Squamatic acid
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| Category | Others |
| Catalog number | BBF-05463 |
| CAS | 569-36-8 |
| Molecular Weight | 390.34 |
| Molecular Formula | C19H18O9 |
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Specification
| Synonyms | Squamatsaure; 2-Hydroxy-4-methoxy-6-methyl-1,3-benzenedicarboxylic acid 1-(4-carboxy-3-hydroxy-2,5-dimethylphenyl) ester; 1,3-Benzenedicarboxylic acid, 2-hydroxy-4-methoxy-6-methyl-, 1-(4-carboxy-3-hydroxy-2,5-dimethylphenyl) ester; 2-Oxy-6-methoxy-4-methyl-isophthalsaeure-3-(3-oxy-2,5-dimethyl-4-carboxy-phenylester) |
| IUPAC Name | 4-(3-carboxy-2-hydroxy-4-methoxy-6-methylbenzoyl)oxy-2-hydroxy-3,6-dimethylbenzoic acid |
| Canonical SMILES | CC1=CC(=C(C(=C1C(=O)O)O)C)OC(=O)C2=C(C(=C(C=C2C)OC)C(=O)O)O |
| InChI | InChI=1S/C19H18O9/c1-7-5-10(9(3)15(20)12(7)17(22)23)28-19(26)13-8(2)6-11(27-4)14(16(13)21)18(24)25/h5-6,20-21H,1-4H3,(H,22,23)(H,24,25) |
| InChI Key | WCWYEXBIRSSVGF-UHFFFAOYSA-N |
Properties
| Boiling Point | 643.3±55.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Lichen-derived caperatic acid and physodic acid inhibit Wnt signaling in colorectal cancer cells
Jarosław Paluszczak, Robert Kleszcz, Elżbieta Studzińska-Sroka, Violetta Krajka-Kuźniak Mol Cell Biochem. 2018 Apr;441(1-2):109-124. doi: 10.1007/s11010-017-3178-7. Epub 2017 Sep 8.
Lichens are a source of secondary metabolites which possess important biological activities, including antioxidant, antibacterial, anti-inflammatory, and cytotoxic effects. The anticancer activity of lichens was shown in many types of tumors, including colorectal cancers (CRC). Several studies revealed that the application of lichen extracts diminished the proliferation of CRC cells and induced apoptosis. Colon carcinogenesis is associated with aberrations in Wnt signaling. Elevated transcriptional activity of β-catenin induces cell survival, proliferation, and migration. Thus, the inhibition of Wnt signaling is a promising therapeutic strategy in colorectal cancer. The aim of this study was the evaluation of the effects of lichen-derived depsides (atranorin, lecanoric acid, squamatic acid) and depsidones (physodic acid, salazinic acid) and a poly-carboxylic fatty acid-caperatic acid, on Wnt signaling in HCT116 and DLD-1 colorectal cancer cell lines. HCT116 cells were more sensitive to the modulatory effects of the compounds. PKF118-310, which was used as a reference β-catenin inhibitor, dose-dependently reduced the expression of the classical β-catenin target gene-Axin2 in both cell lines. Lecanoric acid slightly reduced Axin2 expression in HCT116 cells while caperatic acid tended to reduce Axin2 expression in both cell lines. Physodic acid much more potently decreased Axin2 expression in HCT116 cells than in DLD-1 cells. Physodic acid and caperatic acid also diminished the expression of survivin and MMP7 in a cell line and time-dependent manner. None of the compounds affected the nuclear translocation of β-catenin. This is the first report showing the ability of caperatic acid and physodic acid to modulate β-catenin-dependent transcription.
2. Cladonia uncialis as a valuable raw material of biosynthetic compounds against clinical strains of bacteria and fungi
Elżbieta Studzińska-Sroka, Hanna Tomczak, Natalia Malińska, Marta Wrońska, Robert Kleszcz, Agnieszka Galanty, Judyta Cielecka-Piontek, Dorota Latek, Jarosław Paluszczak Acta Biochim Pol. 2019 Dec 15;66(4):597-603. doi: 10.18388/abp.2019_2891.
Cladonia uncialis is a lichen species with confirmed antibacterial activity and whose genome has been recently sequenced, enabling first attempts in its functional characterization. In this work, we investigated activity of the C. uncialis acetone extract (CUE) and usnic acid (UA) enantiomers against ten clinical microbial strains causing skin infections. The results showed that CUE, containing (-)-UA and squamatic acid, assayed at the same concentrations as UA, was noticeably more active than (-)-UA alone, in its pure form. The studied CUE displayed an activity that was comparable to that of (+)-UA observed for Staphylococcus epidermidis and Enterococcus faecium (18-24 mm zone of growth inhibition), but did not display any activity against fungal strains. The CUE demonstrated low cytotoxicity against HaCaT cells, in comparison to UA enantiomers, which is important for its therapeutic use. Results of the antioxidant assay (DPPH) indicated low antioxidant activity (IC50>200 µg/mL) of CUE, while the total phenolic content was 70.36 mg Gallic Acid Equivalent/g of the dry extract.
3. Lichen Secondary Metabolites Inhibit the Wnt/β-Catenin Pathway in Glioblastoma Cells and Improve the Anticancer Effects of Temozolomide
Aleksandra Majchrzak-Celińska, Robert Kleszcz, Elżbieta Studzińska-Sroka, Agnieszka Łukaszyk, Anna Szoszkiewicz, Ewelina Stelcer, Karol Jopek, Marcin Rucinski, Judyta Cielecka-Piontek, Violetta Krajka-Kuźniak Cells. 2022 Mar 23;11(7):1084. doi: 10.3390/cells11071084.
Lichens are a source of secondary metabolites with significant pharmacological potential. Data regarding their possible application in glioblastoma (GBM) treatment are, however, scarce. The study aimed at analyzing the mechanism of action of six lichen secondary metabolites: atranorin, caperatic acid, physodic acid, squamatic acid, salazinic acid, and lecanoric acid using two- and three-dimensional GBM cell line models. The parallel artificial membrane permeation assay was used to predict the blood-brain barrier penetration ability of the tested compounds. Their cytotoxicity was analyzed using the MTT test on A-172, T98G, and U-138 MG cells. Flow cytometry was applied to the analysis of oxidative stress, cell cycle distribution, and apoptosis, whereas qPCR and microarrays detected the induced transcriptomic changes. Our data confirm the ability of lichen secondary metabolites to cross the blood-brain barrier and exert cytotoxicity against GBM cells. Moreover, the compounds generated oxidative stress, interfered with the cell cycle, and induced apoptosis in T98G cells. They also inhibited the Wnt/β-catenin pathway, and this effect was even stronger in case of a co-treatment with temozolomide. Transcriptomic changes in cancer related genes induced by caperatic acid and temozolomide were the most pronounced. Lichen secondary metabolites, caperatic acid in particular, should be further analyzed as potential anti-GBM agents.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
