Calipteryxin

The medicinal plant Peucedanum japonicum Thunberg: A review of traditional use, phytochemistry, and pharmacology.[Pubmed:39442677]

Fitoterapia. 2024 Dec;179:106270.

Peucedanum japonicum (the family Umbelliferae) is a perennial herbaceous plant with various crucial traditional values for coughs, colds, headaches, and inflammatory responses. For drug developments, the current research aims to offer an overview of the previous results in the three main aspects of traditional use, phytochemistry, pharmacological values, and molecular mechanisms regarding this medicinal species. By chromatographic analysis and separation, more than 120 isolated compounds have been obtained. Khellactone-type coumarins and phenolic compounds are the primary phytochemical classes with some coumarins, such as Calipteryxin, praerutorin A, and pteryxin, being the main metabolites. Pharmacological activities of P. japonicum constituents included anticancer, antioxidative, antimicrobial, antiviral, antiplatelet, and tyrosine inhibitory activities, especially anti-inflammation and anti-obesity. It is worth mentioning that the obtained constituents joined to protect the neurons, bone, and urine systems, and exerted vasorelaxant. In general, the underlying mechanism of anti-inflammatory action can be explained by mitogen-activated protein kinase/nuclear factor-kappa B (MAPK/NF-kappaB) signaling pathway, whereas anti-obesity activity is deduced from regulating lipid metabolism-related genes. It also noted that pteryxin is the most active compound, but the clinical studies and synthesis of new derivatives containing enhanced medicinal values have been still limited, which should be improved.

Pharmacological mechanism underlying anti-inflammatory properties of two structurally divergent coumarins through the inhibition of pro-inflammatory enzymes and cytokines.[Pubmed:26221081]

J Inflamm (Lond). 2015 Jul 29;12:47.

BACKGROUND: The aim of the present study is to investigate the effects of two structurally divergent coumarins, Calipteryxin (1) and (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin (2) from Seseli recinosum, in lipopolysaccharide (LPS)-stimulated murine macrophages. METHODS: The nitrite production was evaluated using Griess reagent. The protein and mRNA expression levels were investigated through Western blot and quantitative real time-PCR analyses. The NF-kappaB and AP-1 DNA-binding activities were assessed using an electrophoretic mobility shift assay. The docking studies were performed with Glide XP in Schrodinger suite (version 2013). RESULTS: The results of the present study revealed that Calipteryxin (1) and (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin (2) treatment showed potent inhibitory effects on pro-inflammatory enzymes and cytokines associated with molecular signaling pathways. Treatment with Calipteryxin and (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin also decreased the production of nitric oxide (NO), tumor necrosis factor alpha (TNF-alpha) and interleukin-1 beta (IL-1beta) in a dose-dependent manner. Additionally, both coumarins inhibited the LPS-induced protein and mRNA expression levels of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in RAW264.7 cells. To explore the potential mechanisms underlying the inhibitory activity of coumarin derivatives, the protein signaling pathways for NF-kappaB, mitogen-activated protein kinase (MAPK) and Akt were examined. Calipteryxin and (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin markedly reduced the LPS-stimulated phosphorylation of IKKalpha/beta, p-IkappaBalpha and IkappaBalpha degradation as well as the nuclear translocation of the p65 subunit of pro-inflammatory transcription factor NF-kappaB. In addition, Calipteryxin and (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin) considerably inhibited the LPS-induced expression of ERK, c-Jun N-terminal kinase (JNK), p38 and Akt proteins. Furthermore, both coumarins significantly inhibited c-Jun expression in the nucleus. CONCLUSIONS: Taken together, these results support the therapeutic potential and molecular mechanism of Calipteryxin and (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin associated with inflammatory diseases.

Application of stepwise gradients in counter-current chromatography: a rapid and economical strategy for the one-step separation of eight coumarins from Seseli resinosum.[Pubmed:23992840]

J Chromatogr A. 2013 Oct 4;1310:66-73.

The targeted purification of compounds with a broad polarity range from traditional medicinal plants is a big challenge for counter-current chromatography (CCC). Gradient elution was introduced in CCC to address this problem. However, once a suitable solvent system is selected, the separation process requires optimization of operational parameters. The present study was conducted to optimize various operational parameters to integrate the flow rate and solvent gradients for the rapid isolation of eight coumarins from Seseli resinosum in a single run. An increase in the system temperature from 15 degrees C to 35 degrees C increased the stationary phase retention and solubility of the sample, whereas the operation time and viscosity of the system were decreased. The high purity of each compound was ensured by collecting the fractions from the main peaks while all the shoulder peaks were mixed and separated under the same conditions with semi-preparative CCC. GC-FID was used to analyze the components of each phase, which was prepared without presaturation to save the time and solvent consumption. Finally, eight coumarins were purified, including (1) d-laserpitin, (2) (3'S,4'S)-3'-angeloyloxy-4'-hydroxy-3',4'-dihydroseselin, (3) (+)-samidin, (4) (3'S,4'S)-3'-acetoxy-4'-angeloyloxy-3',4'-dihydroseselin, (5) deltoin (6), Calipteryxin, (7) (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin, and (8) (-)-anomalin. The present technique has successfully accomplished the goal of one-step separation of these compounds with high purity and recovery in an economic and time efficient manner.

Calipteryxin (CAS 14017-72-2) is a natural product offered by BioCrick for research applications. Customers can buy or order Calipteryxin from BioCrick, a supplier and manufacturer of research chemicals, with product specifications, purity, packaging, and pricing information available upon request.