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Details

Stereochemistry ACHIRAL
Molecular Formula C20H20NO4
Molecular Weight 338.3779
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of JATRORRHIZINE

SMILES

COc1ccc2=CC3=C4C=C(C(=O)C=C4CC[NH+]3C=c2c1OC)OC

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.
1992 May 29
Isoquinoline alkaloids from Mahonia aquifolium stem bark are active against Malassezia spp.
2001
Monoamine oxidase inhibitors from rhizoma of Coptis chinensis.
2001 Feb
Identification of three sulfate-conjugated metabolites of berberine chloride in healthy volunteers' urine after oral administration.
2002 Jan
[Determination of four alkaloids in Berberis plants by HPLC].
2003 Dec
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.
2003 Dec 3
Antimicrobial activity of Mahonia aquifolium crude extract and its major isolated alkaloids.
2004 Aug
[Distribution of four alkaloids in plants of Berberis].
2004 Feb
Separation of protoberberine quaternary alkaloids from a crude extract of Enantia chlorantha by centrifugal partition chromatography.
2004 Jul 2
Structural elucidation and identification of alkaloids in Rhizoma Coptidis by electrospray ionization tandem mass spectrometry.
2004 Nov
[Quality assessment of Coptis chinensis in China].
2005 Apr
Screening and analysis of bioactive compounds with biofingerprinting chromatogram analysis of traditional Chinese medicines targeting DNA by microdialysis/HPLC.
2005 May 27
[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
Rapid determination of protopine, allocryptopine, sanguinarine and chelerythrine in fruits of Macleaya cordata by microwave-assisted solvent extraction and HPLC-ESI/MS.
2006 Nov-Dec
[Determination of 3 kinds of components in huanglian jiedu decoction by HPLC under different UV wavelengths].
2006 Oct
Cytochrome P3A4 inhibitors and other constituents of Fibraurea tinctoria.
2007 Dec
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
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.
2007 Jul 16
Affinity chromatography with immobilized DNA stationary phase for biological fingerprinting analysis of traditional Chinese medicines.
2007 Jun 22
Analysis of berberine and total alkaloid content in cortex phellodendri by near infrared spectroscopy (NIRS) compared with high-performance liquid chromatography coupled with ultra-visible spectrometric detection.
2007 Jun 5
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
Synthesis and antimicrobial activity of 3-alkoxyjatrorrhizine derivatives.
2008 Feb
[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
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
Analysis of major alkaloids in Rhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes.
2008 May
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
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
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 jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC].
2010 Aug
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].
2010 Dec
Increased plasma exposures of five protoberberine alkaloids from Coptidis Rhizoma in streptozotocin-induced diabetic rats: is P-GP involved?
2010 Jun
[In situ intestinal absorption kinetics of berberine and jatrorrhizine from extractive Rhizoma Coptidis in rats].
2010 Mar
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
Determination of protoberberine alkaloids in medicinal plants based on acidic potassium permanganate chemiluminescence system.
2010 Sep-Oct
Patents

Patents

Sample Use Guides

In the model of hyperlipidemia, jatrorrhizine was administered by intragastric injections at up to 100 mg/kg body weight.
Route of Administration: Intragastric
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
FDA UNII
091S1F8V5Q
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
222-817-3
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY
MERCK INDEX
M6579
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY Merck Index
CAS
3621-38-3
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY
PUBCHEM
72323
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY
WIKIPEDIA
JATRORRHIZINE
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY
MESH
C055785
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY
EPA CompTox
3621-38-3
Created by admin on Sat Jun 26 07:44:14 UTC 2021 , Edited by admin on Sat Jun 26 07:44:14 UTC 2021
PRIMARY