Completion of the natural groups of ergot alkaloids: Syntheses and pharmacological profiles ofβ-ergosine andβ-ergoptine

Summary The syntheses and pharmacological potencies of -ergosine and -ergoptine, the missing links in the natural groups of ergot peptide alkaloids are described.86th communication on ergot alkaloids.     

Incorporation of α-aminobutyric acid into ergostine byClaviceps purpurea

Summary Claviceps purpurea 275 F.I. fed with -aminobutyric acid produces ergostine with the corresponding -hydroxy--aminoacid undiluted by endogenous aminoacid. Almost all the -aminobutyric acid not incorporated into the ergostine remains unchanged in the medium. The significance of these results in the biosynthesis of ergot alkaloids is discussed.     

2-Br-α-Ergokryptin: Beeinflussung von Fertilität und Laktation bei der Ratte

Summary The inhibitory actions of -ergocryptin on fertility and lactation in the rat are altered differentially in the 2-bromo derivative of this ergot alcaloid. It is therefore unlikely that the fertility inhibiting and the lactation inhibiting effects of 2-bromo--ergocryptin are governed by a single mechanism of action.     

Effect of dihydroergocristine infusion on tolbutamide-induced insulin secretion in man

Summary The insulinemic response to 1 g of tolbutamide i.v. is greatly enhanced (+145%) after a 60-min infusion of the -lytic dihydrogenated ergot alkaloid, dihydroergocristine (83.3 m/min, corresponding to a total dose of 5 mg) in 7 healthy subjects. No differences are observed in the glycemic responses.Acknowledgment. The authors are grateful to Mr Franco Della Sala, M.D., for his skillful technical assistance.     

An insect growth inhibitor fromTrichilia roka (Meliaceae)

Summary A limonoid sendanin has been identified by spectroscopic data in the fresh fruit of a tropical tree,Trichilia roka (Meliaceae). It has an insect growth inhibitory activity against 4 important cotton insect pests. The absolute configuration of sendanin has been proposed based on CD-data.Insects were kindly supplied by the agenices of the USDA in Tifton, Ga, Phoenix, Az, and Brownsville, Tx. Authentic sample of sendanin was kindly provided by Prof. M. Ochi. The authors thank J. C. James for the CD measurement.     

Synthese und Eigenschaften von Bromocriptin

Summary The bromination of -ergokryptine, a genuine ergot alkaloid of the peptide type, in position 2 of the indol nucleus to 2-bromo--ergokryptine is described. Its transformation to the methanesulfonate led to the prolactin inhibitor bromocriptine-methanesulfonate, Parlodel^®.

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85. Mitteilung über Mutterkornalkaloide.

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Anfragen bitte an diesen Autor richten.     

Scalarolbutenolide,a new sesterterpenoid from the marine spongeSpongia nitens

Summary A new sesterterpenoid, scalarolbutenolide (5), has been isolated from the marine spongeSpongia nitens; its structure, including the absolute stereochemistry, has been established by chemical and spectroscopic studies.This work is a part of the Progetto Finalizzato per l'Oceanografia e i Fondi Marini, C.N.R., Roma.We are indebted to A. Crispino, C. Di Pinto, G. Scognamiglio and R. Turco for their technical assistance.     

12S-Hydroxybromosphaerol,a new bromoditerpene from the red algaSphaerococcus coronopifolius

Summary A minor bromoditerpene, 12S-hydroxybromosphaerol has been isolated from the red algaSphaerococcus coronopifolius, and its structure has been established on the basis of chemical and spectroscopic evidence.This work was carried out under the auspices of Progetto Finalizzato per l'Oceanografia e i Fondi Marini, CNR, Rome.     

Circadian rhythm ofβ-glucuronidase

Summary The circadian rhythm of rat liver-glucuronidase has been studied in animals kept under highly standardized laboratory condition. A clear 24 h rhythm has been observed for this enzyme with a peak activity at 01.00 h and a trough at 13.00 h.The work was carried out in Institut für Anatomie I, Medical School, Hannover (Federal Republic of Germany). Supported by grants from Deutsche Forschungsgemeinschaft, Sonderforschungsbereich 146 and VW Stiftung, Hannover A2 11.2000.     

Sur la présence deβ-alanine dans les tissus des plantes supérieures

Summary -alanine has always been found in peptide hydrolysates of various higher plants, but never in protein hydrolysates. An assumption that the-alanine so found is a constituent of coenzyme A has been suggested.     

A new tryptophan derived alkaloid fromEvodia rutaecarpa (Juss.) Benth. et Hook

Summary The first tryptophan-derived indolopyridoquinazoline alkaloid has been isolated from the fruits ofEvodia rutaecarpa (Jussieu) Bentham et Hook. Its structure is deduced on the basis of spectral data and enantioselective synthesis. The compound has been assigned the absolute configuration (7S,13bS)-7-carboxy-8,13,13b,14-tetrahydro-14-methylindolo[2,33,4]pyrido[2,1-b]quinazolin-5(7H)-one.     

Minor pyrroloterpenoids from the marine spongeCacospongia mollior

Summary 2 pyrroloterpenes, molliorin-d and-e, have been isolated from the spongeCacospongia mollior and their structures have been established by chemical and spectroscopic methods.This work has been carried out in the frame of the Progetto Finalizzato per l'Oceanografia e i Fondi Marini, C.N.R., Roma.     

The metabolism of the male antifertility agent 1-amino-3-chloropropan-2-ol in the rat

Summary The male antifertility agent 1-amino-3-chloropropan-2-ol (ACP,I) has been shown to be metabolized to-chlorohydrin (III) and metabolites of-chlorohydrin. This accounts for the similar antifertility and renal toxicity effects of both compounds.     

The identification of ecdysterone (20-hydroxyecdysone) in 3 species of molluscs (Gastropoda: Pulmonata)

Summary Ecdysterone has been identified in the schistosomiasis vectorBiomphalaria glabrata Say and inHelix aspersa Müller as well as inLymmaea stagnalis L. by chromatography, bioassay, radioimmunoassay, derivatization and by mass spectroscopy. Analysis of the food, faeces and hepatopancreas suggest that the sterol is derived from the diet. The probable function of ecdysterone in relation to calcification of the shell is discussed in this paper.We wish to thank Professor P. Karlson and Dr J. Koolman (Phillips University, Marburg-Lahn, FRG) for providing facilities for RIA. The initial study was begun at the University of Sussex and continued at the Courtauld Institute of Biochemistry, Middlesex Hospital Medical School, London, while D.L.W. was supported by the Ministry of Overseas Development. London and the Medical Research Council of Great Britain (grant G974/525/T). We thank Mr P. Mellon for the mass spectrum and Dr G.B. Russell for his interest in the earlier part of this study. We also thank Professor E. Scherer and Dr Q. Uwe (University of Essen, FRG) for their help in the irradiation ofL. stagnalis.Gauss Str. 82, D-4630 Bochum 5 (Federal Republic of Germany). Research results usingL. stagnalis were submitted for the Philips Europa Wettbewerb für junge Forscher und Erfinder (1979) in a thesis entitled Zur Frage der Existenz von Steroiden und Gonadoliberin bei der Grossen Schlammschnecke (Lymmaea stagnalis L.): ein Beitrag zur Evolution der Insekten- und Wirbeltierhormone.     

BlaB,a protein involved in the regulation of <Emphasis Type="Italic">Streptomyces cacaoi</Emphasis> β-lactamases,is a penicillin-binding protein

Streptomyces cacaoi -lactamase genes are controlled by two regulators named blaA and blaB. Whereas BlaA has been identified as a LysR-type activator, the function of BlaB is still unknown. Its primary structure is similar to that of the serine penicillin-recognizing enzymes (PREs). Indeed, the SXXK and KTG motifs are perfectly conserved in BlaB, whereas the common SXN element found in PREs is replaced by a SDG motif. Site-directed mutations were introduced in these motifs and they all disturb -lactamase regulation. A water-soluble form of BlaB was also overexpressed in the Streptomyces lividans TK24 cytoplasm and purified. To elucidate the activity of BlaB, several compounds recognized by PREs were tested. BlaB could be acylated by some of them, and it can therefore be considered as a penicillin-binding protein. BlaB is devoid of -lactamase, D-aminopeptidase, DD-carboxypeptidase or thiolesterase activity.Received 13 January 2003; received after revision 9 April 2003; accepted 11 April 2003     

The partitioning ofΔ 1-tetrahydrocannabinol into erythrocyte membranes in vivo and its effect on membrane fluidity1into erythrocyte membranes in vivo and its effect on membrane fluidity1

Summary ¹-Tetrahydrocannabinol ( ¹-THC) has been quantified directly in erythrocyte membranes from drug-treated mice using gas chromatography/mass spectrometry. Concentrations of approximately 6 ng ¹-THC/mg membrane protein (10^–5 M) were found when effects of the drug on behavior were prevalent. At these concentrations the drug produced a decrease in membrane order as measured by ESR.This work was supported by grants from the Medical Research Council, the Wellcome Trust and the E. P. Abraham Cephalosporin Trust     

Isolement et identification du 5β-prégnane 11β, 17α, 21-triol 3, 20-dione (Dihydrocortisol) dans l'urine humaine

Summary 5-pregnane 11, 17, 21-triol 3, 20-dione (dihydrocortisol) has been isolated and identified in the urine of patients with feminizing adrenal cortical cancer. This steroid showed the same Rf as synthetic dihydrocortisol in six different chromatographic systems. After acetylation, its Rf was the same as that of 21 monoacetate of dihydrocortisol. After bismuthic or chromic oxydation, it had the same chromatographic Rf as 5-androstane 11-ol 3, 17-dione and 5-androstane 3, 11, 17-trione respectively. After chromic oxydation of its acetate, the Rf was the same as that of 21 monoacetate of cortisone.     

Scarites buparius,a caraboid beetle with an X1X2Y sex-chromosomes system

Summary Scarites buparius has 2n=37 and n=17+X₁X₂Y. This multiple sex-chromosomes system seems to be the result of a reciprocal translocation between the primitive X-chromosome and an autosome. This is the first caraboid beetle, exceptingCicindela spp., that has multiple sex-chromosomes.This work has been supported by a grant of the Comisión Asesora de Investigación Científica y Técnica, No. 1.552.     

The secret of truffles: A steroidal pheromone?

Summary The steroid 5-androst-16-en-3-ol has a pronounced musk-like scent. It is a major constituent of the pheromone of the boar. It occurs also in axillary sweat of men but is devoid of androgenic activity. The presence of this steroid has been demonstrated in truffles (Tuber melanosporum) both by radioimmunoassay and by gas chromatography-mass spectrometry in quantities of 40–60 ng/g fresh material. This offers an explanation for the ability of pigs to detect truffles growing as deep as 1 m under ground.