Two novel creatinine adducts of andrographolide in human urine

Xenobiotica; the Fate of Foreign Compounds in Biological Systems
Feng QiuXinsheng Yao

Abstract

Andrographolide is a major labdane diterpenoid of the traditional Chinese and Ayurvedic medicine. Andrographis paniculate (Burm) Nees, is used in clinical situations in China mainly to treat fever, cold, and inflammation. In our previous study, fifteen metabolites of andrographolide were identified in human urine. However, there are still two other unknown metabolites. The aim of this study was to elucidate the structures of these two metabolites. 3. The two metabolites which are probably epimers were identified as creatinine adducts, and their structures were determined to be 14-deoxy-12-(creatinine-5-yl)-andrographolide-19-O-β-D-glucuronide A (Metabolite 1) and 14-deoxy-12-(creatinine-5-yl)-andrographolide-19-O-β-D-glucuronide B (Metabolite 2) by means of spectroscopic evidences. 4. It is for the first time that the formation of creatinine adducts as a novel metabolic pathway is reported. The mechanism was presumed that β-carbon (C-12) of α, β-unsaturated carbonyl was attacked by a 5-anion intermediate of creatinine formed through elimination of a proton, followed by the double bond migration from 12(13) to 13(14) and elimination of the hydroxyl group at C-14.

References

Apr 1, 1992·Planta medica·B ShuklaB N Dhawan
Aug 5, 2000·Phytotherapy Research : PTR·C CalabreseL J Standish
Nov 18, 2000·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·A PanossianH Wagner
May 9, 2003·Chemical & Pharmaceutical Bulletin·Xiangjiu HeXinsheng Yao
Dec 4, 2003·Journal of Experimental Therapeutics & Oncology·Sriram RajagopalR Rajagopalan
May 13, 2004·Journal of Ethnopharmacology·R Ajaya KumarS Rajagopal
Jun 10, 2004·Chemical & Pharmaceutical Bulletin·Liang CuiXinsheng Yao
Jan 13, 2005·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Liang CuiXinsheng Yao
Nov 29, 2008·European Journal of Pharmacology·María D CarrettaRafael A Burgos
Apr 10, 2009·Drug Metabolism Letters·Liang CuiXinsheng Yao

❮ Previous
Next ❯

Citations

Aug 15, 2013·Natural Product Reports·James R Hanson
Aug 22, 2014·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Stephen C Mitchell
Oct 7, 2020·Natural Product Reports·Quy T N TranChristina L L Chai
Dec 24, 2019·Acta Pharmaceutica Sinica. B·Yuhua LiHuichang Bi

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Chemical & Pharmaceutical Bulletin
Liang CuiXinsheng Yao
Journal of Asian Natural Products Research
Li-Xia ChenXin-Sheng Yao
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
Yanli GuShouzhuo Yao
© 2021 Meta ULC. All rights reserved