Defensive steroids from a carrion beetle (Silpha americana)

Summary The defensive anal effluent discharged bySilpha americana in response to disturbance contains a mixture of steroids stemming from a glandular annex of the rectum. The compounds have been characterized as 15-hydroxyprogesterone (1, principal component), 5-pregnan-15-ol-3, 20-dione (2), 5-pregnan-3, 15-diol-20-one (3), 5-pregnan-7, 15-diol-3,20-dione (4), 5-pregnan-3, 7, 15-triol-20-one (5), 5-pregnan-16-ol-3,20-dione (6), and 5-pregnan-3, 16-diol-20-one (7), none previously found in insects. Bioassays with jumping spiders showed compounds1 and6 to be feeding deterrents at the 1 g level.Paper No. 78 of the series: Defense Mechanisms of Arthropods. Study supported by NIH (Grants AI-02908, AI-12020). We thank Maura Malarcher and Maria Eisner for excellent technical help, and the Squibb Institute of Medical Research for samples of authentic reference compounds.     

17β-Hydroxymethyl-Steroide: Darstellung von Derivaten des 17α-Hydroxy-17β-hydroxymethyl-4-androsten-3-ons

Summary Starting from 17-hydroxy-17-hydroxymethyl-4-androsten-3-one, we synthesized 4-chloro-17-hydroxy-17-hydroxymethyl-4-androsten-3-one-17, 20-acetonide and 17-hydroxy-17-hydroxymethyl-1, 4-androstadien-3-one. 11, 17-dihydroxy-17-hydroxymethyl-4-androsten-3-one was obtained from cortisone via methyl-17-hydroxy-3, 11-dioxo-4-etienate.     

17β-Hydroxymethyl-Steroide: Darstellung von Derivaten des 17β-Hydroxymethyl-4-androsten-3-ons

Summary Starting from methyl 3-oxo-4-etienate, the authors prepared 17-hydroxymethyl-4-androsten-3-one and 11-hydroxy-17-hydroxymethyl-4-androsten-3-one. Chlorination of 17-acetoxymethyl-4-androsten-3-one yielded 4-chloro-17-acetoxymethyl-4-androsten-3-one. 17-Hydroxymethyl-1, 4-androstadien-3-one was obtained from 17-hydroxymethyl-4-androsten-3-one, both by chemical and biological methods.     

The synthesis of ecdysone

Zusammenfassung Ecdyson, ein Häutungshormon der Insekten, wurde ausgehend von Ergosterin in 14 Stufen synthetisiert. Wesentliche Zwischenprodukte waren (20S)-2, 3-Diacetoxy-20-formyl-5-pregn-7-en-6-on und (22R)-2, 3-Diacetoxy-14, 22-dihydroxy-25-(tetrahydropyran-2-yloxy)-5-cholest-7-en-6-on.     

Testosterone metabolism by mouse placenta in vitro

Zusammenfassung 4-C¹⁴-Testosteron wurde durch Mäuseplazenta in vitro zu Steroiden umgesetzt: 3-Hydroxy-5-androstan-3, 17-dion, 3-Hydroxy-5-androstan-3, 17-dion, 4-Androsten-3, 17-dion und 5-Androstan-3, 17-dion. Eine Umsetzung von Testosteron zu Östrogenen wurde nicht nachgewiesen.     

Immunofluorescent localization of β-Corticotropin in the rat pituitary

Zusammenfassung Unter Verwendung eines spezifischen Anti-^1–24-Corticotropin-Serums vom Kaninchen wurde -Corticotropin immunhistologisch in der Rattenhypophyse nachgewiesen. Neben den Epithelien der Pars intermedia konnte kortikotropes Hormon in einem besonderen, mukoiden Zelltypus der Adenohypophyse lokalisiert werden.     

Reduction of high affinity glutamate uptake in rat hippocampus by two polyamine-like toxins isolated from the venom of the predatory waspphilanthus triangulum F

Summary Two components of the venom of the predatory waspPhilanthus triangulum F. significantly reduce — to a greater or less extent — the high affinity uptake of glutamate in rat hippocampus. A concentration of 10 M -PTX caused a reduction of 74%, while the other component, -PTX, at the same concentration, caused a reduction of 18%. Hence the effect of -PTX on high affinity glutamate uptake in the hippocampus is comparable with its effect on high affinity glutamate uptake in insect neuromuscular junctions. Contrary to our previous findings that -PTX has no effect on high affinity glutamate uptake in insect glutamatergic terminal axons, however, -PTX significantly reduces high affinity glutamate uptake in the hippocampus, albeit less effectively than -PTX.     

The molecular structure of the benzilic acid rearrangement product of 3α, 17β-diacetoxy-11-hydroxy-12-oxo-5β-androst-9(11)-ene

Zusammenfassung Die Struktur desp-Brombenzoates des Benzilsäureumlagerungsproduktes von 3, 17-Diacetoxy-11-hydroxy-12-oxo-5-9(11)-androsten wurde durch dreidimensionale Röntgenstrukturanalyse eines Einkristalls als 3-p-Brombenzoat des 11-Carboxy-3, 11, 17-trihydroxy-13-C-nor-5-androstan 11a, 17-Laktons erkannt.     

11β-methyl-19-norsteroids: Novel progestational hormones

Zusammenfassung Die Synthese von 3, 17-Diacetoxy-17-Äthinyl-11-Methylestr-4-en (XII) wird beschrieben. Die Substanz besitzt besonders starke Antifertilitätseigenschaften, wie sie sonst nur Mischungen von Hormonen eigen sind, welche für die Humanfertilität benutzt werden, jedoch ohne deren Nebenwirkungen.     

16-β-methylprednisone from hecogenin

Zusammenfassung Es wird über die Herstellung des 16-Methylprednisons berichtet, welche vom Hecogenin ausgehend über ca. 15 Stufen durchgeführt wird. Als wichtige Zwischenstufe treten 5-Pregn-16-en-3-ol-11, 20-dion-Acetat und 16-Methylen-5-pregnan-3, 17-diol-11, 20-dion auf: letzteres wird durch eine stereospezifische katalytische Reduktion in das entsprechende 16-Methyl-derivat umgewandelt.     

In vivo perfusion of human lung tissue with 7α-3H-dehydroepiandrosterone35S-sulfate. Metabolism of steroid conjugates. IV

Zusammenfassung Bei der in-vivo Perfusion menschlichen Lungengewebes mit 7-³H-DHEA-³⁵S-sulfat zeigte es sich, dass im Lungengewebe sowohl Sulfatase- wie auch Sulfokinaseaktivität enthalten ist. Als Metaboliten konnten neben dem vorherrschenden 5-Androsten-3, 17-diol auch Testosteron, Androstendion, Androsteron, ätiocholanolon sowie Oestrogene nachgewiesen werden.     

Über die Ausscheidung von 3β-Hydroxy-17-Ketosteroiden im Harn von Meerschweinchen

Summary 11-hydroxy-epiandrosterone was isolated and identified from urine of normal untreated female guinea pigs. After cold and hot acid hydrolysis of the urine, we found another 3-hydroxy-17-oxosteroid. Its character was investigated by several methods and we suppose this steroid is9(11)-epiandrosterone, an artificial product of 11-hydroxy-epiandrosterone.     

The benzilic acid rearrangement of 3α,17β-Diacetoxy-11-hydroxy-12-oxo-5β-androst-9(11)-ene

Zusammenfassung Die Bildung von 11-Carboxy-3, 11, 17-trihydroxy-13-C-nor-5-androstan 11a,17-Lakton aus 3, 17-Diacetoxy-11-hydroxy-12-oxo-5-⁹(11)-androsten wird beschrieben. Der Mechanismus und die Stereochemie dieser Umwandlung (Retro-Aldolkondensation und Benzilsäureumlagerung) wird diskutiert.     

The distribution of some enzymes involved in the steroidogenesis of hen's ovary

Riassunto È stata studiata con metodi istochimici la distribuzione della ⁵-3-idrossisteroide deidrogenasi ( ⁵-3-HSDH) e delle 17-idrossisteroide deidrogenasi (17-HSDH), DPN- e TPN-dipendenti, nell'ovario di gallina ovulante. Mentre la ⁵-3-HSDH è presente in tutti i tessuti a secrezione steroide dell'ovario, la 17-HSDH è localizzata solo nelle cellule della granulosa.     

Comparative analysis of human milk and human blood plasma by means of diffusion-in-gel methods

Zusammenfassung Mit Hilfe von Immunoelektrophorese und Doppeldiffusiontechnik wurden in Humanmilch an Blutplasmaproteinen serologisch identifiziert: Praealbumin, Albumin, Acid Seromucoid, ₁-Glykoprotein (3·5 S), Coeruloplasmin, Haptoglobin, ₂- oder-Lipoprotein, Transferrin, Fibrinogen, _2A-Globulin, _2M-Globulin und-Globulin.     

Metabolism in Porifera XII. Further informations on the biosynthesis of 3β-hydroxymethyl-A-nor-steranes in the spongeAxinella verrucosa

Summary Direct incorporation and cold trap experiments suggest that cholest-4-en-3-one is an intermediate in the conversion of cholesterol into 3-hydroxymethyl-A-nor-cholestane in the marine spongeAxinella verrucosa. Cholest-4-en-3-one is further transformed by the sponge into cholest-4-en-3-ol, 5-cholestan-3-one and 5-cholestan-3-ol; these compounds arise from side reactions, which are not part of the major metabolic route leading to 3-hydroxymethyl-A-norsteranes.     

17β-Hydroxymethyl-steroide: Darstellung von 17α-Hydroxy-17β-hydroxymethyl-4-androsten-3-on aus Reichsteins Substanz S

Summary The synthesis of 17-hydroxy-17-hydroxymethyl-4-androsten-3-one fromReichsteins compound S is described. Transformation of 3,3-ethylenedioxy-17-hydroxy-17-hydroxymethyl-5-androsten into 17-methyl-isotestosterone demonstrates the configuration of the substituents at C-17.     

Metabolism in Porifera. IX. Studies on the biological conversion of cholesterol into 19-nor-cholestanol by the spongeAxinella polypoides

Summary The conversion of cholesterol into 19-nor-5-cholestan-3-ol by the spongeAxinella polypoides involves a partial loss (40%) of the 3-hydrogen atom; moreover administration to the sponge of [4-¹⁴C]cholesterol tritiated at C-4 and C-7 showed that the 4- and 7-hydrogen atoms are retained in this conversion. A competitive uptake experiment, [4-¹⁴C]cholesterol vs. [7-³H₂]5-cholestanol, showed that the sponge utilized exclusively cholesterol for the production of 19-nor-5-cholestan-3-ol.Part of this work has been presented at the Nato Conference on Marine Natural Products (Jersey, Great Britain, October, 1976).-This contribution is part of the Programma finalizzato Oceanografia e Fondi marini-sottoprogetto Risorse biologiche C.N.R. Italy.     

Evidence for the extranuclear localization of thymosins in thymus

A new radioimmunoassay has been developed for thymosin ₄ by generating rabbit polyclonal antibodies against the synthetic N-terminal peptide fragment 1–15 coupled to KLH. The synthetic analogue [Tyr¹²]-thymosin ₄ (1–15) was used as tracer. This radioimmunoassay, with a useful range of 10–1000 pmoles, showed cross-reactivity with the second homologous -thymosin of man and rat (thymosin ₁₀) but not of calf (thymosin ₉). This radioimmunoassay, together with an improved radioimmunoassay for the N-terminus of parathymosin , was employed for the measurement of the levels of thymosin ₄ and parathymosin in nuclear and extranuclear extracts of calf thymus. The bulk of these polypeptides was found in the extranuclear material whereas only traces were observed in the nuclear environment, which indicates the extranuclear localisation of - and -thymosins.     

Hydrolysis of amino acid β-naphthylamides by aminopeptidases in the parotid gland

Zusammenfassung Die Aktivität der Aminopeptidasen in Ohrspeicheldrüsen wurde gemessen. Glycyl-Prolin-naphthylamid, Alanin-naphthylamid, Leucin-naphthylamid, Methionin-naphthylamid, und Arginin-naphthylamid wurden von der Mikrosomenfraktion und der löslichen Fraktion schnell gespalten. Das Glycyl-Prolin-naphthylamid spaltende Enzym war in Ohrspeicheldrüsen in relativ grösserer Menge vorhanden. Die Aufspaltung von Glycyl-Prolin-naphthylamid in Glycyl-Prolin und-Naphthylamin wurde papierchromatographisch nachgewiesen.