| | 1 | Author
| M. Wink, D. Schneider, L. Witte | Requires cookie* | | | Title
| Biosynthesis of Pyrrolidine Alkaloid-Derived Pheromones in the Arctiid Moth, Creatonotos transiens: Stereochemical Conversion of Heliotrine  | | | | Abstract
| In larvae and later developmental stages of Creatonotos transiens, which had been reared on the pyrrolizidine alkaloid 75-heliotrine, a new major metabolite was detected by capillary GLC. The structure of this metabolite was determined by GLC-MS (EI, CI-MS) and l3 C NMR to be 1R-heliotrine and 7/?-heliotrine-N-oxide. 7/?-Heliotrine is likely to be the direct precursor for the pheromone R(—)-hydroxydanaidal. | | | |
Reference
| Z. Naturforsch. 43c, 737—741 (1988); received May 4/June 13 1988 | | | |
Published
| 1988 | | | |
Keywords
| Creatonotos, Pyrrolizidine Alkaloids, Heliotrine, Male Pheromone, Hydroxydanaidal | | | |
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| default:Reihe_C/43/ZNC-1988-43c-0737.pdf | | | | Identifier
| ZNC-1988-43c-0737 | | | | Volume
| 43 | |
| 2 | Author
| G.Erhard Veena, R. Oland Greinwald3, PalomaC. Antób, LudgerW. Ittec, F.-C Czygan3 | Requires 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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| default:Reihe_C/47/ZNC-1992-47c-0341.pdf | | | | Identifier
| ZNC-1992-47c-0341 | | | | Volume
| 47 | |
| 3 | Author
| S. Schulz, W. Francke, J. Edgar, D. Schneider | Requires cookie* | | | Title
| Volatile Compounds from Androconial Organs of Danaine and Ithomiine Butterflies | | | | Abstract
| Pyrrolizidine alkaloid derivatives are present in the androconial (male scent) organs of Prittwit-zia hymenaea, Mechanitis isthmia veritabilis, Tithorea harmónia fúria (Lep., Ithomiinae), Amauris echeria and Euploea sylvester (Lep., Danainae). While the ithomiines contain the new pyrrolizidine alkaloid derivative methyl hydroxydanaidoate, the danaines contain the known derivatives danaidone and hydroxydanaidal. In addition, 2,2,6-trimethyl-2-cyclohexen-l,4-dione (oxoisophorone) and related terpenoids have been identified from Amauris, Euploea and Prittwit-zia as well as from the flowers of Buddleja davidii (Loganiaceae). Three new naturally occurring bishomoterpenes as well as mono-and sesquiterpenes and aromatic compounds add to the forma-tion of species specific blends in the scent organs of the butterflies. | | | |
Reference
| Z. Naturforsch. 43c, 99—104 (1988); received July 29 1987 | | | |
Published
| 1988 | | | |
Keywords
| Pyrrolizidine Alkaloids, Oxoisophorone, Bishomoterpenes, Butterfly-Pheromones, Danaines and Ithomiines, Buddleja Flowers | | | |
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| default:Reihe_C/43/ZNC-1988-43c-0099.pdf | | | | Identifier
| ZNC-1988-43c-0099 | | | | Volume
| 43 | |
| 4 | Author
| Eva Von Nickisch-Rosenegkab, Dietrich Schneider1, MichaelW. Inka | Requires cookie* | | | Title
| Time-Course of Pyrrolizidine Alkaloid Processing in the Alkaloid Exploiting Arctiid Moth, Creatonotos transiens | | | | Abstract
| The processing o f dietary pyrrolizidine alkaloids by larvae and adults o f the arctiid moth Creatonotos transiens was studied in time-course experiments: In larvae, pyrrolizidine alkaloid uptake is quickly followed by the transformation o f the alkaloids into their N -oxides. Further more, if 7 S-heliotrine is applied, a stereochemical inversion o f the hydroxyl group at C 7 to 7 /?-heliotrine can be observed within 48 h o f feeding. The rate o f this biotransformation is substantially higher in males which use the 7 /?-form later as a precursor for the biosynthesis o f 7 /?-hydroxydanaidal, a pheromone. The resorbed pyrrolizidine alkaloids are deposited in the integument within 48 h, where they remain stored during the larval, pupal and partly also the imaginal stages. Virtually no alkaloids are lost during ecdysis. Some pyrrolizidine alkaloids can be recovered from the meconium which is released at eclosion by the imagines especially when disturbed. In the adults pyrrolizidine alkaloids are processed in different ways by the two sexes: In females, about 5 0 -8 0 % o f total alkaloids are transferred from the integument to the ovaries and the eggs within 2 -3 days after eclosion. If females mate with alkaloid-rich males they additionally receive with the spermatophore up to 290 |ig pyrrolizidine alkaloid, which are further translocated to the eggs. A biparental endowment o f eggs with acquired defence alkaloids is thus achieved. In males, 3 0 -5 0 % o f pyrrolizidine alkaloids remain in the integu ment; about 10—30% are transferred to the scent organ, the corema, where they are converted into 7 /?-hydroxydanaidal. A nother part (about 40%) is passed to the spermatophore. In the laboratory experiments, the sizes o f the coremata and their respective 7 /?-hydroxydanaidal contents are strongly dependent on the availability o f dietary pyrrolizidine alkaloids during L 6 and especially L 7 stages. In the L7 stage even short-term feeding (4 -6 h) on Senecio jaco-baea is sufficient to induce large coremata. | | | |
Reference
| Z. Naturforsch. 45c, 881—8 (1990); received March 21 1990 | | | |
Published
| 1990 | | | |
Keywords
| Creatonotos transiens, Pyrrolizidine Alkaloid, Pyrrolizidine Alkaloid-N-Oxide, 7 /?-Heliotrine Conversion, A lkaloid Storage | | | |
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| default:Reihe_C/45/ZNC-1990-45c-0881.pdf | | | | Identifier
| ZNC-1990-45c-0881 | | | | Volume
| 45 | |
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