Über die Alkaloide vonRauwolfia ligustrina R. & S. Raugustin,ein neues reserpinähnliches Alkaloid

Summary Twenty-one alkaloids have been identified from the root ofRauwolfia ligustrina R. & S. The more important ones are reserpine, pseudoreserpine and raugustine, a new base which is isomer to pseudoreserpine. The structure of the latter compound is discussed.

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Mitteilung über Rauwolfia-Alkaloide

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Mitteilung sieheC. F. Huebner undE. Schlittler, J. Amer. chem. Soc.79, 250 (1957).     

Zur Pathogenese des Urämiesyndroms. Brenztraubensäure,Acetoin und 2,3-Butylenglykol in Blut von Patienten mit Nieren- und Leberkrankheiten

Summary Acetoin and 2, 3-butylene glycol in blood of renal and hepatic patients are raised, when consciousness is disturbed. There is no correlation between blood levels of acetoin and 2, 3-butylene glycol and the degree of impairment of consciousness. Simultaneous determinations of acetoin and 2, 3-butylene glycol in blood and cerebrospinal fluid show that alterations of the cerebral pyruvic acid metabolism are difficult to detect in circulating blood.

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Mit Unterstützung des «Schweizerischen Nationalfonds» und der Firma F. Hoffmann-La Roche & Co., AG, Basel.

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5. Mitteilung. — 1. Mitt.:H. Thölen, F. Bigler undH. Staub, Path. Microbiol.24, 262 (1961). — 2. Mitt.:F. Bigler, H. Thölen undH. Staub, Helv. physiol. Acta19, C11 (1961). — 3. Mitt.:H. Thölen, F. Bigler undH. Staub, Exper.17, 359 (1961). — 4. Mitt.:F. Bigler, H. Thölen undH. Staub, Schweiz. med. Wschr.91, 1259 (1961).     

Rauwolfia alkaloids,XVI. Deserpidine,a new alkaloid fromRauwolfia canescens

Zusammenfassung AusRauwolfia canescens wurde Deserpidin, C₃₂H₃₈O₈N₂, isoliert und eine Konstitutionsformel für dieses neue Alkaloid vorgeschlagen.

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Communication XV,C. F. Huebner et al., J.A.C.S. (in press).

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From lecture given at Columbia University, New York, January 12th, 1955.     

Nachweis von Scilliglaucosidin in den Zwiebeln vonBowiea volubilis Harvey

Summary Hellebrigenin was converted to Scilliglaucosidin-19-ol and 3-Epi-Scilliglaucosidin-19-ol. This proves the correctness of the assumption ofStoll et al. ³ that the aldehydic group of Scilliglaucosidin is in position C-10.Comparison of a reduction product of Nabogenin, a substance isolated earlier from the bulbs ofBowiea volubilis Harvey, with Scilliglaucosidin-19-ol and 3-Epi-Scilliglaucosidin-19-ol showed its identity with the first named compound. This proves that the so called Nabogenin was a mixture consisting mainly of Scilliglaucosidin.

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8. Mitteilung über die Glykoside vonBowiea vocubilis Harvey und 162. Mitteilung über Glykoside und Aglykone.

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7. Mitt.:A. Katz, Helv. chim. Acta38, 1565 (1955).

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161. Mitt.:H. Kündig-Hegedüs undO. Schindler, Helv. chim. Acta39, 904 (1956).     

Partialsynthese des Aldosterons

Summary The preparation of the (18 11)-lactone of ⁵-3-ethylenedioxy-11-hydroxy-21-acetoxy-20-oxo-pregnen-18-oic acid (XV) is reported. Since this compound has previously been transformed into aldosterone, the reactions described represent the first partial synthesis of this important hormone from readily available 18-unsubstituted natural steroids.

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Über Steroide, 163. Mitteilung; 162. Mitteilung vgl.P. Wieland, K. Heusler undA. Wettstein, Helv. chim. Acta43 (1960), im Druck; XV. Mitteilung überSynthesen in der Aldosteron-Reihe; XIV. Mitteilung vgl.J. Schmidlin undA. Wettstein, Helv. chim. Acta42, 2636 (1959).

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Steroide und Sexualhormone, 215, Mitteilung; 214. Mitteilung vgl.B. Kamber, G. Cainelli, D. Arigoni undO. Jeger, Helv. chim. Acta43 (1960), im Druck.     

Über die Orientierung bei der Kondensation von Benzil mit monosubstituierten Guanidinen

Summary Condensation of benzil with two monosubstituted guanidines in the presence of 50 mol% of potassium hydroxide leads to the formation of 2-(subst. imino)-4, 4-diphenyl-imidazolidin-5-ones (Ia, b); by reduction of the potassium hydroxide used the formation of these products is more or less driven back in favour of the formation of 3-substituted 5, 5-diphenyl-glycocyamidines (Ic, d). A possible explanation for these orientation phenomena is given.

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5. Mitteilung über Hydantoine, Thiohydantoine und Glykocyamidine².

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4. Mitteilung sieheK. Lempert undJ. Breuer Chem. Ber.92, 1710 (1959).     

Über Struktur und Aktivität der den H2O2-Zerfall katalysierenden Cu2+-Komplexe. — VI. Differenzierung von nativer RNS und nativer DNS bzw. denaturierter DNS auf Grund der katalytischen Eigenschaften

Summary The catalysis of H₂O₂ decomposition by Cu²⁺-complexes of RNA and DNA has been investigated. It is shown that both complexes decompose H₂O₂, but only the Cu²⁺-RNA-system shows peroxidative activity too, e.g. only in this case the nucleotide bases are degraded. Thermal denaturation of DNA also leads to a Cu²⁺-complex with peroxidative activity, the latter being dependent on the degree of denaturation.

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V. Mitteilung:S. Petri, H. Sigel undH. Erlenmeyer, Helv. chim. Acta49, 1778 (1966).

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12. Mitteilung überMetallionen und H ₂ O ₂; 11. Mitteilung:H. Ch. Curtius, P. Anders, R. Zell, H. Sigel undH. Erlenmeyer, Helv. chim. Acta49, 2256 (1966).     

Zur Pathogenese des Urämiesyndroms1. Über den Einfluss von Tyramin auf die Acetoinsynthese aus Brenztraubensäure in Rattenleberhomogenat2

Summary Tyramine enhanced the production of acetoin from pyruvate in rat liver homogenates. A stimulation of acetoin synthesis was only observed, when tyramine was oxidized during the incubation. Tyrosol (p-hydroxyphenylethanol) stimulated acetoin synthesis whereasp-hydroxyphenylacetic acid and ammonia were ineffective.

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Mit Unterstützung des »Schweizerischen Nationalfonds» und der Firma F. Hoffmann-La Roche & Co. AG, Basel.

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8. Mitteilung. 1. Mitt.:H. Thölen, F. Bigler undH. Staub, Path. Microbiol. (Basel)24, 262 (1961). — 2. Mitt.:F. Bigler, H. Thölen undH. Staub, Helv. physiol. Acta19, C 11 (1961). — 3. Mitt.:H. Thölen, F. Bigler undH. Staub, Exper.17, 359 (1961). — 4. Mitt.:F. Bigler, H. Thölen undH. Staub, Schweiz. med. Wschr.91, 1259 (1961). — 5. Mitt.:H. Thölen, F. Bigler, A. Heusler, W. Stauffacher undH. Staub, Exper.18, 454 (1962). — 6. Mitt.:F. Bigler, H. Thölen undH. Staub, Schweiz. med. Wschr.92, 746 (1962). — 7. Mitt.:F. Bigler, H. Thölen undH. Staub, in Vorbereitung.     

Über das Cu2+-Bindungsvermögen einiger Aminosäuren und Peptide Metallionen und biologische Wirkung

Summary The capacity of binding copper ions of several aminoacids and peptides has been investigated. A direct colorimetric method measuring comparable values of bound Cu²⁺ has been developed.

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37. Mitteilung; 36. Mitteilung:R. Gall undH. Erlenmeyer, Helv. chim. Acta38, 1421 (1955).     

Zentralerregende Wirkung eines neuen Piperidinderivates

Summary A new piperidine derivative, the 2-diphenylmethylpiperidine, produces already in doses of 0.001 g/kg s.c. a strong increase of the spontaneous motility of various animals. On mice it has about the same potency as d-desoxy-ephedrine and is about 3 times more potent than amphetamin. It also acts markedly antagonistic on various narcotics but has practically no peripheral sympathomimetic effects.

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8. Mitteilung über Alkylenimin-Derivate. 7. Mitteilung sieheB. M. Iselin undK. Hoffmann, J. Am. Chem. Soc.76 (im Druck).     

Synthese der Spiroaminoketal-Gruppierung von Solanum-Alkaloiden

Summary The ring-E opened dihydro derivatives of tomatidine and soladulcidine give the corresponding N-chloroamines with N-chlorosuccinimide. Treatment of these compounds with sodium methoxide yields the spiroaminoketal alkaloids, tomatidine and soladulcidine respectively, in high yields, probably via instable C=N-unsaturated intermediates which undergo spontaneous stereospecific cyclisation.

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Solanum-Alkaloide. XIII. Mitteilung. XII. Mitteilung:K. Schreiber undH. Ripperger, Exper.16, 536 (1960).     

Glucodigifucosid,Neo-Glucodigifucosid und Digitoxigenin-allomethylosid aus den Blättern vonDigitalis lanata Ehrh

Summary The primary glycosides, glucodigifucoside and neo-glucodigifucoside, were isolated from the extract ofDigitalis lanata leaves. They are isomeric glucosides of digiproside and differ in the position of attachment of thed-glucose residue. Digitoxigenin-allomethylosid was isolated from the leaves after enzymatic decomposition.

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23. Mitteilung über Herzglykoside; unter der ausgezeichneten experimentellen Mitarbeit vonH. Gerlach.     

Sauerstoff-Heteroringe. Die Konfiguration und Synthese desd,l-Homopterocarpins

Summary The racemic form of homopterocarpin (V), a constituent of red sandal-wood, has been synthesized by a method which has previously been proposed by the authors. N. M. R. spectral studies in conjunction with the examination of models have enabled the assignment of thecis configuration (V) to homopterocarpin.

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V. Mitteilung. IV. Mitteilung sieheH. Suginome, Exper.18, 161 (1962).     

Über Peptidsynthesen,XLIV. Synthese von Ser4-Glu(NH2)8-Oxytocin (Glumitocin)

Summary Ser⁴-Glu(NH₂)⁸-Oxytocin has been synthesized. The identity of the synthetic compound with the neurohypophysal hormone (Glumitocin) recently isolated from species of cartilaginous is demonstrated.

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Über Peptidsynthesen XLIII. Mitteilung,E. Klieger, Experientia23, 620 (1967).     

Neuere Auffassungen über den Mechanismus der Blutgerinnung

Summary The most important facts and conceptions regarding the mechanism of blood coagulation, supplemented by our own as yet unpublished findings, are represented in a schematically simplified Table. The process of co-agulation is subdivided into five phases, i.e. the prephase (vasoconstriction, agglutination), the first principal phase (formation of thromboplastin), the second principal phase (formation of thrombin), the third principal phase (formation of fibrin), as well as a post-phase (retraction, fibrinolysis). In this new scheme, recently discovered clotting factors and the various inhibitors could easily be incorporated into the classical picture of Morawitz. The scheme is explained briefly.

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9. Mitteilung über Probleme der Blutgerinnung.—8. Mitteilung sieheR. Marbet undA. Winterstein, Die Medizinische1954, 877.     

Nachweis von Corticosteroiden in menschlicher Placenta und Isolierung von 16α-Hydroxytestosteron

Summary The occurrence of cortisol, cortisone, 20-dihydrometabolites of cortisone and several other steroidlike compounds in fresh placental tissue is described. Neither aldosterone, corticosterone nor 11-dehydrocorticosterone has been found. One of the most abundant compounds present has been identified as 16-hydroxy-testosterone.

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184. Mitteilung über Steroide. 183. Mitteilung:E. H. Wehrli, M. Cereghetti, K. Schaffner, J. Urech undE. Vischer, Helv. chim. Acta44, im Druck (1961).     

Neue Totalsynthese einer razemischen Doisynolsäure

Summary A new synthesis is described of a crystalline 7-methyl-doisynolic acid showing a strong estrogenic activity. This acid is probably identical with the stereoisomer C ofAnner andMiescher. Demethylation of this methoxyacid yields a new doisynolic acid of mp. 113–117° (hemihydrate).

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XIII. MitteilungSynthetische Versuche in der Gruppe der östrogenen Hormone; XII. Mitteilung siehe Chem. listy50, 2004 (1956).     

Über Pflanzenwachstumsregulatoren

Summary Experiments withColeus Blumei andTropaeolum showed that triazine compounds inhibit the photosynthesis, and, consequently, prevent the accumulation of starch. The chloroplasts of starchfree coleus leaves kept on a solution containing sugars and simazine are able to form starch again.

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Mitteilung (siehe auch die zwei folgenden ArbeitenExer undRoth).     

β-Ergokryptine,a new alkaloid of the ergotoxine group

Zusammenfassung Es wird die Isolierung eines neuen Isomeren des Ergokryptins beschrieben, das sich von diesem nur durch den Ersatz des Leucin-Restes durch den Isoleucin-Rest im Peptidteil des Moleküls unterscheidet. Das neue Isomere soll als-Ergokryptin und das früher beschriebene Alkaloid als-Ergokryptin bezeichnet werden. Die beiden Isomeren, ebenso ihre Dihydro-Derivate, unterscheiden sich pharmakologisch nur ganz unwesentlich.

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Mitteilung über Mutterkornalkaloide (65. Mitteilung:H. Ott, A. Hofmann andA. J. Frey, J. Am. chem. Soc.88, 1251 (1966)).     

Dien-Synthesen im Aufbau von Östrogenen

Summary The addition of citraconic anhydride to 1-vinyl-6-methoxy-3,4-dihydro-naphthalene according toDiels-Alder's method yielded two isomeric hydro-phenanthrene-dicarboxylic acids. One of these two acids has been converted into 2-methyl-7-methoxy-1,2,3,4,9,10-hexahydro-1,2-dicarboxylic-acid.

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Mitteilung « Über Steroide » (65. Mitt. siehe Helv. chim. Acta30, 1037 [1947]), sowie XX. Arbeit « Über östrogene Carbonsäuren » (XIX. siehe Exper.3, 279 [1947]).