title: Estimation of the Intestinal Absorption and Metabolism Behaviors of 2- and 3-Monochloropropanediol Esters.
abstract: The regioisomers of the di- and mono-oleate of monochloropropanediol (MCPD) have been synthesized and subsequently hydrolyzed with pancreatic lipase and pancreatin to estimate the intestinal digestion and absorption of these compounds after their intake. The hydrolysates were analyzed by HPLC using a corona charged aerosol detection system, which allowed for the separation and detection of the different regioisomers of the MCPD esters. The hydrolysates were also analyzed by GC-MS to monitor the free MCPD. The results indicated that the two acyl groups of 2-MCPD-1,3-dioleate were smoothly hydrolyzed by pancreatic lipase and pancreatin to give free 2-MCPD. In contrast, the hydrolysis of 3-MCPD-1,2-dioleate proceeded predominantly at the primary position to produce 3-MCPD-2-oleate. 2-MCPD-1-oleate and 3-MCPD-1-oleate were further hydrolyzed to free 2- and 3-MCPD by pancreatic lipase and pancreatin, although the hydrolysis of 3-MCPD-2-oleate was 80 % slower than that of 3-MCPD-1-oleate. The intestinal absorption characteristics of these compounds were evaluated in vitro using a Caco-2 cell monolayer. The results revealed that the MCPD monooleates, but not the MCPD dioleates, were hydrolyzed to produce the free MCPD in the presence of the Caco-2 cells. The resulting free MCPD permeated the Caco-2 monolayer most likely via a diffusion mechanism because their permeation profiles were independent of the dose. Similar permeation profiles were obtained for 2- and 3-MCPDs.
authors.affiliation: Ueda Oils and Fats MFG Co. Ltd, 17 Uozakihamamachi, Higashinada-ku, Kobe, 658-0024, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Kaze
authors.affiliation: Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka, 536-8553, Japan. yomi@omtri.or.jp.
authors.forename: Yomi
authors.initials: Y
authors.lastname: Watanabe
authors.affiliation: Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka, 536-8553, Japan.
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Sato
authors.affiliation: Department of Life Science, Faculty of Science and Engineering, Kinki University, 3-4-1 Kowakae, Higashiosaka, Osaka, 577-8502, Japan.
authors.forename: Kaeko
authors.initials: K
authors.lastname: Murota
authors.affiliation: Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan.
authors.forename: Miyako
authors.initials: M
authors.lastname: Kotaniguchi
authors.affiliation: Ueda Oils and Fats MFG Co. Ltd, 17 Uozakihamamachi, Higashinada-ku, Kobe, 658-0024, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Yamamoto
authors.affiliation: Department of Nutrition, Osaka Prefecture University, Habikino, Osaka, 583-8555, Japan.|Center for Research and Development of Bioresources, Osaka Prefecture University, 1-2, Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8570, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Inui
authors.affiliation: Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan.
authors.forename: Shinichi
authors.initials: S
authors.lastname: Kitamura
mesh_terms: D018938:Caco-2 Cells; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000032:analysis* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D005990:Glycerol / Q000031:analogs & derivatives* / Q000737:chemistry; D006801:Humans; D006868:Hydrolysis; D007408:Intestinal Absorption; D007413:Intestinal Mucosa / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D010194:Pancreatin / Q000378:metabolism*; D000517:alpha-Chlorohydrin / Q000737:chemistry*; D011409:Propylene Glycols
chemical_list: D004952:Esters; D005990:Glycerol; D008049:Lipase; D010194:Pancreatin; D000517:alpha-Chlorohydrin; C585004:monochloropropanediol; D011409:Propylene Glycols
keywords: Caco-2; Intestinal absorption; Lipase; Monochloropropanediol; Pancreatin