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Cepharanthine

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-C3014

  • Specification : 98%

  • CAS number : 481-49-2

  • Formula : C37H38N2O6

  • Molecular Weight : 606.71

  • PUBCHEM ID : 10206

  • Volume : 25mg

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Catalogue Number

BF-C3014

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

606.71

Appearance

White crystalline powder

Botanical Source

Stephania epigaea,Stephania japonica

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CCC2=CC3=C(C4=C2C1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)CC7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3

Synonyms

O-Methylcepharanoline/(14S,27R)-22,33-Dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2.1.1.0.0.0]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dod ecaene/6',12'-dimethoxy-2,2'-dimethyl-6,7-[methylenebis-(oxy)]oxyacanthan/CEPHARANTHINE (RG)/(+)-cepharanthine/[methylenebis(oxy)]/Cepharanthine/sepharanthine/Cepharantin/CEPHARANTHINUM/(14S,27R)-22,33-Dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2.1.1.0.0.0]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dodecaene/6',12'-Dimethoxy-2,2'-dimethyl-6,7-[methylenebis(oxy)]oxyacanthan/6,7-methanediyldioxy-6',12'-dimethoxy-2,2'-dimethyl-oxyacanthane/Stephanotis/Cepharanthin

IUPAC Name

(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene

Density

1.2±0.1 g/cm3

Solubility

Flash Point

Boiling Point

Melting Point

140 - 145ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2934990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:481-49-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31132753

Abstract

BACKGROUND:
Cepharanthine (CEP) is a drug used in Japan since the 1950s to treat a number of acute and chronic diseases, including treatment of leukopenia, snake bites, xerostomia and alopecia. It is the only approved drug for Human use in the large class of bisbenzylisoquinoline alkaloids. This natural product, mainly isolated from the plant Stephania cephalantha Hayata, exhibits multiple pharmacological properties including anti-oxidative, anti-inflammatory, immuno-regulatory, anti-cancer, anti-viral and anti-parasitic properties.
PURPOSE:
The mechanism of action of CEP is multifactorial. The drug exerts membrane effects (modulation of efflux pumps, membrane rigidification) as well as different intracellular and nuclear effects. CEP interferes with several metabolic axes, primarily with the AMP-activated protein kinase (AMPK) and NFκB signaling pathways. In particular, the anti-inflammatory effects of CEP rely on AMPK activation and NFκB inhibition.
CONCLUSION:
In this review, the historical discovery and development of CEP are retraced, and the key mediators involved in its mode of action are presented. The past, present, and future of CEP are recapitulated. This review also suggests new opportunities to extend the clinical applications of this well-tolerated old Japanese drug.
Copyright © 2019 Elsevier GmbH. All rights reserved.

KEYWORDS

Alkaloids; Cancer; Cepharanthine; Inflammation; Natural products; Stephania

Title

Cepharanthine: An update of its mode of action, pharmacological properties and medical applications.

Author

Bailly C1.

Publish date

2019 Sep

PMID

30360403

Abstract

Cepharanthine (CEP) is a natural plant alkaloid, and has anti-inflammatory, antineoplastic, antioxidative and anticancer properties. In this study, we investigated whether CEP could sensitize renal carcinoma Caki cells to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis. CEP alone and TRAIL alone had no effect on apoptosis. However, combined CEP and TRAIL treatment markedly enhanced apoptotic cell death in cancer cells, but not in normal cells. CEP induced downregulation of survivin and cellular-FLICE inhibitory protein (c-FLIP) expression at post-translational levels. Ectopic expression of survivin blocked apoptosis by combined treatment with CEP plus TRAIL, but not in c-FLIP overexpression. Interestingly, CEP induced survivin downregulation through downregulation of deubiquitin protein of STAM-binding protein-like 1 (STAMBPL1). Overexpression of STAMBPL1 markedly recovered CEP-mediated survivin downregulation. Taken together, our study suggests that CEP sensitizes TRAIL-mediated apoptosis through downregulation of survivin expression at the post-translational levels in renal carcinoma cells.

KEYWORDS

DR5; STAMBPL1; TRAIL; apoptosis; cepharanthine; survivin

Title

Cepharanthine Enhances TRAIL-Mediated Apoptosis Through STAMBPL1-Mediated Downregulation of Survivin Expression in Renal Carcinoma Cells.

Author

Shahriyar SA1, Woo SM2, Seo SU3, Min KJ4, Kwon TK5.

Publish date

2018 Oct 22

PMID

28359054

Abstract

BACKGROUND:
Cepharanthine (CEP) is a biscoclaurine alkaloid extracted from Stephania cepharantha and has been shown to have an anti-tumour effect on different types of cancers. However, the anti-cancer effect of CEP on human breast cancer cells is still unclear.
METHODS:
We used MTT, clone formation, in vitro scratch, invasion and migration assays to confirm the inhibitory role of CEP on the proliferation of breast cancer cells. Flow cytometry, plasmid construction and western blot analysis were used to study the detailed mechanisms.
RESULTS:
Our study showed that CEP could inhibit cell proliferation by inducing autophagy, apoptosis, and G0/G1 cell cycle arrest of breast cancer cells. Furthermore, we found that CEP induced autophagy and apoptosis by inhibiting the AKT/mTOR signalling pathway.
CONCLUSION:
We found that CEP could inhibit growth and motility of MCF-7 and MDA-MB-231 breast cancer cell. Our study revealed an anti-tumour effect of CEP on breast cancer cells and suggests that CEP could be a potential new clinical therapy for breast cancer.
© 2017 The Author(s)Published by S. Karger AG, Basel.

KEYWORDS

Apoptosis; Autophagy; Breast cancer cells; Cell cycle arrest; Cepharanthine

Title

Cepharanthine Induces Autophagy, Apoptosis and Cell Cycle Arrest in Breast Cancer Cells.

Author

Gao S1, Li X1, Ding X2, Qi W1, Yang Q1,3.

Publish date

2017


Description :

Cepharanthine, an alkaloid derived from Stephania cepharantha Hayata, with possesses anti-inflammatory and antioxidative activities[1][2][3]. Cepharanthine attenuates muscle and kidney injuries induced by limb ischemia/reperfusion (I/R)[3]. Cepharanthine induces autophagy, apoptosis and cell cycle arrest in breast cancer cells[4]. Cepharanthine inhibits the HIV-1 entry process by reducing plasma membrane fluidity[5].