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Punicalagin

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-P1016

  • Specification : 98%

  • CAS number : 65995-63-3

  • Formula : C48H28O30

  • Molecular Weight : 1084.72

  • PUBCHEM ID : 44584733

  • Volume : 20mg

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Catalogue Number

BF-P1016

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

1084.72

Appearance

White crystalline powder

Botanical Source

Punica granatum

Structure Type

Tannins

Category

Standards;Natural Pytochemical;API

SMILES

C1C2C(C3C(C(O2)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O3)O)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6C7=C(C(=C8C9=C7C(=O)OC2=C(C(=C(C3=C(C(=C(C=C3C(=O)O1)O)O)O)C(=C92)C(=O)O8)O)O)O)O)O)O)O

Synonyms

pulchinenoside b4(rg)/1,2,3,11,12,13-Hexahydroxy-5,10-dioxo-8-[3,4,5,11,17,18,19,22,23,34,35-undecahydroxy-8,14,26,31-tetraoxo-9,13,25,32-tetraoxaheptacyclo[25.8.0.0.0.0.0.0]pentatriaconta- 1(35),2,4,6,15,17,19,21,23,27,29,33-dodecaen-10-yl]-5,7,8,10-tetrahydrodibenzo[f,h][1,4]dioxecine-7-carbaldehyde

IUPAC Name

(1R,35R,38R,55S)-6,7,8,11,12,23,24,27,28,29,37,43,44,45,48,49,50-heptadecahydroxy-2,14,21,33,36,39,54-heptaoxaundecacyclo[33.20.0.04,9.010,19.013,18.016,25.017,22.026,31.038,55.041,46.047,52]pentapentaconta-4,6,8,10,12,16,18,22,24,26,28,30,41,43,45,47,49,51-octadecaene-3,15,20,32,40,53-hexone

Density

2.1±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C48H28O30/c49-10-1-6-17(31(59)27(10)55)19-23-21-22-24(47(70)76-38(21)35(63)33(19)61)20(34(62)36(64)39(22)75-46(23)69)18-9(4-13(52)28(56)32(18)60)43(66)74-37-14(5-72-42(6)65)73-48(71)41-40(37)77-44(67)7-2-11(50)25(53)29(57)15(7)16-8(45(68)78-41)3-12(51)26(54)30(16)58/h1-4,14,37,40-41,48-64,71H,5H2

InChl Key

ZJVUMAFASBFUBG-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:65995-63-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30150143

Abstract

Methicillin-resistant Staphylococcus aureus (MRSA) is an important human pathogen that is cross-resistant to most β-lactam antibiotics. We investigated whether oxacillin, which is a β-lactam antibiotic, alone or in combination with punicalagin can affect the penicillin binding protein 2a (PBP2a)-mediated resistance of MRSA. Susceptibility testing of punicalagin with oxacillin was performed using the microdilution and checkerboard assay and the growth curve assay. Binding affinity of punicalagin for cell wall peptidoglycan (PGN) was confirmed by an increased concentration of PGN in bacterial cultures containing punicalagin. The level of PBP2a was analyzed by western blotting. Punicalagin exhibited antimicrobial activity in the viability assay and increased the susceptibility of MRSA to oxacillin. PGN interfered with the antimicrobial activity of punicalagin and prevented the synergistic activity of punicalagin and oxacillin. Increasing the concentration of punicalagin and maintaining a constant concentration of oxacillin resulted in synergistic suppression of the expression of the mec operon (mecA, mecI, and mecR1). The production of PBP2a was suppressed by the addition of punicalagin to oxacillin. Our findings demonstrate that punicalagin potentiates the effect of oxacillin on MRSA by reducing the transcription of mecA (a gene marker for methicillin resistance), which resulted in a reduced level of PBP2a.

Copyright © 2018 The Authors. Production and hosting by Elsevier B.V. All rights reserved.

KEYWORDS

MRSA; PBP2a; Punicalagin; Synergistic; β-lactam

Title

Punicalagin suppresses methicillin resistance of Staphylococcus aureus to oxacillin.

Author

Mun SH1, Kang OH1, Kong R1, Zhou T1, Kim SA1, Shin DW2, Kwon DY3.

Publish date

2018 Aug

PMID

30365643

Abstract

This study evaluated the antifungal activity and cytotoxicity profile of the ellagitannin punicalagin, a compound extracted from the L. pacari A. St.-Hil (Lythraceae) leaf, against Cryptococcus neoformans species complex. Minimum inhibitory concentrations (MIC) were checked using the broth microdilution method. Minimum fungicidal concentrations (MFC) and time of death were used to confirm the antifungal activity of the compound. The in vitro cytotoxicity of punicalagin was tested in BALB/c3T3 fibroblasts and A549 human lung cancer cell line, while the hemolytic potential was tested on sheep erythrocytes. The morphological changes induced in yeast strains by the presence of punicalagin were also analyzed. Tested on eight isolates of the C. neoformans complex punicalagin showed MIC of 0.5 to 4.0 μg/mL and MFC> 256 μg/mL. Punicalagin also demonstrated a good growth inhibitory activity in time-kill curves, but it was not able to achieve a statistically significant reduction of fungal growth suggesting a fungistatic effect of the compound. In vitro cytotoxicity studies using the two cell lines showed that punicalagin has low activity on these cells and no activity on sheep erythrocytes. Morphological changes were seen in the yeasts strains studied when treated with punicalagin. Therefore, punicalagin is a potential antifungal for important pathogenic yeasts and presents a low cytotoxicity profile associated with no hemolytic effects.

Title

Antifungal potential of punicalagin against Cryptococcus neoformans species complex.

Author

Silva TC1, Zara ALSA1, Sa FADS2, Bara MTF2, avila RI2, Costa CR1, Valadares MC2, Santos ASD1, Freitas VAQ1, Silva MDRR1.

Publish date

2018 Oct 22

PMID

29425676

Abstract

BACKGROUND:
Polyphenolic compounds isolated from pomegranate fruit possess several pharmacological activities including anti-inflammatory, hepatoprotective, antigenotoxic and anticoagulant activities. The present work focuses the attention on PDIA3 interaction with punicalagin and ellagic acid, the most predominant components of pomegranate extracts. PDIA3, a member of the protein disulfide isomerase family involved in several cellular functions, is associated with different human diseases and it has the potential to be a pharmacological target.

METHODS:
The interaction of polyphenols with PDIA3 purified protein was explored by fluorescence quenching and calorimetric techniques and their effect on PDIA3 activity was investigated.

RESULTS:
A higher affinity was observed for punicalagin which also strongly affects PDIA3 reductase activity in vitro as a non-competitive inhibitor. Isothermal titration calorimetry confirmed the high affinity of punicalagin for PDIA3. Considering the PDIA3 involvement in oxidative cellular stress response observed in neuroblastoma cells after treatment with hydrogen peroxide, a comparative study was conducted to evaluate the effect of punicalagin on wild type and PDIA3-silenced cells. Punicalagin increases the cell sensitivity to hydrogen peroxide in neuroblastoma cells, but this effect is drastically reduced in PDIA3-silenced cells treated in the same experimental conditions.

CONCLUSIONS:
Punicalagin binds PDIA3 and inhibits its redox activity. Comparative experiments conducted on unsilenced and PDIA3-silenced neuroblastoma cells suggest the potential of punicalagin to modulate PDIA3 reductase activity also in a biological model.

GENERAL SIGNIFICANCE:
Punicalagin can be used as a new PDIA3 inhibitor and this can provide information on the molecular mechanisms underlying the biological activities of PDIA3 and punicalagin.

Copyright © 2018 Elsevier B.V. and Societe Francaise de Biochimie et Biologie Moleculaire (SFBBM). All rights reserved.

KEYWORDS

Ligand-protein binding; Oxidative stress; PDIA3 inhibitor; PDIA3/ERp57; Pomegranate extracts; Punicalagin

Title

Punicalagin, an active pomegranate component, is a new inhibitor of PDIA3 reductase activity.

Author

Giamogante F1, Marrocco I1, Cervoni L1, Eufemi M1, Chichiarelli S1, Altieri F2.

Publish date

2018 Apr


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