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Protopine

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-P3021

  • Specification : 98%

  • CAS number : 130-86-9

  • Formula : C20H19NO5

  • Molecular Weight : 353.37

  • PUBCHEM ID : 4970

  • Volume : 25mg

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Catalogue Number

BF-P3021

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

353.37

Appearance

White crystalline powder

Botanical Source

Toddalia asiatica,Uncaria rhynchophylla,Macleaya cordata,Corydalis yanhusuo,Corydalis adunca

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3

Synonyms

7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one/Protopine/7-Methyl-6,8,9,16-tetrahydro[1,3]dioxolo[5,6]benzo[1,2-c][1,3]dioxolo[4,5]benzo[1,2-g]azecin-15(7H)-on/Biflorine/Protopin/Bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one, 6,8,9,16-tetrahydro-7-methyl-/4,6,7,14-Tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one/BIFLORIN/Hypercorine/4,6,7,14-Tetrahydro-5-Methyl/Tangeratin/Corydinine/Corydalis C

IUPAC Name

15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one

Density

1.3±0.1 g/cm3

Solubility

Dichloromethane; Methanol

Flash Point

284.9±29.8 °C

Boiling Point

547.5±49.0 °C at 760 mmHg

Melting Point

211ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2933590000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:130-86-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31220533

Abstract

We investigated the anti-inflammatory activity of protopine (PTP) and sought to determine its mechanism of action in LPS-stimulated BV2 cells and a carrageenan (CA)-induced mouse model. Treatment with PTP (5, 10, and 20 μM) significantly suppresses the secretion of NO and PGE2 in a concentration-dependent manner without affecting cell viability by downregulating iNOS and COX-2 expression in LPS-induced BV2 cells. PTP also attenuates the production of pro-inflammatory chemokines, such as MCP-1, and cytokines, including TNF-α, IL-1β and IL-6, and augments the expression of the anti-inflammatory cytokine IL-10. In addition, PTP suppresses the nuclear translocation of NF-κB by hindering the degradation of IκB and downregulating the expression of mitogen-activated protein kinases (MAPKs), including p38, ERK1/2 and JNK protein. Furthermore, PTP treatment significantly suppresses CA-induced paw oedema in mice compared to that seen in untreated mice. Expression of iNOS and COX-2 proteins is also abrogated by PTP (50 mg/kg) treatment in CA-induced mice. PTP treatment also abolishes IκB phosphorylation, which hinders the activation of NF-κB. Collectively, these results suggest PTP has potential for attenuating CA- and LPS-induced inflammatory symptoms through modulation of MAPKs/NF-κB signaling cascades.

KEYWORDS

Anti-inflammatory effect; Mitogen-activated protein kinase; Neuro-inflammation; Nuclear factor-kappa B signaling; Protopine.

Title

Protopine Attenuates Inflammation Stimulated by Carrageenan and LPS via the MAPK/NF-κB Pathway

Author

Md Badrul Alam 1 , Mi-Kyoung Ju 2 , Yoon-Gyung Kwon 2 , Sang Han Lee 3

Publish date

2019 Sep

PMID

31861525

Abstract

Corydalis humosa Migo is a traditional Chinese medicine that clears away damp heat, relieves sore. Protopine (PRO) is an alkaloid component isolated from C. humosa Migo. However, the role of protopine in acute kidney injury (AKI) has not yet been reported. This study aims to investigate the effect and mechanism of protopine isolated from C. humosa Migo on lipopolysaccharide (LPS)-induced AKI in mice. Inflammation accumulation was assessed by small animal living imaging. The blood urea nitrogen (BUN), and serum creatinine (Scr) were measured to assess the effects of protopine on renal function in LPS-induced AKI. The levels of tumor necrosis factor (TNF), interleukin-2 (IL-2), interferon-γ (IFN-γ), and (interleukin-10) IL-10 in serum were detected by cytometric bead array. Flow cytometry was used to detect the levels of reactive oxygen species (ROS) in primary kidney cells. The proportions of granulocytes, neutrophils, and macrophages in peripheral blood were examined to evaluate the effect of protopine on immune cells in mice with AKI. Toll-like receptor (TLR4) and apoptotic signaling pathway were detected by Western blot analysis. The results showed that protopine markedly improved the renal function, relieve inflammation, reversed inflammatory cytokines, transformed apoptosis markers, and regulated the TLR4 signaling pathway in mice with AKI induced by LPS. The protopine isolated from C. humosa Migo protected mice against LPS-induced AKI by inhibiting apoptosis and inflammation via the TLR4 signaling pathway, thus providing a molecular basis for a novel medical treatment of AKI.

KEYWORDS

TLR4 signaling pathway; acute kidney injury; apoptosis; inflammation; protopine.

Title

Protopine Protects Mice Against LPS-Induced Acute Kidney Injury by Inhibiting Apoptosis and Inflammation via the TLR4 Signaling Pathway

Author

Beibei Zhang 1 2 , Mengnan Zeng 1 2 , Meng Li 1 2 , Yuxuan Kan 1 2 , Benke Li 1 2 , Ruiqi Xu 1 2 , Yuanyuan Wu 1 2 , Shengchao Wang 1 2 , Xiaoke Zheng 1 2 , Weisheng Feng 1 2

Publish date

2019 Dec 19

PMID

25820387

Abstract

Protopine biosynthesis in Fumaria rostellata and Fumaria officinalis cell suspensions was investigated. For the first time, we reported for calli and cell suspensions obtained from F. rostellata and F. officinalis. Callus induction was initiated on a Murashige and Skoog medium, supplemented with sucrose and various concentrations of plant growth regulators: 2,4-dichlorophenoxyacetic acid (2,4-D) and 6-benzylaminopurine (BAP). The best morphological characteristics, growth behavior, and protopine biosynthesis were observed for two callus lines (5FRL14 and 12FOL1) cultivated under submerged conditions, at low concentration of 2,4-D (0.2 and 0.5 mg/L) and higher concentration of BAP (2.0 and 3.0 mg/L). The maximal yield of protopine was accumulated from cell suspension of F. rostellata (line 5FRL14) cultivated under illumination-49.6 mg/L. Time courses of utilization of sucrose, ammonium, nitrate, and phosphate ions in cultural liquid and acetylcholinesterase inhibitory activity of alkaloid extracts of studied suspensions are also presented.

Title

Protopine Production by Fumaria Cell Suspension Cultures: Effect of Light

Author

Lidiya Georgieva 1 , Ivan Ivanov, Andrey Marchev, Ina Aneva, Panteley Denev, Vasil Georgiev, Atanas Pavlov

Publish date

2015 May


Description :

Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.IC50 Value:Target:In vitro: Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. Pre-treatment of Raw 264.7 cells with protopine reduced the production of pro-inflammatory cytokines [2]. Protopine is a novel microtubule stabilizer with anticancer activity in HRPC cells through apoptotic pathway by modulating Cdk1 activity and Bcl-2 family of proteins [3]. In HepG2 cells, protopine significantly increased CYP1A1 mRNA levels after 24h exposure at concentrations from 25 and 10 μM. Protopine also dose-dependently increased CYP1A1 and CYP1A2 mRNA levels in human hepatocytes [4].In vivo: Assays were performed on MDA-MB-231 human breast cancer cells, and the result showed that protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells; after treatment with protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced [1].