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
Molecular Formula | C15H10O5 |
Molecular Weight | 270.2369 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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The genotoxicity of lucidin, a natural component of Rubia tinctorum L., and lucidinethylether, a component of ethanolic Rubia extracts. | 1988 Jun |
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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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Characterization of lucidin formation in Rubia tinctorum L. | 2005 Oct-Nov |
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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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Antimicrobial anthraquinones from Morinda angustifolia. | 2008 Dec |
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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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Possible contribution of rubiadin, a metabolite of madder color, to renal carcinogenesis in rats. | 2009 Apr |
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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 |
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).
Substance Class |
Chemical
Created
by
admin
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Edited
Fri Dec 15 19:13:42 GMT 2023
by
admin
on
Fri Dec 15 19:13:42 GMT 2023
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Record UNII |
60Q5564O9D
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Record Status |
Validated (UNII)
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Record Version |
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