Identification du glucosiduronate de 5β-pregnane 3α, 21-diol 20-one (THDOC) après administration de cortexone

Summary After administration of cortexone to a normal man, we isolated the 5-pregnana 3, 21-diol 20-one glucuronide in human urine. We found 90% of this corticosteroid in the glucuronide fraction; the remaining 10% was in the free fraction.We found neither the cortexone nor its metabolites dior tetrahydrogenated in the ester-sulphate fraction.The tetrahydrocortexone-glucuronide was identified by paper chromatography and by electrophoresis.     

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.     

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).     

Synthese von 5α- und 5β-Androstan-17β-ol-3-on-17-acetat aus Hyodesoxycholsäure

Summary 5- and 5-androstane-17-ol-3-one-17-acetate have been prepared from 5-androstane-6, 17-diol-3-one-17-acetate by a synthesis involving directedHuang-Minlon-reduction.Separation of 5-androstane-17-ol-3-one from its 5-isomer could readily be achieved by crystallisation of their 3-ethylenketals from acetone.     

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.     

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.     

An antagonism between 3–4 dioxyphenylalanine (DOPA) and 5-hydroxytryptophan (5-HTP)

Riassunto Recentemente è stata formulata l'ipotesi che la 5-idrossitriptamina e la noradrenalina agiscano come mediatori a livello del S.N.C. I risultati ottenuti dall'A. dimostrano che la diossifenilalanina può antagonizzare il potenziamento della narcosi barbiturica indotto dal 5-idrossitriptafano.

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Research fellow from Keio University, Tokyo (Japan).     

Sm3(Fe,Ti)29Nx/α-Fe双相纳米耦合永磁材料的制备

研究了熔体快淬工艺及添加元素Ti对Sm—Fe合金相的形成及结构的影响，成功制备了Sm3（Fe，Ti）29Nx／α-Fe双相纳米耦合永磁材料．研究发现，快淬薄带由Sm3（Fe，Ti）29和α-Fe两相组成，晶化前在纳米晶周围存在部分非晶相，晶化后的晶粒间晶界平直光滑、且晶粒间结合紧密没有界面相，为晶粒间直接接触耦合．对甩带后的样品采用750℃保温10min的晶化退火得到的颗粒比较细小且均匀．氮化磁粉磁滞回线的第二象限没有出现明显的台阶，表现为单相永磁材料的特点，说明硬磁相Sm3（Fe，Ti）29M与软磁相α-Fe晶粒之间的交换耦合作用已形成．     

Control of obesity inA vy /a mice by 5α-androstan-17-one

Summary Treating VY/WfL-A ^vy /a mice with 5-androstan-17-one, a mammalian glucose-6-phosphate dehydrogenase inhibitor, prevented the mice from becoming obese. The weight difference between treated and controlA ^vy /a mice was mainly due to a decreased accumulation of triacylglycerol. The compound did not suppress appetite, had no detectable toxicity and did not affect the lipogenesis rates in the liver and carcass. The weight-controlling effect of 5-androstan-17-one inA ^vy /a mice was reversible upon withdrawal of treatment.The authors wish to thank Mr W.R. Gibson and Drs C.G. Culbertson and P.N. Harris for performing the pathological examinations.     

极小(C_4,K_5;11)-平面图

若n阶平面图G的任一子图都不与H_1同构,且G的任一子图都不与H_2同构,则G称为(H_1,H_2;n)-平面图;平面Ramsey数指不存在(H_1,H_2;n)-平面图的最小n。本文利用对称性及反证等方法,得到了所有的极小(C_4,K_5;11)-平面图,有助于证明平面Ramsey数。     

Totally synthetic (±)-13-Alkyl-3-hydroxy and methoxy-gona-1,3,5(10)-trien-17-ones and related compounds

Zusammenfassung Von mehreren (±) 3-Oxy- und (±) 3-Methoxy-13-alkylgona-1,3,5(10)trien-17-onen und verwandten Verbindungen, einschliesslich von Vertretern der (±) 13-Alkylgon-4-en-3-on-Reihe, werden Totalsynthese und biologische Wirksamkeit beschrieben.     

Conversion of 17α-hydroxypregnenolone to cortisol

Zusammenfassung Nebennierenschnitte von Ratten, Meerschweinchen und Menschen synthetisierten 17-Hydroxyprogesteron, 11-Deoxycortisol und Cortisol aus 17-Hydroxypregnenolon. Diese Verbindung, als Ausgangsprodukt für die Cortisolsynthese, ist ebenso wirksam wie pregnenolon. Die Umwandlung von 17-Hydroxypregnenolon in Dehydroepiandrosteron verläuft weniger vollkommen als zu 17-Hydroxycorticoiden.     

(Z,E)-α-farnesene,main constitutent of the hypertrophied Dufour's gland of the major workers ofPheidole pallidula (Formicidae)

Summary In the European dimorphic ant,Pheidole pallidula, the Dufour's gland of the major workers is hypertrophied and secretes nearly pure (Z, E)--farnesene. This compound is also present in the Dufour's gland of the minor workers but constitutes only around 10% of the volatiles. Chemical polymorphism inP. pallidula is different from that already reported for species ofPheidole from the New World.Aspirante au Fonds National de la Recherche Scientifique.Maître de recherches du Fonds National de la Recherche Scientifique.     

Nα-quinaldyl-L-arginine·HCl,a new defensive alkaloid fromSubcoccinella-24-punctata (Coleoptera,Coccinellidae)

The isolation of N-quinaldyl-L-arginine·HCl (1) from the CoccinellidaeSubcoccinella-24-punctata is reported. The structure, first established on the basis of the analysis of the spectral properties of1, has been confirmed by synthesis. The alkaloid is of endogenous origin and markedly deterrent to ants.     

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.     

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.     

Insulin activates Gαil,2 protein in rat hepatoma (HTC) cell membranes

Insulin action is initiated by binding to its cognate receptor, which then triggers multiple cellular responses by activating different signaling pathways. There is evidence that insulin receptor signaling may involve G protein activation in different target cells. We have studied the activation of G proteins in rat hepatoma (HTC) cells. We found that insulin stimulated binding of guanosine 5′-O-(3-thiotriphosphate) (GTP-γ-³⁵S) to plasma membrane proteins of HTC cells, in a dose-dependent manner. This effect was completely blocked by pertussis toxin treatment of the membranes, suggesting the involvement of G proteins of the Gα _i/Gα _o family. The expression of these Gα proteins was checked by Western blotting. Next, we used blocking antibodies to sort out the specific Gα protein activated by insulin stimulation. Anti-Gα _il,2 antibodies completely prevented insulin-stimulated GTP binding, whereas anti-Gα _o,i3 did not modify this effect of insulin on GTP binding. Moreover, we found physical association of the insulin receptor with Gα _i1,2 by copurification studies. These results further support the involvement of a pertussis toxin-sensitive G protein in insulin receptor signaling and provides some evidence of specific association and activation of Gα _i1,2 protein by insulin. These findings suggest that Gα _i1,2 proteins might be involved in insulin action. Received 23 September 1998; received after revision 23 November 1998; accepted 25 November 1998     

3-Cyclopentyl ether of 17α-ethynylestradiol: A potent anti-gonadotrophic and contraceptive agent in rodents

Riassunto Esperienze condotte in ratti e topi parabionti hanno permesso di stabilire che il 3-ciclopentil etere del 17-etinilestradiolo, estrogeno dotato di elevatissima attività uterotrofica per via orale, è parimenti fornito di forte potere inibente sulla secrezione gonadotropa ipofisaria. Pure a dosi minime esso rivela chiare proprietà anticoncezionali nei ratti femmine. Sia come inibitore ipofisario che come inibitore della fertilità, tale composto si dimostra notevolmente più attivo del 3-metil etere del 17-etinilestradiolo.     

Über 6-(4′-Pyridyl)-3-mercapto-1,2,4-triazin-5-on

Summary In synthesizing 6-(4-pyridyl)-3-mercapto-1,2,4-tria-zin-5-one from the oxime of 4-pyridyl-glyoxylic acid, isonicotinaldehyde-thiosemicarbazone is obtained through decarboxilation as a by-product, which is mainly responsible for the tuberculostatic properties.