文献类型：期刊文献

英文题名：Iodine-induced synthetic method and pharmacokinetic study of cis- and trans-crocetin

作者：Li, Boshen[1,2];Zhang, Yuxuan[1,2];Yang, Zhiqiang[3];Li, Xiaolin[1,2];Yang, Jun[1,2];Luo, Kai[1,2];Wang, Renjie[1,2];Xiao, Chengrong[1];Li, Maoxing[1,2,3,4];Gao, Yue[1]

第一作者：Li, Boshen

通信作者：Li, MX[1];Gao, Y[1];Li, MX[2];Li, MX[3];Li, MX[4]

机构：[1]Beijing Inst Radiat Med, Dept Pharmaceut Sci, Beijing, Peoples R China;[2]Gansu Univ Chinese Med, Coll Pharm, Lanzhou, Peoples R China;[3]Northwest Minzu Univ, Inst Chem Technol, Lanzhou, Peoples R China;[4]Natl Key Lab Kidney Dis, Beijing, Peoples R China

第一机构：Beijing Inst Radiat Med, Dept Pharmaceut Sci, Beijing, Peoples R China

通信机构：[1]corresponding author), Beijing Inst Radiat Med, Dept Pharmaceut Sci, Beijing, Peoples R China;[2]corresponding author), Gansu Univ Chinese Med, Coll Pharm, Lanzhou, Peoples R China;[3]corresponding author), Northwest Minzu Univ, Inst Chem Technol, Lanzhou, Peoples R China;[4]corresponding author), Natl Key Lab Kidney Dis, Beijing, Peoples R China.|[1073501e14fb35863569f]甘肃中医药大学药学院（西北中藏药协同创新中心办公室）;[10735]甘肃中医药大学;

年份：2024

卷号：15

外文期刊名：FRONTIERS IN PHARMACOLOGY

收录：;Scopus(收录号：2-s2.0-85191039895);WOS:【SCI-EXPANDED(收录号:WOS:001206822600001)】；

基金：The author(s) declare that financial support was received for the research, authorship, and/or publication of this article. This study was funded by the Traditional Chinese Medicine Innovation Team and Talent Support Program Project from National Administration of Traditional Chinese Medicine (ZYYCXTDD-202207).

语种：英文

外文关键词：crocetin; iodine-induced; pharmacokinetic; cis isomers; cis-crocetin

摘要：Objective: This experiment aimed to obtain the relatively rare cis-crocetin isomer from natural plants, which predominantly exist in the more stable all-trans configuration. This was achieved through iodine-induced isomerization, followed by purification and structural identification. The study also aimed to compare the pharmacokinetic differences between cis- and trans-crocetin in vivo.Methods: Trans-crocetin of high purity was extracted by hydrolysis from gardenia yellow pigment. Cis-crocetin was then synthesized through an optimized electrophilic addition reaction induced by elemental iodine, and subsequently separated and purified via silica gel column chromatography. Structural identification of cis-crocetin was determined using IR, UV, and NMR techniques. In vivo pharmacokinetic studies were conducted for both cis- and trans-crocetin. In addition to this, we have conducted a comparative study on the in vivo anti-hypoxic activity of trans- and cis-crocetin.Results: Under the selected reaction conditions using DMF as the solvent, with a concentration of 2.5 mg/mL for both trans-crocetin and the iodine solution, and adjusting the illumination time according to the amount of trans-crocetin, the rate of iodine-induced isomerization was the fastest. Cis-crocetin was successfully obtained and, after purification, its structure was identified and found to be consistent with reported data. Cis-crocetin exhibited a faster absorption rate and higher bioavailability, and despite its shorter half-life, it could partially convert to trans-crocetin in the body, thereby extending the duration of the drug's action within the body to some extent.Conclusion: This study accomplished the successful preparation and structural identification of cis-crocetin. Additionally, through pharmacokinetic studies, it uncovered notable variations in bioavailability between cis- and trans-crocetin. These findings serve as a solid scientific foundation for future functional research and practical applications in this field.