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Protosappanin A

$576

  • Brand : BIOFRON

  • Catalogue Number : BD-D0038

  • Specification : HPLC≥98%

  • CAS number : 102036-28-2

  • Formula : C15H12O5

  • Molecular Weight : 272.25

  • PUBCHEM ID : 128001

  • Volume : 5mg

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Catalogue Number

BD-D0038

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥98%

Storage

2-8°C

Molecular Weight

272.25

Appearance

Powder

Botanical Source

Structure Type

Miscellaneous

Category

Standards;Natural Pytochemical;API

SMILES

C1C(=O)COC2=C(C=CC(=C2)O)C3=CC(=C(C=C31)O)O

Synonyms

6H-Dibenz(b,d)oxocin-7(8H)-one,3,10,11-trihydroxy/3,10,11-Trihydroxy-6H-dibenzo[b,d]oxocin-7(8H)-one/Sappanol B/6H-Dibenz(b,d)oxocin-7(8H)-one, 3,10,11-trihydroxy-/6H-Dibenz[b,d]oxocin-7(8H)-one, 3,10,11-trihydroxy-

IUPAC Name

5,14,15-trihydroxy-8-oxatricyclo[10.4.0.02,7]hexadeca-1(16),2(7),3,5,12,14-hexaen-10-one

Applications

Protosappanin A (PTA), an immunosuppressive ingredient and major biphenyl compound isolated from Caesalpinia sappan L, suppresses JAK2/STAT3-dependent inflammation pathway through down-regulating the phosphorylation of JAK2 and STAT3[1].

Density

1.5±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

238.8±25.0 °C

Boiling Point

613.1±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C15H12O5/c16-9-1-2-11-12-6-14(19)13(18)4-8(12)3-10(17)7-20-15(11)5-9/h1-2,4-6,16,18-19H,3,7H2

InChl Key

MUKYVRVYBBYJSI-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:102036-28-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28991528

Abstract

Microglial activation and resultant neuroinflammatory response are implicated in various brain diseases including Alzheimer’s disease and Parkinson’s disease. Treatment with anti-neuroinflammatory agents could provide therapeutic benefits for such disorders. Protosappanin A (PTA) is a major bioactive ingredient isolated from Caesalpinia sappan L.. In this work, the anti-neuroinflammatory effects of PTA on LPS-stimulated BV2 cells were investigated and the underlying mechanisms were explored. Results showed that PTA significantly inhibited the production of TNF-α and IL-1β in LPS-activated BV2 microglia. Moreover, the mRNA expressions of IL-6, IL-1β, and MCP-1 were reduced by PTA in a dose-dependent manner. Furthermore, PTA suppressed JAK2/STAT3-dependent inflammation pathway through down-regulating the phosphorylation of JAK2 and STAT3, as well as STAT3 nuclear translocation against LPS treatment. These observations suggested a novel role for PTA in regulating LPS-induced neuroinflammatory injuries.

Copyright © 2017 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

KEYWORDS

BV2 microglia; JAK2-STAT3; Lipopolysaccharide; Neuroinflammation; Protosappanin A

Title

Protosappanin A exerts anti-neuroinflammatory effect by inhibiting JAK2-STAT3 pathway in lipopolysaccharide-induced BV2 microglia.

Author

Wang LC1, Liao LX2, Zhao MB2, Dong X2, Zeng KW3, Tu PF4.

Publish date

2017 Sep

PMID

25920539

Abstract

OBJECTIVES:
This study aims to investigate antimicrobial ingredients from Sappan Lignum and to evaluate their synergy on methicillin-resistant Staphylococcus aureus strains with antibiotics.

METHODS:
Bioactivity-guided phytochemical procedures were used to screen the active compounds. Minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) were assayed by broth microdilution. The synergy was evaluated through checkerboard microdilution and loss of viability assays.

KEY FINDINGS:
Protosappanins A (PsA) and B (PsB) were identified from Sappan Lignum extracts. They showed active against both S. aureus and MRSA with MIC or MIC50 at 64 (PsA) and 128 (PsB) mg/L alone. When they were used in combination with antibiotics, they showed best synergy with amikacin and gentamicin with MIC50 (mg/L) of amikacin reduced more significantly from 32 to four (with PsA) and eight (with PsB), and the fractional inhibitory concentration index (FICI) ranged between 0.078 and 0.500 (FICI50 = 0.375). Moreover, the resistance of MRSA towards amikacin and gentamicin could be reversed by the Clinical and Laboratory Standards Institute criteria. The combined bactericidal mode could as well be synergy. PsA and PsB showed very low cytotoxicity in comparison with their promising activity against MRSA.

CONCLUSIONS:
Protosappanins A and B showed both alone activities and resistance reversal effects of amikacin and gentamicin against MRSA, which warrant further investigations for potential combinatory therapy of MRSA infection.

© 2015 Royal Pharmaceutical Society.

KEYWORDS

MRSA; Sappan Lignum; protosappanin; resistance reversal effect; synergy

Title

Antimicrobial activity and synergy of antibiotics with two biphenyl compounds, protosappanins A and B from Sappan Lignum against methicillin-resistant Staphylococcus aureus strains.

Author

Zuo GY1, Han ZQ1,2,3, Han J4, Hao XY2, Tang HS1, Wang GC1.

Publish date

2015 Oct;

PMID

25676492

Abstract

Caesalpinia sappan L. (Caesalpiniaceae) has been traditionally used as blood tonic, expectorant, and astringent by boiling with water. Searching for HIV-1 integrase (IN) inhibitors from this plant is a promising approach. The EtOH extract of C. sappan and its isolated compounds were tested for their anti-HIV-1 IN effect using the multiplate integration assay, and the active compounds were determined for their mechanisms by molecular docking technique. Extraction from the heartwoods and roots of C. sappan led to the isolation of nine compounds. Among the compounds tested, sappanchalcone (2) displayed the strongest effect against HIV-1 IN with an IC50 value of 2.3 μM followed by protosappanin A (9, IC50 = 12.6 μM). Structure-activity relationships of compounds from C. sappan were found, in which the vicinal hydroxyl moiety were essential for anti-HIV-1 IN effect of compounds 2 and 9 by binding with the amino acid residues Gln148 and Thr66 in the core domain of the HIV- 1 IN enzyme, respectively.

Copyright © 2015 John Wiley & Sons, Ltd.

KEYWORDS

Caesalpinia sappan; Caesalpiniaceae; anti-HIV-1 IN activity; molecular docking

Title

Anti-HIV-1 Integrase Activity and Molecular Docking Study of Compounds from Caesalpinia sappan L.

Author

Tewtrakul S1, Chaniad P, Pianwanit S, Karalai C, Ponglimanont C, Yodsaoue O.

Publish date

2015 May;