机构：[1]Department of clinical pharmacy, Guangzhou First People's Hospital, South China University of Technology, Guangzhou 510180, P.R. China.[2]School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, P.R. China.[3]Tea Research Institute, Guangdong Academy of Agricultural Sciences, Guangdong Key Laboratory of Tea Resources Innovation & Utilization, Guangzhou 510640, China.
As the final hydrogenated metabolite of curcumin, octahydrocurcumin (OHC) exhibits increased powerful bioactivities. The chiral and symmetric chemical structure indicated that there were two OHC stereoisomers, (3R,5S)-octahydrocurcumin (Meso-OHC) and (3S,5S)-octahydrocurcumin ((3S,5S)-OHC), which may induce different effects on metabolic enzymes and bioactivities. Thus, we detected OHC stereoisomers from rat metabolites (blood, liver, urine and feces) after oral administration of curcumin. In addition, OHC stereoisomers were prepared and then their different influences on cytochrome P450 enzymes (CYPs) and UDP-glucuronyltransferases (UGTs) in L-02 cells were tested to explore the potential interaction and different bioactivities. Our results proved that curcumin could be metabolised into OHC stereoisomers first. In addition, Meso-OHC and (3S,5S)-OHC exhibited slight induction or inhibition effects on CYP1A2, CYP2A6, CYP2C8, CYP2C9, CYP3A4 and UGTs. Furthermore, Meso-OHC exhibited more intensive inhibition toward CYP2E1 expression than (3S,5S)-OHC, ascribed to the different mode of binding to the enzyme protein (P < 0.05), which finally induced more effective liver protection effects in acetaminophen-induced L-02 cell injury.
基金：
Science and Technology Projects
in Guangzhou (202201010514), the Guangdong Basic and
Applied Basic Research Foundation (2021A1515110661), the
Special fund project for the introduction of scientific and technological talents of Guangdong Academy of Agricultural Sciences (R2021YJ-YB3014), the Natural Science Foundation of
Guangdong Province of China (2022A1515011706), and the
National Natural Foundation of China (82074082, 82104472).
语种：
外文
PubmedID：
中科院(CAS)分区：
出版当年[2022]版：
大类|1 区农林科学
小类|2 区食品科技2 区生化与分子生物学
最新[2025]版：
大类|2 区农林科学
小类|2 区生化与分子生物学2 区食品科技
第一作者：
第一作者机构：[1]Department of clinical pharmacy, Guangzhou First People's Hospital, South China University of Technology, Guangzhou 510180, P.R. China.
共同第一作者：
推荐引用方式(GB/T 7714)：
Luo Dandan,Lin Yinsi,Chen Jiannan,et al.Stereoisomers of octahydrocurcumin, the hydrogenated metabolites of curcumin, display stereoselective activity on the CYP2E1 enzyme in L-02 cells[J].Food & function.2023,14(6):2822-2835.doi:10.1039/d2fo03892g.
APA：
Luo Dandan,Lin Yinsi,Chen Jiannan,Huang Xiaoqi,Xie Youliang...&Zhang Zhenbiao.(2023).Stereoisomers of octahydrocurcumin, the hydrogenated metabolites of curcumin, display stereoselective activity on the CYP2E1 enzyme in L-02 cells.Food & function,14,(6)
MLA：
Luo Dandan,et al."Stereoisomers of octahydrocurcumin, the hydrogenated metabolites of curcumin, display stereoselective activity on the CYP2E1 enzyme in L-02 cells".Food & function 14..6(2023):2822-2835
农林科学