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

Molecular Formula	C20H19NO4
Molecular Weight	337.3692
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 65 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2575836	Antagonist 2849
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2575836	Antagonist 2849
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11270727	Inhibitor 8504	4.0 µM [IC50]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11270727	Inhibitor 8504	62.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Bacterial infections 235 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 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27573054	Primary	Preclinical	Unknown Approved Use Unknown
Hypercholesterolemia 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24894270	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].	2010-12	21438408
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.	2010-11-02	20430560
Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics.	2010-11	21049522
Metabolites of protoberberine alkaloids in human urine following oral administration of Coptidis Rhizoma decoction.	2010-11	20549593
Dig1 protects against cell death provoked by glyphosate-based herbicides in human liver cell lines.	2010-10-27	20979644
Simultaneous analysis of seven alkaloids in Coptis-Evodia herb couple and Zuojin pill by UPLC with accelerated solvent extraction.	2010-09	20715137
[Simultaneous determination of jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC].	2010-08	21046728
[Metabolism, transformation and distribution of Coptis chinensis total alkaloids in rat].	2010-08	20931859
Circumvention of multi-drug resistance of cancer cells by Chinese herbal medicines.	2010-07-25	20653978
Determination of bioactive compounds in Cortex Phellodendri by high-performance liquid chromatography.	2010-07-16	20629387
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.	2010-07-15	20561827
Increased plasma exposures of five protoberberine alkaloids from Coptidis Rhizoma in streptozotocin-induced diabetic rats: is P-GP involved?	2010-06	20108175
Rhizoma coptidis and berberine-induced activation of murine microglia N9 cells.	2010-05-04	20211233
[Simultaneous determination of the five alkaloids in Rhizoma Coptidis by nonaqueous capillary electrophoresis].	2010-04	20712125
[In situ intestinal absorption kinetics of berberine and jatrorrhizine from extractive Rhizoma Coptidis in rats].	2010-03	20545203
Quality assurance for Chinese herbal formulae: standardization of IBS-20, a 20-herb preparation.	2010-02-22	20175906
Quaternary alkaloids of Argemone mexicana.	2010-02	20645832
The application of digital image recognition to the analysis of two-dimensional fingerprints.	2010-01-11	20005324
[Preliminary study to investigate dynamic extract process of Huanglian Jiedu Tang and the mechanism of subsidence produce].	2010-01	20349713
Biochemistry and occurrence of o-demethylation in plant metabolism.	2010	21423357
Oren-gedoku-to and its constituents with therapeutic potential in Alzheimer's disease inhibit indoleamine 2, 3-dioxygenase activity in vitro.	2010	20847417
Determination of protoberberine alkaloids in medicinal plants based on acidic potassium permanganate chemiluminescence system.	2009-09-11	19743526
Analgesic and anti-inflammatory activities of ethanol root extract of Mahonia oiwakensis in mice.	2009-09-07	19576980
[Effects of extracts and active components of Rhizoma Coptidis on contraction of circular smooth muscle isolated from guinea pig gastric antrum].	2009-09	19747439
A rapid and simple determination of protoberberine alkaloids in Rhizoma Coptidis by 1H NMR and its application for quality control of commercial prescriptions.	2009-07-12	19345543
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.	2009-07	19472295
Simple and reliable methods for the determination of sixteen marker components for quality control of Daochi pill by HPLC coupled with diode array detection.	2009-06-18	19533595
Development of a rapid resolution liquid chromatographic method for simultaneous analysis of four alkaloids in Rhizoma coptidis under different cultivation conditions.	2009-06-03	19485228
Simultaneous determination of 11 active components in two well-known traditional Chinese medicines by HPLC coupled with diode array detection for quality control.	2009-05-01	19264437
[A new flavonoid glucoside from Huanglianjiedutang decoction].	2009-05	19685742
[Pharmacokinetics of three alkaloids in Huanglianjiedu decoction in rat serum by LC-MS-MS].	2009-05	19673395
[Effect of additives on absorption of Coptis chinensis total alkaloids and pharmacokinetics in mice].	2009-02	19445164
Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN.	2009-02	19156769
Bear bile: dilemma of traditional medicinal use and animal protection.	2009-01-12	19138420
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
Synthesis and antimicrobial activity of 3-octyloxy-8-alkyljatrorrhizine derivatives.	2009	19431018
LC/MS/MS for identification of in vivo and in vitro metabolites of jatrorrhizine.	2008-12	18651596
[Adscription of plasma effective constituents of rat after oral administration of gegen qinlian decoction].	2008-11	19216173
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.	2008-08	18671433
[Variation patterns of Coptis teeta biomass and its major active compounds along an altitude gradient].	2008-07	18839903
Analysis of major alkaloids in Rhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes.	2008-05	18425753
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.	2008-04-21	18395058
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.	2008-03-01	18258496
[Analysis of the main components of coptis-evodia herb couple by HPLC-DAD-MS].	2008-03	18630268
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.	2008-03	17968851
Synthesis and antimicrobial activity of 3-alkoxyjatrorrhizine derivatives.	2008-02	18300191
Cytochrome P3A4 inhibitors and other constituents of Fibraurea tinctoria.	2007-12	17994701
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.	2007-07-16	17634120
Determination of palmatine in canine plasma by liquid chromatography-tandem mass spectrometry with solid-phase extraction.	2007-07-01	17537686
[Distribution of four alkaloids in plants of Berberis].	2004-02	22454993

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:22:02 GMT 2025` Edited by `admin` on `Mon Mar 31 19:22:02 GMT 2025`
Record UNII	091S1F8V5Q
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

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

Preferred Name

English

JATRORRHIZINE

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