title: Isolation and identification of phase 1 metabolites of curcuminoids in rats.
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 metabolites' profiles, possible metabolic pathways of the curcuminoids in rats are proposed.
authors: Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China.
authors: Jun
authors: J
authors: Li
authors: Yue
authors: Y
authors: Liu
authors: Jun-Qi
authors: JQ
authors: Wei
authors: Kun
authors: K
authors: Wang
authors: Li-Xia
authors: LX
authors: Chen
authors: Xin-Sheng
authors: XS
authors: Yao
authors: Feng
authors: F
authors: Qiu
mesh_terms: D000818:Animals; D001711:Biotransformation; D003474:Curcumin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D036381:Diarylheptanoids; D005243:Feces / Q000737:chemistry*; D008297:Male; D053858:Metabolic Networks and Pathways; D015394:Molecular Structure; D051381:Rats; D017208:Rats, Wistar
chemical_list: D036381:Diarylheptanoids; C034786:bisdemethoxycurcumin; D003474:Curcumin; C050229:demethoxycurcumin