PALMATINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22NO4
Molecular Weight	352.4037
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C=C1OC)C3=CC4=C(C=[N+]3CC2)C(OC)=C(OC)C=C4

InChI

InChIKey=QUCQEUCGKKTEBI-UHFFFAOYSA-N

InChI=1S/C21H22NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,9-12H,7-8H2,1-4H3/q+1

HIDE SMILES / InChI

Molecular Formula	C21H22NO4
Molecular Weight	352.4037
Charge	1
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/25526561 | http://www.alliedacademies.org/articles/pharmacological-activities-palmatine-alkaloid-compound-isolated-from-guatteria-friesiana-prospects-for-new-drug-development.pdf

Palmatine is a protoberberine alkaloid. Palmatine is major component of herbal preparations mainly used in traditional medicine Chinese, Korean and Indian. Palmatine can be found in various medicinal plants such as Coptis chinensis, Rhizoma coptidis, Corydalis yanhusuo, Radix tinosporae, among others. It exerts diverse pharmacological and biological properties. Palmatine has been proposed as a promising DNA phototherapy drug, notably due to its ability to produce in situ singlet oxygen only when interacting with DNA.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25526561 \| https://www.ncbi.nlm.nih.gov/pubmed/25829078 \| https://www.ncbi.nlm.nih.gov/pubmed/18421749	Binding Agent 1064
Acetylcholinesterase 207 Target ID: CHEMBL3198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23193393	Inhibitor 8297
Aryl hydrocarbon receptor 26 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24583342	Activator 1430
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25285405	Substrate 661
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25285405	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25043857 https://www.ncbi.nlm.nih.gov/pubmed/27175745 https://www.ncbi.nlm.nih.gov/pubmed/27181460 https://www.ncbi.nlm.nih.gov/pubmed/27444887	Primary	Preclinical	Unknown Approved Use Unknown
Gastric ulcer 67 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27858308	Primary	Preclinical	Unknown Approved Use Unknown
Amnesia 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23193393	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[The changes of some chemical components in banxiaxiexintang decoction of different combinations].	2002 May	12774328
Photostabilization of an entomopathogenic fungus using composite clay matrices.	2003 Feb	12785057
[Study on the solubility changes of Rhizoma Coptidis' main chemical constituents influenced by the proportion of Rhizoma Coptidis and Fructus Evodiae].	2003 Jul	15139107
High-performance capillary electrophoresis for determining the contents of berberine, jatrorrhizine and palmatine in Gegenqinlian decoction.	2003 Jul	12865220
Method validation for determination of alkaloid content in goldenseal root powder.	2003 May-Jun	12852562
Determination of mangiferin, jateorrhizine, palmatine, berberine, cinnamic acid, and cinnamaldehyde in the traditional Chinese medicinal preparation Zi-Shen pill by high-performance liquid chromatography.	2004 Apr	15154983
[Establishment of the control substance of plant drug and fingerprints of Coptis chinensis].	2004 Dec	15663220
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
Sensitivity improvement on detection of Coptidis alkaloids by sweeping in capillary electrophoresis.	2005 Feb 7	15664741
Simultaneous determinations of paeonol and palmatine hydrochloride in Shangshi Aerosols by HPLC method.	2005 Jul 1	15925262
The mechanism of guanine specific photooxidation in the presence of berberine and palmatine: activation of photosensitized singlet oxygen generation through DNA-binding interaction.	2005 Oct	16533018
[Fingerprints of Rhizoma Coptidis from Shizhu by HPLC].	2006 Jul	17059001
Nonaqueous capillary electrophoresis coupled with laser-induced native fluorescence detection for the analysis of berberine, palmatine, and jatrorrhizine in Chinese herbal medicines.	2006 Jun	16833085
RNA specific molecules: cytotoxic plant alkaloid palmatine binds strongly to poly(A).	2006 May 1	16497501
Molecular aspects on the specific interaction of cytotoxic plant alkaloid palmatine to poly(A).	2006 Nov 15	16678250
[Determination of 3 kinds of components in huanglian jiedu decoction by HPLC under different UV wavelengths].	2006 Oct	17225535
[Quality analysis and evaluation of Rhizoma Coptidis under different cultivation conditions].	2006 Oct	17184122
Simultaneous analysis of nine active components in Gegen Qinlian preparations by high-performance liquid chromatography with diode array detection.	2006 Sep	17069251
Hypoglycemic and hypocholesterolemic effects of Coptis chinensis franch inflorescence.	2006 Sep	17031605
Protoberberine alkaloids and their reversal activity of P-gp expressed multidrug resistance (MDR) from the rhizome of Coptis japonica Makino.	2006 Sep	17024849
Identification of palmatine and its metabolites in rat urine by liquid chromatography/tandem mass spectrometry.	2007	17534853
High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.	2007 Apr	17536728
Thin-layer chromatography/desorption electrospray ionization mass spectrometry: investigation of goldenseal alkaloids.	2007 Apr 1	17338504
Cytochrome P3A4 inhibitors and other constituents of Fibraurea tinctoria.	2007 Dec	17994701
Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.	2007 Dec	17891749
DNA-binding affinities and sequence specificities of protoberberine alkaloids and their demethylated derivatives: a comparative study.	2007 Feb	17311227
RNA binding small molecules: studies on t-RNA binding by cytotoxic plant alkaloids berberine, palmatine and the comparison to ethidium.	2007 Feb	17156912
Amplification of DNA-binding affinities of protoberberine alkaloids by appended polyamines.	2007 Feb 15	17127054
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	17084577
Molecular recognition of DNA by small molecules: AT base pair specific intercalative binding of cytotoxic plant alkaloid palmatine.	2007 Jul	17434677
Determination of palmatine in canine plasma by liquid chromatography-tandem mass spectrometry with solid-phase extraction.	2007 Jul 1	17537686
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.	2007 Jul 16	17634120
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.) 3: effect on human lens and retinal pigment epithelial cells.	2007 Jul-Aug	17645667
Affinity chromatography with immobilized DNA stationary phase for biological fingerprinting analysis of traditional Chinese medicines.	2007 Jun 22	17451725
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	17512816
Main antimicrobial components of Tinospora capillipes, and their mode of action against Staphylococcus aureus.	2007 Sep 4	17692848
Interaction of isoquinoline alkaloid palmatine with deoxyribonucleic acids: binding heterogeneity, and conformational and thermodynamic aspects.	2008 Apr	18421749
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
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008 Apr 24	17804078
Pharmacological and therapeutic effects of Berberis vulgaris and its active constituent, berberine.	2008 Aug	18618524
Identification of major alkaloids and steroidal saponins in rat serum by HPLC-diode array detection-MS/MS following oral administration of Huangbai-Zhimu herb-pair Extract.	2008 Aug	18318017
Fast fluorescent staining of protein in sodium dodecyl sulfate polyacrylamide gels by palmatine.	2008 Jan	18081205
The microenvironment of DNA switches the activity of singlet oxygen generation photosensitized by berberine and palmatine.	2008 Jan-Feb	18173721
Self-structure induction in single stranded poly(A) by small molecules: Studies on DNA intercalators, partial intercalators and groove binding molecules.	2008 Jun 1	18387354
Palmatine, a protoberberine alkaloid, inhibits both Ca(2+)- and cAMP-activated Cl(-) secretion in isolated rat distal colon.	2008 Mar	18204477
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
Analysis of major alkaloids in Rhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes.	2008 May	18425753
Simultaneous determination of eight bioactive alkaloids in Corydalis saxicola by high-performance liquid chromatography coupled with diode array detection.	2008 Sep-Oct	18446771

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 0.5 or 1 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Mouse preosteoclastic cell line (RAW 264.7) has a higher sensitivity to palmatine than mouse osteoblastic cell line (MC3T3-E1); the cell survival rates significantly decreased at 40 μM palmatine.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:30:16 GMT 2023` Edited by `admin` on `Fri Dec 15 18:30:16 GMT 2023`
Record UNII	G50C034217
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PALMATINE

Official Name

English

BERBERICININE

Common Name

English

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

Systematic Name

English

PALMATINE (NEGATIVE MARKER) (CONSTITUENT OF GOLDENSEAL) [DSC]

Common Name

English

O,O-DIMETHYLDEMETHYLENEBERBERINE

Common Name

English

PALMATINE [INCI]

Common Name

English

PALMATINE [MI]

Common Name

English

PALMATINE CATION

Common Name

English

PALMATINE ION

Common Name

English

Palmatine [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

19009