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Protosappanin B

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-P2013

  • Specification : 98%

  • CAS number : 102036-29-3

  • Formula : C16H16O6

  • Molecular Weight : 304.3

  • PUBCHEM ID : 13846690

  • Volume : 20mg

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Catalogue Number

BF-P2013

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

304.3

Appearance

Powder

Botanical Source

Caesalpinia sappan,Caesalpinia decapetala

Structure Type

Phenolics

Category

Standards;Natural Pytochemical;API

SMILES

C1C2=CC(=C(C=C2C3=C(C=C(C=C3)O)OCC1(CO)O)O)O

Synonyms

(7S)-7-(Hydroxymethyl)-7,8-dihydro-6H-dibenzo[b,d]oxocine-3,7,10,11-tetrol/6H-Dibenz[b,d]oxocin-3,7,10,11-tetrol, 7,8-dihydro-7-(hydroxymethyl)-, (7S)-

IUPAC Name

(10S)-10-(hydroxymethyl)-8-oxatricyclo[10.4.0.02,7]hexadeca-1(16),2(7),3,5,12,14-hexaene-5,10,14,15-tetrol

Density

1.5±0.1 g/cm3

Solubility

Methanol; Acetone

Flash Point

350.2±31.5 °C

Boiling Point

655.5±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H16O6/c17-7-16(21)6-9-3-13(19)14(20)5-12(9)11-2-1-10(18)4-15(11)22-8-16/h1-5,17-21H,6-8H2/t16-/m0/s1

InChl Key

QRTYTQTVJQUCEP-INIZCTEOSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:102036-29-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30705351

Abstract

The aim of the study was to investigate the effects of protosappanin B on the proliferation and apoptosis of bladder cancer cells. The effects of protosappanin B (12.5, 25, 50, 100, or 200 μg/mL, 48 h) on proliferation of SV-HUC-1, T24 and 5637 cells was assessed using the MTT assay. The effects of protosappanin B (100, 150, 200, 250, or 300 μg/mL, 48 h) on cell apoptosis and cell cycle were analyzed using flow cytometry. T24 and 5637 cells treated with 200 µg/mL protosappanin B showed morphological changes (shrinkage, rounding, membrane abnormalities, and reduced adhesion), but protosappanin B had no proliferation arrest effect on SV-HUC-1 cells. Protosappanin B caused concentration-dependent inhibition of cell growth, with IC50 of 82.78 µg/mL in T24 cells and 113.79 µg/mL in 5637 cells. Protosappanin B caused concentration-dependent increases in T24 and 5637 cell apoptosis (100-300 µg/mL). The effects of protosappanin B on the cell cycle in both cell types was G1 arrest with reductions in the proportion of S-phase cells and proliferation index. A proteomics analysis showed that protosappanin B modulated a number of genes involved in the cell cycle. In conclusion, protosappanin B inhibits the proliferation and promotes the apoptosis of T24 and 5637 human bladder cancer cells in a concentration-dependent manner, possibly via interference with cell cycle regulation, preventing G1-to-S transition.

Title

Protosappanin B Promotes Apoptosis and Causes G 1 Cell Cycle Arrest in Human Bladder Cancer Cells

Author

Xihua Yang 1 , Lili Zhao 1 , Tingting Zhang 2 , Junfeng Xi 1 , Shuze Liu 3 , Liansheng Ren 4 , Yaqin Zheng 5 , Huanhu Zhang 6

Publish date

2019 Jan 31

PMID

25657114

Abstract

Protosappanin B (PTB) is a bioactive dibenzoxocin derivative isolated from Caesalpinia sappan L. Here, we investigated the neuroprotective effects and the potential mechanisms of PTB on oxygen-glucose deprivation (OGD)-injured PC12 cells. Results showed that PTB significantly increased cell viability, inhibited cell apoptosis and up-regulated the expression of growth-associated protein 43 (a marker of neural outgrowth). Moreover, our study revealed that PTB effectively maintained mitochondrial homeostasis by up-regulation of mitochondrial membrane potential (MMP), inhibition of cytochrome c release from mitochondria and inactivation of mitochondrial caspase-9/3 apoptosis pathway. Further study showed that PTB significantly promoted cytoplasmic component degradation of p53 protein, a key negative regulator for mitochondrial function, resulting in a release of Bcl-2 from p53-Bcl-2 complex and an enhancing translocation of Bcl-2 to mitochondrial outer membrane. Finally, we found the degradation of p53 protein was induced by PTB via activation of a MDM2-dependent ubiquitination process. Taken together, our findings provided a new viewpoint of neuronal protection strategy for anoxia and ischemic injury with natural small molecular dibenzoxocin derivative by activating ubiquitin-dependent p53 protein degradation as well as increasing mitochondrial function.

KEYWORDS

Mitochondrial dysfunction; Protosappanin B (PubChem CID: 102036-29-3); Ubiquition-dependent degradation; p53.

Title

Protosappanin B Protects PC12 Cells Against Oxygen-Glucose Deprivation-Induced Neuronal Death by Maintaining Mitochondrial Homeostasis via Induction of Ubiquitin-Dependent p53 Protein Degradation

Author

Ke-Wu Zeng 1 , Li-Xi Liao 1 , Ming-Bo Zhao 1 , Fang-Jiao Song 2 , Qian Yu 2 , Yong Jiang 1 , Peng-Fei Tu 3

Publish date

2015 Mar 15

PMID

27976417

Abstract

Caesalpinia sappan L. is a traditional medicinal plant which is used for promoting blood circulation and cerebral apoplexy therapy in China. Previous reports showed that the extracts of Caesalpinia sappan L. could exert vasorelaxant activity and anti-inflammation activity. Protosappanin B is a major constituent of C. sappan L., and showed several important bioactivities. The separation was achieved by an Acquity UPLC BEH Symmetry Shield RP18 column (1.7 μm, 2.1 × 100 mm) column with the gradient mobile phase consisting of 5 mm ammonium acetate aqueous solution and acetonitrile. Detection was carried out by using negative-ion electrospray tandem mass spectrometry via multiple reaction monitoring. Plasma samples were preprocessed by an extraction with ethyl acetate, and apigenin was used as internal standard. The current UPLC-MS/MS assay was validated for linearity, accuracy, intraday and interday precisions, stability, matrix effects and extraction recovery. After oral and intravenous administration, the main pharmacokinetic parameters were as follows: peak concentrations, 83.5 ± 46.2 and 1329.6 ± 343.6 ng/mL; areas under the concentration-time curve, 161.9 ± 69.7 and 264.9 ± 56.3 μg h/L; and half-lives, 3.4 ± 0.9 and 0.3 ± 0.1 h, respectively. The absolute bioavailability in rats of protosappanin B was 12.2%. The method has been successfully applied to a pharmacokinetic and bioavailability study of protosappanin B in rats.

KEYWORDS

Bioavailability; Pharmacokinetic; UPLC-MS/MS; protosappanin B.

Title

A UPLC/MS/MS Method for Determination of Protosappanin B in Rat Plasma and Its Application of a Pharmacokinetic and Bioavailability Study

Author

Wei-Ying Chen 1 , Xian-Zhen Zhou 2 , Li-Lan Wu 1 , Yun-Shan Wu 1 , Shu-Mei Wang 2 , Bo Liu 1 , De-An Guo 1 3

Publish date

2017 Jul


Description :

Protosappanin B is a phenolic compound extracted from Lignum Sappan. Anti-cancer activity[1]. Protosappanin B induces apoptosis and causes G1 cell cycle arrest in human bladder cancer cells[2].