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Alphitolic acid

Catalog No.GC71997 Copy One-Click Copy Product Info

Alphitolic acid, a pentacyclic triterpenoid with a lupane skeleton, exhibits anti-inflammatory and cytotoxic activities.

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Alphitolic acid Chemical Structure

Cas No.: 19533-92-7

Size Price Stock Qty
1 mg
$498.00
In stock

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Sample solution is provided at 25 µL, 10mM.



Description of Alphitolic acid

Alphitolic acid, a pentacyclic triterpenoid with a lupane skeleton, exhibits anti-inflammatory and cytotoxic activities [1]. Alphitolic acid can regulate various metabolism-related genes such as AR and FABP1, altering the metabolic state of cancer cells and thereby inhibiting cell growth[2]. Alphitolic acid can be used as a model compound to develop liquid chromatography methods for identifying related compounds and to screen therapeutic targets for type 2 diabetes in the pharmacodynamics experiments[3].

In vitro, Alphitolic acid treatment for 72 hours significantly inhibited the proliferation of SCC4 cells and SCC2095 cells, with IC50 values of 12µM and 15µM, respectively[4]. Alphitolic acid pretreatment (22.7µM) for 1 hour significantly inhibited the production of NO and TNF-α in RAW 264.7 macrophages induced by Lipopolysaccharides (LPS)+IFN-γ[5]. 100µM of Alphitolic acid pretreatment for 1 hour significantly inhibited the expression of inducible nitric oxide synthase (iNOS) in J774A.1 cells stimulated by LPS, and reduced the level of NO[6].

In vivo, Alphitolic acid treatment (1.56mg/ear) via topical administration for 5min inhibited 12-O-tetradecanoylphorbol 13 acetate (TPA)-induced topical inflammation in the ears of adult male CF-1 mice [7].

References:
[1] Park S, Cho J, Jeon H, et al. Expedient synthesis of alphitolic acid and its naturally occurring 2-O-ester derivatives[J]. Journal of Natural Products, 2019, 82(4): 895-902.
[2] Wang X, Wan X, Zhu T, et al. Metabolomics combined with network pharmacology reveals the anti-hepatoma effects of terpenoids from Polygonatum kingianum var. grandifolium and Polygonatum sibiricum Redouté as well as differences in their terpenoid metabolites[J]. BMC Plant Biology, 2025, 25(1): 769.
[3] Shen C, Wang Y, Zhang H, et al. Exploring the active components and potential mechanisms of Rosa roxburghii Tratt in treating type 2 diabetes mellitus based on UPLC-Q-exactive Orbitrap/MS and network pharmacology[J]. Chinese Medicine, 2023, 18(1): 12.
[4] Bai L Y, Chiu C F, Chiu S J, et al. Alphitolic acid, an anti-inflammatory triterpene, induces apoptosis and autophagy in oral squamous cell carcinoma cells, in part, through a p53-dependent pathway[J]. Journal of Functional Foods, 2015, 18: 368-378.
[5] Raju R, Gunawardena D, Ahktar M A, et al. Anti-inflammatory chemical profiling of the Australian rainforest tree Alphitonia petriei (Rhamnaceae)[J]. Molecules, 2016, 21(11): 1521.
[6] Masullo M, Montoro P, Autore G, et al. Quali-quantitative determination of triterpenic acids of Ziziphus jujuba fruits and evaluation of their capability to interfere in macrophages activation inhibiting NO release and iNOS expression[J]. Food Research International, 2015, 77: 109-117.
[7] Aguirre M C, Delporte C, Backhouse N, et al. Topical anti-inflammatory activity of 2α-hydroxy pentacyclic triterpene acids from the leaves of Ugni molinae[J]. Bioorganic & medicinal chemistry, 2006, 14(16): 5673-5677.

Protocol of Alphitolic acid

Cell experiment [1]:

Cell lines

SCC4 cells

Preparation Method

SCC4 cells were cultured in DMEM/F12 medium supplemented with 10% foetal bovine serum (FBS), 5mg/ml of penicillin, and 5mg/ml of streptomycin at 37℃ in the presence of 5% CO2. Cells (5×103) were seeded and incubated in 96-well, flat-bottomed plates in 10% FBS-supplemented DMEM/F12 for 24h, and were exposed to Alphitolic acid at the different concentrations (0, 10, 15, 20, 25, and 30µM) in 5% DMEM/F12 medium for 72h. Subsequently, cell viability analysis was conducted.

Reaction Conditions

0, 10, 15, 20, 25, and 30µM; 72h

Applications

Alphitolic acid treatment induced cell apoptosis in SCC4 cells in a dose-dependent manner.
Animal experiment [2]:

Animal models

Balb/C mice

Preparation Method

Adult male CF-1 mice (20-25g) were kept on a 14:10h light-dark cycle, with water and food provided ad libitum, and were fasted overnight before the experiments. Alphitolic acid (1.56mg/ear) was dissolved in acetone and applied topically on the inner (10μl) and outer (10μl) surface of the right ear of the mice. After 5 min, 5μg TPA was administered topically on the right ear and acetone on the left ear as a solvent control. After 4.5h, all the mice were sacrificed by cervical dislocation, and a section of 6mm diameter of the right and left ears was collected for analysis.

Dosage form

1.56mg/ear for once; topical application

Applications

Alphitolic acid treatment inhibited TPA-induced topical inflammation in the ears of mice.

References:
[1] Bai L Y, Chiu C F, Chiu S J, et al. Alphitolic acid, an anti-inflammatory triterpene, induces apoptosis and autophagy in oral squamous cell carcinoma cells, in part, through a p53-dependent pathway[J]. Journal of Functional Foods, 2015, 18: 368-378.
[2] Aguirre M C, Delporte C, Backhouse N, et al. Topical anti-inflammatory activity of 2α-hydroxy pentacyclic triterpene acids from the leaves of Ugni molinae[J]. Bioorganic & medicinal chemistry, 2006, 14(16): 5673-5677.

Chemical Properties of Alphitolic acid

Cas No. 19533-92-7 SDF
Formula C30H48O4 M.Wt 472.7
Solubility DMSO : 50 mg/mL (105.78 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) Storage 4°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 Alphitolic acid

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.1155 mL 10.5775 mL 21.1551 mL
5 mM 423.1 μL 2.1155 mL 4.231 mL
10 mM 211.6 μL 1.0578 mL 2.1155 mL
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In vivo Formulation Calculator (Clear solution) of Alphitolic acid

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
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3. All of the above co-solvents are available for purchase on the GlpBio website.

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Average Rating: 5 ★★★★★ (Based on Reviews and 30 reference(s) in Google Scholar.)

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