The Cleavage of Androsterone β-D-glucopyranosiduronic Acid in Organic Media

Burstein, Shlomo; Jacobsohn, Gert M.; Lieberman, Seymour

doi:10.1021/ja01490a048

Cited by 32 publications

(11 citation statements)

References 2 publications

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“…However, the stability of conjugates in contact Authors Han and with such solvents is questionable. Lopez and Lindsay (1993b) have reported instability of alkylphenol conjugates when they were placed in contact with certain organic solvents, similar to other reports (Burstein and Lieberman, 1958;Burstein et al, 1960). Our objectives were to determine the stability of phenolic conjugates when placed in contact with selected solvents, and to identify conditions to help develop analytical procedures that would not distort quantitative relationships between free and conjugated forms of alkylphenols from fatty foods.…”

Section: Introductionsupporting

confidence: 53%

“…In two-phase systems, hydrolysis of conjugates in organic media follows first-order reaction kinetics and occurs in two stages (Burstein et al, 1960;Marsh, 1966). The first stage involves partitioning of conjugate into the organic phase, followed by solvolysis of conjugate in the nonionizing solvent.…”

Section: Stability Of Conjugates In Bulky Water:solvent Systemsmentioning

confidence: 99%

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Stability of Metabolically Conjugated Precursors of Meat and Milk Flavor Compounds in Various Solvents

Han

Lindsay

1995

Journal of Food Science

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The stability of selected metabolic conjugates (phenylglucuronide, phenylphosphate, and naphthylsulfate) was determined in model systems composed of water and various ratios (3 : 1, 1: 1, 1:3) of selected solvents (hexane, chloroform, ethyl acetate, diethyl ether, or methanol) held at either 22°C or 40°C for 30 min under various pH conditions (PH 1.5, 3.2, or 6.5). Notable hydrolysis occurred only for the more polar solvents held in contact with acidic aqueous phases. Conditions were identified for minimizing hydrolysis of conjugates during extraction of fat and free alkylphenols from milk and meat products with diethyl ether. They were pH near neutral, short exposure time, near ambient temperature, presence of excess water, and saturation of aqueous phase with sodium chloride.

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Section: Introductionsupporting

confidence: 53%

Section: Stability Of Conjugates In Bulky Water:solvent Systemsmentioning

confidence: 99%

Stability of Metabolically Conjugated Precursors of Meat and Milk Flavor Compounds in Various Solvents

Han

Lindsay

1995

Journal of Food Science

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“…During this chromatography, free steroids and steroid monoglucuronides were eluted before the elution of these two fractions. The conjugates were cleaved by solvolysis under condi¬ tions in which it is known that only steroid sulphates are hydrolysed (Burstein 8c Lieberman 1958t5;Burstein et al 1960 ) and amniotic fluid (Luukkainen et al 1970). …”

Section: Discussionmentioning

confidence: 99%

Identification and Determination of Neutral Steroid Sulphates in Human Foetal Adrenal and Liver Tissue

Huhtaniemi

Luukkainen

Vihko

1970

Acta Endocrinologica

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The endogenous neutral steroids in adrenal and liver tissue obtained from foetuses of 12\p=n-\17 weeks gestation were investigated. After extractions, the steroids were fractionated into a monosulphate and a disulphate fraction on Sephadex LH-20. The conjugates were cleaved by solvolysis, and purified on silicic acid and their trimethyl silyl ethers were analysed by gas-liquid chromatography and gas chromatography-mass spectrometry. Only neutral steroid monosulphates were found. The following compounds were identified in the monosulphate fraction of adrenal tissue: dehydroepiandrosterone, 16\g=a\-hydroxydehydroepiandrosterone, pregnenolone and 17\g=a\-hydroxypregnenolone,and of liver tissue; dehydroepiandrosterone, 16\g=a\-hydroxydehydroepiandrosterone, androst-5-ene\x=req-\ 3 \ g = b \ , 1 6 \ g = a \ , 1 7 \ g = b \ -t r i o l , pregnenolone, 17\g=a\-hydroxypregnenoloneand 16\g=a\-hydroxypregnenolone. The identifications and the results of the quantitative determinations of endogenous neutral steroid sulphates suggest that pregnenolone is synthesised in vivo in the foetal adrenal and converted to 17\g=a\-hydroxypregnenoloneand dehydroepiandrosterone sulphates. The latter compound is further transformed to 16\g=a\-hydroxydehydroepiandrosterone sulphate. No 16\g=a\-hydroxylationof pregnenolone was observed in adrenal tissue, whereas liver tissue seems to form 16\g=a\-hydroxypregnenolone. Reduction of a 17-keto group to 17\g=b\-hydroxyl and a 20\ x=req-\ keto group to 20\g=a\-hydroxyl seems to take place in liver but not in adrenal tissue.

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“…Solvolysis was performed under conditions in which only steroid sulphates are cleaved (Bur stein 8c Lieberman 1958; Burstein et al 1960). electrophoresis, paper chromatography and TLC the steroid con¬ jugates isolated from urine showed the same mobilities as the reference steroid disulphates.…”

Section: Nature Of Conjugationmentioning

confidence: 99%

Neutral Steroids in Urine During Pregnancy

Jänne

Vihko

1970

Acta Endocrinologica

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A disulphate fraction of the steroids in the urine of pregnant females was separated by chromatography on Sephadex LH-20. The steroids in this fraction showed the mobility of steroid disulphates on thin-layer chromatography, paper chromatography and high-voltage paper electrophoresis. After solvolysis, the free steroids were fractionated on silicic acid and by thin-layer chromatography. Fractions containing dihydroxylated C19 and C21 steroids were obtained. Using gas-liquid chromatography and gas chromatography-mass spectrometry, the following 18 steroids were identified in the disulphate fraction of neutral steroids in late-pregnancy urine: 5\g=a\-androstane-3\g=a\,17\g=a\-diol,androst-5\x=req-\ ene-3\g=b\,17\g=a\-diol,androst-5-ene-3\g=b\,17\g=b\-diol,18-hydroxyandrosterone, 17\ g=a\ \ x=r eq-\ hydroxydehydroepiandrosterone, 16\ g=b\ -hydroxydehydroepiandrosterone,

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The Cleavage of Androsterone β-D-glucopyranosiduronic Acid in Organic Media

Cited by 32 publications

References 2 publications

Stability of Metabolically Conjugated Precursors of Meat and Milk Flavor Compounds in Various Solvents

Stability of Metabolically Conjugated Precursors of Meat and Milk Flavor Compounds in Various Solvents

Identification and Determination of Neutral Steroid Sulphates in Human Foetal Adrenal and Liver Tissue

Neutral Steroids in Urine During Pregnancy

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