19533-92-7
Chemical Structure
Alphitolic acid
Synonym(s): Aophitolic acid
- CAS No.: 19533-92-7
- Formula:C30H48O4
- Molecular Weight:472.70
IUPAC Name: (1R,3aS,5aR,5bR,7aR,9R,10R,11aR,11bR,13aR,13bR)-9,10-dihydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
InChIKey: PFCVZKFJHRCLCC-PGOIBATFSA-N
SMILES: OC([C@]12[C@@]([C@@H](CC2)C(C)=C)([H])[C@]3([H])[C@@](CC1)([C@]4([C@]([C@@]5([C@@](C(C)([C@H]([C@@H](C5)O)O)C)([H])CC4)C)([H])CC3)C)C)=O
Biological Activity: Alphitolic acid (Aophitolic acid), an anti-inflammatory triterpenoid compound, is a selective HMGCS2 inhibitor (IC50 17.17 μM, Kd 5.6 μM). Alphitolic acid inhibits ORAI1/STIM1-mediated CRAC currents, store-operated calcium entry, the Akt-mTOR-NF-κB signaling pathway, p70S6K/S6/IκBα phosphorylation, NF-κB/Bcl-2 expression, and NO/TNF-α production, while upregulating p53 and downregulating MDM2. Alphitolic acid induces apoptosis (apoptosis) and autophagy (autophagy) through Beclin 1, Atg7, LC3B-II, and autophagosomes, inhibits oral squamous cell carcinoma proliferation/viability, and exhibits antibacterial/antimalarial/antioxidant activities. Alphitolic acid can be used in research on inflammatory diseases, allergic diseases, Tamoxifen (HY-13757A)-resistant breast cancer, oral squamous cell carcinoma, and inflammation[1][2][3][4][5].
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Alphitolic acid | Alphitolic acid (Aophitolic acid), an anti-inflammatory triterpenoid compound, is a selective HMGCS2 inhibitor (IC50 17.17 μM, Kd 5.6 μM). Alphitolic acid inhibits ORAI1/STIM1-mediated CRAC currents, store-operated calcium entry, the Akt-mTOR-NF-κB signaling pathway, p70S6K/S6/IκBα phosphorylation, NF-κB/Bcl-2 expression, and NO/TNF-α production, while upregulating p53 and downregulating MDM2. Alphitolic acid induces apoptosis (apoptosis) and autophagy (autophagy) through Beclin 1, Atg7, LC3B-II, and autophagosomes, inhibits oral squamous cell carcinoma proliferation/viability, and exhibits antibacterial/antimalarial/antioxidant activities. Alphitolic acid can be used in research on inflammatory diseases, allergic diseases, Tamoxifen (HY-13757A)-resistant breast cancer, oral squamous cell carcinoma, and inflammation. | |||||||||||||||||||||
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References
- [1]. Park SJ, et al. Anti-Inflammatory Effects of Alphitolic Acid Isolated from Agrimonia coreana Nakai Extracts Are Mediated via the Inhibition of ICRAC Activity in T Cells. Int J Mol Sci. 2023 Dec 9;24(24):17309.
- [2]. Hwang S, et al. Targeting HMG-CoA synthase 2 suppresses tamoxifen-resistant breast cancer growth by augmenting mitochondrial oxidative stress-mediated cell death. Life sciences. 2023 Sep 01;328:121827.
- [3]. Li-Yuan Bai, 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. ournal of Functional Foods. 18 (2015) 368-378.
- [4]. Raju R, et al. Anti-Inflammatory Chemical Profiling of the Australian Rainforest Tree Alphitonia petriei (Rhamnaceae). Molecules (Basel, Switzerland). 2016 Nov 11;21(11):1521.
- [5]. Gossan DP, et al. Triterpene glycosides from the aerial parts of Gouania longipetala. Phytochemistry. 2017 Feb;134:71-77.
