Arginine-vasopressin,lysine-vasopressin,and oxytocin,C14-labeled in the glycine residue

Zusammenfassung Die Synthese von Arginin-Vasopressin, Lysin-Vasopressin und Oxytocin, deren Glycinrest eine¹⁴C-Markierung trägt, wird mit Hilfe der Festkörpermethode nachMerrifield beschrieben.

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Supported by National Institutes of Health grants No. AM-13567 and No. AM-10080 and the Atomic Energy Commission.

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Abbreviations follow the rules of the IUPAC-IUB Commission on Biochemical Nomenclature in Biochemistry5, 2485 (1966). All optically-active amino acids are ofl-configuration. The following additional abbreviations were used: N-hydroxysuccinimide ester (OSu), ethanol (EtOH), methanol (MeOH), acetic acid (AcOH),n-butanol (n-BuOH), pyridine (Pyr) and N,N-dicyclohexylcarbodiimide (DCCI). Protected peptides and hormones were visualized on thinlayer plates according to the procedure byH. Zahn andE. Rexroth, Z. analyt. Chem.148, 181 (1955). The biological activities of the hormones were measured against the U.S.P. Posterior Pituitary Reference Standard; the four-point design was used for these bioassays and standard errors were calculated according to the method ofC. I. Bliss,The Statistics of Bioassay (Academic Press, New York, N.Y. 1952).

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Acknowledgments. The authors wish to thank Mr.D. Schlesinger for some of the amino acid derivatives used, and MissM. Wahrenburg and Mrs.A. Silverman for bioassays.     

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).     

Muntjac chromosomes: A new karyotype forMuntiacus muntjak

Zusammenfassung Es gibt bemerkenswerte Unterschiede der Karyotypen vonMuntiacus muntjak vaginalis undM. m. muntjak. Jeder hat einen unterschiedlichen DNA-Wert, aber beide Werte sind niedriger als diejenigen des Menschen. Die Karyotypen-Evolution ist nicht abgeklärt, aber die Befunde zeigen, dass eine taxonomische Revision notwendig ist.

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We thank CaptainIllar Muul (U. S. Army Medical Research Unit, Kuala Lumpur) for donation of the skin biopsy ofMuntiacus muntjak muntjak, andK. Imredy, B. Bacon andM. Larson for technical assistance. Supported by NIH Grant No. HD 03298.     

Polyploidisierung von Getreidearten durch Lindan-haltige Beizmittel

Summary After treatment ofHordeum vulgare, Secale cereale, Triticum aestivum andAvena sativa with Lindan-containing seed dressings, the somatic chromosomes in the root tip mitoses were analyzed. Most of the chromosome sets in the root tip cells have been polyploidized. Using pure Lindan (-hexachlorocyclohexane), it could be shown that this insecticide is responsible for the induction of polyploidy.

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Für gewissenhafte Mithilfe bei den cytologischen Untersuchungen danken wir FrauG. Westermeier, Frl.E. Kunzmann und HerrnO. L. Koller.     

Mass spectrometry in structural and stereochemical problems spegazzinine and spegazzinidine

Zusammenfassung Auf Grund von Protonresonanz und massenspektrometrischen Messungen werden die Strukturen III und VII für die Aspidosperma-Alkaloide Spegazzinidin und Spegazzinin vorgeschlagen.

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This paper represents part III. For preceding paper seeB. Gilbert, J. Ferreira, R. J. Owellen, C. E. Swanholm, H. Budzikiewicz, L. J. Durham, andC. Djerassi, Tetrahedron Letters,1962, 59.

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This paper represents Part VI in the La Plata seriesEstudios sobre Plantas; for paper V seeT. Nakano, C. Djerassi, R. A. Corral, andO. O. Orazi, J. org. Chem.26, 1184 (1961).     

Alkaloid studies XXVI. The constitution of pyrifolidine

Zusammenfassung Die Struktur desAspidosperma-Alkaloids Pyrifolidin (I) wird durch Protonresonanz und durch Vergleich mit Aspidospermin und Aspidocarpin bewiesen. Dieses Alkaloid ist in seiner absoluten Konfiguration ein Antipode des Aspidospermins.

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Paper XXV,C. Djerassi, A. A. P. G. Archer, T. George, B. Gilbert, J. N. Shoolery, andL. F. Johnson, Exper.16, 532 (1960).

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Acknowledgement. Financial support has been provided by grant H-5048 of the National Heart Institute, National Institutes of Health (U.S. Public Health Service), and by the Conselho Nacional de Pesquisas (Brazil). The postdoctorate research fellowship ofB. Gilbert in Rio de Janeiro was financed from a grant of the Rockefeller Foundation in support of a collaborative research program between Stanford University and the Instituto de Quimica Agricola, Rio de Janeiro (Brazil).     

The role of glycine in the biosynthesis of a terpene

Zusammenfassung Mit doppelt markiertem Glycin konnte gezeigt werden, dass das Kohlenstoffatom der Methylgruppe viel besser als das Kohlenstoffatom der Karboxylgruppe in die Isoprengruppe des Ophiobolins B ausCochiobolus miyabeanus eingebaut wird. Die Radioaktivität wird in Ophiobolin B eingebaut, wenn die folgenden Verbindungen verwendet werden: [3-¹⁴C]-Serin, [¹⁴C-Methyl]-Sarcosin, [¹⁴C-Methyl]-Methionin, und [¹⁴C] Formate.

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a)Studies on Biosynthesis. Part V. for Part IV, seeM. Anchel, A. K. Bose, K. S. Khanchandani andP. T. Funke, Phytochem.9, 2135 (1970). b) Presented in part at the 3rd Natural Products Symposium, University of West Indies, Jamaica, January 1970.

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The support of this research by Stevens Institute of Technology is gratefully acknowledged. We wish to thank Dr.J. H. Davis and Prof.L. Z. Pollara for their interest and encouragement and Drs.H. Levy, P. T. Funke, M. S. Manhas, P. K. Bhattacharyya andM. Anchel for valuable discussions and help with some of the experiments. We are particularly thankful to Dr.L. Canonica for providing us with cultures ofCochiobolus miyabeanus that made our work on ophiobolin B possible.     

Detection and substitution-pattern determination of guanidines

Summary The guanidine function can be detected and its substitution pattern determined taking into account the¹H-NMR signals of the N–H and N–C–H groups. Satisfactory results were obtained with mono-to penta-substituted guanidines (as picrate salts).Part XX ofStudies on Plants; preceding part,R. A. Corral, O. O. Orazi andI. A. Benages, Tetrahedron29, 205 (1973).     

Untersuchungen über die Tumorbildung beim amphidiploiden Bastard vonNicotiana langsdorffii undNicotiana glauca

Summary The occurrence of tumours of the amphidiploid hybrid ofNicotiana glauca andN. langsdorfii can — as was found in organculture — be connected with the specific formation of callus ofN. glauca. Those factors ofN. glauca which hinder callus growth, are obviously disturbed by the hybridization withN. langsdorffii, so thatN. glauca's potency in forming callus can manifest itself uninhibitedly and thus produce tumours.

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Den Herren Prof. Dr.G. de Lattin (Zoologisches Institut der Universität des Saarlandes) und Prof. Dr.F. Anders (Genetisches Institut der Justus Liebig-Universität, Giessen) bin ich für die Förderung dieser Arbeit zu grösstem Dank verpflichtet.     

Reserpinin,ein neues Alkaloid ausRauwolfia serpentina Benth

Summary Reserpinine, a minor alkaloid ofRauwolfia serpentina Benth. accompanying Reserpine, has been isolated, and its structural formula is proposed.

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10. Mitteilung über Rauwolfia Alkaloide. — 9. Mitteilung sieheF. Bader, D. F. Dickel undE. Schlittler, Amer. Soc.76 (1954) (im Druck).     

Das Na-Transportsystem während der Erregungsprozesse am Ranvier-Knoten isolierter markhaltiger Nervenfasern

Summary (1) An attempt is made to interpret the action potential of medullated nerve fibres of the frog in terms of permeability changes to Na ions.(2) In keeping with a suggestion byHodgkin andHuxley, the following assumptions are made: (a) a carrier system is responsible for transporting Na ions across the nodal membrane; (b) in a resting fibre (high membrane potential) its transport capacity is small; (c) depolarization has a dual effect on the transport system, namely activation of carrier groups as a quick reaction and inactivation of the whole system as a slower reaction.(3) The following experimental observations are interpreted on the ground of these assumptions: threshold for depolarization, threshold for repolarization, absolute and relative refractory period, alteration of the action potential on application of a hypertonic (5%) NaCl solution.

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Eine vorläufige Mitteilung erfolgte auf der Tagung des Schweiz. Vereins für Physiologie usw. in Fribourg 1956. Helv. physiol. Acta14, C35–36 (1956).     

New dopamine receptor stimulant drug

Zusammenfassung Es wird der Nachweis erbracht, dass2(p-nitrobenzylthio)-Imidazolin (3H) · HCl (NBTI) Dopamin-Rezeptoren von Mäusen, Ratten und Affen direkt zu stimulieren vermag.

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The authors wish to thank Dr.G. Ullyot, SKF Laboratories, for gifts of NBTI and chlorpromazine; Dr.H. Corrodi, AB Hässle, Göteborg, Sweden, for the methyl ester hydrochlorides ofl-Dopa,-methyl-p-tyrosine andp-chlorophenylalanine; McNeil Laboratories, Inc., Fort Washington, Pennsylvania, for the haloperidol; and Schering Corporation, Bloomfield New Jersey, for perphenazine. Thanks are also due toA. Schindler for his skillful technical assistance.

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Final paper in press, Eur. J. Pharmac. (1972).     

Synthetic peptides related to caerulein1. Note 1

Riassunto Vengono descritte le proprietà di una serie di peptidi sintetici affini alla ceruleina e si discutono brevemente i rapporti fra attività e struttura.

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A. Anastasi, V. Erspamer andR. Endean, Experientia23, 699 (1967).

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This work was in part supported by grants from the Consiglio Nazionale delle Ricerche, Roma.     

La nature de la substance minérale de l'os

Summary In answer to objections put forward byBrandenberger andSchintz against their theory concerning the chemical nature of bone salts, the authors afford supplementary evidence about the real crystalline and chemical entity of hydrated tricalcium phosphate. According to the conditions, the precipitate contains either dicalcium phosphate or lime and this affects the nature of the product obtained by calcination.The mineral bone substance is not a hydroxylapatite because it turns either to carbonato-apatite or oxyapatite according to carbon dioxide being kept or not in the crystal lattice. The X-ray patterns of those two apatites are undoubtedly different.

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Réponse à une note deE. Brandenberger etH. R. Schinz, Exper.4, 59 (1948).     

Alkaloids of apocynaceae IV. Dregamine,a new alkaloid fromVoacanga dregei E. M.

Zusammenfassung Dregamine, ein neues Alkaloid aus der ApocynaceaeVoacanga dregei E. M. wurde isoliert und charakterisiert. Diese Verbindung stellt einen neuen Vertreter der Klasse der 2-Acyl-indole dar.

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Alkaloids of Apocynaceae III,M. Gorman, N. Neuss, J. A. Deyrup, andN. J. Cone, J. Amer. chem. Soc. (1959), in press.     

Alkaloid studies LV. 19-dehydroyohimbine,a novel alkaloid fromAspidosperma pyricollum

Zusammenfassung Ausser den bekannten Alkaloiden Ulein (I), Apparicin (II), Demethylaspidospermin (III), Yohimbin (IV) und-Yohimbin (V) wurde noch ein unbekanntes Alkaloid aus der Rinde vonAspidosperma pyricollum Muell.-Arg. isoliert, dessen Struktur als 19-Dehydroyohimbin (VI) chemisch sowie spektroskopisch bewiesen wurde.

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Paper LIV,H. Monteiro, H. Budzikiewicz, C. Djerassi, R. R. Arndt, andW. H. Baarschers, Chem. Commun.1965, 317.

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On leave from the CSIR National Chemical Laboratory, Pretoria (South Africa).     

Antibiotics from higher plants.Thalictrum rugosum. Thalrugosamine,a newBisbenzylisoquinoline alkaloid active vsMycobacterium smegmatis

Zusammenfassung Charakterisierung und Strukturaufklärung eines neuen Alkaloides, Thalrugosamin ausThalictrum rugosum.

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Acknowledgment. The authors are indebted to the Warren-Teed Division of Rohm and Haas and the NIH (No. AI 09846) for financial support,Rodger White (Warren-Teed) andFrank W. Denison (Abbott Laboratories) for biological data andRueyping Leu for expert technical assistance.     

Einbauunterschiede in den Zellschichten des Cortex nach Markierung mitd,l-Prolin-H3 bei der Maus

Summary Autoradiographic studies of the mouse brain following incorporation ofd,l-proline-H³ andl-histidine-H³ show a wide variation of the regional uptake ofd,l-proline into the cerebral nerve cells, in contrast tol-histidine. In the cerebral cortex proline is to be found only in the nerve cells of the lamina ganglionaris (V) and lamina multiformis/infima (VI/VII). Subsequent translocation of radioactivity is indicative of an axoplasmic flow of proline-labelled substances into the distal parts of the neuronal processes.

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Mit dankenswerter Unterstützung durch das Landesamt für Forschung Nordrhein-Westfalen.     

High-frequency fusion of fungal protoplasts

Zusammenfassung Es gelang, die intraspezifische Protoplastfusion vonAspergillus flavus, A. nidulans, A. niger, Penicillium frequentans undP. ramigena mit grosser H?ufigkeit zu verwirklichen. Die Fusionsh?ufigkeit wurde durch Komplementation von Mangelmutanten festgestellt.

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The authors thank Dr.M. Czakó, Dr.M. Pesti and Mr.L. Manczinger for producing and characterizing some of the required mutants, andéva Sziráki andMagdolna Romvári for skilful technical assistance.     

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).