Synthese von 22,26-Imino-cholestan-Derivaten

Summary 3, 16-diacetoxy-5-pregnane-20-one and the analogue pregn-5-ene derivative have been converted into (22R, 25R)-22, 26-imino-5-cholestane-3, 16-diol. The configuration at C-22 and C-25 was determined by transformation into the known (22R, 25R)-5-solanidane-3-one. Application of the Ruschig method led to (25R)-22,26-imino-5-cholest-22(N)-ene-3, 16-diol.

---

---

Solanum-Alkaloide. XVI. Mitteilung. — XV. Mitteilung:K. Schreiber undH. Ripperger, Tetrahedron Letters Nr.27, 9 (1960).     

Steroids and related natural products. 14α-Methyl testosterone

Zusammenfassung Eine Zwanzigstufenumwandlung von Isocholesterol (rohes Lanosterol) zu 14-Methyltestosteron wurde ausgeführt und die Reaktionsfolge von 3-Hydroxy-4,4,14-trimethyl-20-oxo-5-pregnan zu 14-Methyltestosteron beschrieben.

---

---

Part XIV. Part XIII,G. P. Mueller andG. R. Pettit, Exper.18, 404 (1962).

---

A preliminary report of this study was presented (August 27, 1962) at The Second International Symposium on the Chemistry of Natural Products, Prague (Czechoslovakia).

---

This investigation was supported by PHS Research Grants CY-4074(C3) and CA 04074-05 from the National Cancer Institute, Public Health Service.     

7α-hydroxylation of dehydroepiandrosterone in human testis and epididymis in vitro

Zusammenfassung Zerhackte menschliche Hoden und Epididymis wurden mit Dehydroepiandrosteron ohne Kofaktoren bebrütet und es wurden unter anderem 7-und 7-Hydroxydehydroepiandrosteron und 5-Androsten-3, 7, 17-triol charakterisiert. Die Ausbeute an 7-hydroxylierten Metaboliten war fast gleich in Hoden und Epididymis.

---

---

The authors wish to thank Mr.J. Novák for his excellent technical assistance. We are indebted to Dr.J. E. Jirásek for generous performance of histological control of tissue and to Dr.S. Röhling for his kind pernission of radioactivity measurements.     

Metabolism of a pharmacologically active pyrrolidine derivative (prolintane) by lactam formation

Zusammenfassung Prolintan, N-1-(-Benzylbutyl)-Pyrrolidin, wurde in Kaninchen durch ein Mikrosomensystem der Leber in das entsprechende Laktam, N-1-(-Benzylbutyl)-Pyrrolidin-2-on, umgebaut. Das gleiche Stoffwechselprodukt fand sich auch im Gewebe von Ratten, denen das Medikament gegeben wurde; allenfalls Spuren davon wurden im Urin der Ratten ausgeschieden.

---

---

We thank Dr.D. C. Remy for a sample of syntheticdl-1-(-propylphenethyl)-pyrrolidin-2-one.     

Hormonal rupture of larval diapause in the tickRhipicephalus sanguineus (Lat.)

Zusammenfassung Die Diapause von Larven der ZeckeRhipicephalus sanguineus (Lat.) wird durch- and-Ecdyson beendet.

---

---

We would like to thank Dr.J. B. Siddal for generously providing-ecdysone, Dr.T. Takemoto for-ecdysone and Dr.N. Krishnan for the juvenile hormone analogue,trans, trans-10, 11-epoxy faresenic acid methyl ester.     

Wirkung von 6β-Methoxy-9β,10α-pregna-4,6-dien-3,20-dion

Summary 6-Methoxy-9,10 -pregna-4,6-diene-3,20-dione inhibites the ⁴-3-oxosteroid-5-reduction in microsomes and the ⁴-3-oxosteroid-5-reduction in the soluble fraction of male rat liver. The 3- and 3-hydroxysteroid dehydrogenase are not inhibited by this substance.

---

---

Diese Arbeit wurde von der Firma Hoffmann-La Roche, Basel, unterstützt.     

Sur l'inversion de l'action hypertensive de la prostaglandine F2α, chez le rat

Summary In normal rats, prostaglandin F₂ is a potent vasoconstrictor. The corresponding systemic hypertension is progressively attenuated by tachyphylaxis, revealing a longlasting fall of blood pressure. Tachyphylaxis is accelerated by previous injection of arachidonic acid and bradykinin. The vasodepressive activity of PGF₂ is inhibited by indomethacin.

---

---

Nous remercions vivement le docteurPike (Upjohn, Kalamazoo) qui nous a fourni gracieusement ces prostaglandines.     

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.

---

---

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

Synthese von Solanidin aus Demissidin

Summary The steroidal alkaloid solanidine (solanid-5-ene-3-ol, II) which occurs in the potato plantSolanum tuberosum L. has been synthesized from demissidine (5-solanidane-3-ol, I), an alkaloid from the Mexican wild potatoSolanum demissum Lindl. The synthesis involves the following steps: 5-solanidane-3-one, 2,4-dibromo-5-solanidane-3-one, solanid-4-ene-3-one, 3-acetoxy-solanida-3,5-diene, and solanidine (II).

---

---

Solanum-Alkaloide. XVII. Mitteilung. — XVI. Mitteilung:K. Schreiber undG. Adam, Exper.17, 490 (1961).     

Subzelluläre Verteilung der Brenzcatechinamine in Herz und Nebennieren von Meerschweinchen nach Vorbehandlung mitl-α-Methyl-Dopa

Summary -Methyl-noradrenalin synthesized after pretreatment of the guinea-pig with -methyl-dopa was found to be localized, like noradrenalin, mainly in the granular fraction 100 000g of the heart and in the fraction of the chromaffin granules of the suprarenal medulla (15000 g). -Methyl-adrenalin could not bo found.

---

---

Ausgeführt mit Unterstützung der Deutschen Forschungsgemeinschaft.     

Enzymatische Hydrierungen im Ring A von Steroiden mittels Streptomyzeten

Summary A strain ofStreptomyces griseus has been found to convert ⁴-3-keto steroids into the corresponding saturated 3-keto-5-compounds and, on prolonged incubation, into the 3-hydroxy-5-derivatives.

---

---

10. Mitt. über mikrobiologische Reaktionen; 9. Mitt. sieheJ. Urech, E. Vischer undA. Wettstein, Helv. chim. Acta43, 1077 (1960).

---

170. Mitt. über Steroide; 169. Mitt. sieheR. Neher undA. Wettstein, Helv. chim. Acta43, 1171 (1960).

---

Auszugsweise vorgetragen am VII. Internationalen Kongress für Mikrobiologie, Stockholm 1958.     

The effect of monoamine synthesis-inhibitors on the ovarian compensatory hypertrophy

Resumen La administración continuada de-metilpara-tirosina, un inhibidor de la síntesis de catecolaminas, impide la hipertrofia compensadora del ovario en ratas. Este efecto es prevenido por la simultânea injección de DOPA, un. precursor de las catecolaminas. El grado de la hipertrofia compensadora del ovario no fue modificado por lap-cloro-fenilalanina, un inhibidor de la síntesis de serotonina. El estudio histológico de los ovarios de los animales tratados con MPT sugiere que ésta bloquea la ovulación, no modificando aparentemente la secreción tonica de las gonadotrofinas FSH y LH.

---

---

A grant from the Consejo Nacional de Investigaciones Científicas y Tecnicas of Argentina supported this research.-methylp-Tyrosine was a gift from Dr.Karl Pfister of Merck Sharp & Dohme Research Laboratories.     

Serum glycoprotein levels in athletes in training

Résumé Les sportifs examinés au repos, après plusieurs jours consécutifs d'entraînement ou de compétitions ont un niveau nettement plus élevé que le groupe de contrôle pour l'₁-antitrypsine, l'₂-HS-glycoprotéine, l'₂-macroglobuline, la transferrine, la céruloplasmine et le cuivre sériques. La signification biologique possible de ces faits est discutée.

---

---

With support from the Deutsche Forschungsgemeinschaft and Kuratorium für Sportmedizin.

---

Dozenten-Stipendiat der Alexander-von-Humboldt-Stiftung.     

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.

---

---

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

Interaction of polyene antibiotics and serum lipoproteins

-.     

Ein neues Verfahren zur Herstellung von 19-Norsteroiden

Summary The new methods for the production of 19-norsteroids described involve the conversion of 5-halogen-6-hydroxy-steroids into the corresponding 5-halogen-6:19-ethers either with lead tetraacetate or by the hypoiodite reaction^8,10. The 6:19-oxygen bridge is then opened reductively either directly or after oxidation of the 6:19-ethers to lactones or preferably after introduction of a ^4,6-3-oxo grouping. Acylolytic cleavage of the ⁴-3-oxo-6:19-ethers followed by alkaline hydrolysis gives ^4,6-3-oxo-19-hydroxy-steroids. The 19-hydroxycompounds formed are easily converted into 19-norsteroids by known methods.

---

---

Über Steroide, 189. (vorläufige) Mitteilung; 188. Mitt. vgl.J. Kalvoda, J. Schmidlin, G. Anner undA. Wettstein, Exper.18, 398 (1962).     

Steroidal sapogenins. XXX stereochemistry of the side chain

Zusammenfassung Die optischen Drehungen einiger 20, 25d; 20, 25l; 20, 25d; und 20, 25-l-Sapogenine wurden bestimmt. Die ersten drei Serien gaben übereinstimmend linksdrehende Werte, aber die letztere Gruppe erwies sich als rechtsdrehend.Die Struktur der vier Serien der Sapogenine folgte aus der Analyse dieser Befunde. Der mögliche Mechanismus bei der Entstehung dieser Verbindungen aus Pseudosapogeninen wurde besprochen. Die Autoren gelangen zum Schluss, dass sterische Faktoren an C₂₀ und C₂₅ die Richtung der Ringschliessung beeinflussen.

---

Steroidal sapogenins. XXX stereochemistry of the side chain

     

Uptake of D-glucose anomers by rat retina

Summary Uptake ofd-glucose anomers by isolated rat retina was studied. After 3 min incubation at 37°C in the presence of or anomer (750 g/ml), a significantly greater uptake (1.32 mg/g wet tissue) of -anomer was observed compared with that of -d-glucose (1.11 mg/g wet tissue). This result and other data suggest that the carrier ford-glucose transport in the retina prefers the -anomer stereospecifically.Acknowledgment. The authors are grateful to Mr S. Suzuki for his technical assistance.     

Aryl and aniline hydroxylases in rat nuclear membranes after pretreatment with pregnenolone 16α-carbonitrile,phenobarbital and methylcholanthrene

Résumé L'aryl hydrocarbure hydroxylase nucléaire répond seulement au méthylcholanthrène tandis que le phénobarbital et la prégnénolone 16-carbonitril ne l'affectent pas. Les trois substances n'induisent pas l'aniline hydroxylase nucléaire. Cependant elles sont des puissants inducteurs de l'aryl et l'aniline hydroxylase microsomiale.

---

---

We thank Dr.H. Gelboin for the 3-hydroxybenzo(a)pyrene, Dr.J. Babcock for pregnenolone 16-carbonitrile, and Dr.M. Bornens for his helpful discussions.