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Planta Med 2012; 78(12): 1351-1356
DOI: 10.1055/s-0032-1314990
Pharmacokinetic Investigations
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Isolation and Identification of Phase 1 Metabolites of Curcuminoids in Rats

Jun Li
1   Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China
2   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China
,
Yue Liu
1   Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China
2   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China
,
Jun-Qi Wei
1   Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China
2   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China
,
Kun Wang
1   Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China
2   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China
,
Li-Xia Chen
1   Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China
2   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China
,
Xin-Sheng Yao
1   Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China
2   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China
,
Feng Qiu
1   Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China
2   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, China
› Author Affiliations
Further Information

Publication History

received 19 January 2012
revised 02 June 2012

accepted 04 June 2012

Publication Date:
29 June 2012 (online)

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Abstract

Curcuminoids are natural food coloring additives with anti-inflammatory, antioxidant, and anticarcinogenic activity, which contain mainly three diarylheptanoids: curcumin, demethoxycurcumin, and bisdemethoxycurcumin. In this paper, the metabolites of curcuminoids in the feces and urine of rats after oral administration by gavage were investigated. Four new metabolites, 3-hydroxy-[1-(4-hydroxyphenyl)-7-(3-hydroxyphey)] heptane-A (M1), 3-hydroxy-[1-(4-hydroxyphenyl)-7-(3-hydroxyphey)] heptane-B (M2), 3-hydroxy-1,7-bis(3-hydroxyphenyl) heptane-A (M3) and 3-hydroxy-1,7-bis(3-hydroxyphenyl) heptane-B (M4), along with five known metabolites (M5–M9), were isolated from the feces of male Wistar-derived rats and nine known metabolites (M5–M8, M10–M14) were isolated from the urine. Their structures were elucidated by extensive spectroscopic analysis. The finding that the metabolites occurred as several pairs of enantiomers was confirmed by chiral column chromatography. Based on the metabolitesʼ profiles, possible metabolic pathways of the curcuminoids in rats are proposed.

Key words

Curcuma longa - Zingiberaceae - curcuminoids - rat - metabolites from faeces and urine - enantiomers

Supporting Information

 

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