Home
Resources
Publications
Metabolic Profile of 1,5-dicaffeoylquinic Acid in Rats, an in Vivo and in Vitro Study

Metabolic Profile of 1,5-dicaffeoylquinic Acid in Rats, an in Vivo and in Vitro Study

Bo Yang, Zhiyun Meng, Junxing Dong, Liangping Yan, Libo Zou, Zhongming Tang, Guifang Dou

Drug Metab Dispos. 2005 Jul;33(7):930-6.

PMID: 15802385

Abstract:

To explore the metabolism of 1,5-dicaffeoylquinic acid (1,5-DCQA) in rats, liquid chromatography-mass spectrometry in parallel to diode-array detection was used for the rapid detection/characterization of the metabolites formed in bile, urine, and plasma of rats following oral administration of 1,5-DCQA (160 mg/kg). The methylation and glucuronidation of 1,5-DCQA occurring in vitro using rat liver and small intestinal microsomes and cytosols were studied in comparison with those occurring in vivo, and the enzymes involved were also determined. In addition, the anti-HIV (human immunodeficiency virus) activity of three important metabolites was preliminarily evaluated in MT-4 cells infected with HIV-1. A total of 22 metabolites in vivo and in vitro were identified, including four isomeric O-mono-methylated metabolites (M8-M11), nine isomeric O-di-methylated metabolites (M3, M6, M22, and M12-M17), four isomeric O-mono-methyl-glucuronidated metabolites (M2 and M19-M21), four isomeric O-di-methyl-glucuronidated metabolites (M1, M4, M5, and M7), and one glucuronidated metabolite (M18). The O-methylation positions of three important metabolites (M8, M9, and M12) were determined (3''-, 3'-, and 3',3''-) by comparing with synthesized standards. The efficacy experiments showed that M8, M9, and M12 could inhibit HIV replication with IC(50) values of about 25, 25, and 46 microM, respectively. These results suggest that O-methylation and glucuronidation are two important metabolic pathways of 1,5-DCQA, that both rat liver and small intestine can catalyze such reactions by catechol-O-methyltransferase and UDP-glucuronosyltransferases, and that the HIV-1 inhibitory activity of M8, M9, and M12 is comparable to or slightly weaker than that of 1,5-DCQA.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP19870463	1,5-Dicaffeoylquinic acid		19870-46-3	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: