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Details

Stereochemistry ACHIRAL
Molecular Formula C20H20NO4
Molecular Weight 338.3771
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of JATRORRHIZINE

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

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

PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
[Distribution of four alkaloids in plants of Berberis].
2004 Feb
Hypoglycemic activity of jatrorrhizine.
2005
[Quality assessment of Coptis chinensis in China].
2005 Apr
[Chemical constituents from Corydalis humosa].
2005 Jul
Screening and analysis of bioactive compounds with biofingerprinting chromatogram analysis of traditional Chinese medicines targeting DNA by microdialysis/HPLC.
2005 May 27
Capillary electrochromatography with a neutral monolithic column for classification of analytes and determination of basic drugs in human serum.
2005 Sep
Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry.
2006
[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].
2006 Apr
Pharmacokinetics of berberine and its main metabolites in conventional and pseudo germ-free rats determined by liquid chromatography/ion trap mass spectrometry.
2006 Dec
[Fingerprints of Rhizoma Coptidis from Shizhu by HPLC].
2006 Jul
Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA.
2006 Jul 1
Acetylcholinesterase inhibitors from Stephania venosa tuber.
2006 May
Determination of quinolizidine alkaloids in Sophora flavescens and its preparation using capillary electrophoresis.
2006 May
[Liquid chromatography-tandem electrospray ionization ion trap mass spectrometric assay for the metabolites of jatrorrhizine in rat urine].
2006 Sep
Hypoglycemic and hypocholesterolemic effects of Coptis chinensis franch inflorescence.
2006 Sep
Simultaneous determination of eight components in Radix Tinosporae by high-performance liquid chromatography coupled with diode array detector and electrospray tandem mass spectrometry.
2007 Feb 19
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
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
LC/MS/MS for identification of in vivo and in vitro metabolites of jatrorrhizine.
2008 Dec
[Variation patterns of Coptis teeta biomass and its major active compounds along an altitude gradient].
2008 Jul
[Analysis of the main components of coptis-evodia herb couple by HPLC-DAD-MS].
2008 Mar
Analysis of major alkaloids in Rhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes.
2008 May
[Adscription of plasma effective constituents of rat after oral administration of gegen qinlian decoction].
2008 Nov
Synthesis and antimicrobial activity of 3-octyloxy-8-alkyljatrorrhizine derivatives.
2009
[Effect of additives on absorption of Coptis chinensis total alkaloids and pharmacokinetics in mice].
2009 Feb
Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN.
2009 Feb
Bear bile: dilemma of traditional medicinal use and animal protection.
2009 Jan 12
Pulsatilla decoction and its active ingredients inhibit secretion of NO, ET-1, TNF-alpha, and IL-1 alpha in LPS-induced rat intestinal microvascular endothelial cells.
2009 Jul
A rapid and simple determination of protoberberine alkaloids in Rhizoma Coptidis by 1H NMR and its application for quality control of commercial prescriptions.
2009 Jul 12
Development of a rapid resolution liquid chromatographic method for simultaneous analysis of four alkaloids in Rhizoma coptidis under different cultivation conditions.
2009 Mar-Apr
[A new flavonoid glucoside from Huanglianjiedutang decoction].
2009 May
[Pharmacokinetics of three alkaloids in Huanglianjiedu decoction in rat serum by LC-MS-MS].
2009 May
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
[Effects of extracts and active components of Rhizoma Coptidis on contraction of circular smooth muscle isolated from guinea pig gastric antrum].
2009 Sep
Analgesic and anti-inflammatory activities of ethanol root extract of Mahonia oiwakensis in mice.
2009 Sep 7
Simple and reliable methods for the determination of sixteen marker components for quality control of Daochi pill by HPLC coupled with diode array detection.
2009 Sep-Oct
Biochemistry and occurrence of o-demethylation in plant metabolism.
2010
Oren-gedoku-to and its constituents with therapeutic potential in Alzheimer's disease inhibit indoleamine 2, 3-dioxygenase activity in vitro.
2010
[Simultaneous determination of the five alkaloids in Rhizoma Coptidis by nonaqueous capillary electrophoresis].
2010 Apr
[Simultaneous determination of jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC].
2010 Aug
[Metabolism, transformation and distribution of Coptis chinensis total alkaloids in rat].
2010 Aug
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].
2010 Dec
Quaternary alkaloids of Argemone mexicana.
2010 Feb
Circumvention of multi-drug resistance of cancer cells by Chinese herbal medicines.
2010 Jul 25
Determination of bioactive compounds in Cortex Phellodendri by high-performance liquid chromatography.
2010 May-Jun
Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics.
2010 Nov
Dig1 protects against cell death provoked by glyphosate-based herbicides in human liver cell lines.
2010 Oct 27
Simultaneous analysis of seven alkaloids in Coptis-Evodia herb couple and Zuojin pill by UPLC with accelerated solvent extraction.
2010 Sep
Determination of protoberberine alkaloids in medicinal plants based on acidic potassium permanganate chemiluminescence system.
2010 Sep-Oct
Patents

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
MI  
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
ECHA (EC/EINECS)
222-817-3
Created by admin on Tue Oct 22 13:23:51 UTC 2019 , Edited by admin on Tue Oct 22 13:23:51 UTC 2019
PRIMARY
MERCK INDEX
M6579
Created by admin on Tue Oct 22 13:23:51 UTC 2019 , Edited by admin on Tue Oct 22 13:23:51 UTC 2019
PRIMARY Merck Index
CAS
3621-38-3
Created by admin on Tue Oct 22 13:23:51 UTC 2019 , Edited by admin on Tue Oct 22 13:23:51 UTC 2019
PRIMARY
WIKIPEDIA
JATRORRHIZINE
Created by admin on Tue Oct 22 13:23:51 UTC 2019 , Edited by admin on Tue Oct 22 13:23:51 UTC 2019
PRIMARY
MESH
C055785
Created by admin on Tue Oct 22 13:23:51 UTC 2019 , Edited by admin on Tue Oct 22 13:23:51 UTC 2019
PRIMARY
EPA CompTox
3621-38-3
Created by admin on Tue Oct 22 13:23:51 UTC 2019 , Edited by admin on Tue Oct 22 13:23:51 UTC 2019
PRIMARY