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In the Arctiid Moth Creatonotos Transiens A Organ Specific Storage of Dietary Pyrrolizidine Alkaloids in the Arctiid Moth Creatonotos transiens A. Egelhaaf, K. Cölln, B. Schmitz, M. Buck Zoologisches Institut der Universität, Im Weyertal 119, D-5000 Köln 41, Bundesrepublik Deutschland M. Wink* Pharmazeutisches Institut der Universität, Saarstraße 21, D-6500 Mainz, Bundesrepublik Deutschland D. Schneider Max-Planck-Institut für Verhaltensphysiologie, D-8130 Seewiesen/Starnberg, Bundesrepublik Deutschland Z. Naturforsch. 45c, 115-120(1990); received September 25, 1989 Creatonotos, Arctiidae, Pyrrolizidine Alkaloids, Heliotrine Metabolism, Storage Larvae of the arctiid moth Creatonotos transiens obtained each 5 mg of heliotrine, a pyrroli­ zidine alkaloid, via an artificial diet. 7 S-Heliotrine is converted into its enantiomer, 7 Ä-heliotrine, and some minor metabolites, such as callimorphine. IS- and 7 /?-heliotrine are present in the insect predominantly (more than 97%) as their N-oxides. The distribution of heliotrine in the organs and tissues of larvae, prepupae, pupae and imagines was analyzed by capillary gas-liquid chromatography. A large proportion of the alkaloid is stored in the integu­ ment of all developmental stages, where it probably serves as a chemical defence compound against predators. Female imagines had transferred substantial amounts of heliotrine to their ovaries and subsequently to their eggs; males partly directed it to their pheromone biosyn­ thesis. Introduction and -dissipating organ, the corema [6, 7]. The The East-Asian arctiid moth Creatonotos tran­ quantity of this morphogenetic effect is directly de­ siens, is polyphagous and thus also feeds on a pendent upon the dosis, but independent of the number of plants which contain noxious secondary temporal spreading of the feeding program. All metabolites. Whereas alkaloids of the tropane-, this clearly indicated already that the larvae quinolizidine-, or purine-type are not resorbed but sequester all or some of the ingested PA. To date eliminated with the faeces, pyrrolizidine alkaloids we do not know, when exactly the sensitive period (PA) are selectively taken up and processed by for the corema induction begins (some time in the these insects [1-3]. The resorption of PA seems to late final larva?); but we found that this period ter­ be catalyzed by specific carrier proteins [4], In all minates during the second prepupal day [9, 10], In stages and both sexes, PA fed specimens appeared the process of the growth of the corema anlage, the to be protected from several predators [5]. ingested PA are a sufficient (yet perhaps not indis­ In the males, PA further serve as modulators for pensable [8]) factor in addition to the pupation the development of an abdominal scent-producing hormone, the ecdysone [9, 10]. The scent-hair bearing corema dissipates 7 R-hy- droxydanaidal, a pheromone which derived in all Abbreviations: GLC, gas-liquid chromatography; MS, our laboratory experiments from dietary PA mass spectrometry; El, electron impact; Cl, chemical [6 - 12]. ionization; PA, pyrrolizidine alkaloids; L7, last larval PA thus have three functions in this specialized instar. herbivore: they act (as in some other lepidoptera; * New address: Institut für Pharmazeutische Biologie, see [1, 5, 13]) as defence substances and as phero­ Universität Heidelberg, Im Neuenheimer Feld 364, D-6900 Heidelberg, Bundesrepublik Deutschland. mone precursors, but only in Creatonotos can they Reprint requests to A. Egelhaaf, D. Schneider or also act as a morphogen for the male pheromone M. Wink. gland. Verlag der Zeitschrift für Naturforschung, D-7400 Tübingen The aim of this study was to follow the path of a 0341-0382/90/0100-0115 $01.30/0 pure PA, which last instar larvae ingested. We ana- Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung This work has been digitalized and published in 2013 by Verlag Zeitschrift in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der für Naturforschung in cooperation with the Max Planck Society for the Wissenschaften e.V. digitalisiert und unter folgender Lizenz veröffentlicht: Advancement of Science under a Creative Commons Attribution Creative Commons Namensnennung 4.0 Lizenz. 4.0 International License. 116 A. Egelhaaf et al. ■ Storage of Pyrrolizidine Alkaloids in an Arctiid Moth Table I. Distribution of pyrrolizidine alkaloids in Creatonotos transiens. Larvae obtained 5 mg 75-heliotrine each. Alkaloids were extracted from tissue preparations and analyzed by capillary GLC. Alkaloid content/tissue is given as |ig PA (IS- and 7 /?-heliotrine) including PA-N-oxides which were reduced prior to extraction. Data are means of at least 2 animals. - = Tissue not analyzed/not available; Haem. = haemolymph; Fat b. = fat body; Int. = integument: Sex o. = sex organ; Cor. = corema; Rest = not defined tissues; Faec. = faeces; Exuv. = exuviae; % rec. = % PA recovered excluding faeces and exuviae. Developmental Alkaloid content (fig/tissue or organ) Stage Sex Haem. Fat b . Int. Wings Guts Sex o. Eggs Cor. Rest Faec. Exuv . % rec. Larvae M 26 45 547 132 1 .0 _ _ 98 308 1.7 17 F 28 13 343 24 0 . 8 -- 11 1091 1 . 0 8 Prepupae(1d) M 37 19 520 - 13 0 . 2 -- 18 -- 1 2 F 2 1 61 876 - 8 0.7 -- 27 - - 2 0 Prepupae ^2d) M 34 108 509 - 109 2.5 -- 147 -- 16 F 18 35 473 - 37 7.8 -- 80 -- 14 Pupae(1 d) M 71 - 699 - 41 2 . 2 -- 264 -- 2 2 F 15 - 198 - 5 --- 170 -- 8 Pupae (5d) M 17 6 664 - 39 6 -- 309 -- 2 0 F 8 18 557 - 1 0 --- 204 -- 16 Pupae ( 8 d) M 25 - 329 - 3 0 . 8 - 129 459 - 4 19 F 3 - 166 ----- 90 - 3 5 Imago M -- 568 27 2 7 - 2 1 --- 1 2 F - - 76 1 0 2 500* 17+ - 387 -- 2 0 * In 3 females the ovary could be isolated, for the other animals the ovary fraction was included in the “rest” section. + Data underrepresent the real value since only a fraction of the eggs was recovered. See [ 8 ] for the latest measurements. lyzed the major tissues through the subsequent de­ Alkaloid analysis velopmental stages, beginning with the wander- Organs were homogenized in 500 )^1 0.5 m HC1 raupe, a stage which does no longer feed. in Eppendorf vials and stored at -20 °C until fur­ ther processing. In order to reduce PA-N-oxides Materials and Methods the homogenates were treated with zinc powder Animals for at least 3 h. Alkaloids were extracted by liquid- solid extraction using Chem elut columns (ICT, A laboratory population of Creatonotos tran­ Analytichem; [2, 15]). Crude alkaloid extracts were siens (Walker) was maintained on a semi-artificial analyzed by capillary GLC on a Perkin Elmer in­ diet [14]. The origin (Bali, Indonesia) of this labo­ strument (GLC 8500) equipped with flame ioniza­ ratory population is important because of the un­ tion and nitrogen specific detectors. GLC condi­ clear systematic status of this species and its sub­ tions: 30 mxO.l mm DB-5 column (J&W; ICT species from different localities. L7 (last instar) Frankfurt); oven: 170 °C, 2 min isothermal, then larvae were each fed 5 mg of the pure (commercial­ to 300 °C at 30 °C/min; detectors: 320 °C; injector: ly available) PA 7S'-heliotrine. This dosis was of­ 250 °C, split injection (1:20); carrier gas: helium, fered in the diet. At given intervals, wanderraupen 90 kPa. - GLC and GLC-MS (EI, Cl) was per­ (late L7) or later developmental stages (prepupae, formed as in a previous study [15]. pupae, imagines) were dissected to obtain the fol­ lowing organs or tissues: haemolymph, fat body, Results and Discussion gut, integument, ovaries, eggs, testes, coremata, wings, exuviae and faeces. The comparatively Identification o f heliotrine and its metabolites large variation of the PA amounts recovered from Heliotrine containing diet is readily accepted by the different tissues (in particular from the “rest” the larvae [3, 5], Alkaloid extracts obtained from fraction, see Table I) appears to be mainly a natu­ whole larvae, pupae and imagines contained the ral phenomenon and only to a minor degree indic­ original 7 S-heliotrine and metabolites derived ative of technical difficulties to obtain “clean” from it [15]. Up to 20% of the heliotrine and samples of fresh tissue for the chemical analysis. its PA metabolites could be recovered from the A. Egelhaaf et al. ■ Storage of Pyrrolizidine Alkaloids in an Arctiid Moth 17 PUPAE (8d) ALKALOID ALKALOID CONTENT (%) HFIGSCR HFIGSCR IMAGINES 80 o ¥ 60 - haemolymph fat body 40 integument gut gonads corema 20 - wings rest H F I G S C W R Fig. 1. Distribution of heliotrine in different tissues and developmental stages of both sexes of Creatonotos transiens. For females, the amounts found in the ovaries were omitted from this illustration but attributed to the rest fraction (cf. Table I). Other experimental details as in Tables I and III. 118 A. Egelhaaf et al. ■ Storage of Pyrrolizidine Alkaloids in an Arctiid Moth animals and up to a further 20% from the faeces alkaloidal compounds by detoxification processes (Table I). The low PA recovery rate from the and thus escaped our detection process? Experi­ animals is in part explained by other experiments ments in progress support the latter explanation [2] where feeding of more than 3 mg PA per [17]. larva seemed to overcharge the intestinal uptake A major chemical change is apparent in the PA mechanism with PA excretion as a consequence. extracts, namely a conversion of the “free” alka­ The fate of the “’missing’' portion (up to 60% of loid into its more hydrophilic and less cell-mem- the original PA) needs to be studied and we ask: brane permeable N-oxides (Table II). This occurs was the heliotrine converted to alkaloids which are rather soon after the PA feeding [17], The site of either not extractable or not sufficiently volatile this change is still unknown but might be the gut for GLC studies or was it mainly degraded to non- wall or the haemocoel.
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