Literature DB >> 24221631

Metabolic links between the biosynthesis of pyrrolizidine alkaloids and polyamines in root cultures of Senecio vulgaris.

T Hartmann1, H Sander, R Adolph, G Toppel.   

Abstract

Isotope feeding and inhibitor experiments were performed in order to elucidate the pathway common to polyamine and alkaloid biosynthesis in root cultures of Senecio vulgaris L. α-Difluoromethylarginine, a specific inhibitor of arginine decarboxylase, prevented completely the incorporation of radioactivity from [(14)C]arginine and [(14)C]ornithine into spermidine and the pyrrolizidine alkaloid senecionine N-oxide. In contrast, α-difluoromethylornithine, a specific ornithine-decarboxylase inhibitor, had no effect on the flow of radioactivity from labelled ornithine and arginine into polyamines and alkaloids. Thus, putrescine, the common precursor of polyamines and pyrrolizidine alkaloids, is exclusively derived via the arginine-agmatine route. Ornithine is rapidly transformed into arginine. Recycling of the guanido moiety of agmatine back to ornithine can be excluded. Putrescine and spermidine were found to be reversibly interconvertable and to excist in a highly dynamic state. In contrast, senecionine N-oxide did not show any turnover but accumulated as a stable metabolic product. In-vivo evidence is presented that the carbon flow from arginine into the polyamine/alkaloid pathway may be controlled by spermidine. The possible importance of the metabolic coupling of pyrrolizidine-alkaloid biosynthesis to polyamine metabolism is discussed.

Entities:  

Year:  1988        PMID: 24221631     DOI: 10.1007/BF00402884

Source DB:  PubMed          Journal:  Planta        ISSN: 0032-0935            Impact factor:   4.116


  14 in total

1.  An improved preparation of tertiary amine N-oxides.

Authors:  J Cymerman Craig; K K Purushothaman
Journal:  J Org Chem       Date:  1970-05       Impact factor: 4.354

2.  Analysis of polyamines in higher plants by high performance liquid chromatography.

Authors:  H E Flores; A W Galston
Journal:  Plant Physiol       Date:  1982-03       Impact factor: 8.340

Review 3.  The pyrrolizidine alkaloids.

Authors:  D J Robins
Journal:  Fortschr Chem Org Naturst       Date:  1982

4.  Activities of arginine and ornithine decarboxylases in various plant species.

Authors:  H Birecka; A J Bitonti; P P McCann
Journal:  Plant Physiol       Date:  1985-10       Impact factor: 8.340

5.  Arginine decarboxylase and polyamines required for embryogenesis in the wild carrot.

Authors:  R P Feirer; G Mignon; J D Litvay
Journal:  Science       Date:  1984-03-30       Impact factor: 47.728

6.  DL-alpha-(Difluoromethyl)arginine: a potent enzyme-activated irreversible inhibitor of bacterial decarboxylases.

Authors:  A Kallio; P P McCann; P Bey
Journal:  Biochemistry       Date:  1981-05-26       Impact factor: 3.162

7.  Reversed-phase ion-pair liquid chromatographic procedure for the simultaneous analysis of S-adenosylmethionine, its metabolites and the natural polyamines.

Authors:  J Wagner; C Danzin; P Mamont
Journal:  J Chromatogr       Date:  1982-02-12

8.  Selective uptake of pyrrolizidine N-oxides by cell suspension cultures from pyrrolizidine alkaloid producing plants.

Authors:  K von Borstel; T Hartmann
Journal:  Plant Cell Rep       Date:  1986-02       Impact factor: 4.570

9.  Alkaloid patterns and biosynthetic capacity of root cultures from some pyrrolizidine alkaloid producing Senecio species.

Authors:  G Toppel; L Witte; B Riebesehl; K V Borstel; T Hartmann
Journal:  Plant Cell Rep       Date:  1987-12       Impact factor: 4.570

10.  Enzymic conversion of agmatine to putrescine in Lathyrus sativus seedlings. Purification and properties of a multifunctional enzyme (putrescine synthase).

Authors:  K S Srivenugopal; P R Adiga
Journal:  J Biol Chem       Date:  1981-09-25       Impact factor: 5.157

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  10 in total

1.  The first step in the biosynthesis of cocaine in Erythroxylum coca: the characterization of arginine and ornithine decarboxylases.

Authors:  Teresa Docimo; Michael Reichelt; Bernd Schneider; Marco Kai; Grit Kunert; Jonathan Gershenzon; John C D'Auria
Journal:  Plant Mol Biol       Date:  2012-02-07       Impact factor: 4.076

2.  Homospermidine synthase, the first pathway-specific enzyme of pyrrolizidine alkaloid biosynthesis, evolved from deoxyhypusine synthase.

Authors:  D Ober; T Hartmann
Journal:  Proc Natl Acad Sci U S A       Date:  1999-12-21       Impact factor: 11.205

3.  Sequestration of ingested [(14)C]senecionineN-oxide in the exocrine defensive secretions of chrysomelid beetles.

Authors:  A Ehmke; M Rowell-Rahier; J M Pasteels; T Hartmann
Journal:  J Chem Ecol       Date:  1991-12       Impact factor: 2.626

4.  Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides in Senecio vulgaris L.

Authors:  T Hartmann; A Ehmke; U Eilert; K von Borstel; C Theuring
Journal:  Planta       Date:  1989-01       Impact factor: 4.116

5.  Cell-specific expression of homospermidine synthase, the entry enzyme of the pyrrolizidine alkaloid pathway in Senecio vernalis, in comparison with its ancestor, deoxyhypusine synthase.

Authors:  Stefanie Moll; Sven Anke; Uwe Kahmann; Robert Hänsch; Thomas Hartmann; Dietrich Ober
Journal:  Plant Physiol       Date:  2002-09       Impact factor: 8.340

6.  Studies on the biosynthesis of tropane alkaloids in Datura stramonium L. transformed root cultures : 2. On the relative contributions of L-arginine and L-ornithine to the formation of the tropane ring.

Authors:  R J Robins; A J Parr; N J Walton
Journal:  Planta       Date:  1991-01       Impact factor: 4.116

7.  Studies on the biosynthesis of tropane alkaloids in Datura stramonium L. transformed root cultures : 1. The kinetics of alkaloid production and the influence of feeding intermediate metabolites.

Authors:  R J Robins; A J Parr; E G Bent; M J Rhodes
Journal:  Planta       Date:  1991-01       Impact factor: 4.116

8.  Phenotypic plasticity of Senecio vulgaris from contrasting habitat types: growth and pyrrolizidine alkaloid formation.

Authors:  P M Frischknecht; K Schuhmacher; H Müller-Schärer; T W Baumann
Journal:  J Chem Ecol       Date:  2001-02       Impact factor: 2.626

9.  Lepidoptera and pyrrolizidine alkaloids Exemplification of complexity in chemical ecology.

Authors:  M Boppré
Journal:  J Chem Ecol       Date:  1990-01       Impact factor: 2.626

10.  Homospermidine in transgenic tobacco results in considerably reduced spermidine levels but is not converted to pyrrolizidine alkaloid precursors.

Authors:  Mohamed I S Abdelhady; Till Beuerle; Dietrich Ober
Journal:  Plant Mol Biol       Date:  2009-06-21       Impact factor: 4.076

  10 in total

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