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1Author    M. Wink, T. Hartmann, L. WitteRequires cookie*
 Title    Enzymatic Synthesis of Quinolizidine Alkaloids in Lupin Chloroplasts  
 Abstract    The enzymatic sequence responsible for the biosynthesis o f tetracyclic quinolizidine alkaloids could be localized in chloroplasts isolated from Lupinus polyphyllus leaves and L. albus seedlings by differential centrifugation. U pon feeding of cadaverine to isolated chloroplasts lupanine is produced as the m ain alkaloid. Chloroplasts treated with digitonine produce sparteine and 17-oxosparteine instead o f lupanine, thus indicating that the biosynthetic sequence is interrupted. The intermediacy of 17-oxosparteine could be confirmed since exogeneous 17-oxosparteine is con­ verted into lupanine by intact chloroplasts. 17-Oxosparteine synthase (see Z. N aturforsch. 34 c, 704 1979) the key enzyme of quinolizidine alkaloid biosynthesis could be solubilized from chloro­ plasts treated with detergents or osmotic shock. 
  Reference    Z. Naturforsch. 35c, 93—9 (1980); received Septem ber 26 1979 
  Published    1980 
  Keywords    Quinolizidine Alkaloids, Enzymatic Synthesis, Isolated Chloroplasts, Lupinus polyphyllus 
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 TEI-XML for    default:Reihe_C/35/ZNC-1980-35c-0093.pdf 
 Identifier    ZNC-1980-35c-0093 
 Volume    35 
2Author    M. Wink, L. WitteRequires cookie*
 Title    Quinolizidine Alkaloids as Nitrogen Source for Lupin Seedlings and Cell Cultures  
 Abstract    The alkaloid patterns during germination and seedling development of Lupinus polyphyllus, L. angustifolius, L. albus, L. pubescens, Cytisus scoparius, Baptisia australis, Spartium junceum and Laburnum anagyroides were studied by capillary glc and EI-MS and CI-MS. The alkaloid contents were relatively high in the seeds and decreased by 20—100% during germination and the early developmental stages. The plants with fully developed leaves were able to synthesize new alkaloids. The decrease of alkaloid concentrations during germination was interpreted in terms of alkaloid turnover and use of the alkaloidal nitrogen for seedling development. The ability of plants to rely on the alkaloidal nitrogen as a nitrogen source could also be shown in lupin cell cultures which could survive and even grow on media which contained sparteine as the sole nitrogen source. 
  Reference    Z. Naturforsch. 40c, 767—775 (1985); received August 19/September 4 1985 
  Published    1985 
  Keywords    Alkaloid Turnover, Quinolizidine Alkaloids, Lupinus, Germination, Nitrogen Source 
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 TEI-XML for    default:Reihe_C/40/ZNC-1985-40c-0767.pdf 
 Identifier    ZNC-1985-40c-0767 
 Volume    40 
3Author    Michael Wink, Thomas Hartmann, Ludger Witte, Joachim RheinheimerRequires cookie*
 Title    Interrelationship between Quinolizidine Alkaloid Producing Legumes and Infesting Insects: Exploitation of the Alkaloid- Containing Phloem Sap of Cytisus scoparius by the Broom Aphid Aphis cytisorum  
 Abstract    Aphids (Aphis cytisorum) which infest broom plants (Cytisus scoparius) accumulate up to 500 ng alkaloid/g fr. wt. The alkaloids, which are similar to those of the plants, consist of 17-oxo-sparteine, sparteine, 12,13-dehydrosparteine, and lupanine. Infested plants contain >,50% less alkaloids than aphid-free plants. In Lupinus aphid resistance which is due to their high alkaloid content is more expressed: Whereas bitter varieties are free from aphids, only the sweet alkaloid-free plants are susceptible to aphid infestation. The accumulation of alkaloids in aphids indicates that the quinolizidine alkaloids are translocated via the phloem in legume plants. This assumption is supported by direct evidence: analysis of phloem sap from Lupinus contains up to 5 mg alkaloid whereas xylem sap is virtually free of alkaloids. The interrelationship between quinolizidine alkaloids and hervivores is discussed. 
  Reference    Z. Naturforsch. 37c, 1081—1086 (1982); received August 31 1982 
  Published    1982 
  Keywords    Quinolizidine Alkaloids, Aphids, Insect Resistance, Phloem Transport, Cytisus scoparius 
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 TEI-XML for    default:Reihe_C/37/ZNC-1982-37c-1081.pdf 
 Identifier    ZNC-1982-37c-1081 
 Volume    37 
4Author    M. WinkRequires cookie*
 Title    Chemical Defense of Leguminosae. Are Quinolizidine Alkaloids Part of the Antimicrobial Defense System of Lupins?  
 Abstract    Growth o f 6 bacteria (Serratia marcescens, Bacillus megaterium , Bacillus subtilis, Streptococcus viridis, Micrococcus luteus, and M ycobacterium ph lei) was inhibited by 50% if the growth m edium contained sparteine at concentrations between 0 .5 -1 0 m M . Total growth inhibition, which was bacteriostatic in nature, was achieved at 20 m M . The growth o f 6 phytopathogenic fungi was also affected: at a sparteine concentration o f 15 m M the growth o f Alternaria porri was reduced by 40% as compared to the untreated control. R espective values were 18% inhibition for Piricularia oryzae, 33% for H elminthosporium carbonum, 15% for R hizoctonia solani, 5% for Fusarium oxysporum, and 42% for Asperquillus oryzae. Since the concentrations o f quinolizidine alkaloids range from 1 -2 0 0 m M (roots, leaves, or stems) or 1 0 -2 0 0 m m ol/k g (seeds) in Legum inosae, it is discussed whether quinolizidine alkaloids are involved in the antim icrobial defense o f lupins, in addition to their potential role as allelopathic or herbivore repellent defense com pounds. 
  Reference    Z. Naturforsch. 39c, 548 (1984); received January 23 1984 
  Published    1984 
  Keywords    Quinolizidine Alkaloids, Growth Inhibition, Bacteria, Fungi, Antim icrobial Defense 
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 TEI-XML for    default:Reihe_C/39/ZNC-1984-39c-0548.pdf 
 Identifier    ZNC-1984-39c-0548 
 Volume    39 
5Author    Roland Greinwald, Gabriele Lurz, Ludger Witte, Franz-Christian CzyganRequires cookie*
 Title    A Survey of Alkaloids in Spartium junceum L. (Genisteae-Fabaceae)  
 Abstract    The alkaloid pattern of Spartium junceum has been investigated. Cytisine, N-methylcytisine, anagyrine, rhombifoline and epi-baptifoline occur as major compounds in most of the samples studied. Considerable quantitative differences were found between various parts of the plant. The alkaloid content changed strongly dependent on the seasons. Only a limited variation can be ascribed to geographical origin. 
  Reference    Z. Naturforsch. 45c, 1085—1089 (1990); received February 15/September 26 1990 
  Published    1990 
  Keywords    Spartium junceum, Fabaceae, Genisteae, Quinolizidine Alkaloids, Gas Chromatography/Mass Spectrometry, Chemotaxonomy 
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 TEI-XML for    default:Reihe_C/45/ZNC-1990-45c-1085.pdf 
 Identifier    ZNC-1990-45c-1085 
 Volume    45 
6Author    G.Erhard Veena, R. Oland Greinwald3, PalomaC. Antób, LudgerW. Ittec, F.-C Czygan3Requires cookie*
 Title    Alkaloids of Adenocarpus hispanicus (Lam.) DC Varieties  
 Abstract    A lkaloid extracts from different organs o f Adenocarpus hispanicus ssp. hispanicus and A de­ nocarpus hispanicus ssp. gredensis were analyzed by capillary GC. Twenty-four com pounds could be identified by the high sensitive method o f GLC-M S: the pyrrolizidine alkaloids de-corticasine, N -acetylnorloline and N-butyrylnorloline, the bipiperidyl alkaloid amm oden-drine, the phenylethylamine tyramine and 19 quinolizidine alkaloids. In contrast to Adenocar­ pus com plicatus, Adenocarpus foliolosus and Adenocarpus viscosus the alkaloid pattern o f A de­ nocarpus hispanicus is characterized by the occurrence o f quinolizidine alkaloids with sparteine predominating in the leaves and numerous dehydroderivatives o f sparteine. Remarkable is the total absence o f adenocarpine which was described as a main com pound o f the three former species. Our results strongly support the opinion that the genus Adenocarpus should be divided into two phytochem ical groups. 
  Reference    Z. Naturforsch. 47c, 341 (1992); received December 12 1991/February 18 1992 
  Published    1992 
  Keywords    Adenocarpus hispanicus, Genisteae, Quinolizidine Alkaloids, Bipiperidyl Alkaloids, Pyrrolizidine Alkaloids 
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 TEI-XML for    default:Reihe_C/47/ZNC-1992-47c-0341.pdf 
 Identifier    ZNC-1992-47c-0341 
 Volume    47 
7Author    Planchuelo-R Avelo3b, L. Udger, W. Ittec, M. Ichael, W. Ink3Requires cookie*
 Title    Quinolizidine Alkaloid Profiles of South American Lupins: Lupinus linearis and the Lupinus gibertianus Complex  
 Abstract    The alkaloid composition of leaves of Lupinus linearis D esr. (3 ecotypes) and L. gibertia­ nus Smith (6 ecotypes) from A rgentina and Brazil were studied by capillary gas-liquid chrom atography and GLC-mass spectrom etry (EI-M S). Both species are closely related according to morphological criteria. This view is supported by the alkaloid profiles which are very similar and share a series of new and uncom m on alkaloids. M ain alkaloids are lupanine, 13-hydroxylupanine, esters of 13-hydroxylupanine (e.g. 13-angeloyloxylupanine, 13-tigloyloxylupanine, 13-benzoyloxylupanine, 13-ci5/frans-cinnamoyloxylupanine). M inor alkaloids are: sparteine, 1 1 ,1 2 -dehydrosparteine, am m odendrine, tetrahydrorhom bifoline, angustifoline, a-isolupanine, 5,6-dehydrolupanine, 11,12-dehydrolupanine, N-formylangusti-foline, 13-ds-cinnamoyloxymultiflorine. New m inor alkaloids which have been tentatively identified by GLC-MS are 13-hydroxy-17-oxolupanine and corresponding esters (13-an-geloyloxy-17-oxolupanine, 13-tigloyloxy-17-oxolupanine, 13-benzoyloxy-17-oxolupanine, 13-cis-cinnamoyloxy-17-oxolupanine, and 13-fran.s--cinnamoyloxy-17-oxolupanine). 
  Reference    Z. Naturforsch. 48c, 702—706 (1993); received June 281993 
  Published    1993 
  Keywords    Lupinus, Leguminosae, Quinolizidine Alkaloids, Chem otaxonom y, A lkaloid Profile 
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 TEI-XML for    default:Reihe_C/48/ZNC-1993-48c-0702.pdf 
 Identifier    ZNC-1993-48c-0702 
 Volume    48 
8Author    Michael WinkRequires cookie*
 Title    Chemical Defense of Lupins. Mollusc-Repellent Properties of Quinolizidine Alkaloids  
 Abstract    Polyphagous molluscs such as H elix pom atia and Arion rufus generally do not feed on plants containing alkaloids. O f 19 species tested 10 species were totally avoided, the other 9 species were less attacked than Lactuca sativa, which was readily taken. Plants containing quinolizidine alkaloids were studied in detail. Those species with the a-pyridone alkaloids cytisine and N-methylcytisine were avoided to a higher extent than plants with lupanine as the major alkaloid. Since the repellency observed could be due to other natural products present in the plants besides the alkaloids, the feeding response o f H elix pom atia was tested on artificial diets containing quinolizidine alkaloids in various concentrations as the only variable. If the snails had the choice they clearly preferred alkaloid-free food or a diet with only low alkaloid concen­ trations. Half-maximal repellency o f cytisine is less than 2 m M , o f sparteine 1 -5 m M , and o f lupanine 1 -8 mM. Since the in vivo concentrations o f sparteine, cytisine, and lupanine are equal to or higher than the inhibitory concentrations required it is concluded that quinolizidine alkaloids constitute a potential antimolluscan principle o f legum es. 
  Reference    Z. Naturforsch. 39c, 553 (1984); received March 22 1984 
  Published    1984 
  Keywords    Quinolizidine Alkaloids, M ollusc Repellency, C oevolution, Plant-H erbivore Interaction, Snails, Chemical Defense 
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 TEI-XML for    default:Reihe_C/39/ZNC-1984-39c-0553.pdf 
 Identifier    ZNC-1984-39c-0553 
 Volume    39 
9Author    Kaleab Asres, Bandreas Tei, Bmichael WinkRequires cookie*
 Title    Quinolizidine Alkaloids of Platycelphium vöense (Engl.) Wild (Leguminosae)  
 Abstract    13 Alkaloids were identified in leaves and twigs of Platycelphium vöense (a monotypic genus in the tribe Sophoreae) by capillary G LC and GLC-MS. Cytisine, N-methylcytisine, anagyrine and 5,6-dehydrolupanine fig­ ured as major and N-formylcytisine, N-acetylcytisine, baptifoline, thermopsine, isolupanine, and rhombifoline as minor alkaloids in both leaves and twigs. Lupanine occurred in considerable amount in the leaves and as a minor component in the twigs. The rare alkaloid, 6ß-hydroxylupanine, was detected only in the leaves while N-ethylcytisine was shown to be a minor constituent of the twigs only. 
  Reference    Z. Naturforsch. 52c, 129—131 (1997); received October 17/November 11 1996 
  Published    1997 
  Keywords    Platycelphium vöense, Leguminosae, Quinolizidine Alkaloids, Capillary Gas Chromatography (G L C ), GLC-Mass Spectrometry 
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 TEI-XML for    default:Reihe_C/52/ZNC-1997-52c-0129_n.pdf 
 Identifier    ZNC-1997-52c-0129_n 
 Volume    52