DIHYDROSANGUINARINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H15NO4
Molecular Weight	333.3374
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC2=C(C=CC3=C2OCO3)C4=C1C5=C(C=C4)C=C6OCOC6=C5

InChI

InChIKey=CIUHLXZTZWTVFL-UHFFFAOYSA-N

InChI=1S/C20H15NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-7H,8-10H2,1H3

HIDE SMILES / InChI

Molecular Formula	C20H15NO4
Molecular Weight	333.3374
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/16280262 | https://www.ncbi.nlm.nih.gov/pubmed/21500094

The quaternary benzo[c]phenanthridine alkaloid sanguinarine (SG) is the main component of Sangrovit, a natural livestock feed additive. Dihydrosanguinarine (DHSG) has been identified as an SG metabolite in rats. Therefore, the conversion of SG to DHSG is a likely elimination pathway of SG in mammals. Dihydrosanguinarine can also be isolated from Macleaya macrocarpa. DHSG has also been shown to have antiparasytic and anti fungal properties. It has been identified as a potential antiparasitic treatment for Ichthyopthirius multifiliis infection in Squaliobarbus curriculus.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Two antimicrobial alkaloids from Bocconia arborea.	1999 Aug	10433482
Identification of benzophenanthridine alkaloids from Bocconia arborea by gas chromatography-mass spectrometry.	2002 May-Jun	12099109
Direct determination of alkaloid contents in Fumaria species by GC-MS.	2002 Nov-Dec	12494757
Argemone oil induced cellular damage in the reproductive tissues of transgenic Drosophila melanogaster: protective role of 70 kDa heat shock protein.	2003	12898646
Achiral and chiral determination of benzophenanthridine alkaloids from methanol extracts of Hylomecon species by high performance liquid chromatography.	2003 Feb	12643585
[Studies on the alkaloids from the herb of Corydalis adunca].	2005 Feb	15719638
Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS.	2005 Sep-Oct	16223088
Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification.	2006 Feb	17080644
A liquid chromatographic-mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat.	2006 Jan 2	16280262
Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism.	2007 Apr	17077972
Metabolism of sanguinarine: the facts and the myths.	2007 Feb	17305495
Disposition of sanguinarine in the rat.	2007 May	17523056
[Alkaloid constituents of Corydalis adunca].	2007 Nov	18323203
Differential induction of protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cultures by methyl jasmonate and yeast extract.	2008 Feb	18309269
Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures.	2008 Jan 22	18211706
The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study.	2008 Jul	18495316
Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures.	2008 May 20	18420297
[Alkaloids from Macleaya cordata].	2009 Jul	19873781
Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells.	2009 Jun	19346183
Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.	2009 Mar 13	18774138
Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms.	2009 Sep	19629460
Antifungal activity of the benzo[c]phenanthridine alkaloids from Chelidonium majus Linn against resistant clinical yeast isolates.	2009 Sep 25	19647059
Antibacterial activity of Hylomecon hylomeconoides against methicillin-resistant Staphylococcus aureus.	2010 Apr	19578993
In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds.	2010 Aug	20686258
Phytochemical and antimicrobial characterization of Macleaya cordata herb.	2010 Dec	20600683
Interaction of sanguinarine and its dihydroderivative with the Na+/K+-ATPase. Complex view on the old problem.	2010 Jun 16	20385218
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.	2010 Nov 18	21083930
Fluorescence of sanguinarine: spectral changes on interaction with amino acids.	2010 Oct 7	20683512
A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain.	2013 Dec 12	24120516
NQO1 involves in the imine bond reduction of sanguinarine and recombinant adeno-associated virus mediated NQO1 overexpression decreases sanguinarine-induced cytotoxicity in rat BRL cells.	2014 Feb 10	24300172

Sample Use Guides

In Vivo Use Guide

male Wistar rats: at concentrations of 100 and 500 ppm Dihydrosanguinarine (DHSG) in feed for 90 days (average doses of 14 and 58 mg DHSG/kg body weight/day)

Route of Administration: Oral

In Vitro Use Guide

The antifungal activities of dihydrosanguinarine, isolated from the leaves of Macleaya microcarpa, was evaluated on 12 plant pathogenic fungi. Among the 11 tested plant pathogenic fungi in vitro, compound showed the highest antifungal activity against B. cinerea Pers, with 95.16% mycelial growth inhibition at 50 µg mL⁻¹.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:42:47 GMT 2023` Edited by `admin` on `Fri Dec 15 19:42:47 GMT 2023`
Record UNII	3H1ZKG80F7
Record Status	`Validated (UNII)`
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Name

Type

Language

DIHYDROSANGUINARINE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID00189627