Decarbomethoxy apocuanzine,a new indole alkaloid fromVoacanga chalotiana

Résumé On a extrait de l'écorce des racines deVoacanga chalotiana un nouvel alcalode indolique, la décarbométhoxyapocuanzine. L'étude de son spectre de RMN et la corrélation chimique avec la cuanzine (2) permettent d'attribuer à cet alcalode la structure1.

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Riassunto Dalla corteccia della radice dellaVoacanga chalotiana ê stata isolata la decarbometossi apocuanzina (1), un nuovo alcaloide indolico la cui struttura è stata definita per via spettroscopica e mediante correlazione chimica con la cuanzina (2).

     

Ceralbol,a new sesterterpenic alcohol isolated from insect wax

Summary The isolation and structural elucidation of ceralbol (1), a new sesterterpene from the insect waxCeroplastes albolineatus are reported.Contribution No. 465 from Instituto de Quimica de la Universidad Nacional Autonoma de Mexico.This work was supported by a grant from Syntex laboratories, S.A., Mexico, D.F.     

The isolation and structure of 13,18-dehydroglaucarubinone,a new antineoplastic quassinoid fromSimarouba amara

Summary An investigation of the Guyana plantSimarouba amara Aubl. (Simaroubaceae) for antineoplastic quassinoids led to isolation and structural determination of the new quassinoids 2-acetylglaucarubine (1a) and 13,18-dehydroglaucarubinone (2). The previously known 2-acetylglaucarubinone (3a) and glaucarubinone (3b) were also obtained. The new quassinoid2 was found significantly to inhibit growth of the murine lymphocytic leukemia P388.Antineoplastic agents 59. For part 58 refer to M. T. Edgar, G.R. Pettit and T.H. Smith, J. org. Chem., in preparation.Acknowledgments. We wish to thank Mr B. Septe for providing the¹³C-NMR-data. Dr Jean H. Schmidt and Miss Linda M. Lange for assistance with biological studies.—G.R. Pettit is grateful to the National Cancer Institute (performed pursuant to contract No. N01-67048 with the Division of Cancer Treatment, NCI, National Institutes of Health, Dept. of Health, Education and Welfare), Public Health Services Research grant No. CA 16049-03 from the National Cancer Institute, the Fannie E. Rippel Foundation, Talley Industries, and the Phoenix Coca-Cola Bottling Co., for partial support of this investigation.     

Presence of calcium ions as a requisite for the in vitro stimulation of TSH-release by hypothalamic TRF

Résumé L'incubation in vitro de fragments d'hypophyse (rat) dans le liquide de Krebs-Ringer sans calcium (Ca⁺⁺) inhibe l'action du facteur hypothalamique TRF (TSH-releasing factor) qui normalement stimule la sécrétion de l'hormone thyréotrope (TSH). La ré-introduction de l'ion Ca⁺⁺ (2.54 mM) rétablit la réponse (sécrétion de TSH) au facteur TRF.

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Supported by USPHS research grants Nos. AM 08290.04, HD 02577.01, training grant No. GM 956.04; also No. FR 00254 to Common Research Computer Facility, Texas Medical Center. We are pleased to acknowledge the excellent assistance of Mrs.Nancy Pace in the assays involved here.     

Antimutagenic unusual amino acids from plants

Summary Five unusual amino acids were identified as antimutagens against spontaneous mutation ofSalmonella typhimurium TA100: L-azetidine-2-carboxylic acid (1) from Liliaceae plants, -(methylenecyclopropyl)glycine (2) fromLitchi chinensis seeds, and 2-amino-4-methylhex-5-ynoic acid (3), hypoglycin A (4), and (2S, 4R)-2-amino-4-hydroxyhept-6-ynoic acid (5) fromEuphoria longana seeds. The absolute stereochemistry of5 was determined by its chiral synthesis from L-allylglycine, proving that5 is the C-4 epimer of the amino acid previously isolated from dried longan seeds.This work was partly supported by a Grant-in-Aid form the Ministry of Education, Science, and Culture, Japan, No. 57740283 (to HK).     

RandomX-chromosome inactivation in interspecific hybrids ofMeriones libycus (♂) ×Meriones shawi (♀) (Rodentia: Gerbillinae)

Résumé Des cultures obtenues à partir d'hybrides femelles entre deux espèces deMeriones à 44 chromosomes et différant par l'acrocentrie (M. shawi) ou la métacentrie (M. libycus) de l'X ont permis l'étude de clones cellulaires. C'est alors tantôt l'X métacentrique, tantôt l'X acrocentrique qui se révèle inactivé («latereplicating»). Bien que la proportion 1/1, significative d'une inactivation due uniquement au hasard, n'ait pas été rigoureusement observée, ces résultats sont nettement en faveur de l'hypothèse deLyon.

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Supported by Project No. 417 from the U.S. Children's Bureau and National Science Foundation (Grant No. GB 5676X).     

A lytic factor associated with brucellaphage causing ‘lysis-from-without’

Résumé Des bactériophages de Brucella se sont montrés capables de provoquer une lyse extra-cellulaire, en cultures liquides deB. abortus, en présence de glycine et d'acide éthylène-diamine-tétraacétique. Des traitements au sérum anti-bactériophage, aux enzymes protéolytiques, ou la centrifugation différentielle dans le chlorure de césium n'ont pu séparer l'activité lytique de la particule infectieuse elle-même.

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This study was supported by Public Health Service research grant No. AI 06161 from the National Institute of Allergy and Infectious Diseases and by a World Health Organization research grant. The authors are grateful to Dr.D. Pratt for helpful suggestions and assistance with the density gradient centrifugation.     

Isolation of 2-S-cysteinyldopa and 2,5-S,S-dicysteinyldopa from the urine of patients with melanoma

Summary Urine from patients with melanoma metastases is shown to contain, in addition to the previously described 5-S-cysteinyldopa (I), 2 closely related metabolites which have been isolated and identified as 2-S-cysteinyldopa (II) and 2, 5-S, S-dicysteinyldopa (III).Supported by grants from the Swedish Cancer Society (No. 626-B76-05XB and 869-B75-01P), the Swedish Medical Research Council (No. B76-04X-00056-12), and the Walter, Ellen and Lennart Hesselman Foundation for Scientific Research. Professor Prota was a visiting scientist of the Swedish Cancer Society (No. 626-B75-04V). The authors are indebted to Dr Soshuke Ito for samples of 2-S-cysteinyldopa and 2,5-S,S-dicysteinyldopa.     

Chromosome preparations of opossum leucocytes

Résumé C'est la première fois que l'on décrit une technique pour la préparation des chromosomes de leucocytes d'opossum. Cette technique a l'avantage d'être simple et elle permet en outre de préciser les détails morphologiques de certains chromosomes de l'opossum. Par exemple, les chromosomesX de la femelle de l'opossum laineux (Caluromys derbianus) sont aisément identifiés comme étant la plus petite paire submétacentrique du complément.

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Supported in part by grants from U. S. Public Health Service (No. HD 00033-02) and Baylor University College of Medicine General Research Grant (No. P-66-6) and a grant from the James Picker Foundation.     

Transformation of progesterone byCaldariella acidophila,an extreme thermophilic bacterium

Summary Caldariella Acidophila, a thermophilic bacterium, converts porgesterone (1) to pregn-4-en-3,6,20-trione (2), 5a-pregnan-3, 6, 20-trione (3), pregn-4-en-20a-ol-3-one (4), pregn-4-6-ol-3, 20-dione (5) and pregn-4-en-6a-ol-3, 20-dione (6). Different patterns of these metabolites were obtained by modifying the incubation conditions and using differently treated biocatalysis.     

1,1-Dimethyl-5,6-dihydroxyindolinium chloride from a deep water marine sponge,Dercitus sp.

Summary 1,1-Dimethyl-5,6-dihydroxyindolinium chloride (1a)was identified from a deep water sample of the marine sponge,Dercitus sp., and its structure was elucidated by spectral methods.Acknowledgments. This is Harbor Branch Oceanographic Institution, Inc., SeaPharm Project Contribution No. 612. We thank Drs K. Rinehart, Jr, S. Pomponi and E. Armstrong for sponge collection.     

Competition between strains ofDrosophila willistoni andD. pseudoobscura

Resumen El resultado de la competencia entreDrosophila willistoni yD. pseudoobscura depende de la constitución genética de las estirpes que compiten y de la temperatura. A 20 °C las dos especies coexisten, lo cual indica que el principio de exclusión competitiva no es universalmente válido.

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Supported by NSF grant No. GB-1256 (International Biological Program), and PHS Career Development Award No. K3GM37265.     

Structure and stereochemistry of attenuol,a new lignan fromKnema attenuata (Wall.) Warb.

Summary A new lignan attenuol has been isolated from the bark ofKnema attenuata (Wall.) Warb. Its structure (I) is deduced on the basis of analytical and spectral data. The compound has been assigned the absolute configuration as 2S,3R-dimethyl-1S-(p-hydroxyphenyl)-6,7-methylenedioxytetralin (III).Contribution No. 487 from the Ciba-Geigy Research Centre.Acknowledgments. We thank Dr H. Fuhrer and Dr P. Moser of Ciba-Geigy Ltd. Basle for the NMR spectral data and ORD determinations and Dr S. Selvavinayakam and his colleagues for the analytical results.     

Zonaroic acid from the brown seaweedDictyopteris undulata (=zonarioides)

Summary A sesquiterpene-substituted 4-hydroxybenzoic acid, zonaroic acid (5), is described from the brown seaweedDictyopteris undulata (=zonarioides). The absolute stereochemistry in the zonarol (1)-chromazonarol (2) and zonaroic acid (5) series has also been defined. The occurrence of5 along with zonarol (1), the corresponding sesquiterpene-substituted hydroquinone, suggests that 4-hydroxybenzoic acid is the ring precursor as in ubiquinone biogenesis.     

Structure de la sarpédobiline,pigment biliaire de Lépidoptère

Summary On the basis of NMR studies, mass spectrometry, chemical reactions and correlations with phorcabilin1, the structure2 is proposed for sarpedobilin, a butterfly blue bile pigment first isolated fromPapilio graphium sarpedon. This structure represents a new natural heterocyclic system.

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Nous remercions les Professeurs E. Lederer et J. Bergerard pour leur intérêt et le CEA Saclay pour une subvention ayant facilité l'achat des molécules isotopiques. Nous remercions aussi le D^r H. J. Veith, Darmstadt (République fédérale d'Allemagne), pour les mesures en spectrométrie de masse par désorption de champ.     

Epidermal sensitivity to hypoxia in the lugworm

Summary Physiological and anatomical data support the idea that in the caudal epidermis of the lugworm,Arenicola marina (L.), there are chemoreceptors detecting variations of oxygen partial pressure in the ambient water.This research was partly supported by a C.N.R.S. grant, AI No. 582 085. We thank Dr P. Dejours and Dr J. Taxi for helpful comments and discussion, Mrs S. Dejours for editing the English of this paper, M.F. Baucher, A. Dorme, F. Kleinbauer, the staff of the Station Biologique de Roscoff and the Service de Microscopie Electronique, C.N.R.S., boulevard Raspail, Paris, for technical assistance.     

Annonacin,a novel,biologically active polyketide fromAnnona densicoma

Summary A new linear polyketide, Annonacin (I), has been isolated from active extracts of the stembark ofAnnona densicoma Mart. Annonacin (I) is highly cytotoxic and is active in an assay designed to detect antimitotic agents. The structure of (I) was determined by analysis of spectroscopic data.25 September 1986     

Tartessol,a new diterpene fromSideritis grandiflora Salzm

Résumé Un nouveau diterpène tartessol (1) a été isolé de laSideritis grandiflora Salzm. (Labiées) est sa structure est proposée comme étantent-14-acétoxy-15-beyèren-18-ol.

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Part XVIII in the series Studies on diterpenes from genusSideritis. For Part XVII seeT. G. de Quesada, B. Rodríguez andS. Valverde,Phytochemistry, in press.

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The authors thank Dr.J. Borja, Botany Department, Faculty of Pharmacy, Madrid, for the collection and botanical classification of the plant material and Dr.Juana Bellanato, Institute of Optics, C.S.I.C., Madrid, for the high resolution IR spectra.     

Diketopiperazines containing L-proline from Streptomyces lavendulae and their stereochemistry in solution

Summary l-Valyl-l-proline (I),l-leucyl-l-proline (II),l-phenylalanyl-l-proline (III) andl-isoleucyl-l-proline (IV) anhydrides were isolated from the cultures ofStreptomyces lavendulae No. 314 and, on the basis of¹³C-NMR and CD spectra, their stereochemistry in solution is described.Acknowledgments. The authors would like to express their sincere thanks to Prof. H. Ogura, Kitasato University, for kind supply of the authenticl-valyl-l-proline anhydride and to Mr. A. Takakuwa, JASCO, for measuring the CD curves with J-40 automatic recording spectropolarimeter.     

Seasonal variations in testicular monoamine oxidase in the house sparrow (Passer domesticus) and uinta ground squirrels (Spermophilus armatus)

Résumé Des moinaux familiers (Passer domesticus) et des écureuils (Spermophilus armatus) des montagnes Uinta ont été capturés à différentes époques de l'année et l'activité de laMao a été mesurée dans leurs testicules. Chez les deux espèces l'activité de la MAO était la plus grande lorsque le poids des testicules était le plus élevé et la plus basse avant et après la saison du rut. Chez le moineau, l'augmentation de l'activité de MAO a précédé le développement des testicules.

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We thank the Atomic Energy Commission Grant No. At(11-1)-1602, Utah State University research project No. U-300 and Ecol. Grant No. 19 for their support of this research.R. L. Urry, present address: Division of Urology, University of Rochester, School of Medicine and Dentistry, Rochester, New York, 14642.J. L. Frehn was on sabbatical leave from his present position in the Department of Biology, Illinois State University, Normal, Illinois, 61761. We thankPhyllis Tayler for her technical help in this investigation.