Biological properties of alkaloids. Influence of quinolizidine alkaloids and gramine on the germination and development of powdery mildew,Erysiphe graminis f.sp.hordei

Summary The quinolizidine alkaloids sparteine, lupanine and 13-tigloyl-oxylupanine and the indole alkaloid gramine inhibited the germination of conidia ofErysiphe graminis f.sp.hordei Marchal and also the further development to appressoria. Half-maximal inhibitory concentrations of these alkaloids were 1–5 mmol/l. This result provides further evidence for a role of alkaloids as chemical defense compounds in plants.     

Host-plant pyrrolizidine alkaloids inNyctemera annulata Boisduval: Their persistence through the life-cycle and transfer to a parasite

Summary Larvae ofNyctemera annulata Boisduval ingest pyrrolizidine alkaloids fromSenecio spathulatus A. Rich. which subsequently appear in the adult months and their eggs; the acquisition of the alkaloids by a parasite of theN. annulata larvae provides a further illustration of their ability to persist in insects.Acknowledgments. We thank Dr R. Yamdagni of the Chemistry Department, University of Calgary, Canada, and Dr O. Madsen of the Organic Chemistry Department, The Technical University of Denmark, Lyngby, Denmark, for much help with the MS data collection. We are also very grateful to Dr C.C.J. Culvenor, CSIRO Animal Health Lab., Parkville, Victoria, Australia, who most generously provided us with authentic reference specimens of pyrrolizidine alkaloids.     

Pyrrolizidine alkaloids inDanaus plexippus L. andDanaus chrysippus L.

Summary Danaus plexippus L. andDanaus chrysippus L. have been found to store pyrrolizidine alkaloids obtained from adult food plants and it is suggested that the alkaloids contribute to the unpalatability of the butterflies to potential predators.Acknowledgment. We thank Dr.C. C. J. Culvenor for rearing some of the butterflies andJ. M. Smith for plant collection. The plants were identified by the national Herbarium, Melbourne.     

Betel nut residues in archaeological samples of human teeth from the Mariana Islands

Two tetrahydropyridine alkaloids, arecaidine and guvacine that are characteristic of betel nut (Areca catechu L.) have been detected in the deliberately stained labial surface of female teeth excavation on Rota, Mariana Islands. This was accomplished using selected ion monitoring techniques in conjunction with gas chromatography/electron impact-mass spectrometry. These alkaloids were not present on the buccal surface of the teeth and indicate the use of betel nut to effect the staining.     

New tamjamine class alkaloids from the marine ascidianAtapozoa sp. and its nudibranch predators. Origin of the tambjamines inAtapozoa

Summary Two new tambjamine class alkaloids, possessing ichthyodeterrent properties, have been isolated from the organic extracts of the marine ascidianAtapozoa sp. and its nudibranch predators. The structure of the new metabolites were elucidated through interpretation of their physical and spectral data and by comparison with spectral data for related compounds. Microscopic examination ofAtapozoa considering the yellow color of the tambjamines suggested thatAtapozoa is capable of the de novo biosynthesis of these metabolites.     

Effects of phthalimide on growth and alkaloid formation ofDatura metel L.

Summary When administered toDatura metel L. by foliar or root application, the new plant growth regulator phthalimide exercises a favorable effect on the vegetative growth and also stimulates the formation of tropane alkaloids.     

Biosynthesis of roquefortine and 3,12-dihydroroquefortine by the culturePenicillium farinosum

Summary A new culturePenicillium farinosum synthesizing roquefortine and 3, 12-dihydroroquefortine was found. UnlikeP. roqueforti, a known producer of these compounds, the culture under study does not synthesize clavine alkaloids. The maximal roquefortine content was observed in the late logarithmic and early stationary growth phases while the maximal 3, 12-dihydroroquefortine content was obtained in the beginning of the stationary phase.Thanks are due to Drs V. M. Adanin and M. Yu. Nefedova for mass- and IR-spectra.     

Vincanorin und Vincarein,zwei neue Alkaloide ausVinca minor L.

Summary The isolation of two new alkaloids fromVinca minor L. (Apocynaceae) is described. Vincarein, C₂₁H₂₄N₂O₄, and Vincanorin, C₁₉H₂₂N₂O, both probably belong to the group of indol alkaloids.     

Isolation of alkaloids fromAthrotaxis selaginoides

Summary A novel series of alkaloids has been obtained from the Tasmanian plantAthrotaxis selaginoides, the first to be isolated from the plant family Taxodiaceae.     

Biogenesis ofElaeocarpus andPeripentadenia alkaloids

Summary A pathway for the biogenesis of alkaloids ofElaeocarpus andPeripentadenia spp. (Elaeocarpaceae) is put forward, which involves methionine as the source of the central C3 unit in the structures of all these bases except mearsine, for which acetate units appear to furnish all the carbon atoms in its structure.     

Voacamidin und Voacristin,zwei neue Alkaloide ausVoacanga africana Stapf

Summary From the bark and the root-bark ofVoacanga africana Stapf, two new alkaloids have been isolated and characterized.     

Pyrrolizidine alkaloids in overwintering monarch butterflies (Danaus plexippus) from mexico

Summary North American populations of the monarch butterfly,Danaus plexippus, have been found to contain pyrrolizidine alkaloids and their N-oxides. Analytical methods (TLC, GC, and GC/MS) have been developed to isolate, quantitate, and structurally elucidate the alkaloids. Examples of at least two classes of pyrrolizidine alkaloids have been identified, the macrocyclic diesters, senecionine, integerrimine, and seneciphylline, and the monoesters, echinatine, intermedine, and lycopsamine.21 November 1986This work was supported by NSF (Grants BSR-81-19391 and BSR-81-19382), and a Stauffer Chemical Company fellowship. We thank David Hodapp, Mark Stelljes, and Cordula Bruenner for technical help, Dr T.P. Krick, University of Minnesota, St. Paul, Minn., USA, for assistance in GC/MS analysis of PAs, and Dr J.A. Edgar, CSIRO, Parkville, Victoria, Australia, for samples of authentic reference compounds.     

Directed biosynthesis of analogues of ergot peptide alkaloids withClaviceps purpurea

Summary Analogues of peptide ergot alkaloids can be obtained by feeding a producing culture ofClaviceps purpurea with an analogue of one of the amino acids of the peptide chain of the alkaloid.     

Displacement activity of some natural cularine alkaloids at striatal3H-SCH 23 390 and3H-raclopride binding sites

Five natural cularines isolated from the aerial parts ofSarcocapnos crassifolia (Fumariaceae) and a cularioid isolated from the bark ofGuatteria ouregou (Annonaceae) were tested for their ability to displace³H-SCH 23 390 and³H-raclopride from their striatal binding sites. Celtisine, breoganine and cularidine were able to inhibit the binding at D-1 and D-2 dopaminergic sites at nanomolar concentrations. Other alkaloids were active at micromolar concentrations. These data suggest that the presence of an oxepine system in the isoquinoline skeleton could lead to compounds which would be very active and possibly selective at dopaminergic receptor sites.     

Alkaloide ausSchizozygia caffaeoides (Boj.) Baill.

Summary FromSchizozygia caffaeoides (Boj.) Baill. (Apocynaceae), one major and ten minor new alkaloids have been isolated and characterised. Most of them are N-acylindoline derivatives, partly with the hitherto unknown 5,6-methylendioxyindoline system. Some possible correlations between these alkaloids are discussed.

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Den Herren Dres.H. Fritz, R. W. Schmid undH. Wagner und ihren Mitarbeitern danken wir für Spektren und Mikroanalysen.     

Antimitotic effect of nimbidin — A first report

Summary The antimitotic activity of nimbidin, a drug from the plantMelia azadirecta indica, was assessed by its effect on the meristematic cells of onion root tips. The effect was almost similar to those of colchicine and vinca alkaloids. Recovery trials showed that the drug induces lethal damage in a considerable proportion of treated cells and may hence have applications in cancer chemotherapy.     

3-Ethyl-2,5-dimethylpyrazine,a component of the trail pheromone of the antMessor bouvieri

Summary 3-Ethyl-2,5-dimethylpyrazine, found in the poison gland of workers, induces trail following in the Mediterranean harvester antMessor bouvieri. The poison gland contains on average 9 ng of this trail pheromone component. The alkaloids anabasine and anabaseine are also present in this gland, but induce no reaction in workers. Trail following is also induced by substances present in the Dufour gland, but the combined effect of both glands shows no synergism.     

A blocked mutant ofClaviceps purpurea accumulating chanoclavine-I-aldehyde

Summary An alkaloid-blocked mutant ofClaviceps purpurea was isolated from a strain which produces ergotoxine alkaloids. The mutant accumulates chanoclavine-I and the corresponding aldehyde. It lacks the ability to form tetracyclic ergolines.Dedicated to Prof. Dr Dr h.c. K. Mothes on the occasion of his eightieth birthday.     

Role of the δ 8 double bond of agroclavine in lysergic acid amide biosynthesis byClaviceps purpurea

Summary Agroclavine, given to actively-growing sclerotial tissue of a strain ofClaviceps purpurea which can not normally elaborate ergot alkaloids, was transformed by this tissue into lysergic acid amide with overall efficiency of approximataly 40%. By contrast, festuclavine (8, 9-dihydro-agroclavine) was not transformed, indicating specificity in the mechanism of lysergyl biosynthesis.     

Über zwei neue kristallisierte Alkaloide ausErythrophleum guineense Don

Summary In addition to cassaine, two new alkaloids have been isolated from the bark ofErythrophleum guineense Don, in crystalline form. Their empirical formulæ have been established by analysis of the free bases and of some of their crystalline salts.