Caperatic acid
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| Category | Others |
| Catalog number | BBF-05122 |
| CAS | 29227-64-3 |
| Molecular Weight | 402.52 |
| Molecular Formula | C21H38O7 |
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Specification
| Synonyms | 1,2,3-Heptadecanetricarboxylic acid, 2-hydroxy-, 1-methyl ester (8CI); 5-Methyl hydrogen 3-C-carboxy-2,4-dideoxy-2-tetradecylpentarate |
| IUPAC Name | 2-hydroxy-2-(2-methoxy-2-oxoethyl)-3-tetradecylbutanedioic acid |
| Canonical SMILES | CCCCCCCCCCCCCCC(C(=O)O)C(CC(=O)OC)(C(=O)O)O |
| InChI | InChI=1S/C21H38O7/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19(23)24)21(27,20(25)26)16-18(22)28-2/h17,27H,3-16H2,1-2H3,(H,23,24)(H,25,26) |
| InChI Key | HMJJWFFZRCLIDN-UHFFFAOYSA-N |
Properties
| Boiling Point | 549.3±50.0°C (Predicted) |
| Melting Point | 132-133.5°C |
| Density | 1.100±0.06 g/cm3 (Predicted) |
Reference Reading
1. Lichen-Derived Depsides and Depsidones Modulate the Nrf2, NF-κB and STAT3 Signaling Pathways in Colorectal Cancer Cells
Katarzyna Papierska, Violetta Krajka-Kuźniak, Jarosław Paluszczak, Robert Kleszcz, Marcin Skalski, Elżbieta Studzińska-Sroka, Wanda Baer-Dubowska Molecules. 2021 Aug 7;26(16):4787. doi: 10.3390/molecules26164787.
The study aimed to evaluate the possible modulation of Nrf2, NF-ĸB and STAT3 signaling pathways in the colorectal cancer (CRC) cells line DLD-1 and HCT116 by secondary metabolites of lichens. An attempt was made to indicate the most promising targets in these signaling pathways. Attention was also paid to the effects of the compounds tested on CRC cells using anakoinosis-that is, simultaneous analysis of several signaling pathways. The effects of the tested natural compounds on the activity of selected transcriptional factors related to CRC were analyzed by Western blot and RT-PCR assays. The highest activity against CRC cells was shown by physodic and salazinic acids from the studied secondary metabolites of lichens. As a result, an increase in the activation of transcription factor Nrf2 and the expression of its selected target genes was observed. Physodic and salazinic acids induced the opposite effect in relation to the NF-κB and STAT3 pathways. These results confirmed our earlier observations that lichen-derived compounds have the ability to modulate signaling pathway networks. While caperatic acid affected Wnt/β-catenin to the most extent, salazinic acid was the most potent modulator of Nrf2, NF-κB and STAT3 pathways. Physodic acid seemed to affect all the investigated pathways.
2. Is Caperatic Acid the Only Compound Responsible for Activity of Lichen Platismatia glauca within the Nervous System?
Elżbieta Studzińska-Sroka, Aleksandra Majchrzak-Celińska, Monika Bańdurska, Natalia Rosiak, Dominik Szwajgier, Ewa Baranowska-Wójcik, Marcin Szymański, Wojciech Gruszka, Judyta Cielecka-Piontek Antioxidants (Basel). 2022 Oct 20;11(10):2069. doi: 10.3390/antiox11102069.
Lichens are a source of various biologically active compounds. However, the knowledge about them is still scarce, and their use in medicine is limited. This study aimed to investigate the therapeutic potential of the lichen Platismatia glauca and its major metabolite caperatic acid in regard to their potential application in the treatment of central nervous system diseases, especially neurodegenerative diseases and brain tumours, such as glioblastoma. First, we performed the phytochemical analysis of the tested P. glauca extracts based on FT-IR derivative spectroscopic and gas chromatographic results. Next the antioxidant properties were determined, and moderate anti-radical activity, strong chelating properties of Cu2+ and Fe2+ ions, and a mild effect on the antioxidant enzymes of the tested extracts and caperatic acid were proved. Subsequently, the influence of the tested extracts and caperatic acid on cholinergic transmission was determined by in vitro and in silico studies confirming that inhibitory effect on butyrylcholinesterase is stronger than against acetylcholinesterase. We also confirmed the anti-inflammatory properties of P. glauca extracts and caperatic acid using a COX-2 and hyaluronidase inhibition models. Moreover, our studies show the cytotoxic and pro-apoptotic activity of the P. glauca extracts against T98G and U-138 MG glioblastoma multiforme cell lines. In conclusion, it is possible to assume that P. glauca extracts and especially caperatic acid can be regarded as the source of the valuable substances to finding new therapies of central nervous system diseases.
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 ╳
