We Offer Worldwide Shipping
Login Wishlist

Epiberberine

$272

  • Brand : BIOFRON

  • Catalogue Number : BD-D0021

  • Specification : HPLC≥98%

  • CAS number : 6873-09-2

  • Formula : C20H18NO4

  • Molecular Weight : 336.36

  • PUBCHEM ID : 160876

  • Volume : 10mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

BD-D0021

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥98%

Storage

-20℃

Molecular Weight

336.36

Appearance

Red needle crystallization

Botanical Source

Coptis chinensis Franch./Alkaloid from Berberis floribunda, Coptis chinensis, Coptis trifolia and Nandina domestica

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC5=C(C4=C3)OCO5)OC

Synonyms

Benz(a)-1,3-benzodioxolo(4,5-g)quinolizinium,11,12-dihydro-8,9-dimethoxy/epiberberinium/8,9-dimethoxy-11,12-dihydro-[1,3]dioxolo[4,5-h]isoquino[2,1-b]isoquinolinylium/Benz(a)-1,3-benzodioxolo(4,5-g)quinolizinium, 11,12-dihydro-8,9-dimethoxy-/8,9-Dimethoxy-11,12-dihydro[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-13-ium/Benzo[a]-1,3-benzodioxolo[4,5-g]quinolizinium, 11,12-dihydro-8,9-dimethoxy-/pseudo-Epiberberin/Epiberberin

IUPAC Name

16,17-dimethoxy-5,7-dioxa-1-azoniapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),9,11,14,16,18-octaene

Applications

Epiberberine is an alkaloid isolated from Coptis chinensis, acts as a potent AChE and BChE inhibitor, and a non-competitive BACE1 inhibitor, with IC50s of 1.07, 6.03 and 8.55 μM, respectively. Epiberberine has antioxidant activity, with peroxynitrite ONOO- scavenging effect (IC50, 16.83 μM), and may protect against Alzheimer disease[1]. Epiberberine inhibits the early stage of differentiation of 3T3-L1 preadipocytes, downregulates the Raf/MEK1/2/ERK1/2 and AMPKα/Akt pathways[2]. Epiberberine has the potential effect in the research of diabetic disease[3].

Density

Solubility

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

Flash Point

Boiling Point

Melting Point

260ºC

InChl

InChI=1S/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1

InChl Key

FPJQGFLUORYYPE-UHFFFAOYSA-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#:6873-09-2) 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

30638299

Abstract

A new strategy by converging ultrafiltration high-performance liquid chromatography with ultraviolet and mass spectrometry and pH-zone-refining counter-current chromatography was developed for the rapid screening and separation of potential acetylcholinesterase inhibitors from the crude alkaloidals extract of Zanthoxylum nitidum. An optimized two-phase solvent system composed of chloroform/methanol/water (4:3:3, v/v) was used in this study. And, in the optimal solvent system, 45 mM hydrochloric acid was added to the aqueous stationary phase as the retainer, while 5 mM triethylamine was added to the organic mobile phase as the eluter. As a result, with the purity of over 95%, five alkaloids including jatrorrhizine (1, 340 mg), columbamine (2, 112 mg), skimmianine (3, 154 mg), palmatine (4, 226 mg), and epiberberine (5, 132 mg) were successfully purified in one step from 3.0 g crude alkaloidals extract. And their structures were identified by ultraviolet, mass spectrometry, 1 H and 13 C NMR spectroscopy. Notably, compounds 2, 4 and 5 were firstly reported in Z. nitidum. In addition, acetylcholinesterase inhibitory activities of compounds 1-5 were evaluated, and compounds 3, 4 and 5 exhibited stronger acetylcholinesterase inhibitory activity (IC50 values at 8.52 ± 0.64, 14.82 ± 1.21 and 3.12 ± 0.32 μg/mL, respectively) than berberine (IC50 value at 32.86 ± 2.14 μg/mL, positive control). The results indicated that the proposed method is an efficient technique to rapidly screen acetylcholinesterase inhibitors from complex samples, and could be served as a large-scale preparative technique for separating ionizable active compounds.

© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS

Zanthoxylum nitidum; acetylcholinesterase inhibitors; counter-current chromatography; ultrafiltration

Title

Large-scale separation of acetylcholinesterase inhibitors from Zanthoxylum nitidum by pH-zone-refining counter-current chromatography target-guided by ultrafiltration high-performance liquid chromatography with ultraviolet and mass spectrometry screening.

Author

Liu M1, Liu Q1, Chen M1, Huang X1, Chen X1,2.

Publish date

2019 Mar

PMID

30391811

Abstract

Angiotensin converting enzyme (ACE), fusing with FLAG tag, was overexpressed in human embryonic kidney 293T cells. This recombinant FLAG-tagged ACE was immobilized on anti-FLAG antibody coated magnetic beads by affinity method in crude cell lysate for the first time. The enzyme-immobilized magnetic beads (ACE-MB), without further cleavage procedure, were used directly to establish a cost-effective and reliable method for screening ACE inhibitors by coupling with fluorescence detection. The enzymatic activity of the ACE-MB was validated based on its Michaelian kinetic behavior towards hippuryl-histidyl-leucine by UHPLC-MS/MS method firstly. Then, several conditions were optimized including amount of magnetic beads, incubation temperature and time in the procedure of ACE immobilization and amount of ACE-MB in the microplate operation. Moreover, this screening assay was validated with Z’ factors between 0.71 and 0.81 using four known ACE inhibitors (captopril, lisinopril, fosinopril and fosinoprilat). The developed method was applied for the screening of ACE inhibitors from a small compound library of 45 natural products. As a result, epiberberine and fangchinoline with certain ACE inhibitory activities were screened out in the assay and validated. The results demonstrate the usefulness of this screening method using ACE immobilized on magnetic beads and the advantage of great efficiency with respect to both time and reagents for screening ACE inhibitors.

Copyright © 2018. Published by Elsevier B.V.

KEYWORDS

Angiotensin converting enzyme; FLAG tag; High throughput screening; Magnetic beads; Recombinant enzyme

Title

A method using angiotensin converting enzyme immobilized on magnetic beads for inhibitor screening.

Author

Tang W1, Jia B1, Zhou J1, Liu J1, Wang J1, Ma D2, Li P3, Chen J4.

Publish date

2019 Feb 5

PMID

30378366

Abstract

A mixed-mode chromatographic method based on surface electrostatic exclusion and reversed-phase chromatography was established for the determination of alkaloids present in Coptis chinensis. The effects of two mobile phase additives, formic acid and acetic acid, on retention, peak shape and selectivity of the alkaloids in Coptis chinensis were investigated using the self-made C18HCE column. Acetic acid (0.1%, v/v) used as the additive was found to be optimum for effective separation of the main alkaloids present in Coptis chinensis. The main chromatographic peaks of Coptis chinensis were recognized by the established method and references, which were coptisine, epiberberine, columbamine, jatrorrhizine, berberine and palmatine, respectively. With reference to the content determination method of Coptis chinensis in the 2015 edition of pharmacopoeia, the linear relationship of berberine in the range of 0.5-100 mg/L was good, the correlation coefficient was 0.9996, and the average recovery was 93.74%. The contents of alkaloids in Coptis chinensis in different batches of Hubei and Chongqing were determined. The method is simple, reliable and accurate, and can be used as reference for separation and analysis of other basic compounds.

KEYWORDS

Coptis chinensis; alkaloids; electrostatic exclusion/reversed-phase mixed chromatographic mode; peak shape; selectivity

Title

[An analytical method for alkaloids of Coptis chinensis based on mixed-mode surface electrostatic exclusion/reversed-phase chromatography].

Author

Zhang H1, Guo Z2,3, Yu W2,3, Yan J2,3, Jin G2,3, Wang L1.

Publish date

2018 Oct 8