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Alphitolic acid (Aophitolic acid) is an anti-inflammatory triterpene could found in quercus aliena. Alphitolic acid blocks Akt–NF-κB signaling to induce apoptosis. Alphitolic acid induces autophagy. Alphitolic acid has anti-inflammatory activity and down-regulates the NO and TNF-α production. Alphitolic acid can be used for cancer and inflammation research .
In Vitro
Alphitolic acid (Aophitolic acid) (0-30 µM; 72 hours; HSC-3, SCC2095, and SCC4 cells) has anti-proliferative activity in oral cancer cells in a dose-dependent manner, induces apoptosis and blocks Akt–NF-κB signaling. Alphitolic acid (Aophitolic acid) (0-25 µM; 3-72 hours; SCC4 cells) induces autophagy with increases the expression of autophagosome marker LC3B-II and two autophagyregulatory proteins. Alphitolic acid (Aophitolic acid) (0-25 µM; 72 hours; SCC4 cells) increases p53 phosphorylation and expression, decreases in the expression of the oncogenic E3 ligase MDM2. Alphitolic acid (Aophitolic acid) (0-25 µM; 72 hours; RAW 264.7 macrophages) has anti-inflammatory activity and down-regulates the NO and TNF-α production with IC 50 values of 17.6 and 22.7 µM, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: HSC-3, SCC2095 and SCC4 cells Concentration: 0, 10, 15, 20, 25 and 30 µM Incubation Time: 72 hours Result: Suppressed the proliferation of SCC4 and SCC2095 cells with IC 50 values of 12 and 15 µM, respectively. Apoptosis AnalysisCell Line: SCC4 cells Concentration: 0, 10, 20 and 30 µM Incubation Time: 72 hours Result: Increased the percentage of apoptotic cells from 11.8% to 25.1% in a dose-dependent manner. Western Blot AnalysisCell Line: SCC4 cells Concentration: 0, 10, 15 and 20 µM Incubation Time: 72 hours Result: Decreased the expression of phosphorylation of Akt and its downstream substrates, including p70S6K, S6, and IκBα. Down-regulated the expression of NF-κB and its downstream target gene product Bcl-2. Western Blot AnalysisCell Line: SCC4 cells Concentration: 0, 10, 15, 20 and 25 µM Incubation Time: 3, 6, 12, 24, 48 and 72 hours Result: Increased autophagosome marker LC3B-II in a dose- and time-dependent manner. Increased the expression of autophagy-related protein 7 (Atg7).
In Vivo
Alphitolic acid (Aophitolic acid) (47-756 µg/ear; i.h.; adult male CF-1 mice) has anti-inflammatory activity in vivo. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Adult male CF-1 miceDosage: 47, 94, 330, 378 and 756 µg/ear Administration: subcutaneous injection Result: Had anti-inflammatory activity with an ED 50 of 0.11 and 0.20 µM in a dose-dependent.
Form:Solid
Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Classe | Prenol lipids |
| Subclass | Triterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Triterpenoids |
| Alternative Parents | 18-hydroxysteroids Oxosteroids Secondary alcohols Cyclic alcohols and derivatives 1,2-diols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Triterpenoid - 18-hydroxysteroid - 18-oxosteroid - Hydroxysteroid - Oxosteroid - Steroid - Cyclic alcohol - 1,2-diol - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Alcohol - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Aliphatic homopolycyclic compound |
| Descrizione | This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
| External Descriptors | dihydroxy monocarboxylic acid - pentacyclic triterpenoid |
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| Peso molecolare | 472.700 g/mol |
|---|---|
| XLogP3 | 7.200 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Exact Mass | 472.355 Da |
| Monoisotopic Mass | 472.355 Da |
| Topological Polar Surface Area | 77.800 Ų |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Complexity | 894.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 11 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |