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
SMILES
OCC1=C(O)C2=C(C=C1O)C(=O)C3=C(C=CC=C3)C2=O
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
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
PubMed
Title | Date | PubMed |
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Carcinogenicity and DNA adduct formation observed in ACI rats after long-term treatment with madder root, Rubia tinctorum L. | 1998 Dec |
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Lucidin type anthraquinone glycosides from Putoria calabrica. | 2002 May |
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Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography. | 2006 Nov 10 |
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Chemical constituents of Morinda citrifolia roots exhibit hypoglycemic effects in streptozotocin-induced diabetic mice. | 2008 May |
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Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity? | 2009 |
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1,3-Dihydr-oxy-2-methoxy-methyl-9,10-anthraquinone from Rennellia elliptica Korth. | 2009 May 29 |
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Anthraquinones from the roots of Knoxia valerianoides inhibit the formation of advanced glycation end products and rat lens aldose reductase in vitro. | 2010 Feb |
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Chemical structure determination of DNA bases modified by active metabolites of lucidin-3-O-primeveroside. | 2010 Jan |
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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 May 21 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2070492
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25686628
Lucidin was active against Entamoeba histolytica (MIC 31.25 μg/mL) and Giardia intestinalis (MIC 7.8 μg/mL).
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SUBSTANCE RECORD