The Stability Of Curcumin Metabolites, Degradation Products And Feces

The rhizomes of Curcuma Longa, a tropical herb indigenous to southern Asia, has played an important role in the pharmaceutical, food and textile industries in China, Japan and southeastern Asia for thousands of years. It has been widely used as an aromatic stomachic, carminative, anthelmintic, laxative, and as condiments in foods as well as for liver ailment. Therefore, in the international market curcuminoids enjoyed a high reputation. The United Nations Food and Agriculture Organization (FAO) and World Health Organization (WHO) announce that curcuminoids were the high security natural pigment.With regard to the chemical constituents of this plant, curcuminoids were shown to be the one major active principles. Curcuminoids, consist mainly of three diarylheptanoids: curcumin(CUR), demethoxycurcumin(DMC), and bisdemethoxycurcumin(BDMC). These are recognized for their beneficial effects such as a choleretic, as anti-oxidant, anti-inflammatory agents, for treating human immunodeficiency virus infections and as anticarcinogens. In this dissertation,1) The pure compounds of three curcuminoids were purified from Curcuma Longa and the NMR data were assigned.2) The stability and degradation products of CUR and DMC were investigated. The stability of CUR in different conditions was examined by using UV spectrophotometer. The degradation products were isolated by open ODS column and PHPLC. Their structures were determined on the basis of physicochemical properties and spectroscopic methods such as ¹H-NMR, ¹³C-NMR, and UV spectrum. The isolated compounds from photodecomposition of curucmin were identified as vanillin(1), vanillic acid(2), 2-hydroxy-acetovanillone(3), protocatechualdehyde(4), acetoferulone(5), trans-ferulic acid(6), cis-ferulic acid (7), vanillic acid methyl ester(8); the compounds from alkali liquor were identified as vanillin(1), vanillic acid(2), trans-ferulic acid(6). The isolated compounds from photodecomposition of demethoxycurucmin were identified as vanillin(1), vanillic acid(2), acetoferulone(5), trans-ferulic acid(6), 4-Hydroxybenzaldehyde(9), 4-hydroxy acetocinnamone(10) 4-hydroxy cinnamic acid(11). The above results will provide important information for chemical and biological properties. 3) The metabolites of curcumin in rat feces were studied, and several metabolites were detected. The results are important for the understanding of curcuminoids metabolism in rats and should provide information and reference for the further metabolic investigation of curcuminoids in human.