Spectrophotometric determination of unsaturated pyrrolizidine alkaloids

Mattocks, A. R.

doi:10.1021/ac60248a006

Cited by 145 publications

(69 citation statements)

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“…After eclosion, the imago and the meconium were placed individually in separate vials with 2 ml of absolute methanol. PA ascorbate and individual imagoes, meconia and feces were analyzed by a colorimetric method to determine the amount of PAs TM [17][18][19]. One tenth of the total liquid volume was dried and oxidized for 25 min at 100 ~ with 0.5 ml of 30 % H20 2 + 5 mg/ml Na2P20 7 diluted 1:200 with absolute MeOH.…”

Section: Methodsmentioning

confidence: 99%

Evolutionary implications of pyrrolizidine alkaloid assimilation by danaine and ithomiine larvae (Lepidoptera: Nymphalidae)

Trigo

Motta

1990

Experientia

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Summary. Larvae of danaine and ithomiine butterflies assimilate pyrrolizidine alkaloids painted on their larval host plants. This finding supports the theory of the common ancestral use of these compounds by Ithomiinae and Danainae. Key words. Pyrrolizidine alkaloids; Ithomiinae; Danainae; phylogenetic relationships; assimilation of host-plant defensive chemicals.Larvae of more than 95 % of the species of Ithomiinae butterflies feed on plants of the family Solanaceae 1. However, four primitive genera (Tellervo, Tithorea, Elzunia and Aeria) feed on Apocynaceae (tribe Parsonsieae), whose leaves may contain pyrrolizidine alkaloids (PAs) 2-5. In some Ithomiinae, these alkaloids function as male pheromone precursors 6-1~ and as a chemical defense against predation by the spider Nephila clavipes al -13. Larvae of Tellervo and Tithorea sequester PAs from their host plants 4, 5, while Aeria probably uses host plant compounds as precursors for PA biosynthesis s. The adults of Solanaceae-feeding Ithomiinae assimilate PAs from their food sources (nectar of Boraginaceae and Asteraceae) and decomposing leaves of Boraginaceae (mainly Heliotropium), since Solanaceae do not contain PAs 11-t3. It has been suggested that the ancestral host plant of the closely related Danainae and Ithomiinae 14, 15 contained PAs, leading to a dependence of these bufferflies on these alkaloids which has been retained up to the present 6, 7. Danaus plexippus larvae assimilated PAs from a PA-free host plant which was treated with these alkaloids, suggesting that this danaine maintains the capacity for PA sequestration and storage probably used by its ancestors to obtain PAs from their host plants 16 In this work we show that Ithomiinae larvae which feed on PA-free plants also retain the capacity for PA sequestration and storage. On the basis of this finding we discuss the possible common ancestry of Ithomiinae and Danainae, and of their larval host plants. Material and methodsEggs and larvae of species of Ithomiinae, Danainae, Pieridae, and their host plants (table 1) were obtained in the regions of Campinas and Jundiai, Silo Paulo, Brazil. The Danainae were included as a closely related group (sistergroup of Ithomiinae is) and the Pieridae as a control, since they do not utilize plants with PAs in their life cycle. Larvae were reared at room temperature (about 25 ~ on leaves of their respective food plants. The leaves were changed daily. The third instar larvae were fed daily with PA ascorbate painted on the host-plant leaves, until pupation. The PA ascorbate salt was prepared with the free bases of PAs from Eupatorium laevigatum (echinatine and three other non-identified alkaloids 5) plus ascorbic acid (15:8 w/w). The PA ascorbate was utilized because it is water soluble (free bases are poorly miscible with water and soluble in organic solvents). PA N-oxides, which are soluble in water, could also be utilized, but the data on transformation from free bases to N-oxides would be lost. Controls were included for each butterfly species; they were given...

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Section: Methodsmentioning

confidence: 99%

Evolutionary implications of pyrrolizidine alkaloid assimilation by danaine and ithomiine larvae (Lepidoptera: Nymphalidae)

Trigo

Motta

1990

Experientia

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“…Further analysis of the PA composition was done with GC-MS (Witte et al 1992). Total PA concentration was determined spectrophotometrically, modified after Mattocks (1967). The concentration of individual PAs was calculated by total PA concentration fraction of individual PA measured by GC analysis.…”

Section: Pa Analysismentioning

confidence: 99%

Diversity of pyrrolizidine alkaloids in Senecio species does not affect the specialist herbivore Tyria jacobaeae

et al. 2002

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The evolution of the diversity of related secondary metabolites in plants is still poorly understood. It is often thought that the evolution of plant secondary metabolites is driven by specialist insect herbivores and under this coevolutionary model it is expected that related compounds differ in their effects on specialist herbivores. Here we focus on the diversity of pyrrolizidine alkaloids (PAs) in Senecio species and their effects on Tyria jacobaeae, a specialist moth on Senecio jacobaea. As a first step to determine the effects of related PAs on T. jacobaeae, we studied larval performance on plants from 11 S. jacobaea populations and eight Senecio species with different PA compositions. Although the populations of S. jacobaea differed in their PA compositions, there was no difference in larval performance among the populations. Larval performance differed among the eight species but we could not show a correlation with PA composition. Oviposition choice experiments showed a strong correlation between oviposition preference and larval performance on the eight species but oviposition preference did not seem to be correlated with PAs. We found no indications that related PAs differ in effects on the specialist T. jacobaeae; therefore it seems unlikely that T. jacobaeae is a driving force behind the evolution of the diversity of PAs. Alternatively, we propose that the evolution of the diversity of PAs is driven by selection pressure from generalist herbivores or that the diversity of PAs may even be selectively neutral.

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“…A linear dose-response relationship was obtained when aliquotes of dilute, methanolic extracts from dry leaves of Senecio rupestris were analyzed either by ELISA or by colour spectrophotometric determination (Table I) [Mattocks, 1967;Roeder et al, 19921. Senecio rupestris contains senecionine (2) and integemmine (3) in different amounts (Roeder and Wiedenfeld, 1983; Unpublished results).…”

Section: Analysis Of Biological Samplesmentioning

confidence: 99%

Analysis of pyrrolizidine alkaloids: A competitive enzyme‐linked immunoassay (ELISA) for the quantitative determination of some toxic pyrrolizidine alkaloids

Roeder

Pflueger

1995

Natural Toxins

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Spectrophotometric determination of unsaturated pyrrolizidine alkaloids

Cited by 145 publications

References 2 publications

Evolutionary implications of pyrrolizidine alkaloid assimilation by danaine and ithomiine larvae (Lepidoptera: Nymphalidae)

Evolutionary implications of pyrrolizidine alkaloid assimilation by danaine and ithomiine larvae (Lepidoptera: Nymphalidae)

Diversity of pyrrolizidine alkaloids in Senecio species does not affect the specialist herbivore Tyria jacobaeae

Analysis of pyrrolizidine alkaloids: A competitive enzyme‐linked immunoassay (ELISA) for the quantitative determination of some toxic pyrrolizidine alkaloids

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