Monohydroxy Derivatives Research Articles

Benzo[A]pyrene metabolism in organ cultures of human endometrium

Twenty-six specimens of normal human endometrium were obtained for studies of [ 3H]benzo[ a]pyrene metabolism in short-term organ culture. The tissues were capable of converting benzo[ a]pyrene (BP) to oxygenated derivatives which co-chromatographed with dihydrodiols, quinones and monohydroxy derivatives of BP. A sulfate conjugate of a monohydroxy BP was also found among the acetone/ethyl acetate soluble products. When the acetone/ethyl acetate soluble metabolites were analyzed using high-pressure liquid chromatography (HPLC), the proportion of metabolites were found to vary greatly from specimen to specimen. Eight women smoked cigarettes but the BP metabolite profiles from organ cultures of endometrial tissue from these women did not differ from those who did not smoke. The average value for sulfate conjugates of monohydroxy BP was significantly lower in endometrial tissue from three postmenopausal women (ages 49, 57 and 58) than among premenopausal women. Specimens from premenopausal women which had been in organ culture for 2 weeks prior to the addition of [ 3H]BP produced metabolite profiles similar to those of specimens from postmenopausal women with a greatly reduced proportion of BP-phenol sulfate conjugates. These data suggest that the absence of hormonal stimulus (i.e., advanced age or conditions of organ culture) may affect the metabolism of BP in human endometrial tissue.

Urinary and biliary metabolites of phenanthrene in the coalfish (Pollachius virens).

Metabolites present in the urine and bile of coalfish (Pollachius virens) 48 hrs after the intragastric administration of phenanthrene (75 mg/kg) were studied. Using gas chromatographic-mass spectrometric methods small amounts of unchanged compound, all five of the possible monohydroxy derivatives and the 1,2- and 9,10-dihydrodiols of phenanthrene were identified inthese samples. The major metabolite detected was phenanthrene-1,2-dihydrodiol which was excreted mainly as glucuronide and/or sulfate conjugates.

Chronic toxicity of 2,5,4′-trichlorobiphenyl in young rhesus monkeys: I. Body distribution, elimination, and metabolism

Four adult rhesus monkeys, two males and two females, were fed 14 C-labeled 2,5,4′-trichlorobiphenyl (2,5,4′-TCB) as 5 ppm of the daily diet. After 84 days, one male and one female were sacrificed and body distributions were determined. The greatest concentrations of 2,5,4′-TCB were observed in bile (60.9 g/g, male; 28.8 g/g, female). High values were also found in fat (5.03 g/g, male; 9.79 g/g, female), adrenal cortex (1.04 g/g, male; 1.55 g/g, female), and skin (1.08 g/g, male; 0.97 g/g, female). The lymph nodes and bone marrow of the female contained approximately 10 times as much 2,5,4′-TCB as the male. After 28 days of recovery the remaining male and female were sacrificed. The concentration of 2,5,4′-TCB in all of their tissues was greatly reduced. The t ½ for clearance of 2,5,4′-TCB in rhesus monkeys is 4.5 to 4.8 days. The major metabolites found in the urine were conjugated and free monohydroxy derivatives of 2,5,4′-TCB. No clinical signs of edema, alopecia, or acne were observed during the course of the study.

Chemical ionization mass spectra of natural monohydroxy- and monoacyloxy-substituted dihydropyranocoumarins and dihydrofurocoumarins

The chemical ionization mass spectra of ten compounds of the group of natural monohydroxy and monoacyloxy derivatives of dihydropyranocoumarins and dihydrofurocoumarins have been studied. Their difference from the electron impact mass spectra has been shown. The structural-analytical possibilities of the method of chemical ionization for this series of substances has been determined.

Contributions to ecological chemistry CXV1 metabolism of 2,5,4,′—trichlorobiphenyl-14C and 2,4,6,2′,4′ — pentachlorobiphenyl-14C in the marsh plantVeronica Beccabunga

Under the experimental conditions used, 2, 4, 6, 2′, 4′ -pentachlorobiphenyl is more persistent than2, 5, 4′ -trichlorobiphenyl. 2, 5, 4′ —Trichlorobiphenyl is metabolized to at least two monohydroxy derivatives which occur in free form as well as conjugated in the plant tissues (Fig. 2).

Apomorphine: Chemistry, Pharmacology, Biochemistry

This chapter discusses the chemistry, pharmacology, and the biochemistry of apomorphine. Apomorphine (APO) is a tertiary base with the empirical formula C 17 H 17 NO 2 . Its molecular skeleton consists of four fused six-membered rings, giving the molecule a semirigid structure. Its molecular skeleton is that of an aporphine alkaloid; owing to the catechol moiety in ring D, it oxidizes rapidly and becomes green on exposure to air and in solution. APO can be acetylated to diacetylapomorphine without loss of potency. However, etherification leads invariably to less active or inactive compounds. 11-Hydroxy-10-methoxyaporphine (apocodeine) and 10,11-methylenedioxyaporphine are about four times less potent than APO in inducing stereotyped gnawing in rats, while 10,11 -dimethoxyaporphine is inactive. Monohydroxy derivatives of aporphine are inactive. The N -methyl group of 10-or 11-hydroxyaporphine is replaced by a N - n -propyl substituent, some activity is retained; these compounds are nevertheless less potent than APO. It is concluded that the 10, 11-dihydroxy substitution pattern of APO is an absolute requirement for optimal activity.

Determination of Methaqualone in Urine by Metabolite Detection Via Gas Chromatography

Abstract Pharmaceutical preparations of the sedative and hypnotic agent methaqualone have been widely prescribed and dispensed under a variety of trade names, including Quaalude®, Sopor®, and Parest®. Cases of methaqualone abuse and overdose have been well documented [1–3]. The ready availability and frequent abuse of methaqualone have led to the development of methods of analysis for methaqualone and its metabolites in biologic fluids. Nowak et al used thin-layer chromatography (TLC) to study the metabolism of methaqualone in laboratory animals [4]. Only a small fraction of the dose was detected as the unchanged drug in the urine of the rat, while the major portion of the dose was hydroxylated and excreted as glucuronide conjugates. Preuss et al isolated twelve metabolites from urine of human subjects who had ingested methaqualone [5]. By comparison of these twelve metabolites with a series of synthesized monohydroxy derivatives of methaqualone they were able to identify five monohydroxy metabolites of the drug.

Metabolism of 2,2'-dichlorobiphenyl-14C in two plant-water-soil-systems.

Under the experimental conditions used, 2, 2′ -dichlorobiphenyl proved to be non-persistent. It is metabolized (Fig. 1) to at least two monohydroxy derivatives and probably one dihydroxy derivative and a dechlorinated product. The monohydroxy derivatives occur in free form, as well as conjugated in the plant tissues.

Preparation, Gas Chromatographic Behavior, and Spectroscopic Properties of Hydroxylated Chlorobiphenyls

Abstract Some useful methods for the preparation of chlorobiphenylols have been investigated. Twenty monohydroxy and dihydroxy derivatives of chlorobiphenyls are described; 10 are new compounds and several are known metabolic products from animals or microorganisms. The relationship between structure of the chlorobiphenylols and gas chromatographic retention time as well as electron capture detector response, including those of derivatives, has been examined. The ultraviolet, fluorescence, and mass spectra of these hydroxylated derivatives have also been examined with a view towards analysis and structure elucidation of metabolites.

20α-Hydroxysteroid oxidoreductase fromActinomyces roseochromogenus ATCC 3347. Industion, primary purification, substrate specificity

The formation of 20α-hydroxysteroid oxidoreductase with a constitutive enzyme ofActinomyces roseochromogenus is activated by certain predominantly monohydroxy derivatives of pregnane. Some steroids suppress the formation of the enzyme. Intact cells ofA. roseochromogenus and a cell-free enzyme system possess identical substrate specificities which are close to the substrate specificity of the 20α-hydroxysteroid oxidoreductase of rat testes and reduce only 20-oxopregnanes with a 17-oxygen function. The specific role of the 17-oxogen function appears at the substrate-enzyme level.

A preliminary report on the intermediates in the conversion [formula omitted] of cholesterol to pregnenolone in adrenal preparations

The reaction sequences cholesterol → 20α-hydroxycholesterol → 20α, 22R-di-hydroxycholesterol → pregnenolone, and cholesterol → 22R-hydroxycholesterol → 20α, 22Rrdihydroxycholesterol → pregnenolone have been studied quantitatively under conditions of first-order kinetics with adrenocortical preparations. The sequence of 22R-hydroxycholesterol was much more important than that of 20α-hydroxycholesterol, but only a small fraction of the pregnenolone formation from cholesterol via the monohydroxy derivatives could be accounted for. A much more substantial fraction could be accounted for by assuming an enzymatic, concerted attack of oxygen on cholesterol to form 20α, 22R-dihydroxycholesterol which then is oxidatively cleaved to pregnenolone. This study establishes several pathways leading from cholesterol to pregnenolone.

The glycosides of the roots from Glossostelma carsoni (N.E. Br.) Bullock

AbstractPentacyclic triterpenes, sterols, cardenolides and pregnane derivatives could be identified in extracts from roots of Glossostelma carsoni (N.E. BR.) Bullock. From the first group, the following substances could be isolated in crystalline form: β‐amyrin, lupeol, their 3‐O‐acetyl derivatives, and 3‐O‐isovaleryl‐β‐amyrin. The sterols were isolated in the form of two mixed but crystalline fractions. The less polar fraction was shown to be a mixture of β‐sitosterol, campesterol, stigmasterol, and cholesterol (stereoisomers are not excluded); the more polar fraction is probably a mixture of monohydroxy derivatives of the four above mentioned sterols.

スサビノリの脂質について-III

Carotenoids which were extracted in the previous paper from “Nori”, a dry product of Porphyra yezoensis, were separated into following six pigment groups on alumina column (Figs. 1, 2 and 3, and Table 1). 1) The V pigment which amounted to 59-65% of the total carotenoids was not identical with all-trans lutein but with probable mono-cis isomer (Figs. 4, 5 and 6). 2) The II pigment was β-carotene amounting to 19-24% of the total. 3) Compared with chromatographic results of β-carotene samples which were kept in solvents for one week or four months at room temperature, the I (4-9%) and III (1TO ?? 3%) pigments were concluded to be stereoisomers of β-carotene (Figs. 7 and 8). 4) The IV and VI pigments were not under enough examination. The former was presumed to contain decomposed β-carotene and mono-hydroxy derivatives, however. 5) Other carotenoids such as α-carotene, zeaxanthin etc. could not be observed, even if any, by the chromatographic method shown in Figs. 1 and 2.

Aspects of stereochemistry—II* : Intramolecular hydrogen bonding in some monohydroxy derivatives of tetrahydrofuran, tetrahydropyran and 1:3-dioxan

Aspects of stereochemistry—II* : Intramolecular hydrogen bonding in some monohydroxy derivatives of tetrahydrofuran, tetrahydropyran and 1:3-dioxan

Aspects of stereochemistry—II : Intramolecular hydrogen bonding in some monohydroxy derivatives of tetrahydrofuran, tetrahydropyran and 1:3-dioxan

The extent of intramolecular hydrogen bonding between hydroxyl groups and ring oxygens, as determined by infra-red spectroscopy in the hydroxyl stretching region, in a series of monohydroxy derivatives of tetrahydropyran, tetrahydrofuran and 1:3-dioxan provides direct experimental evidence for the stabilities of different conformations of certain of the alcohols. The synthesis of tetrahydropyran-3-ol is described and the mechanism of the reaction of perbenzoic acid with glycals is discussed.

The path of carotenoid synthesis in a photosynthetic bacterium

Exponentially growing cells of the photosynthetic bacterium Rhodospirillum rubrum contain a mixture of carotenoids: lycopene, P481, spirilloxanthin, and their monohydroxy derivatives. When such cells are resuspended in buffer and incubated anaerobically in the light, the total amount of carotenoid pigment in the cells remains constant, but there is a net synthesis of spirilloxanthin at the expense of the other carotenoids originally present. This synthesis proceeds from lycopene through P481. Added to a photosynthetically growing culture of R. rubrum at a final concentration of 7 · 10 −5 M, diphenylamine causes a complete arrest of normal carotenoid synthesis, accompanied by a rapid accumulation of carotenoids more saturated than lycopene. Phytoene, phytofluene, hydroxyphytofluene, ζ-carotene, hydroxy-ζ-carotene, neurosporene and hydroxyneurosporene are the principal accumulating compounds. If the diphenylamine is removed and the cells are resuspended in buffer and incubated anaerobically in the light, an endogenous synthesis of normal carotenoids takes place at the expense of all the accumulated precursors with the probable exception of phytoene. The kinetic analysis of this endogenous synthesis reveals the sequential relationships between the participating carotenoids.

Pteridines as substrates of mammalian xanthine oxidase: I. The end-product of the enzymic oxidation of pteridines

1. 1. The oxidation by mammalian xanthine oxidase of pteridine, its monohydroxy derivatives and of 2,4-dihydroxypteridine has been investigated. All these compounds, with the exception of 6-hydroxypteridine, are attacked by the enzyme. 2. 2. In all cases the same end-product is obtained, which has been identified as 2,4,7-trihydroxypteridine. 3. 3. These observations indicate that the 6-hydroxyl group in xanthopterin can not originate through interaction of its precursor with xanthine oxidase.

Retene Investigations. XVIII. The Mannich Reaction with Monohydroxy Derivatives of Phenanthrene and Retene.

Retene Investigations. XVIII. The Mannich Reaction with Monohydroxy Derivatives of Phenanthrene and Retene.