Glycidol Fatty Acid Ester and 3-Monochloropropane-1,2-Diol Fatty Acid Ester in Commercially Prepared Foods

Glycidyl fatty acid esters (GEs), which are the main pollutant in processed oils, are potential mutagens or carcinogens. 3-Monochloropropane-1,2-diol fatty acid esters (3-MCPDEs) are also well-known food processing contaminants. 3-MCPDEs are believed to be a precursor to GEs in foodstuffs. In vivo, lipase breaks down the phosphate ester of GEs and 3-MCPDEs to produce glycidol and 3-MCPD, respectively, which are genotoxic carcinogens. Thus, it is important to determine human exposure to GEs and 3-MCPDEs through foodstuffs. There are only reports on the amount of GE and 3-MCPDE in cooking oils and cooked foods. The content in multiple types of foods that are actually on the market was not clarified. In this study, 48 commercially prepared foods were analyzed to identify other sources of exposure to GE and 3-MCPDE. All of them contained relatively high amounts of GEs and 3-MCPDEs. The correlation between GEs and 3-MCPDEs in individual foods was examined. There was a correlation between the amounts of GEs and 3-MCPDEs in the food products (r = 0.422, p < 0.005). This is the first report on the content in multiple types of commercially prepared foods that are actually on the market was clarified.

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Estradiol Fatty Acid Esters in Adipose Tissue and Serum of Pregnant and Pre- and Postmenopausal Women

The Journal of Clinical Endocrinology & Metabolism ◽

10.1210/jc.2007-1372 ◽

2007 ◽

Vol 92 (11) ◽

pp. 4327-4331 ◽

Cited By ~ 14

Author(s):

Maija Badeau ◽

Veera Vihma ◽

Tomi S. Mikkola ◽

Aila Tiitinen ◽

Matti J. Tikkanen

Keyword(s):

Adipose Tissue ◽

Fatty Acid ◽

Postmenopausal Women ◽

Fatty Acid Ester ◽

Acid Ester ◽

Physiological Role ◽

Fatty Acid Esters ◽

17Β Estradiol ◽

Acid Esters ◽

Free Estradiol

Abstract Context: The 17β-estradiol fatty acid esters are hormone derivatives with long-lasting estrogenic effect. They are transported in serum lipoproteins and thought to be sequestered in adipose tissue. Objective: Our objective was to determine the 17β-estradiol fatty acid ester concentrations in serum and adipose tissue in women of various hormonal states. Design: After several chromatographic steps separating esterified from free estradiol, time-resolved fluoroimmunoassay was used as a quantifying tool. Participants: Samples were obtained from pregnant women undergoing cesarean section (n = 13), or premenopausal (n = 8) and postmenopausal women (n = 6) during gynecological surgery. Main Outcome Measures: 17β-Estradiol and 17β-estradiol fatty acid ester concentrations in serum, and visceral and sc adipose tissue were examined. Results: The ratio of esterified to free estradiol in plasma increased with decreasing estradiol level from 0.5% in pregnant, to 15% in premenopausal and 110% in postmenopausal women. Estradiol esters constituted about 10% of the free estradiol present in adipose tissue in pregnancy. In nonpregnant women, most of the adipose tissue estradiol was in esterified form, the median ester to free ratio being elevated to 150–490%. After menopause, the overwhelming majority of estradiol in both free and esterified form was present in adipose tissue. Conclusions: The overall higher ester to free estradiol ratio in adipose tissue than in serum indicates active esterification capacity in adipose tissue. The predominance of esterified and free estradiol in postmenopausal adipose tissue compared with serum suggests in situ production and storage. Whether the estradiol esters have an independent physiological role in adipose tissue remains to be clarified.

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Steroid fatty acid esters in adrenals and plasma: effects of ACTH

Journal of Endocrinology ◽

10.1677/joe.0.1270505 ◽

1990 ◽

Vol 127 (3) ◽

pp. 505-511 ◽

Cited By ~ 15

Author(s):

B. Bélanger ◽

S. Caron ◽

A. Bélanger ◽

A. Dupont

Keyword(s):

Fatty Acid ◽

Guinea Pig ◽

Fatty Acid Ester ◽

Acid Ester ◽

Human Subjects ◽

Fatty Acid Esters ◽

Marked Rise ◽

Plasma Effects ◽

Short Time ◽

Acid Esters

ABSTRACT The presence and production of 5-ene-steroid fatty acid esters (SFA) has been previously reported in bovine adrenals. A study was conducted, using a series of chromatographic procedures and radioimmunoassays, to determine the levels of SFA in adrenals from man, cattle, dog, rat and guinea-pig, and to assess, in both rats and guinea-pigs, the effect of ACTH on SFA production by adrenals and their subsequent secretion into the circulation. The effects of ACTH on plasma SFA and non-conjugated steroid levels were also investigated in human subjects. Our data indicated that adrenal pregnenolone fatty acid ester (PREG-FA) levels were below 40% of PREG levels in cattle, dog, rat and guinea-pig while, in man, PREG-FA levels were threefold those of PREG. A large proportion of dehydroepiandrosterone (DHEA) and 5-androstene-3β,17β-diol were present as fatty acid ester derivatives in the adrenals of all species, with the exception of cattle. In both rats and guineapigs, administration of ACTH caused a sharp increase in adrenal PREG of approximately threefold which lasted for 6 h, while the concentration of adrenal PREG-FA was slightly increased for a short time. In plasma, however, a marked rise in PREG-FA occurred, while the changes in PREG levels were much lower than those of its acylated counterpart. In man, PREG and DHEA concentrations were rapidly stimulated two-fold in the first 30 min following the administration of ACTH, while PREG-FA and DHEA-FA levels were increased by approximately 2·5-fold (P<0·01) at 120 and 180 min. Our data suggest that there is a rapid turnover of SFA in adrenals which causes accumulation of non-polar steroids in the plasma. Journal of Endocrinology (1990) 127, 505–511

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Quantitative Determination of Estradiol Fatty Acid Esters in Human Pregnancy Serum and Ovarian Follicular Fluid

Clinical Chemistry ◽

10.1093/clinchem/47.7.1256 ◽

2001 ◽

Vol 47 (7) ◽

pp. 1256-1262 ◽

Cited By ~ 15

Author(s):

Veera Vihma ◽

Herman Adlercreutz ◽

Aila Tiitinen ◽

Paula Kiuru ◽

Kristiina Wähälä ◽

...

Keyword(s):

Fatty Acid ◽

Fatty Acid Ester ◽

Follicular Fluid ◽

Acid Ester ◽

Late Pregnancy ◽

Fatty Acid Esters ◽

Time Resolved ◽

Human Pregnancy ◽

Ovarian Follicular Fluid ◽

Acid Esters

Abstract Background: Lipophilic estradiol derivatives carried by lipoprotein particles in blood may mediate antioxidant or endocrine effects. We developed a new quantitative method to determine the concentration of circulating lipophilic estradiol fatty acid esters in human early- and late-pregnancy serum and in ovarian follicular fluid. Methods: After extraction from serum or follicular fluid, estradiol fatty acid esters were separated from nonesterified estradiol by Sephadex LH-20 column chromatography. The estradiol ester fraction was hydrolyzed by saponification and further purified by several chromatographic steps. The hydrolyzed estradiol esters were measured by time-resolved fluoroimmunoassay. Results: The average estradiol fatty acid ester concentration in serum increased 10-fold during pregnancy, from 40.4 pmol/L (expressed as pmol/L estradiol; range, 25.0–64.2 pmol/L) in early pregnancy (n = 8) to 404 pmol/L (196–731 pmol/L) in late pregnancy (n = 10). The ratio of estradiol ester to nonesterified estradiol remained relatively constant during pregnancy, at 0.4–0.6%. In 10 follicular fluid samples, the mean estradiol ester concentration was 106 nmol/L (56.9–262 nmol/L). Compared with serum, a greater proportion of estradiol in follicular fluid (3.0–10%) was in the esterified form. Conclusion: The new method provides a means to measure circulating estradiol fatty acid ester concentrations in human pregnancy serum.

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Separation of fatty acid esters and fatty acid ester derivatives using preparative scale sequential gas-liquid chromatographic equipment

Chromatographia ◽

10.1007/bf02269105 ◽

1978 ◽

Vol 11 (12) ◽

pp. 703-714 ◽

Cited By ~ 4

Author(s):

P. E. Barker ◽

S. E. Liodakis

Keyword(s):

Fatty Acid ◽

Fatty Acid Ester ◽

Acid Ester ◽

Fatty Acid Esters ◽

Preparative Scale ◽

Liquid Chromatographic ◽

Acid Esters

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Effect of sucrose fatty acid esters, monoglycerol and polyglycerol fatty acid ester on in vitro growth of Botrytis cinerea PEAS. and on postharvest control of rot in fruits

food preservation science ◽

10.5891/jafps.28.227 ◽

2002 ◽

Vol 28 (5) ◽

pp. 227-234 ◽

Cited By ~ 1

Author(s):

Yasuo TATSUMI ◽

Tomomi HADATE ◽

Satoko MATSUO ◽

Kazunori TSUNO

Keyword(s):

Fatty Acid ◽

Botrytis Cinerea ◽

Fatty Acid Ester ◽

Acid Ester ◽

Fatty Acid Esters ◽

In Vitro Growth ◽

Sucrose Fatty Acid Esters ◽

Acid Esters ◽

Postharvest Control

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Does External Exposure of Glycidol-Related Chemicals Influence the Forming of the Hemoglobin Adduct, N-(2,3-dihydroxypropyl)valine, as a Biomarker of Internal Exposure to Glycidol?

Toxics ◽

10.3390/toxics8040119 ◽

2020 ◽

Vol 8 (4) ◽

pp. 119

Author(s):

Yuko Shimamura ◽

Ryo Inagaki ◽

Hiroshi Honda ◽

Shuichi Masuda

Keyword(s):

Propylene Oxide ◽

Allyl Alcohol ◽

Edible Oils ◽

Dietary Exposure ◽

Fatty Acid Esters ◽

Internal Exposure ◽

High Background ◽

Glycidyl Fatty Acid Esters ◽

Acid Esters

Glycidyl fatty acid esters (GE) are constituents of edible oils and fats, and are converted into glycidol, a genotoxic substance, in vivo. N-(2,3-dihydroxypropyl)valine (diHOPrVal), a hemoglobin adduct of glycidol, is used as a biomarker of glycidol and GE exposure. However, high background levels of diHOPrVal are not explained by daily dietary exposure to glycidol and GE. In the present study, several glycidol-related chemicals (glycidol, (±)-3-chloro-1,2-propanediol, glycidyl oleate, epichlorohydrin, propylene oxide, 1-bromopropane, allyl alcohol, fructose, and glyceraldehyde) that might be precursors of diHOPrVal, were administered to mice, and diHOPrVal formation from each substance was examined with LC-MS/MS. DiHOPrVal was detected in animals treated with glycidol and glycidyl oleate but not in mice treated with other chemicals (3-MCPD, epichlorohydrin, propylene oxide, 1-bromopropane, allyl alcohol, fructose, and glyceraldehyde). The amount of diHOPrVal per administered dose produced from other chemicals was negligible compared to the amounts associated with dietary glycidol and GE. The present study provides important knowledge for exploring other sources for internal exposure to glycidol.

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