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
Direct determination of alkaloid contents in Fumaria species by GC-MS.	2002 Nov-Dec	12494757
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
Metabolism of sanguinarine: the facts and the myths.	2007 Feb	17305495
Differential induction of protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cultures by methyl jasmonate and yeast extract.	2008 Feb	18309269
Antifungal activity of the benzo[c]phenanthridine alkaloids from Chelidonium majus Linn against resistant clinical yeast isolates.	2009 Sep 25	19647059
Phytochemical and antimicrobial characterization of Macleaya cordata herb.	2010 Dec	20600683
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)`
Record Version

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Name

Type

Language

DIHYDROSANGUINARINE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID00189627