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Oxypeucedanin hydrate Sale

(Synonyms: 水合氧化前胡素,(-)-Prangol) 目录号 : GC39030

A furanocoumarin with diverse biological activities

Oxypeucedanin hydrate Chemical Structure

Cas No.:2643-85-8

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产品描述

(+)-Oxypeucedanin hydrate is a furanocoumarin that has been found in A. japonica and has diverse biological activities.1,2,3 It is active against the Gram-positive bacteria B. cereus, S. aureus, and S. faecalis (MICs = 9.76-78.12 ?g/ml), the Gram-negative bacteria E. coli, S. dysenteriae, P. aeruginosa, K. pneumoniae, and S. typhi (MICs = 39.06-625 ?g/ml), and the fungi C. albicans and M. audouinii (MIC = 39.06 ?g/ml for both).2 (+)-Oxypeucedanin hydrate inhibits proliferation of human MK-1 gastric and HeLa cervical cancer cells, as well as murine B16/F10 melanoma cells (EC50s = 47.2, 80.3, and 42 ?g/ml, respectively).1 It also inhibits proliferation of sensitive and multidrug-resistant murine L5178Y lymphoma cells (IC50s = 41.96 and 60.58 ?M, respectively).3

1.Fujioka, T., Furumi, K., Fuhii, H., et al.Antiproliferative constituents from Umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonicaChem. Pharm. Bull. (Tokyo)47(1)96-100(1999) 2.Dongfack, M.D.J., Lallemand, M.-C., Kuete, V., et al.A new sphingolipid and furanocoumarins with antimicrobial activity from Ficus exasperataChem. Pharm. Bull. (Tokyo)60(8)1072-1075(2012) 3.Mottaghipisheh, J., Nové, M., Spengler, G., et al.Antiproliferative and cytotoxic activities of furocoumarins of Ducrosia anethifoliaPharm. Biol.56(1)658-664(2018)

Chemical Properties

Cas No. 2643-85-8 SDF
别名 水合氧化前胡素,(-)-Prangol
Canonical SMILES CC(C)(O)[C@H](O)COC1=C(C=CO2)C2=CC(O3)=C1C=CC3=O
分子式 C16H16O6 分子量 304.29
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 3.2863 mL 16.4317 mL 32.8634 mL
5 mM 0.6573 mL 3.2863 mL 6.5727 mL
10 mM 0.3286 mL 1.6432 mL 3.2863 mL
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Research Update

Facile and Rapid Isolation of Oxypeucedanin hydrate and Byakangelicin from Angelica dahurica by Using [Bmim]Tf2N Ionic Liquid

Molecules 2021 Feb 5;26(4):830.PMID:33562719DOI:10.3390/molecules26040830.

Ionic liquids (ILs) have sparked much interest as alternative solvents for plant materials as they provide distinctive properties. Therefore, in this study, the capacity of ILs to extract Oxypeucedanin hydrate and byakangelicin from the roots of Angelica dahurica (A. dahurica) was investigated. The back-extraction method was examined to recover target components from the IL solution as well. Herein, [Bmim]Tf2N demonstrated outstanding performance for extracting Oxypeucedanin hydrate and byakangelicin. Moreover, factors including solvent/solid ratio, extraction temperature and time were investigated and optimized using a statistical approach. Under optimum extraction conditions (solvent/solid ratio 8:1, temperature 60 °C and time 180 min), the yields of Oxypeucedanin hydrate and byakangelicin were 98.06% and 99.52%, respectively. In addition, 0.01 N HCl showed the most significant ability to back-extract target components from the [Bmim]Tf2N solution. The total content of both Oxypeucedanin hydrate (36.99%) and byakangelicin (45.12%) in the final product exceeded 80%. Based on the data, the proposed approach demonstrated satisfactory extraction ability, recovery and enrichment of target compounds in record time. Therefore, the developed approach is assumed essential to considerably reduce drawbacks encountered during the separation of Oxypeucedanin hydrate and byakangelicin from the roots of A. dahurica.

High-performance liquid chromatographic method for the determination and pharmacokinetic study of Oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma

J Pharm Biomed Anal 2007 May 9;44(1):166-72.PMID:17344014DOI:10.1016/j.jpba.2007.02.002.

A high-performance liquid chromatographic method was developed and validated for the determination and pharmacokinetic study of Oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma. The coumarin components and the internal standard isopsoralen were extracted from plasma samples with the mixture of tert-butyl methyl ether and n-hexane (4:1, v/v). Chromatographic separation was performed on a C(18) column (200 mm x 4.6mm, 5 microm) with the mobile phase acetonitrile-methanol-water-acetic acid (20:15:65:2, v/v/v/v) at a flow-rate of 1.0 ml/min. Only the peak of Oxypeucedanin hydrate and byak-angelicin could be detected in dog plasma after oral administration of ethanol extracts of A. dahurica mainly containing xanthotoxol, osthenol, imperatorin, Oxypeucedanin hydrate and byak-angelicin. The calibration curves of Oxypeucedanin hydrate and byak-angelicin were linear over a range of 22.08-8830.00 and 6.08-2430.00 ng/ml in dog plasma, respectively. The quantification limit of Oxypeucedanin hydrate and byak-angelicin in dog plasma was 22.08 and 6.08 ng/ml, respectively. The intra- and inter-day precision was less than 7.6% and 8.5% and the accuracy was from 91.9% to 106.1%. The lowest absolute recoveries of Oxypeucedanin hydrate and byak-angelicin were 85.7% and 87.0%, respectively. The method was successfully applied to the pharmacokinetic studies of Oxypeucedanin hydrate and byak-angelicin in dog plasma after oral administration of ethanol extracts from A. dahurica.

Effect of co-administration of Acori Tatarinowii Rhizoma volatile oil on pharmacokinetic fate of xanthotoxol, Oxypeucedanin hydrate, and byakangelicin from Angelicae Dahuricae Radix in rat

J Sep Sci 2020 Jun;43(12):2349-2362.PMID:32222035DOI:10.1002/jssc.201901250.

A combination of Angelicae Dahuricae Radix and Acori Tatarinowii Rhizoma has been widely used as the herb pair in traditional Chinese medicine to treat stroke, migraine, and epilepsy. However, the underlying synergistic mechanism of the herb pair remains unknown. This study was aimed at investigating the effects of Acori Tatarinowii Rhizoma volatile oil on the pharmacokinetic parameters of xanthotoxol, Oxypeucedanin hydrate, and byakangelicin from Angelicae Dahuricae Radix in rat, and in vitro absorption behavior of the three compounds using rat everted gut sac, in situ single-pass intestinal perfusion, and Caco-2 cell monolayer models. The pharmacokinetic study exhibited clear changes in the key pharmacokinetic parameters of the three main coumarins through co-administering with Acori Tatarinowii Rhizoma volatile oil (50 mg/kg), the area under curve and the maximum plasma concentration of xanthotoxol increased 1.36 and 1.31 times; the area under curve, the maximum plasma concentration, mean residence time, half-life of elimination, and the time to reach peak concentration of Oxypeucedanin hydrate increased by 1.35, 1.18, 1.24, 1.19 and 1.49 times, respectively; the area under curve, mean residence time, half-life of elimination, and time to reach peak concentration of byakangelicin climbed 1.29, 1.27, 1.37, and 1.28 times, respectively. The three coumarin components were absorbed well in the jejunum and ileum in the intestinal perfusion model, when co-administered with Acori Tatarinowii Rhizoma volatile oil (100 μg/mL). The in vivo and in vitro experiments showed good relevance and consistency. The results demonstrated that the three coumarin compounds from Angelicae Dahuricae Radix were absorbed through the active transportation, and Acori Tatarinowii Rhizoma volatile oil could promote the intestinal absorption and transport of these compounds by inhibiting P-glycoprotein (P-gp)-mediated efflux.

Simultaneous determination of byak-angelicin and Oxypeucedanin hydrate in rat plasma by column-switching high-performance liquid chromatography with ultraviolet detection

J Chromatogr B Biomed Sci Appl 2001 Apr 5;753(2):309-14.PMID:11334345DOI:10.1016/s0378-4347(00)00569-7.

A simple and sensitive column-switching HPLC method was developed for the simultaneous determination of two furocoumarin compounds, byak-angelicin and Oxypeucedanin hydrate, which are the main components of hot water extract of Angelica dahurica root (AE), in rat plasma. Plasma sample was simply deproteinated with perchloric acid. After centrifugation, the supernatant was injected into a column-switching HPLC system consisting of a clean-up column (Symmetry Shield RP 8, 20x3.9 mm I.D.) and analytical column (Symmetry C18, 75x4.6 mm I.D.) which were connected with a six-port switching valve. The flow-rate of the mobile phase (acetonitrile-water, 20:80) was maintained at 1 ml/min. Detection was carried out at wavelength 260 nm with a UV detector. The column temperature was maintained at 40 degrees C. The calibration curves of byak-angelicin and Oxypeucedanin hydrate were linear over the ranges 19.6 to 980 ng/ml (r2>0.997). The accuracy of these analytes was less than 4.4%. The intra- and inter-day relative standard deviations of byak-angelicin and Oxypeucedanin hydrate were within 12.0% and 12.7%, respectively. The present method was applied for the analysis of plasma concentration from rats after administration of AE.

Comparative Antiseizure Analysis of Diverse Natural Coumarin Derivatives in Zebrafish

Int J Mol Sci 2021 Oct 22;22(21):11420.PMID:34768849DOI:10.3390/ijms222111420.

Coumarins are a well-known group of plant secondary metabolites with various pharmacological activities, including antiseizure activity. In the search for new antiseizure drugs (ASDs) to treat epilepsy, it is yet unclear which types of coumarins are particularly interesting as a systematic analysis has not been reported. The current study performed behavioral antiseizure activity screening of 18 different coumarin derivatives in the larval zebrafish pentylenetetrazole (PTZ) model using locomotor measurements. Activity was confirmed for seven compounds, which lowered seizure-like behavior as follows: oxypeucedanin 38%, Oxypeucedanin hydrate 74%, notopterol 54%, nodakenetin 29%, hyuganin C 35%, daphnoretin 65%, and pimpinellin 60%. These coumarins, together with nodakenin, underwent further antiepileptiform analysis by local field potential recordings from the zebrafish opticum tectum (midbrain). All of them, except for nodakenetin, showed pronounced antiepileptiform activity, decreasing PTZ-induced elevation in power spectral density (PSD) by 83-89% for oxypeucedanin, Oxypeucedanin hydrate, and notopterol, 77% for nodakenin, 26% for nodakenetin, 65% for hyuganin C, 88% for daphnoretin, and 81% for pimpinellin. These data demonstrate the potential of diverse coumarin scaffolds for ASD discovery. Finally, the structural differences between active and inactive coumarins were investigated in silico for Oxypeucedanin hydrate and byacangelicin for their interaction with GABA-transaminase, a hypothetical target.