Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China.
Planta Med. 2012 Aug;78(12):1351-6. doi: 10.1055/s-0032-1314990. Epub 2012 Jun 29.
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.
姜黄素类是具有抗炎、抗氧化和抗癌活性的天然食用色素添加剂，主要包含三种二芳基庚烷：姜黄素、脱甲氧基姜黄素和双脱甲氧基姜黄素。本文研究了灌胃给予大鼠后姜黄素类在粪便和尿液中的代谢物。从雄性 Wistar 衍生大鼠的粪便中分离得到了四个新的代谢物，3-羟基-[1-(4-羟基苯基）-7-(3-羟基苯基）庚烷-A（M1）、3-羟基-[1-(4-羟基苯基）-7-(3-羟基苯基）庚烷-B（M2）、3-羟基-1,7-双（3-羟基苯基）庚烷-A（M3）和 3-羟基-1,7-双（3-羟基苯基）庚烷-B（M4），以及从尿液中分离得到了九个已知代谢物（M5-M9）。通过广泛的光谱分析阐明了它们的结构。通过手性柱色谱证实了这些代谢物以几对对映异构体的形式存在。基于代谢物的图谱，提出了姜黄素类在大鼠体内的可能代谢途径。
