium channel The two-pore-domain or tandem pore domain potassium channels are a family of 15 members that form what is known as leak channels which possess Goldman-Hodgkin-Katz (open) rectification. These channels are regulated by several mechanisms includin ...

KCNK3 Potassium channel subfamily K member 3 is a protein that in humans is encoded by the ''KCNK3'' gene. This gene encodes K2P3.1, one of the members of the superfamily of potassium channel proteins containing two pore-forming P domains. K2P3.1 is an ...

KCNK9 Potassium channel subfamily K member 9 is a protein that in humans is encoded by the ''KCNK9'' gene. This gene encodes K2P9.1, one of the members of the superfamily of potassium channel proteins containing two pore-forming P domains. This open ch ...

, and

KCNK18 Potassium channel subfamily K member 18 (KCNK18), also known as TWIK-related spinal cord potassium channel (TRESK) or K2P18.1 is a protein that in humans is encoded by the ''KCNK18'' gene. K2P18.1 is a potassium channel containing two pore-formin ...

are primarily responsible for sanshool's effects. Hydroxy-alpha sanshool excites D-hair

afferent nerve fiber Afferent nerve fibers are the axons (nerve fibers) carried by a sensory nerve that relay sensory information from sensory receptors to regions of the brain. Afferent projections ''arrive'' at a particular brain region. Efferent nerve fibers a ...

s, a distinct subset of the sensitive light touch receptors in the skin, and targets novel populations of Aβ and C-fiber nerve fibers.

Extraction

To isolate the molecule from the pepper in form of an extract, steam distillation can be used: Dried peels of the fruit are immersed in a mixture of lower alcohols (for example ethanol) and water with a mass percentage between 35% and 65% of the alcohol. The solution gets heated up in the process of steam distillation where the aqueous part evaporates and takes parts of the hydroxy-alpha- sanshool up, too. The distillate separates in two phases: the aqueous ethanol phase and the oil phase which contains the desired molecule. Steam distillation extraction methods demonstrate yields of approximately 60%.

References

{{DEFAULTSORT:Hydroxy Alpha Sanshool Fatty acid amides Tertiary alcohols Polyenes

Mechanism

Extraction

See also

References