+86-28-82633987
Product name: Hydroxy-β-sanshool
Synonym name:
Catalogue No.: BP4107
Cas No.: 97465-69-5
Formula: C16H25NO2
Mol Weight: 263.381
Botanical Source: Zanthoxyli pericarpium
Physical Description:
Type of Compound: Alkaloids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Description:
Hydroxy-β-sanshool is a pungent compound, it can cause oral numbness.
References:
J Agric Food Chem. 2018 Jun 6;66(22):5621-5634.
Dynamic Proteome Alteration and Functional Modulation of Human Saliva Induced by Dietary Chemosensory Stimuli.
METHODS AND RESULTS:
Saliva flow measurements and SDS-PAGE separation of human whole saliva freshly collected after oral stimulation with citric acid (sour), aspartame (sweet), iso-α-acids (bitter), mono sodium l-glutamate (umami), NaCl (salty), 6-gingerol (pungent), hydroxy-α-sanshool (tingling), and Hydroxy-beta-sanshool (numbing), followed by tryptic digestion, nano-HPLC-MS/MS, and label-free protein quantitation demonstrated a stimulus- and time-dependent influence of the dietary chemosensates on salivation and the salivary proteome composition. Gene ontology enrichment analysis showed evidence for stimulus-induced alterations of the saliva proteome to boot an efficient molecular defense network of the oral cavity, e.g., 6-gingerol increased salivary lactoperoxidase activity, catalyzing the oxidation of thiocyanate to produce the antimicrobial and antifungal hypothiocyanate, from 0.37 ± 0.02 to 0.91 ± 0.05 mU/mL 45 s after stimulation. In comparison, oral citric acid stimulation induced an increase of myeloperoxidase activity, catalyzing the chloride oxidation to generate antimicrobial hypochloride in saliva, from 0.24 ± 0.04 to 0.70 ± 0.1 mU/mL as well as an increase of salivary levels of lysozyme, exhibiting antimicrobial activity on Gram-positive bacteria, from 6.0-10 to 100-150 μg/mL.
CONCLUSIONS:
Finally, microbial growth experiments clearly demonstrated for the first time that the increase of the salivary lysozyme abundance upon oral citric acid stimulation translates into an enhanced biological function, that is an almost complete growth inhibition of the two lysozyme-sensitive Gram-positive bacteria tested.
HPLC of Hydroxy-β-sanshool
HNMR of Hydroxy-β-sanshool
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
49.3300
2.5036
2.5031
.1263
1.0974
16.1389
High
75.6296
3.2087
Yes
Yes
Yes
No
No
No
0.0
No
Yes
Yes
Yes
Hydroxy-β β-sanshool is an important class of natural alkylamine compounds, mainly found in Sichuan pepper (Zanthoxylum spp.) and green pepper oil. As one of the main active ingredients in Sichuan pepper's unique spiciness and numbing sensation, hydroxy-β-sanshalogen not only gives Sichuan pepper a distinctive flavor experience but also demonstrates multiple bioactivities in pharmacological research, especially showing significant potential in anti-inflammatory fields. In recent years, with the deepening development of natural product pharmacology, hydroxy-β-sanmatin has become a research hotspot due to its unique molecular structure and multi-target mechanism, attracting widespread attention.
This review aims to systematically summarize the chemical structure and physicochemical properties of hydroxy-β-sanjiadan, plant origins and extraction methods, with a focus on its pharmacological activity and mechanism of action, explore its druggability and pharmacokinetic characteristics, and finally look ahead to its clinical application potential and future research directions, providing comprehensive reference for researchers in related fields.
Hydroxy-β-sanyanjiazine belongs to the alkylamide class of natural products, with a molecular formula of C16H25NO2 and a molecular weight of 263.3810. Its structural features include an alkyl side chain binding to an amide group, while the molecule contains a hydroxyl functional group, giving it specific polarity and biological activity. The compound has a LogP value of 2.5036, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and bioavailability. Its polar surface area (TPSA) is 49.33 Ų, indicating that the molecule has a certain polarity that facilitates binding to biological macromolecule targets.
Hydroxy-β-sanmatin has relatively low water solubility (0.1263 mg/mL), which matches its hydrophobic alkyl chain structure. Notably, this compound has a high ability to penetrate the blood-brain barrier, suggesting its potential to act in the central nervous system. In terms of safety, hydroxy-β-sanshalogen does not show hERG channel inhibitory activity, and Ames-induced mutagenic test results are negative, indicating low potential cardiotoxicity and genotoxicity risks.
Hydroxy-β-sanshalogen is mainly found in Sichuan peppercorn (Zanthoxylum bungeanum Maxim.) and green pepper oil, and is a representative component of various sanshalogen compounds in Sichuan pepper. As a traditional Chinese medicine and seasoning, Sichuan peppercorns are widely distributed in China and East Asia. Its fruits and seeds are rich in volatile oils and non-volatile alkyl amides, with a high content of hydroxy-β-sanphyllacin.
There are various methods for extracting hydroxy-β-sanshaloscaphanin, with common ones including solvent extraction, ultrasound-assisted extraction, and supercritical CO2 extraction. Traditional solvent extraction mostly uses ethanol, methanol, or ethyl acetate as solvents, combined with reflux or ultrasound assistance to improve extraction efficiency. Supercritical CO2 extraction has been widely used in recent years for the extraction of Sichuan pepper oil and its active ingredients, thanks to its excellent selectivity, absence of solvent residues, and environmental friendliness. After extraction, purification is usually performed by column chromatography and preparative high-performance liquid chromatography (prep-HPLC) to obtain high-purity hydroxy-β-sanshaloscaphanin.
The anti-inflammatory activity of hydroxy-β-sanshaloshankan is one of its most notable pharmacological properties. Multiple in vitro and in vivo studies have shown that this compound can significantly inhibit the production of inflammatory mediators and activate inflammatory signaling pathways. Its targets include various inflammation-related factors, including IL-6, TNF-α, NOS2, PTGS1 (COX-1), PTGS2 (COX-2), CASP1 (caspase-1), NFKB1, STAT3, and others.
In macrophage models, hydroxy-β-sanshalogen can inhibit LPS-induced inflammatory factor release, reduce the expression levels of IL-6 and TNF-α, and alleviate inflammatory responses. Additionally, this compound exerts anti-inflammatory effects by regulating the NF-κB and STAT3 signaling pathways, inhibiting the transcriptional activity of pro-inflammatory genes. CASP1 inhibition helps block the activation of inflammasomes, further reducing the release of pro-inflammatory cytokines.
Hydroxy-β-sanphyllaine acts as a regulator of TRPV1 and TRPA1 channels, participating in neural perception and pain transmission processes. TRPV1 and TRPA1 are important ion channels for sensing spiciness and pain. Hydroxy-β-sanshalogen activates or modulates these channels, producing a unique numbing sensation while also providing analgesic and neuroprotective effects. Its high blood-brain barrier penetration supports its potential applications in the central nervous system.
In addition to its anti-inflammatory and neuromodulatory effects, hydroxy-β-sanshalogen also exhibits certain antioxidant activity, scavenging free radicals and reducing oxidative stress damage. Additionally, some studies suggest it may be involved in regulating lipid metabolism and immune responses, but the related mechanisms still require further investigation.
The biological activity of hydroxy-β-sanshaloshanin mainly depends on its regulation of various molecular targets, forming a complex signaling network. Its key mechanisms include:
Inhibition of pro-inflammatory cytokine expression: Hydroxy-β-sanshalogen reduces the release of inflammatory mediators by inhibiting the expression of IL-6 and TNF-α, thereby alleviating inflammatory responses.
Regulating the NF-κB signaling pathway: NF-κB is a core transcription factor in inflammatory responses. Hydroxy-β-sanjiazin exerts anti-inflammatory effects by blocking NF-κB activation and suppressing the transcription of pro-inflammatory genes.
Blocking the STAT3 signaling pathway: STAT3 is involved in cell proliferation and inflammatory responses. Hydroxy-β-sanshalogen regulates cytokine expression by inhibiting STAT3 phosphorylation, thereby suppressing inflammation.
Inhibition of CASP1 activity: CASP1 is a key enzyme in inflammasomes. Hydroxy-β-sanshalogen reduces inflammatory responses by inhibiting CASP1, blocking the maturation and release of IL-1β.
Regulating TRPV1 and TRPA1 ion channels: Hydroxy-β-sanphylin acts as an agonist or regulator of TRPV1 and TRPA1, affecting calcium ion influx and participating in pain perception and neural regulation.
Inhibition of PTGS1 and PTGS2 (COX-1 and COX-2): By inhibiting cyclooxygenase activity, it reduces prostaglandin synthesis, lowering inflammation and pain responses.
Regulates NOS2 expression: Hydroxy-β-sancapanine inhibits induced nitric oxide synthase (iNOS/NOS2), reduces excess nitric oxide production, and alleviates oxidative stress and inflammation.
In summary, hydroxy-β-sanshalogen achieves its anti-inflammatory and neuromodulatory pharmacological effects through multi-target and multi-pathway synergistic effects.
The druggability parameters of hydroxy-β-sanshaloshanshin indicate that it has good potential for drug development. The molecular weight is 263.38, following the Lipinski rule, with a moderate LogP value of 2.5, which is beneficial for oral absorption and cell membrane penetration. The TPSA is 49.33 Ų, indicating suitable polarity for easy target binding.
Low water solubility may limit its bioavailability, but formulation optimization (such as nanocarriers, liposomes, etc.) can improve its solubility and stability. Its high blood-brain barrier penetration ability offers possibilities for treating central nervous system diseases.
In terms of safety, hydroxy-β-sanshalosin does not inhibit hERG channels, reducing the risk of cardiotoxicity, and the Ames test was negative, indicating a low genotoxicity risk and meeting safety requirements.
Pharmacokinetic research is still in its early stages. Current data suggest that hydroxy-β-sannarin is well absorbed orally and widely distributed in the body, especially enriched in the nervous system. Its metabolic pathway may involve oxidation and binding reactions in liver enzyme systems, with excretion mainly via bile and urine. Future studies are needed to systematically study its absorption, distribution, metabolism, and excretion (ADME) characteristics to guide clinical drug regimen design.
Hydroxy-β-sanshaloshan, as a multifunctional active ingredient derived from natural sources, has broad clinical application prospects. Its remarkable anti-inflammatory effects give it potential therapeutic value in chronic inflammatory diseases such as arthritis, inflammatory bowel disease, and respiratory inflammation. By modulating TRPV1 and TRPA1 channels, hydroxy-β-sanphyllain can also be used as an adjunct therapy for neuropathic pain, neuroinflammation, and related central nervous system diseases.
In addition, hydroxy-β-sanshalosphaginine is safe and abundantly available, making it suitable for development as an oral or topical formulation. In the future, modern drug delivery technologies can be combined to enhance bioavailability and targeting, expanding the scope of clinical applications.
However, clinical research on hydroxy-β-sanjiazine remains limited, lacking systematic clinical trial data. Future research should focus on in-depth evaluation of its pharmacodynamics, toxicology, and pharmacokinetics, clarify its optimal route of administration and dosage, and explore its potential for combined use with existing anti-inflammatory drugs.
Hydroxy-β-sansanyanin, as an important alkylamide natural product in Sichuan pepper oil, demonstrates broad pharmacological activity and good druggability due to its unique chemical structure and multi-target anti-inflammatory mechanism. Its potential in anti-inflammation, neuromodulation, and analgesia provides a valuable example for pharmacological research of natural products.
In the future, by combining modern medicinal chemistry, molecular biology, and pharmacokinetic technologies, the mechanism of action and clinical value of hydroxy-β-sanshalosin will be further revealed, helping to promote its translation from laboratory research to clinical practice, foster the development of innovative natural products, and provide new strategies and options for the treatment of inflammatory and neurological diseases.
Shenshuai
Wenjing
Hedandan
