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Hydroxy-γ-sanshool

Katalog-Nr.GC36281

Hydroxy-γ-sanshool is a natural alkaloid extracted from Zanthoxylum plants and belongs to the class of unsaturated fatty acid amide compounds.

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Hydroxy-γ-sanshool Chemische Struktur

Cas No.: 78886-66-5

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1mg
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5mg
260,00 $
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Sample solution is provided at 25 µL, 10mM.

Description of Hydroxy-γ-sanshool

Hydroxy-γ-sanshool is a natural alkaloid extracted from Zanthoxylum plants and belongs to the class of unsaturated fatty acid amide compounds[1]. Hydroxy-γ-sanshool has multiple physiological activities such as neuroactivation, analgesia, anti-inflammatory, and antioxidant[2, 3]. Hydroxy-γ-sanshool can activate TRPV1 channels in human sensory neurons and trigger calcium ion influx[4].

In vitro, treatment of human colon adenocarcinoma HCT-116 cells with Hydroxy-γ-sanshool (0-130µM) for 24-48h inhibited cell growth, induced cell morphological distortion, induced cell cycle arrest in the G1 phase, caused programmed cell death, reduced the mRNA and protein levels of Cyclin D1, CDK4, and PCNA, and increased the mRNA and protein levels of P21, P53, Fas, and Caspase 8[5].

In vivo, oral administration of Hydroxy-γ-sanshool (2.5mg/kg) to mice induced by dextran sulfate sodium (DSS)-induced oxidative stress increased the hepatic antioxidant capacity (T-AOC) and the levels of colonic GSH-Px and SOD[6].

References:
[1] Lu I C, Hu P Y, Lin C H, et al. Alkamides in Zanthoxylum Species: Phytochemical Profiles and Local Anesthetic Activities[J]. International Journal of Molecular Sciences, 2024, 25(22): 12228.
[2] Yan H, Zhou F, Liu Y, et al. Zanthoxylum bungeanum Maxim: A Review of Its Phytochemistry, Pharmacology, and Pharmacokinetics[J]. Natural Product Communications, 2023, 18(10): 1934578X231209153.
[3] Li R L, Zhang Q, Liu J, et al. Hydroxy‐α‐sanshool Possesses Protective Potentials on H2O2‐Stimulated PC12 Cells by Suppression of Oxidative Stress‐Induced Apoptosis through Regulation of PI3K/Akt Signal Pathway[J]. Oxidative Medicine and Cellular Longevity, 2020, 2020(1): 3481758.
[4] Luo J, Ke J, Hou X, et al. Composition, structure and flavor mechanism of numbing substances in Chinese prickly ash in the genus Zanthoxylum: A review[J]. Food Chemistry, 2022, 373: 131454.
[5] Zhaojun C, Lulin T, Xin F, et al. Hydroxy-γ-sanshool from Zanthoxylum bungeanum (prickly ash) induces apoptosis of human colorectal cancer cell by activating P53 and Caspase 8[J]. Frontiers in Nutrition, 2022, 9: 914638.
[6] Chen Z, Tan L, Li L, et al. Sanshools from Zanthoxylum genus and their antioxidant properties in vitro and in vivo[J]. Frontiers in Sustainable Food Systems, 2024, 8: 1256568.

Protocol of Hydroxy-γ-sanshool

Cell experiment [1]:

Cell lines

HCT-116 cells

Preparation Method

Cells were exposed to various concentrations (0, 50, 90, or 130µM) of Hydroxy-γ-sanshool (HRS) for 24 or 48h, with assessment of apoptosis and cell cycle arrest as well as regulatory gene and protein expression associated with apoptosis and the cell cycle.

Reaction Conditions

0, 50, 90, 130µM; 24, 48h

Applications

Hydroxy-γ-sanshool inhibited cell growth, induced morphological distortion, and arrested the cell cycle at G1 phase, and also caused programmed cell death in a dose-dependent manner. Hydroxy-γ-sanshool significantly inhibited mRNA and protein levels of Cyclin D1, CDK4, PCNA, and increased mRNA and protein levels of P21, P53, Fas, and Caspase 8.

Animal experiment [2]:

Animal models

C57BL/6 mice

Preparation Method

Mice were randomly divided into the following six groups: the normal control group, Dextran sulfate sodium (DSS)-model group, DSS+Hydroxy-α-sanshool (HAS) group, DSS+Hydroxy-γ-sanshool (HBS) group, DSS+Hydroxy-γ-sanshool (HRS) group, DSS+γ-sanshool (RS) group. The intragastric dose of sanshool was 2.5mg/kg. After mice were termination, the liver and colon were collected at −80°C.

Dosage form

2.5mg/kg; p.o.

Applications

After intragastric administration of sanshool, HRS increased the the level of hepatic T-AOC and colon GSH-Px and SOD. Hydroxy-γ-sanshool exhibited efficacy in mitigating DSS-induced oxidative stress in the colon of mice.

References:
[1]Zhaojun C, Lulin T, Xin F, et al. Hydroxy-γ-sanshool from Zanthoxylum bungeanum (prickly ash) induces apoptosis of human colorectal cancer cell by activating P53 and Caspase 8[J]. Frontiers in Nutrition, 2022, 9: 914638.
[2]Chen Z, Tan L, Li L, et al. Sanshools from Zanthoxylum genus and their antioxidant properties in vitro and in vivo[J]. Frontiers in Sustainable Food Systems, 2024, 8: 1256568.

Chemical Properties of Hydroxy-γ-sanshool

Cas No. 78886-66-5 SDF
Canonical SMILES C/C=C/C=C/C=C\CC/C=C/C=C/C(NCC(C)(C)O)=O
Formula C18H27NO2 M.Wt 289.41
Löslichkeit Soluble in DMSO Storage Store at -20°C,protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Hydroxy-γ-sanshool

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 3.4553 mL 17.2765 mL 34.5531 mL
5 mM 0.6911 mL 3.4553 mL 6.9106 mL
10 mM 0.3455 mL 1.7277 mL 3.4553 mL
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