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

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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
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
Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism.	2007 Apr	17077972
[Alkaloid constituents of Corydalis adunca].	2007 Nov	18323203
Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms.	2009 Sep	19629460
In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds.	2010 Aug	20686258
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

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.

Name

Type

Language

DIHYDROSANGUINARINE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID00189627