LUCIDIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O5
Molecular Weight	270.2369
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCC1=C(O)C=C2C(=O)C3=C(C=CC=C3)C(=O)C2=C1O

InChI

InChIKey=AMIDUPFSOUCLQB-UHFFFAOYSA-N

InChI=1S/C15H10O5/c16-6-10-11(17)5-9-12(15(10)20)14(19)8-4-2-1-3-7(8)13(9)18/h1-5,16-17,20H,6H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28972744 | https://www.ncbi.nlm.nih.gov/pubmed/25574682 | https://www.ncbi.nlm.nih.gov/pubmed/2070492 | https://www.ncbi.nlm.nih.gov/pubmed/9886573

Lucidin-3-O-primeveroside (LuP) is an anthraquinone derivative present in Rubia tinctorum L. (madder root), which has been used as a coloring agent and food additive. LuP can be metabolically converted to genotoxic compound lucidin, which subsequently forms lucidin-specific N2-2'-deoxyguanosine (N2-dG) and N6-2'-deoxyadenosine (N6-dA) DNA adducts. Lucidin is mutagenic and carcinogenic in rodents but has low carcinogenic risks in humans. Lucidin adduct destabilizes DNA structure and reduces fidelity and processivity of DNA synthesis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28972744 \| https://www.ncbi.nlm.nih.gov/pubmed/25574682 \| https://www.ncbi.nlm.nih.gov/pubmed/2070492 \| https://www.ncbi.nlm.nih.gov/pubmed/9886573	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Determination of lucidin-specific DNA adducts by liquid chromatography with tandem mass spectrometry in the livers and kidneys of rats given lucidin-3-O-primeveroside.	2012-05-21	22494063
Anthraquinones from the roots of Knoxia valerianoides inhibit the formation of advanced glycation end products and rat lens aldose reductase in vitro.	2010-02	20195820
Chemical structure determination of DNA bases modified by active metabolites of lucidin-3-O-primeveroside.	2010-01	20000472
1,3-Dihydr-oxy-2-methoxy-methyl-9,10-anthraquinone from Rennellia elliptica Korth.	2009-05-29	21583274
Possible contribution of rubiadin, a metabolite of madder color, to renal carcinogenesis in rats.	2009-04	19167447
Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity?	2009	20107583
Antimicrobial anthraquinones from Morinda angustifolia.	2008-12	18621113
Chemical constituents of Morinda citrifolia roots exhibit hypoglycemic effects in streptozotocin-induced diabetic mice.	2008-05	18451522
Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography.	2006-11-10	16962601
Characterization of lucidin formation in Rubia tinctorum L.	2004-11-13	16310368
[Examination of the anthraquinone composition in root-stock and root samples of Rubia tinctorium L. plants of different origins].	2004	16318223
Chemical and enzymatic hydrolysis of anthraquinone glycosides from madder roots.	2003-06-10	12793459
Lucidin type anthraquinone glycosides from Putoria calabrica.	2002-05	12036036
Mutagenicity of natural anthraquinones from Rubia tinctorum in the Drosophila wing spot test.	2001-03	11301857
Carcinogenicity and DNA adduct formation observed in ACI rats after long-term treatment with madder root, Rubia tinctorum L.	1998-12	9886573
Evaluation of DNA-binding activity of hydroxyanthraquinones occurring in Rubia tinctorum L.	1991-07	2070492
[Studies on coloring constituents in commercial madder color].	1989	2636908
The genotoxicity of lucidin, a natural component of Rubia tinctorum L., and lucidinethylether, a component of ethanolic Rubia extracts.	1988-06	3069188

Patents

Sample Use Guides

In Vivo Use Guide

Male Parkes mice were treated orally for 4 days with lucidin (2 mg/d) and DNA was isolated from liver, kidney, duodenum and colon. Analysis by 32P-postlabelling revealed that lucidin formed DNA adducts in all the tissues examined but that the adduct patterns were organ-specific.

Route of Administration: Oral

In Vitro Use Guide

Lucidin was active against Entamoeba histolytica (MIC 31.25 μg/mL) and Giardia intestinalis (MIC 7.8 μg/mL).

Name

Type

Language

NSC-30546

Preferred Name

English

LUCIDIN

Common Name

English

9,10-ANTHRACENEDIONE, 1,3-DIHYDROXY-2-(HYDROXYMETHYL)-

Systematic Name

English

HENINE

Common Name

English

DIHYDROXY-2-(HYDROXYMETHYL)ANTHRAQUINONE, 1,3-

Systematic Name

English

1,3-DIHYDROXY-2-(HYDROXYMETHYL)ANTHRAQUINONE

Systematic Name

English

LUCIDIN [HSDB]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID10197278