Home
Resources
Publications
Chemical Structure Determination of DNA Bases Modified by Active Metabolites of lucidin-3-O-primeveroside

Chemical Structure Determination of DNA Bases Modified by Active Metabolites of lucidin-3-O-primeveroside

Yuji Ishii, Toshiya Okamura, Tomoki Inoue, Kiyoshi Fukuhara, Takashi Umemura, Akiyoshi Nishikawa

Chem Res Toxicol. 2010 Jan;23(1):134-41.

PMID: 20000472

Abstract:

Lucidin-3-O- primeveroside (LuP) is one of the components of madder root (Rubia tinctorum L.; MR) which is reported to be carcinogenic in the kidney and liver of rats. Since metabolism of LuP generates genotoxic compounds such as lucidin (Luc) and rubiadin (Rub), it is likely that LuP plays a key role in MR carcinogenesis. In the present study, the chemical structures of Luc-specific 2'-deoxyguanosine (dG) and 2'-deoxyadenosine (dA) adducts following the reactions of dG and dA with a Luc carbocation or quinone methide intermediate derived from Acetoxy-Luc were determined by liquid chromatography with photodiode array and electron spray ionizaion-mass spectrometry (LC-PDA-ESI/MS). The identification of the two measurable adducts as Luc-N(2)-dG and Luc-N(6)-dA was confirmed by NMR analysis. Subsequently, using a newly developed quantitative analytical method using LC-ESI/MS, the formation of Luc-N(2)-dG and Luc-N(6)-dA from the reaction of calf thymus DNA with Luc in the presence of S9 mixture was observed. The fact that this reaction with Rub also gave rise to the same dG and dA adducts strongly suggests that Rub genotoxicity involves a metabolic conversion to Luc. The precise determination of the modified DNA bases generated by LuP and the method for their analysis may contribute to further comprehension of the mode of action underlying carcinogenesis by MR and related anthraquinones.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP29706590	Lucidin 3-primeveroside		29706-59-0	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: