Identification of 3α, 17α, 21-trihydroxy-5α-pregnane (allotetrahydro-17α-hydroxy-cortexone) and 3α,21-dihydroxy-5α-pregnane (allo-tetrahydro-cortexone) in human urine

Résumé Le 3, 17, 21-trihydroxy 5-pregnane (allo-tétrahydro-17-hydroxy-cortexone) et le 3,21-dihydroxy 5-prégane (allo-tétrahydro-cortexone) ont été identifiés dans l'urine humaine. Ces composés avaient les mêmes migrations chromatographiques avant ou après acétylation ou oxydation que les respectifs stéroïdes de synthèse.     

Isolement et identification du 5β-prégnane 11β, 17α, 21-triol 3, 20-dione (Dihydrocortisol) dans l'urine humaine

Summary 5-pregnane 11, 17, 21-triol 3, 20-dione (dihydrocortisol) has been isolated and identified in the urine of patients with feminizing adrenal cortical cancer. This steroid showed the same Rf as synthetic dihydrocortisol in six different chromatographic systems. After acetylation, its Rf was the same as that of 21 monoacetate of dihydrocortisol. After bismuthic or chromic oxydation, it had the same chromatographic Rf as 5-androstane 11-ol 3, 17-dione and 5-androstane 3, 11, 17-trione respectively. After chromic oxydation of its acetate, the Rf was the same as that of 21 monoacetate of cortisone.     

Preliminary note on certain pharmacological properties of 3β, 16α-dihydroxyallopregnan-20-one

Zusammenfassung 3, 16- Dihydroxyallopregnan-20-one hat die Eigenschaft, bei der Mehrzahl adrenopriver, salzbelasteter Ratten im Harn eine Natrium-Mehrausscheidung hervorzurufen.     

Disparition de la 5-hydroxytryptamine dans les granulations des glandes de la peau deDiscoglossus pictus et deRana temporaria après injection de réserpine

Summary 30 min after an intraperitoneal injection of reserpine (5 or 10 mg/kg) in the frog (Rana temporaria) and in the toad (Discoglossus pictus), a substance which has the properties of 5-hydroxytryptamine (argentaffine reaction, azoreaction, indoreaction and fluorescence in U.V. after formaldehyde) disappears from the skin glands; the histochemical reactions are more positive again 1 1/2 to 2 h after the injection of reserpine.     

Zur Umsetzung von 3α-Hydroxy-5β-Steroiden mit Blei(IV)-acetat

Summary On treatment of 3-hydroxy-5-steroids with lead tetra-acetate formation of 3, 9-oxides is observed. The yields of this ring closure reaction decrease significantly in the order 11-keto, ^{9, 11}-ene and ring-C saturated compounds.     

Etude du métabolisme de mescalines fluorées par Pieris brassicae (Insecte,Lépidoptère)

Summary The action of -fluorinated mescalins on induction of diapause in the cabbage butterfly. Pieris brassicae, has been studied. The introduction of fluorine into mescalin has no influence on this activity. This result suggests solvolysis of fluorine and in vivo formation of a common ethylimine intermediate. Activity decreases, however, with substitution of the nitrogen.     

Activité inhibitrice de certains α,β,β-triaryléthylènes vis-à-vis des sécrétions anté-hypophysaires

Summary An investigation has been made of the inhibitory effects on the secretions of the anterior pituitary of four ,,-triarylethylenes with weak oestrogenic activity. These substances have been found to vary in the degree to which they inhibit each of the secretions investigated.     

Un nouveau type de détermination chromosomique du sexe chez les mammifèresEllobius lutescens Th. etMicrotus (Chilotus) oregoni Bachm. (Muridés-Microtinés)

Summary (1)Ellobius lutescens andMicrotus oregoni show the same type of sex-chromosomes. The diploid number is odd in both sexes, seventeen.(2) The odd element ofEllobius is morphologically alike in the male and in the female. InM. oregoni, the odd element of the male is acrocentric, that of the female metacentric.(3) Following a hypothesis ofWhite, it seems very probable that the heterochromosome of the male is built of the primitiveY (short arm) and the primitiveX (long arm) linked together. In the female of the same species (M. oregoni), the sex-chromosome represents both theX fused together.(4) Only the half of the Zygotes may develope, the other half being lethal.(5) The close kinship betweenEllobius andM. oregoni is certain, a parallel evolution appearing as highly improbable.     

Effects of 2-β-D-glucosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one onSchizaphis graminum (rondani) (insecta,aphididae) feeding on artificial diets

Summary 2--Glucosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA-Glc), the main hydroxamic acid from maize and wheat, and its aglucone, decreased survival ofSchizaphis graminum reared on artificial diets. Both compounds were toxic for aphids and acted as feeding deterrents, at concentrations as low as 1 mM. The natural concentrations of glucosides of hydroxamic acids in wheat leaves reach up to 6 mmoles/kg fresh weight, thus falling within the range in which DIMBOA-Glc causes delecterious effects to diet-fed aphids.To whom correspondence should be addressed. THis work was supported by grants from International Foundation for Science (484), Universidad de Chile (N-1654) and the Agency for International Development.     

3-Amino-1-(3,4-dichloro-α-methyl-benzyl)-2-pyrazolin-5-one (Bay g 2821), a potent diuretic from a new substance class

Summary Chemistry, salidiuretic activity and mechanism of action of 3-amino-1-(3,4-dichloro--methyl-benzyl)-2-pyrazolin-5-one (Bay g 2821), a new diuretic, are described. Owing to the initial rapid onset of activity, the reserve in capacity and the additional long duration of activity, this substance represents a potent diuretic and antihypertensive agent.     

Bildung von 17α-Hydroxy-Δ5-pregnenolon und 3β-Hydroxy-17-keto-Δ5-androsten (DHA) in Nebennieren- und Testes-Gewebe

Summary The transformation of ⁵-pregnenolone into 17-hydroxy-⁵-pregnenolone, and of the latter into DHA, is shown to occur in homogenates and fractions thereof, both of bovine adrenal and testicular tissue. The relative significance of these reactions for the biogenesis of androgens in normal and neoplastic tissue is discussed.

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173. Mitteilung über Steroide; 172. Mitteilung:P. Wieland, K. Heusler undA. Wettstein, Helv. chim. Acta43, 2066 (1960).     

Characterization of 17β-estradiol 3-(β-D-glucopyranoside) and 17-(α-D-glucopyranoside) as the metabolites of 17β-estradiol in the cultured ovaries of the silkworm,Bombyx mori

Summary The structures of the metabolites formed upon incubation of 17-estradiol with the ovaries of silkworm,Bombyx mori, have been determined as 17-estradiol 3-(-D-glucopyranoside) (1) and 17-(-D-glucopyranoside) (2) by spectroscopic means.     

Propriétés antiacétylcholinestérasiques du diiodométhylate debis-(diméthylamino-3-phénoxy)-1-3 propane,de ses dérivés phénoliques et des esters carbamiques correspondants

Summary Thein vitro anti-acetylcholinesterase properties ofbis-(dimethylamino-3-phenoxy)-1-3 propane dimethiodide (2842 CT) of two phenolics derivatives (3443 CT and 3116 CT) and of the two corresponding carbamic esters (3152 CT et 3113 CT) have been compared using human red blood corpuscles as enzyme source; under specified conditions, the Cl-50 are respectively 8 × 10^–7 M for 2842 CT, 3.5 × 10^–9 for the two phenolic compounds, and 1.5 × 10^–9 for the carbamic esters. The potencies of these phenols are very close to those of the carbamates, being a bit higher or lower depending on the concentration of the inhibitor and on the time of the readingThe two phenolic compounds, like 2842 CT, react readily with the enzyme contrarily to the carbamic esters which combine slowly. On the other hand the inhibition by the phenolic derivatives is as stable against washing as that by the carbamates. The carbamates, but not the phenols, show the slow displacement phenomenon.Some of these characteristics are compatible with the hypothesis that carbamic compounds could act through liberated phenolic functions but others indicate that carbamic groups have a role of their own.     

Sur la caractérisation de dérivés guanidiques d'origine biologique par électrophorèse et chromatographie sur papier (chromatoélectrophorèse)

Summary Paper chromatography has been used in conjonction with electrophoresis in a perpendicular direction (chromatoelectrophoresis), in order to characterize various guanidoderivatives of biological interest and also citrulline. The isolation of definite spots can be obtained with a satisfactory selectivity by this procedure, at a higher speed than by bidimensional chromatography; and the use of a few coloured reactions (ninhydrine,Sakaguchi, diacetyle--naphtol andp-dimethylaminobenzaldehyde) on the same electrochromatogram has been successfully practised in this field.     

Effets de la réserpine sur le développement d'Oedipoda coerulescens L. (Acridien,Orthoptère)

Summary Inhibitory effects of reserpine on ecdysis and chromatic adaptation inOedipoda appear to be linked with changes observed in both neural and neuro-endocrine regulating systems.     

Isolierung von 4α-methyl-5α-stigmasta-7,24(28)-dien-3β-ol ausSolanum tuberosum sowie über die Identität dieser Verbindung mitα 1-Sitosterin

Summary The sterol fraction from leaves of the potato plant,Solanum tuberosum, was found to contain a minor constituent, the structure of which has been established as 4-methyl-5-stigmasta-7,24(28)-diene-3-ol (I). This sterol is most probably identical with ₁-sitosterol and has the same constitution as citrostadienol, differing only in the configuration of the ^{24 (28)}-double bond.

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Sterine und Triterpenoide. III. Mitteilung. — II. Mitteilung s. 3.     

Synthesis ofO 1.5-(β-D-galactopyranosyl) [DMet2, Hyp5] enkephalin amide,a new highly potent analgesic enkephalin-related glycosyl peptide

Summary A new series of O-glycosyl enkephalins has been prepared, following a convergent strategy, with high chemical yields. The galactosyl analogue,O ^1.5-(-D-galactopyranosyl) [DMet², Hyp⁵] enkephalin amide proved to be one of the most potent in vivo opioid agonists synthesized up to now.     

Cyanidin-3-β-glucoside,a newly recognized basis for resistance in cotton to the tobacco budwormheliothis virescens (Fab.) (lepidoptera: Noctuidae)

Summary Cyanidin-3--glucoside was shown to be an important factor of resistance in cottonGossypium hirsutum L. leaves to the tobacco budwormHeliothis virescens (Fab.). This provides a potential basis for achieving insect resistance in non-glanded cotton and other crops infested byHeliothis.In cooperation with the Mississippi Agriculture and Forestry Experiment Station, Mississippi State. Mention of a trademark, proprietary product or vendor does not constitute a guarantee or warranty of the product by the U.S. Department of Agriculture and does not imply its approval to the exclusion of other products or vendors that may also be suitable.     

Leydig cell andΔ 5-3β-hydroxysteroid dehydrogenase activity in the testis of toad (Bufo melanostictus) following cold exposuredehydrogenase activity in the testis of toad (Bufo melanostictus) following cold exposure

Summary Leydig cell nuclear area and ⁵-3-hydroxysteroid dehydrogenase activity were increased in the testis ofBufo melanostictus 2 days after a single short-term cold exposure. Both parameters returned to normal values 4 days later.