JATRORRHIZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H20NO4
Molecular Weight	338.3771
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(CC[N+]3=CC4=C(C=CC(OC)=C4OC)C=C23)C=C1O

InChI

InChIKey=MXTLAHSTUOXGQF-UHFFFAOYSA-O

InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/957909 | https://www.ncbi.nlm.nih.gov/pubmed/19431018 | https://www.ncbi.nlm.nih.gov/pubmed/27573054 | https://www.ncbi.nlm.nih.gov/pubmed/2575836 | https://www.ncbi.nlm.nih.gov/pubmed/11270727

Jatrorrhizine is an active component of the traditional Chinese herb Coptis chinensis, which has been used to prevent and treat metabolic disorders. It is also found plants such as Enantia chlorantha, Thalictrum lucidumm, Thalictrum revolutum. Jatrorrhizine possesses antifungal, antibacterial activity. It has low toxicity and was studied in mouse models of obesity and hypercholesterolemia. The mechanism of action of Jatrorrhizine is not fully elucidated. The compound blocks alpha-1 and alpha-2 adrenoreceptors, monoamine oxidase A and B.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2575836	Antagonist 2778
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2575836	Antagonist 2778
Monoamine oxidase A 49 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11270727	Inhibitor 8297	4.0 µM [IC50]
Monoamine oxidase B 72 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11270727	Inhibitor 8297	62.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19431018	Primary	Basic research	Unknown Approved Use Unknown
Fungal infection 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12916091	Primary	Basic research	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27573054	Primary	Preclinical	Unknown Approved Use Unknown
Hypercholesterolemia 47 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24894270	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Monoamine oxidase inhibitors from rhizoma of Coptis chinensis.	2001 Feb	11270727
Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids.	2003 Aug	12916091
[Determination of four alkaloids in Berberis plants by HPLC].	2003 Dec	15617491
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.	2003 Dec 3	14640583
High-performance capillary electrophoresis for determining the contents of berberine, jatrorrhizine and palmatine in Gegenqinlian decoction.	2003 Jul	12865220
[Establishment of the control substance of plant drug and fingerprints of Coptis chinensis].	2004 Dec	15663220
[Distribution of four alkaloids in plants of Berberis].	2004 Feb	22454993
Structural elucidation and identification of alkaloids in Rhizoma Coptidis by electrospray ionization tandem mass spectrometry.	2004 Nov	15532075
Study on noncovalent complexes of cytotoxic protoberberine alkaloids with double-stranded DNA by using electrospray ionization mass spectrometry.	2004 Oct 4	15341959
Hypoglycemic activity of jatrorrhizine.	2005	16463653
Binding of the bioactive component jatrorrhizine to human serum albumin.	2005 Feb 11	15715992
[Chemical constituents from Corydalis humosa].	2005 Jul	16252721
Using oxidized carbon nanotubes as matrix for analysis of small molecules by MALDI-TOF MS.	2005 Jun	15907704
Spectrometric studies of cytotoxic protoberberine alkaloids binding to double-stranded DNA.	2005 Mar 1	15698803
Determination of quinolizidine alkaloids in Sophora flavescens and its preparation using capillary electrophoresis.	2006 May	16167304
[Quality analysis and evaluation of Rhizoma Coptidis under different cultivation conditions].	2006 Oct	17184122
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.	2007 Jul 16	17634120
Analysis of alkaloids in Coptis chinensis Franch by accelerated solvent extraction combined with ultra performance liquid chromatographic analysis with photodiode array and tandem mass spectrometry detections.	2008 Apr 21	18395058
Online structural elucidation of alkaloids and other constituents in crude extracts and cultured cells of Nandina domestica by combination of LC-MS/MS, LC-NMR, and LC-CD analyses.	2008 Aug	18671433
LC/MS/MS for identification of in vivo and in vitro metabolites of jatrorrhizine.	2008 Dec	18651596
[Variation patterns of Coptis teeta biomass and its major active compounds along an altitude gradient].	2008 Jul	18839903
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.	2008 Mar	17968851
Simultaneous determination of berberine, palmatine and jatrorrhizine by liquid chromatography-tandem mass spectrometry in rat plasma and its application in a pharmacokinetic study after oral administration of coptis-evodia herb couple.	2008 Mar 1	18258496
[Adscription of plasma effective constituents of rat after oral administration of gegen qinlian decoction].	2008 Nov	19216173
Chinese herbal medicinal ingredients inhibit secretion of IL-6, IL-8, E-selectin and TXB2 in LPS-induced rat intestinal microvascular endothelial cells.	2009	19874221
Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN.	2009 Feb	19156769
[A new flavonoid glucoside from Huanglianjiedutang decoction].	2009 May	19685742
[Pharmacokinetics of three alkaloids in Huanglianjiedu decoction in rat serum by LC-MS-MS].	2009 May	19673395
Simultaneous determination of 11 active components in two well-known traditional Chinese medicines by HPLC coupled with diode array detection for quality control.	2009 May 1	19264437
[Effects of extracts and active components of Rhizoma Coptidis on contraction of circular smooth muscle isolated from guinea pig gastric antrum].	2009 Sep	19747439
Biochemistry and occurrence of o-demethylation in plant metabolism.	2010	21423357
[Simultaneous determination of jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC].	2010 Aug	21046728
[Metabolism, transformation and distribution of Coptis chinensis total alkaloids in rat].	2010 Aug	20931859
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].	2010 Dec	21438408
[Preliminary study to investigate dynamic extract process of Huanglian Jiedu Tang and the mechanism of subsidence produce].	2010 Jan	20349713
The application of digital image recognition to the analysis of two-dimensional fingerprints.	2010 Jan 11	20005324
Screening the bioactive compounds in aqueous extract of Coptidis rhizoma which specifically bind to rabbit lung tissues beta2-adrenoceptor using an affinity chromatographic selection method.	2010 Jul 15	20561827
[In situ intestinal absorption kinetics of berberine and jatrorrhizine from extractive Rhizoma Coptidis in rats].	2010 Mar	20545203
Determination of bioactive compounds in Cortex Phellodendri by high-performance liquid chromatography.	2010 May-Jun	20629387
Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics.	2010 Nov	21049522
Metabolites of protoberberine alkaloids in human urine following oral administration of Coptidis Rhizoma decoction.	2010 Nov	20549593
Simultaneous determination of baicalin, baicalein, wogonin, berberine, palmatine and jatrorrhizine in rat plasma by liquid chromatography-tandem mass spectrometry and application in pharmacokinetic studies after oral administration of traditional Chinese medicinal preparations containing scutellaria-coptis herb couple.	2010 Nov 2	20430560
Determination of protoberberine alkaloids in medicinal plants based on acidic potassium permanganate chemiluminescence system.	2010 Sep-Oct	19743526

Patents

Sample Use Guides

In Vivo Use Guide

In the model of hyperlipidemia, jatrorrhizine was administered by intragastric injections at up to 100 mg/kg body weight.

Route of Administration: Intragastric

In Vitro Use Guide

Antifungal activity of jatrorrhizine was tested on dermatophytes and yeast strains isolated from superficial human lesions. The solution of jatrorrhizine was added to Sabouraud 2% dextrose agar. 5 μl of the suspension of each active growing test fungus was inoculated on the surface of testing and control agar plates and incubated for 15 days at 25 ± 1 °C. Two days after the fungi started growth on control plates the minimal inhibitory concentration was determined as the lowest tested concentration that inhibited visible growth of the test fungi.

Name

Type

Language

JATRORRHIZINE

Common Name

English

7,8,13,13A-TETRADEHYDRO-3-HYDROXY-2,9,10-TRIMETHOXYBERBINIUM

Common Name

English

NEPROTIN

Common Name

English

5,6-DIHYDRO-3-HYDROXY-2,9,10-TRIMETHOXYDIBENZO(A,G)QUINOLIZINIUM

Systematic Name

English

JATRORRHIZINE [MI]

Common Name

English

JATEORRHIZINE

Common Name

English

Code System Code Type Description

FDA UNII

091S1F8V5Q