Quantitative Analysis of Sanshool Compounds in Japanese Pepper (<i>Xanthoxylum piperitum</i>DC.) and Their Pungent Characteristics

Sugai, Etsuko; Morimitsu, Yasujiro; Kubota, Kikue

doi:10.1271/bbb.69.1958

Cited by 53 publications

(42 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Szechuan pepper extracts also contain hydroxy-β-sanshool, but this isomer plays a minor role in eliciting the tingling psychophysical effects of Xanthoxylum plants 10 . Indeed, we found that application of hydroxy-β-sanshool (100 μM-1 mM) did not excite sensory neurons ( Supplementary Fig.…”

Section: Sanshool Targets Members Of the Kcnk K + Channel Familymentioning

confidence: 99%

“…In contrast to the intense, burning pain associated with 'hot' chili peppers of the Capsicum family, Szechuan peppers elicit a wholly unique sensation that is best described as a tingling paresthesia or numbing 9,10 , suggestive of an interaction with neurons involved in tactile sensation and innocuous touch 11 . Hydroxy-α-sanshool (sanshool) is the active ingredient in Szechuan peppers, and although there has been some preliminary analysis of its effects on cultured sensory neurons 9,11,12 , its cellular and molecular site of action remains enigmatic.…”

mentioning

confidence: 99%

“…For example, sanshool was initially proposed to activate subsets of primary afferent fibers that respond to cooling, heat or light touch 11 , whereas a more recent study suggests that most, if not all, sensory neurons respond to sanshool. Furthermore, two studies reach different conclusions as to the involvement of specific molecular targets, most notably the capsaicin receptor (TRPV1), in this response 10,12 .…”

mentioning

confidence: 99%

See 2 more Smart Citations

Pungent agents from Szechuan peppers excite sensory neurons by inhibiting two-pore potassium channels

et al. 2008

View full text Add to dashboard Cite

In traditional folk medicine, Xanthoxylum plants are referred to as 'toothache trees' because their anesthetic or counter-irritant properties render them useful in the treatment of pain. Psychophysical studies have identified hydroxy-α-sanshool as the compound most responsible for the unique tingling and buzzing sensations produced by Szechuan peppercorns or other Xanthoxylum preparations. Although it is generally agreed that sanshool elicits its effects by activating somatosensory neurons, the underlying cellular and molecular mechanisms remain a matter of debate. Here we show that hydroxy-α-sanshool excites two types of sensory neurons, including small-diameter unmyelinated cells that respond to capsaicin (but not mustard oil) as well as large-diameter myelinated neurons that express the neurotrophin receptor TrkC. We found that hydroxy-α-sanshool excites neurons through a unique mechanism involving inhibition of pH-and anesthetic-sensitive two-pore potassium channels (KCNK3, KCNK9 and KCNK18), providing a framework for understanding the unique and complex psychophysical sensations associated with the Szechuan pepper experience.Somatosensation, or the sense of touch, is the process whereby we detect changes in ambient temperature or pressure. This sensory modality is mediated by subsets of primary afferent neurons that detect chemical, thermal or mechanical stimuli over a range of stimulus intensities. Generally speaking, pain-producing (noxious) stimuli are detected by neurons (referred to as nociceptors) that have small-to medium-diameter somata that correspond to unmyelinated C and lightly myelinated Aδ nerve fibers. In contrast, innocuous stimuli, such as light touch, are detected by large-diameter neurons corresponding to more heavily Reprints and permissions information is available online at

show abstract

Section: Sanshool Targets Members Of the Kcnk K + Channel Familymentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Pungent agents from Szechuan peppers excite sensory neurons by inhibiting two-pore potassium channels

et al. 2008

View full text Add to dashboard Cite

show abstract

“…Sanshools, linear polyunsaturated fatty acid amides, are the major contributors to the characteristic taste of this plant (Yasuda et al, 1982). To date, about 50 compounds in this structural class have been isolated from various species of the genus Zanthoxylum and related plants (Yasuda et al, 1980;Mizutani et al, 1988;Xiong et al, 1997;Sugai et al, 2005). Linear polyunsaturated fatty acid amide metabolites exhibit antioxidant activities, modulatory effects on relaxing the circle muscle of the gastric body, and anthelmintic properties (Navarrete and Hong, 1996;Hashimoto et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

New polyunsaturated fatty acid amides isolated from the seeds of Zanthoxylum piperitum

et al. 2008

View full text Add to dashboard Cite

Five linear fatty acid amides (1-5) of the sandshool class, including two new compounds, were isolated from Zanthoxylum piperitum seeds. Based on combined spectral analyses, the structures of new compounds 4 and 5 were determined to be 2',3'-dihydroxy-alpha-sanshool and 2',3'-dihydroxy-beta-sanshool, respectively. These compounds exhibited weak cytotoxicity in the A-549 (human lung cancer) cell line.

show abstract

“…This result supports the finding that MN-I and MNK-III taste exceptionally pungent and sweet because of their large contents of cinnamaldehyde. In addition, various component analyses of Cinnamomum cassia [17][18][19] indicated that major natural pungent compounds, such as capsaicin (Hot pepper) [20], piperine (Pepper) [21], a-sanshool (Japanese pepper) [22], 6-gingerol, 6-shogaol (Ginger) [23], tadeonal (Benitade) [24], and allyl isothiocyanate (Wasabi) [25], were not reported. Therefore, the principal source of pungency in Cinnamomi Cortex also seems to be cinnamaldehyde.…”

Section: Discussionmentioning

confidence: 99%

Influence of composition upon the variety of tastes in Cinnamomi Cortex

Yokomi

Ito

2009

J Nat Med

View full text Add to dashboard Cite

Cinnamomi cortex, which is normally referred to as cinnamon, is a very popular spice as well as an important natural medicine. High-quality cinnamon is traditionally believed to taste sweet and be strongly pungent without astringency. Cinnamomi cortex with larger amounts of cinnamaldehyde was sweeter in taste comparisons. The contents of tannins and sugars in cinnamon powder had little effect on the taste. Evaluations of the sweetness and pungency of cinnamaldehyde solutions (0.1, 0.25, 0.50, 0.75, 1.0, and 5.0 mg/ml) were performed using volunteers. The scores for sweetness increased significantly from 0.10 to 0.50 mg/ml (P < 0.05, Mann-Whitney U-test), but there was no significant difference above 0.75 mg/ml. The concentration threshold for the sweet taste of cinnamaldehyde appeared to be less than 0.75 mg/ml, and the more concentrated solutions gave excessive pungency. Therefore, two contrastive tastes of Cinnamomi cortex, sweet and pungent, were both attributed to cinnamaldehyde. Consequently, its taste, one of its indices of quality, seems to vary mainly according to the content of cinnamaldehyde.

show abstract

Quantitative Analysis of Sanshool Compounds in Japanese Pepper (Xanthoxylum piperitumDC.) and Their Pungent Characteristics

Cited by 53 publications

References 11 publications

Pungent agents from Szechuan peppers excite sensory neurons by inhibiting two-pore potassium channels

Pungent agents from Szechuan peppers excite sensory neurons by inhibiting two-pore potassium channels

New polyunsaturated fatty acid amides isolated from the seeds of Zanthoxylum piperitum

Influence of composition upon the variety of tastes in Cinnamomi Cortex

Contact Info

Product

Resources

About