title: Curcuminoid Demethylation as an Alternative Metabolism by Human Intestinal Microbiota.
abstract: Curcumin and other curcuminoids from Curcuma longa are important bioactive compounds exhibiting various pharmacological activities. In addition to the known reductive metabolism of curcuminoids, an alternative biotransformation of curcuminoids by human gut microbiota is reported herein. A curcuminoid mixture, composed of curcumin (1), demethoxycurcumin (2), and bisdemethoxycurcumin (3), was metabolized by the human intestinal bacterium Blautia sp. MRG-PMF1. 1 and 2 were converted to new metabolites by the methyl aryl ether cleavage reaction. Two metabolites, demethylcurcumin (4) and bisdemethylcurcumin (5), were sequentially produced from 1, and demethyldemethoxycurcumin (6) was produced from 2. Until now, sequential reduction of the heptadienone backbone of curcuminoids was the only known metabolism to occur in the human intestine. In this study, a new intestinal metabolism of curcuminoids was discovered. Demethylation of curcuminoids produced three new colonic metabolites that were already known as promising synthetic curcumin analogues. The results could explain the observed beneficial effects of turmeric.
authors.affiliation: Metalloenzyme Research Group and Department of Integrative Plant Science, Chung-Ang University , Anseong 17546, Korea.
authors.forename: Supawadee
authors.initials: S
authors.lastname: Burapan
authors.affiliation: Metalloenzyme Research Group and Department of Integrative Plant Science, Chung-Ang University , Anseong 17546, Korea.
authors.forename: Mihyang
authors.initials: M
authors.lastname: Kim
authors.affiliation: Metalloenzyme Research Group and Department of Integrative Plant Science, Chung-Ang University , Anseong 17546, Korea.
authors.forename: Jaehong
authors.identifier: http://orcid.org/0000-0002-5328-3927
authors.initials: J
authors.lastname: Han
mesh_terms: D001419:Bacteria / Q000145:classification / Q000302:isolation & purification / Q000378:metabolism*; D030024:Curcuma / Q000378:metabolism*; D003474:Curcumin / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism*; D036381:Diarylheptanoids; D000069196:Gastrointestinal Microbiome; D006801:Humans; D007413:Intestinal Mucosa / Q000378:metabolism*; D007422:Intestines / Q000382:microbiology*; D008745:Methylation; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000378:metabolism*
chemical_list: D036381:Diarylheptanoids; D010936:Plant Extracts; D003474:Curcumin; C050229:demethoxycurcumin
keywords: curcumin; curcuminoids; demethoxycurcumin; demethylation; human intestinal metabolism; turmeric