On the evolution of the diversity of pyrrolizidine alkaloids

the role of insects as selective forces
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Universiteit Leiden , [Leiden
Pyrrolizidines., Plant chemical defenses., Insect-plant relationships., Phytophagous insects --
StatementMirka Máčel.
Classifications
LC ClassificationsQK898.P97 M33 2003
The Physical Object
Pagination109 p. :
ID Numbers
Open LibraryOL3374923M
LC Control Number2004464066

Studies into the evolution of pyrrolizidine alkaloid biosynthesis using Senecio species have identified homospermidine synthase as the enzyme responsible for the synthesis of the first specific.

Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1–9 were found in the aerial parts, 7 and 8 in the roots, and 6–10, together with eleven fatty acids, in the seeds of this plant species.

They are especially numerous and diverse in the tribe Senecioneae and form a powerful defense mechanism against herbivores.

Studies into the evolution of pyrrolizidine alkaloid biosynthesis using Senecio species have identified homospermidine synthase as the enzyme responsible for the synthesis of the first specific intermediate.

These studies further indicated that the homospermidine synthase-encoding gene Cited by:   Dissertation. The evolution of chemical diversity in plants: pyrrolizidine alkaloids and cytochrome Ps in Jacobaea.

Plants produce an astonishing variety of secondary metabolites (SMs) which are thought to play vital roles in the fitness of plants through ecological interactions. In this thesis this question was studied using the pyrrolizidine alkaloids (PAs) of Jacobaea species as the study system from an evolutionary and biosynthetic perspective.

PA variations were studied among and within Jacobaea species, and species-specific PA profiles. Pyrrolizidine alkaloid concentrations and profiles were highly diverse in a biogeographical survey of the exotic plant Senecio pterophorus. Plants were potentially more toxic in the invasive range than in the native by: On the evolution of the diversity of pyrrolizidine alkaloids: the role of insects as selective forces.

Phd. dissertation, Leiden University Macel M, Klinkhamer PGL, Vrieling K, Meijden E. Diversity of pyrrolizidine alkaloids in Senecio species does not affect the specialist herbivore Tyria by: Among the diversity of secondary metabolites which are produced by plants as means of defence against herbivores and microbes, pyrrolizidine alkaloids (PAs) are common in Boraginaceae, Asteraceae and some other plant families.

Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in Cited by: Pyrrolizidine alkaloids occur in a variety of plants used as food and herbal medicines in many parts of the world, particularly in Africa and Asia.

The first natural substances shown to cause liver tumors were pyrrolizidine alkaloids from plants. Pyrrolizidine alkaloids, sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine.

Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores. More than PAs and PA N-oxides have been identified in over 6, plants, and about half of them exhibit.

Species of several unrelated families within the angiosperms are able to constitutively produce pyrrolizidine alkaloids as a defense against herbivores. In pyrrolizidine alkaloid (PA) biosynthesis, homospermidine synthase (HSS) catalyzes the first specific step.

HSS was recruited during angiosperm evolution from deoxyhypusine synthase (DHS), an enzyme Cited by: Evolution of pyrrolizidine alkaloid biosynthesis in Apocynaceae: revisiting the defence de-escalation hypothesis Tatyana Livshultz1, Elisabeth Kaltenegger2, Shannon C.

Straub3, Kevin Weitemier4, Elliot Hirsch1, Khrystyna Koval1, Lumi Mema1 and Aaron Liston4 1Department of Biodiversity, Earth, and Environmental Sciences, Academy of Natural Sciences of Drexel Cited by: 7.

Within a class of particular metabolites all plants species produce not one but a variety of related metabolites. Ragwort plants for example produce over 30 different pyrrolizidine alkaloids.

Details On the evolution of the diversity of pyrrolizidine alkaloids PDF

How to explain this chemical diversity. We put up several hypothesis to explain the diversity within a particular metabolite class. 1 Evolution through time of Pyrrolizidine Alkaloids detection and quantification Filipe Monteiro-Silva,a Gerardo González-Aguilarb aDepartamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, Porto, PortugalCited by: 1.

Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in herbivores and humans.

Description On the evolution of the diversity of pyrrolizidine alkaloids PDF

Almost all genera of the. Diversity of pyrrolizidine alkaloids in Seneciospecies does not affect the specialist herbivore Tyria jacobaeae Received: 19 November / Accepted: 29 August / Published online: 9 October Springer-Verlag Abstract The evolution of the diversity of related secondary metabolites in plants is still poorly understood.

Diversity6 Table 1. List of plant species of the Boraginaceae containing PAs. Species Pyrrolizidine alkaloids References Alkanna orientalis 7-Angeloylretronecine, 9-angeloylretronecine, 7-tigloylretronecine, 9-tigloylretronecine, 7-seneioylretronecine, 9-senecioylretronecine, triangularine, dihydroxytriangularine, triangularicine.

The effects of pyrrolizidine alkaloids (PAs) were tested on five generalist insect herbivore species of several genera using artificial diets or neutral substrates to which PAs were added. We found evidence that structurally related PAs differed in their effects to the thrips Frankliniella occidentalis, the aphid Myzus persicae, and the locust.

On ingestion of PAs, parent alkaloid or metabolites can be found in the serum and only later in the urine and faeces indicating that absorption across the gastrointestinal tract occurs7,8,9,10,11,12,13, Studies using a limited number of representative PAs have shown that three main pathways of metabolism occur Activation pathway File Size: KB.

chemical constituents of plants, secondary metabolites, pyrrolizidine alkaloids, insect pests, plant-insect relations, antifeedants, feeding behavior Abstract: The evolution of the diversity in plant secondary compounds is often thought to be driven by insect herbivores, although there is little empirical evidence for this assumption.

Macel, M. On the evolution of the diversity of pyrrolizidine alkaloids: The role of insects as selective forces. PhD Dissertation. University of Leiden. Macel, M. Attract and deter: a dual role for pyrrolizidine alkaloids in plant–insect interactions.

Cited by: Alkaloids can be toxic too (e.g. atropine, tubocurarine). Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly evoke a bitter taste.

The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut. tion and maintenance of the diversity of structurally related secondary plant compounds.

As a model system to study the evolution of the diversity of secondary metabolites, we used the pyrrolizidine alkaloids (PAs) in Senecio species. Senecionine-type PAs, comprising over structures, are abundant in the.

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Pyrrolizidine alkaloid containing plants are the most widespread and expensive poisonous plant problem that affects plants, insects, animals and humans. April PPRL Outline Plants Toxin Metabolism Poisoning Susceptibility Clinical.

Pyrrolizidine alkaloidosis is a disease caused by chronic poisoning found in humans and other animals caused by ingesting poisonous plants which contain the natural chemical compounds known as pyrrolizidine alkaloids.

Pyrrolizidine alkaloidosis can result in damage to the liver, kidneys, heart, brain, smooth muscles, lungs, DNA, lesions all over the body, and could be a.

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties. Diversity6 (2), DOI: /d Dorothee Langel, Dietrich Ober, Pieter B. Pelser. The evolution of pyrrolizidine alkaloid biosynthesis and diversity Cited by: Laboratory and field tracer experiments with 14C-labelled senecionine N-oxide (SO) and distant biosynthetic precursors such as [14C]putrescine revealed that pyrrolizidine alkaloid N-oxides (PAs) in Senecio vernalis show no significant turnover over periods of up to 29 d.

However, PAs are spatially mobile, they are continuously allocated, and labelled PAs are even detectable in Cited by: Hepatotoxic pyrrolizidine alkaloids in Emilia sonchifolia from Taiwan. Journal of Food Composition and Analysis42, DOI: / Dorothee Langel, Dietrich Ober, Pieter B.

Pelser. The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the by: The full text of this article hosted at is unavailable due to technical by: 3 SUMMARY Pyrrolizidine alkaloids (PAs) which may find their way into human and animal food in Australia are derived mainly from the plants Heliotropium europaeum, Echium plantagineum, Symphytum spp.

and Crotalaria retusa. The Sympthytum spp. (comfrey) are deliberately ingested while the remaining species are weeds in variousFile Size: 61KB. The evolution of pathways within plant secondary metabolism has been studied by using the pyrrolizidine alkaloids (PAs) as a model system.

PAs are constitutively produced by plants as a defense against herbivores. The occurrence of PAs is restricted to certain unrelated families within the angiosperms. Homospermidine synthase (HSS), the first specific enzyme in Cited by: Defensive properties of pyrrolizidine alkaloids against in the early evolution of the secondary metabolite diversity.

In this review, we discuss the impact that Table 1 Overview of studies on pyrrolizidine alkaloids and the effect on the growth of microorganisms. PAs studied showed a.Livshultz and her team traced the evolution of a gene that is involved in the production of a class of chemicals that are highly toxic to humans and other mammals, called pyrrolizidine alkaloids.