Novel deep eutectic solvent-based liquid phase microextraction for the extraction of estrogenic compounds from environmental samples
Nazir FattahiMojtaba ShamsipurZiba NematifarNasrin BabajaniMasoud MoradiShahin SoltaniShahram Akbari
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Steroid hormones, such as estrone (E1), 17β-estradiol (E2), 17β-ethinylestradiol (EE2) and estriol (E3) are a group of lipophilic active substances, synthesized biologically from cholesterol or chemically. A pH-switchable hydrophobic deep eutectic solvent-based liquid phase microextraction (DES-LPME) technique was established and combined with gas chromatography-mass spectroscopy for the determination of estrogenic compounds in environmental water and wastewater samples. A DES was synthesized using l-menthol as HBA and (1S)-(+)-camphor-10-sulfonic acid (CSA) as HBD, and used as a green extraction solvent. By adjusting the pH of the solution, the unique behavior of the DES in the phase transition and extraction of the desired analytes was investigated. The homogenization process of the mixture is done only by manual shaking in less than 30 seconds and the phase separation is done only by changing the pH and without centrifugation. Some effective parameters on the extraction and derivatization, such as molar ratio of DES components, DES volume, KOH concentration, HCl volume, salt addition, extraction and derivatization time and derivatization prior or after extraction were studied and optimized. Under the optimum conditions, relative standard deviation (RSD) values for intra-day and inter-day of the method based on 7 replicate measurements of 20 ng L-1 of estrogenic compounds and 10 ng L-1 for internal standard in different samples were in the range of 2.2-4.6% and 3.9-5.7%, respectively. The calibration graphs were linear in the range of 0.5-100 ng L-1 and the limits of detection (LODs) were in the range of 0.2-1.0 ng L-1. The relative recoveries of environmental water and wastewater samples which have been spiked with different levels of target compounds were 91.0-108.8%.Keywords:
Estriol
Deep eutectic solvent
Estriol
Conjugate
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In women of reproductive age, the primary source of circulating estrogens is the ovaries. There are three forms of estrogen circulating in our bloodstream: estradiol, estrone and estriol. The normal ratio of these three types of estrogens ideally should be 10–20%, 10–20%, and 60–80% respectively. The estrogen that accounts for most of the tissue stimulation is called estradiol. Estrone is a little bit less potent with estriol being the weakest. Brain converts estrone and estradiol to 2- and 4-hydroxylated derivatives known as catechol estrogens
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Catechol
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The object of the present study was to prove that rat-liver tissue will convert either estrone or estradiol to estriol in vitro and to study and compare the extent of this conversion by liver tissue from male, female, and castrated rats and the effect on this conversion of treatment of the animals with sex hormones. While there is no doubt as to the in vitro conversion of estradiol and estrone to estriol, which amounts to about 30 to 40%, there are no statistically significant effects of gonadectomy or treatment with sex hormones on rate of. conversion. A significantly larger conversion of estrone to estriol was observed in livers from male rats than in those from females.
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INTRODUCTION IT HAS been established that the urine of laying hens contains estrone (Ainsworth and Common, 1962), 16-epi-estriol (Hertelendy and Common, 1964) and estradiol-17β (Hertelendy et al., 1965). The presence of estriol and 16, 17-epi-estriol in laying hens’ urine has been demonstrated chromatographically (Mathur and Common, 1967). Studies on the in vivo conversions of injected 14C-labelled estrogens have shown that the hen's urine probably contains also 17-epi-estriol, 16-ketoestradiol, 16-ketoestrone and estradiol-17α (MacRae et al., 1960; Ainsworth et al., 1962, 1964; Hertelendy and Common, 1965; Mulay and Common, 1967). Estrone, estradiol-17β and 16-ketoestrone are quantitatively the most important urinary estrogens of the hen (Ainsworth et al., 1962; Common et al., 1965); there is very considerably less 16-epi-estriol plus 17-epi-estriol than estrone (Mathur et al., 1966). Relatively little is known about the state of combination of hens’ urinary estrogens. Accordingly, we have investigated this matter by injecting 14C-labelled estrone or estradiol-17β into . . .
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1. A method is given for the extraction and fractionation of rabbit urines which frees these urines of inactive chromogens but permits a quantitative recovery of estrone and estriol for the colorimetric determination of these compounds. 2. Estrone and estriol content of rabbit urine extracts can be determined by the concentration of the colored compound they form upon diazotization with sulfanilic acid and by the modified phenolsulfonic acid test of Cohen and Marrian. Estriol can be determined by the specific reaction first described by David. The technique for these tests is presented. 3. Estriol (300 micrograms) injected into rabbits (a) in heat, (b) pregnant, (c) pseudopregnant, (d) hysterectomized in heat, (e) hysterectomized pseudopregnant, (f) ovariectomized, is excreted in the urine as estriol. Rabbit does in the luteal phase (b, c, and e) excrete 3 to 4 times the amount of estriol excreted by females without corpora lutea (a, d, and f). 4. When estrone (300 micrograms) is injected into the same types of rabbit does types a, b, and c excrete both estrone and estriol, type f excretes both estrone and estriol shortly after ovariectomy, but only estrone at 2 months after castration. Hysterectomized animals (types d and e) never excrete estriol after estrone injection. The total urinary estrin (estrone plus estriol) in estrone-injected animals is increased 2 to 3 times in animals in the luteal phase (b, c, and e). 5. It is concluded that the uterus is the site of conversion of estrone to estriol, and that the conversion cannot take place in a uterus completely free of ovarian control (e.g., in long time ovariectomized animals). 6. In neither estrone-injected nor estriol-injected females is all the injected hormone recovered in the urine. The maximum recovery is 66 per cent. When estrone-benzoate (600 micrograms) is injected 94-98 per cent of the hormone is recovered from animals in the luteal phase (types c and e) and about 79 per cent in an ovariectomized female (type f). These data are taken to indicate that luteal secretions give partial protection against destruction to the hormones. 7. The observation that in certain of the urine extracts the hormone titer by bioassay is somewhat higher than the colorimetric titer may indicate that there is a slight conversion of estrone to estradiol, particularly since no equilenin was found in any of the extracts by colorimetric test. 8. The simultaneous injection of 300 micrograms of estrone and 500 micrograms of progesterone 4 days after an initial injection of 300 micrograms of estrone results in: (1) an increased estrin excretion in females in heat, hysterectomized unmated, and ovariectomized, and a slight decrease in the pseudopregnant female; (2) the appearance of estriol in the urine of the long time ovariectomized animal with no urinary estriol in a control ovariectomized animal receiving no progesterone. These findings are taken to prove that the conversion of estrone to estriol occurs in the uterus under the influence of progesterone. Since animals in heat produce small amounts of estriol after estrone injection it is inferred that the ovaries of estrus rabbits produce small amounts of corpus luteum hormone in the absence of formed corpora lutea.
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Estrone sulfate, estrone, estradiol and estriol were measured through the course of pregnancy in 85 women. Of the unconjugated estrogens, estradiol had the highest plasma concentration, being approximately twice that of estrone and four times that of estriol. Estrone sulfate level was twice that of estradiol. All estrogens measured showed the same pattern of increase with time. When plotted against fetal and placental weights, the increase in plasma concentration of all estrogens correlated better with fetal weight than with placental weight.
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Estriol, ring D—α-ketols and estrone were measured in the urine of 9 normal males aged 17–50 yr, and 12 postmenopausal females, aged 47–72 yr. Mean values (μg/24 hr) with ranges were as follows: Males: estriol, 8.3 (3.9–13.5); ring D—α-ketols, 5.6 (2.3–10.1); estrone, 5.0 (1.5–8.3). Females: estriol, 6.0 (1.5–14.9); ring D—α-ketols, 2.8 (1.3–4.2); estrone, 2.2 (0.4–4.9). The ring D—α-ketolic fraction appears to consist, on the average, of approximately equal amounts of 16α-hydroxyestrone and a 16-ketoestradiol-17β(16-ketoestradiol) fraction perhaps containing some 16β-hydroxyestrone. Analysis of C14—ring D—α-ketols from the urine of 3 subjects given estrone-16-C14 suggests that 16α-hydroxyestrone and the 16-ketoestradiol fraction arise from estrone, perhaps via some common intermediate. No proof could be obtained for the conversion in vivo of 16-ketoestradiol to 16α-hydroxyestrone, either directly or via the triols.
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Normal young and postmenopausal women were placed into groups according to the ratio of the estrogens in their urine. Women whose ratio was greater than 1.3 if young and greater than 3.2 if postmenopausal were compared to women whose ratio was less than 0.7 and less than 2.1 for young and postmenopausal, respectively. Between the respective high- and low-ratio groups, there were no significant differences for circulating levels of estriol, metabolic clearance rates of estriol, or blood production rates of estriol, estrone, or estradiol. Women who had had breast cancer were compared to a group of normal controls and were also found to have similar blood production rates for estriol, estrone, and estradiol. The ratios of the blood production rates of estriol to estrone and estradiol were similar for the high and low groups for young and postmenopausal women and also between the breast cancer women and their controls. It appears, therefore, that the difference in urinary estrogen ratios is primarily due to different pathways of metabolism of the free circulating estrogens and not to differences in the production rates of the estrogens. Estriol is produced at only 10% the rate of estrone and estradiol.
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WORK on the urinary conversion products of injected 14C-labeled estrone and estradiol-17β* (MacRae and Common, 1960; Ainsworth et al., 1962) suggested that estrone and estradiol-17β are quantitatively more important urinary estrogens in the hen and that there is less 16-epi-estriol than estrone or estradiol-17β and less estriol than 16-epi-estriol. However, direct quantitative chemical information about estrogen excretion by the hen is comparatively scanty. Common et al. (1965) have reported chemically determined values for daily urinary estrone excretion by four hens. The values (uncorrected for methodological loss) for hens that were not laying were within the range 0.4 μg. to 2.0 μg. per day. The values for two hens during periods of sustained egg-laying were within the range 2.2 μg. to 5.0 μg. per day, and the highest individual values for daily estrone excretion by these two hens (4.7 μg. and 7.5 μg.) were observed 3 to 5 days before the …
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