Sequestration of plant secondary compounds by butterflies and moths

Summary A number of aposematic butterfly and moth species sequester toxic substances from their host plants. Some of these insects can detect the toxic compounds during food assessment. Some pipevine swallowtails use aristolochic acids among the host finding cues during oviposition and larval feeding and accumulate the toxins in the body tissues throughout all life stages. Likewise, a danaine butterfly,Idea leuconoe, which sequesters high concentrations of pyrrolizidine alkaloids in the body, lays eggs in response to the specific alkaloid components contained in the apocynad host. Insect species sharing the same poisonous host plants may differ in the degree of sequestration of toxins. Two closely ralated aposematic geometrid moth species,Arichanna gaschkevitchii andA. melanaria, sequester a series of highly toxic diterpenoids (grayanotoxins) in different degrees, while a cryptic geometrid species,Biston robstus, does not sequester the toxins, illustrating the diversity in adaptation mechanisms even within the same subfamily. By contrast, a number of lepidopteran species store the same compounds though feeding upon taxonomically diverse plant species. A bitter cyanoglycoside, sarmentosin, was characterised from several moth species in the Geometridae, Zygaenidae and Yponomeutidae, and from the apollo butterflies,Parnassius spp. (Papilionidae), although each species feeds on different groups of plants.Interspecific similarities and differences in life history and ecology are discussed in relation to variable characteristics of sequestration of plant compounds among these lepidopteran insects.     

Effect of Cd++ on germination,growth and active principles of Datura metel L.∗

The effects of Cd⁺⁺ concentration increment in soil and/or in atmosphere, on germination, growth and alkaloid contents of Datura metel L. were investigated. We observed a significant reduction of growth following addition of Cd⁺⁺ in soil. Minor effects on growth were evident when the plants were sprayed with CdCl₂ solution (10mgCd⁺⁺/l).

Scanning electron microscope observation showed stomata widely open and conspicuous cuticular striations in the foliar epidermis of polluted plants.

GLC analysis of extracts evidenced a significant variation in active principle content among plants undergoing different treatments.     

超高效液相色谱-三重四极杆串联质谱法测定蜂蜜中吡咯里西啶类生物碱

建立了蜂蜜中5种吡咯里西啶类生物碱的超高效液相色谱-串联质谱测定方法.蜂蜜样品用50%甲醇超声提取,强阳离子交换固相萃取柱净化富集,超高效液相色谱-三重四极杆串联质谱MRM模式检测,外标法定量.以Waters BEH C18(100 mm×2.1 mm,1.7μm)色谱柱分离,以含0.1%甲酸的乙腈和0.1%甲酸水溶液进行梯度洗脱.倒千里光碱、千里光宁、千里光菲啉和野百合碱在0.2—100.0μg·kg-1,克氏千里光宁在1.0—200.0μg·kg-1的浓度范围内各化合物线性关系良好,相关系数r均大于0.999,定量限在0.2—0.8μg·kg-1之间.在3个加标水平下,空白基质蜂蜜中的5种生物碱的平均回收率为82.0%—110.0%之间,相对标准偏差(RSD)小于12.5%.方法准确可靠,适合于蜂蜜中吡咯里西啶类生物碱的测定.     

Evidence for two genetically and chemically defined host races of Tyria jacobaeae (Arctiidae, Lepidoptera)

Summary. A widely distributed host race of Tyria jacobaeae lives on Senecio jacobaea and related species and accumulates pyrrolizidine alkaloids (“PA race”), another race, which is restricted to the Alps and found on Petasites paradoxus, sequesters sesquiterpenes, such as petasol and isopetasol. Nucleotide sequences of the mitochondrial 16S rDNA gene show 1% sequence divergence, indicating that genetical differences exist between the PA exploiting and the terpene-sequestering host races of T. jacobaeae. This finding suggests that both host races of T. jacobaeae must have been separated for some time already, possibly since the Pleistocene. Received 2 May 2001; accepted 1 June 2001.     

Risk assessment of the use of PAS100 green composts in sheep and cattle production in Scotland

A generalized quantitative risk assessment for the use of source-segregated green waste (SSGW) compost use in livestock production is presented. This assessment focussed on potential risks associated with a specific product, PAS100 compost that meets the UK publicly available specification 100 and represents the majority of compost available for use in extensive Scottish livestock systems. A hazard screening approach was used to identify all potentially hazardous agents present in compost. A total of 497 potentially hazardous agents were screened, with 147 finally put forward for quantitative risk assessment. Scenarios modelled in the assessment included surface application of compost to grazing land and also incorporation into soil and subsequent uptake by fodder crops. Risk estimates were compared to those associated with six comparator materials, including various sludges, slurries and farm yard manures. Overall, five potentially hazardous agents (PCB28, PCB138, PCB153, 1,2,3,4,6,7,8-HpCDD, Clopyralid) returned a hazard quotient >1 but within margins of uncertainty, indicating that further investigation may be required. Within the limitations of available information, SSGW compost was found to pose less risk to grazing livestock, or the environment, than other commonly-used soil amendments. While this assessment relates to a specific product/standard used in the UK, the methodology could easily be applied to other composts/products/situations. Therefore these results have wider applicability.     

Chemical composition and antifungal activity of Chelidonium majus extracts – antagonistic action of chelerythrine and sanguinarine against Botrytis cinerea

This study discusses the similarities and differences between the antifungal activity of Chelidonium majus L. extracts and chelerythrine/sanguinarine, the main alkaloids in these extracts, against the plant pathogenic fungus, Botrytis cinerea. The obtained data show that the Ch. majus L. extracts inhibit the growth of B. cinerea very effectively. The extracts activity is significantly greater than that of chelerythrine/sanguinarine standard solutions alone and it does not always reflect the total content of alkaloids in the extracts. It has been proved that B. cinerea exhibits very diverse resistance to chelerythrine and sanguinarine. The IC₅₀ values for chelerythrine and sanguinarine equal 5.41?mg/mL and 1.76?mg/mL, respectively. In the mixture the antifungal activity of chelerythrine and sanguinarine is antagonistic in the concentration dependent way. Based on the presented data it is not clear, however, which alkaloids present in the Ch, majus extracts at significantly lower concentration levels enhance the activity of chelerythrine and sanguinarine so that the extracts activity is considerably greater than that of both main alkaloids mixtures.     

Phenological fate of plant-acquired pyrrolizidine alkaloids in the polyphagous arctiid Estigmene acrea

Summary. The alkaloid profiles of the life history stages of the highly polyphagous arctiid Estigmene acrea were established. As larvae individuals had free choice between a plain diet (alkaloid-free) and a diet that was supplemented with Crotalaria-pumila powder with a known content and composition of pyrrolizidine alkaloids (PAs). Idiosyncratic retronecine esters (insect PAs) accounted for approximately half of the PAs recovered from the larvae. These alkaloids were synthesized by the larvae through esterification of dietary supinidine yielding the estigmines, and esterification of retronecine yielding the creatonotines. The retronecine is derived from insect-mediated degradation of the sequestered pumilines (macrocyclic PAs of the monocrotaline type). With one exception, the PA profiles established for larvae were found almost unaltered in all life-stages as well as larval exuviae and pupal cocoons. The exception is the males, which in comparison to pupae and adult females, showed a significantly decreased quantity of the creatonotines and pumilines. These data support the idea that the creatonotines are direct precursors of the PA-derived male courtship pheromone, hydroxydanaidal. Crosses of PA-free males with PA-containing females and vice versa confirmed an efficient trans-mission of PAs from males to females and then from females to eggs. In single cases a male bestowed almost his total PA load to the female, and a female her total load to the eggs. The results are discussed with respect to pheromone formation, PA transmission between life-stages, and the defensive role of PAs against predators and parasitoids     

Corematal function in <Emphasis Type="Italic">Utetheisa ornatrix</Emphasis> (Lepidoptera: Arctiidae): Hydroxydanaidal is devoid of intrinsic defensive potency

Summary. Hydroxydanaidal, the pyrrolizidine alkaloid-derived male corematal pheromone active in the close-range precopulatory interactions of the moth Utetheisa ornatrix, appears not to contribute to the chemical defense of this moth. The compound failed to manifest feeding deterrency as an additive to mealworms, in assays with a lycosid spider (Lycosa ceratiola). Moreover, contact with the male’s coremata, such as appears to occur inevitably in consequence of courtship in Utetheisa, does not in itself reduce the palatability of the female moth.     

Pyrrolizidine alkaloid content in <Emphasis Type="Italic">Senecio</Emphasis>: ontogeny and developmental constraints

Summary. The ontogeny of pyrrolizidine alkaloid (PA) synthesis and constraints on defence level during the seedling stage were examined in the annual Senecio vulgaris and the monocarpic perennial Senecio jacobaea. In both species, PAs were actively synthesized from the onset of seedling growth so that juvenile stages did not go through an undefended stage. Roots are known to be the exclusive sites where PAs are produced. Root biomass was the single most important biomass parameter explaining variation in total PAs per seedling. All correlation coefficients between—relative growth rate and PA concentration were negative, but none was significant. However, a significant negative—correlation was found between shoot to root ratio and PA concentration in S. jacobaeaseedlings, suggesting a dilution effect of the PAs. Earlier studies have shown that the shoot to root ratio is positively correlated with relative growth—rate of established S. jacobaea plants. It is therefore suggested that young S. jacobaea plants with a high shoot to root ratio and hence a high growth capacity necessarily have lower PA defence levels than plants with a low shoot to root ratio. Received 10 July 2002; accepted 16 November 2002.     

Detoxification of pyrrolizidine alkaloids by the harvestman <Emphasis Type="Italic">Mitopus morio</Emphasis> (Phalangidae) a predator of alkaloid defended leaf beetles

Summary. The harvestman Mitopus morio (Phalangidae) is a generalist predator. It is known to prey on larvae of the chrysomelid leaf beetle Oreina cacaliae defended by plant acquired pyrrolizidine alkaloids (PAs). Tracer feeding experiments were performed to determine how harvestmen tolerate protoxic PAs. Minced meat containing either [¹⁴C]senecionine or [¹⁴C]senecionine N-oxide was fed to M. morio and subsequently feces and bodies were analyzed. Labeled alkaloid N-oxide remained stable and was eliminated almost unaltered with the feces; only 10% was recovered as tertiary PA. In contrast, approximately 80% of labeled tertiary alkaloid (senecionine) ingested with the diet was N-oxidized and eliminated; the remaining 20% consisted of unchanged senecionine and a polar metabolite of unknown structure. Harvestmen process their diet by excreting digestive juice, indicated by bleaching of the meat color. Analysis of the processed diet revealed some N-oxidation of [¹⁴C]senecionine, suggesting the gut as the site of Noxidation. Analysis of the bodies of harvestmen 80 hours after the tracer feeding pulse revealed only trace amounts of the polar metabolite. Neither senecionine nor its N-oxide could be detected in the body extracts. The results are discussed in relation to the strategies of PA adapted insects to avoid accumulation of tertiary PAs in living tissues.