Pyrrolizidine alkaloids distribution

From the hair-pencils of butterflies in Danainae and Ithomiinae (Papilion-oidea Nymphalidae), a wider variety of pyrrolizines (la-d, and 6a-d) have been identified than from Arctiidae moths. These compounds are biosynthesized from pyrrolizidine alkaloids, which are included in host plants fed by the larvae and protect them from the attacks of other herbivores [122]. In addition to novel lactones (7, 8a, and 8b) derived from an acid part of the alkaloids, many volatiles of more than 100 compounds (aromatics, terpenoids, hydrocarbons, and others) constitute scent bouquets of the male butterflies [123]. For example, the hair-pencil of Idea leuconoe (Danainae) which is distributed in South-East Asia contained 16 compounds (6b, 8a, 8b, 9, and others), and a mixture of the major volatiles applied to a butterfly dummy elicited an abdomen-curling acceptance posture in the females as a crude extract of the male hair-pencils did [ 124]. A chiral GC analysis revealed the absolute config-... 

Pyrrolizidine alkaloids have a wide distribution, but are characteristic of certain genera of the Boraginaceae (e.g. Heliotropium, Cynoglossum, and Symphytum), the Compositae/Asteraceae (e.g. Senecio) and the Leguminosae/Fabaceae (e.g. Crotalaria). The pyrrolizidine bases rarely occur in the free form, but are generally found as esters with rare mono- or di-basic acids, the necic acids. Thus, senecionine (Figure 6.18) from Senecio species is a diester of retronecine with senecic acid. Inspection of the ten-carbon skeleton... 

Russian comfrey (Symphytum x uplandicum Nyman) is widely recommended as a medicinal herb and an item of human diet. A previous investigation of this species led to the isolation of three alkaloids which were not fully characterized (cf. Vol. 7, p. 57). Culvenor and co-workers have separated eight pyrrolizidine alkaloids from the leaves of this perennial plant by counter-current distribution.21 The known alkaloids echimidine (51), symphytine (52), lycopsamine (53), and intermedine (54) were present. In addition, four new alkaloids, i.e. 7-acetyl-lycopsamine (55), 7-acetylintermedine (56), symlandine (57), and uplandicine (58), were characterized by spectroscopic methods, and by hydrolysis. The total alkaloidal extract caused chronic hepatotoxic effects in rats, and the authors... 

Toxicity has been demonstrated in analogues of pyrrolizidine alkaloids with a pyrrole or dihydropyrrole ring. The vascular changes in the lungs of rats after intravenous injection of pyrrole carbamates have been reported.60 The distribution of radioactivity in rats given tritium-labelled synthanecine A (16) bis-N-ethyl-carbamate and bis-hydroxymethyl-l-methylpyrrole has been studied.61 Biliary excretion is important for the disposal of pyrrolic metabolites from retrorsine and synthanecine A bis-N-ethylcarbamate, but not for the parent compounds.62... 

HARTMANN, T., ZIMMER, M., Organ-specific distribution and accumulation of pyrrolizidine alkaloids during the life history of two annual Senecio species. J. Plant Physiol., 1986,122,67-80. 

Eastman DF, Dimenna GP, Segall HJ. Covalent binding of two pyrrolizidine alkaloids, senecionine and seneciphylline, to hepatic macromolecules and their distribution, excretion, and transfer into milk of lactating mice. Drug Metab Dis 1982 10 236-40. 

The occurrence of pyrrolizidine derivatives in the Lepidoptera is not confined to butterflies, but has also been observed in the tiger moth, where their function may be similar to that established in one species of butterfly. Male tiger moths (fam. Arctiidae) possess scent organs in the form of inflatable coremata which have a pheromone-distributing function. Some of these species are known to use plants containing pyrrolizidine alkaloids, e.g. Heliotropium europaeum and Echium... 

Incorporations, similar to that for putrescine, were observed for spermine (46) and spermidine (47) (also measured against arginine C-labels on asterisked carbons), and there was a similar distribution of the label. These amines can, like putrescine, then be converted into pyrrolizidine alkaloids via the hypothetical (44) both polyamines are known to be degraded to pyrrolines, resembling (44), plus 1,3-diaminopropane on oxidation with plant polyamine oxidases. 

The occurrence and distribution of pyrrolizidine alkaloids in members of the tribes Eupatorieae " and Senecioneae have been reviewed. 

Table Distribution of the Pyrrolizidine alkaloid types within the taxa of Pyrrolizidine alkaloid containing species (see Lit. Pelle-...

Senecio vulgaris (Asteraceae) is a perennial plant that came to Japan in the Meiji Era (1868—1912) and spread as a naturalized plant aU over the country. In contrast, Senecio pierotii (Asteraceae) is a perennial plant that grows in the swamps of the mountains in Japan. Pyrrolizidine alkaloids, which possess a pyrrolizidine nucleus, were isolated from a number of Senecio plants, inclu-deing S. vulgaris and S. pierotti. These alkaloids are distributed in Senecio plants, and several other genera of plants in the Asteraceae, Boraginaceae, and Fabaceae. Because their principal source is Senecio plants, these pyrrolizidine alkaloids are also known as Senecio alkaloids. 

Distribution of Pyrrolizidine Alkaloids Pyrrolizidine Alkaloids in Animals Pyrrolizidine Alkaloids and Parasitic Plants ITie Role of Pyrrolizidine Alkaloids in Livestock Poisoning... 

Friesen JB, Burkhouse PC, Biesboer DD, Leete E (1992) Influence of alkaloid precursors on the alkaloid content of Nicotiana alata root cultures. Phytochemistry 31 3059-3063 Frblich C, Hartmann T, Ober D (2006) Tissue distribution and biosynthesis of 1,2-unsaturated pyrrolizidine alkaloids in Phalaenopsis hybrides (Orchidaceae). Phytochemistry 67 1493-1502... 

FrbUch C, Ober D, Hartmann T (2007) Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species. Phytochemistry 68 1026-1037... 

The already mentioned occurrence of certain alkaloids or alkaloid types in unrelated plants creates some problems for the chemotaxonomist (Matveyev, 1959 Sharapov, 1962). The pyrrolizidine alkaloids, for example, are produced by plants like Crotalaria in Fabaceae, Senecio in Com-positae, Lolium in Glumiflorae, Cynoglossum in Boraginaceae, and Secu-rinega in Euphorbiaceae (Crowley and Culvenor, 1962 Culvenor and Smith, 1967 Culvenor et aL, 1968a,b). The alkaloids derived from the pyridine nucleotide cycle are distributed in unrelated plants. The most common... 

Pyrrolizidine Alkaloid Analogues. Part 2. Further Hydroxymethyl-l-methyl-3-pyrrolines (Synthanecines), and the Preparation and Esterification of Some Hydroxymethylpyrroles. J. Chem. Soc., Perkin Trans. 1 1978, 896 — The Distribution of Radioactivity in Rats given pH]2,3-Bisacetoxymethyl-l-methylpyrrole, a Pneumotoxic Analogue of Labile Pyrrolizidine Alkaloid Metabolites. Toxicol. Lett. 3,79 (1979). 

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