The biosynthesis of retronecine

Grue-Sørensen, Gunnar; Spenser, Ian D.

doi:10.1139/v82-095

Cited by 28 publications

(7 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The sample of cadaverine, intramolecularly doubly labelled ("bond-labelled") with I3C and "N (Experiment 5) was prepared in three steps from sodium ("C,"N)cyanide and 1-bromo-4-phthalimidobutane by the reaction sequence shown in Scheme 2, in analogy with the preparation of a similarly labelled sample of putrescine (10).…”

Section: Methods and Resultsmentioning

confidence: 99%

Biosynthesis of the lupine alkaloids. I. Lupinine

Golebiewski¹,

Spenser²

1985

Can. J. Chem.

Self Cite

View full text Add to dashboard Cite

The mode of incorporation into lupinine of cadaverine, intramolecularly doubly labelled with,15N and with,13C at the C-atom adjacent to 15N, i.e., 13C, 15N-"bond-labelled", was determined by,13C nmr spectroscopy; lupinine is generated from two cadaverine-derived C5-units by a route which excludes a "dimeric" intermediate with C2v symmetry. The mode of incorporation of 2H from L-(2-2H)lysine, from (R)- and (S)-(1-2H)cadaverine, and from (2-2H)-Δ1-piperideine into lupinine was determined by 2H nmr spectroscopy. The results corroborate the conclusions from the 13C,15N experiment and they establish the stereochemistry of six of the steps in the biosynthetic conversion of L-lysine into lupinine.

show abstract

Section: Methods and Resultsmentioning

confidence: 99%

Biosynthesis of the lupine alkaloids. I. Lupinine

Golebiewski¹,

Spenser²

1985

Can. J. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Thus, two molecules of [ 1 ,5-"C2]cadaverine are incorporated into lupinine (1) with about 1/4 of the radioactivity at C-11 , and about Y2 at C-(4 + 6).2 This labelling pattern is analogous to that obtained for the pyrrolizidine alkaloid retronecine with [ 1 ,4-14C2]putrescine3 and, in more detail, with W-labelled putrescines. 4 The use of [13C-'5N] doubly labelled putrescine indicated that retronecine is derived from a later C4-N-C4 symmetrical intermediate ,536 and this intermediate was shown to be homospermidine (6). 537 We now present evidence that the analogous N-(5-aminopentyl)-l,5-diaminopentane (7) is not an intermediate in lupinine biosynthesis.…”

mentioning

confidence: 80%

Quinolizidine alkaloid biosynthesis: incorporation of [1-amino-15N, 1-13C]cadaverine into lupinine

Rana¹,

Robins²

1984

J. Chem. Soc., Chem. Commun.

View full text Add to dashboard Cite

“…Finally, feeding Senecio isatideus with [1,2- 13 C 2 ]-putrescine gave rise to four pairs of doublets, namely C-1/C-9, C-2/C-3, C-5/C6 and C-7/C-8, with four different coupling constants (Figure 7C). To investigate which C-N bond remains intact during retronecine biosynthesis [1- 15 N,1- 13 C], double labeled putrescine was synthesized and fed to Senecio vulgaris [66,67] or Senecio isatideus [58,65]. Analysis of the necine base showed an equal amount of retronecine with a 15 N and a 13 C label at C-3 and retronecine with a 15 N and a 13 C label at C-5 (Figure 7D).…”

Section: Biosynthesis Of Pyrrolizidine Alkaloidsmentioning

confidence: 99%

Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants

2019

View full text Add to dashboard Cite

Pyrrolizidine alkaloids (PAs) are heterocyclic secondary metabolites with a typical pyrrolizidine motif predominantly produced by plants as defense chemicals against herbivores. They display a wide structural diversity and occur in a vast number of species with novel structures and occurrences continuously being discovered. These alkaloids exhibit strong hepatotoxic, genotoxic, cytotoxic, tumorigenic, and neurotoxic activities, and thereby pose a serious threat to the health of humans since they are known contaminants of foods including grain, milk, honey, and eggs, as well as plant derived pharmaceuticals and food supplements. Livestock and fodder can be affected due to PA-containing plants on pastures and fields. Despite their importance as toxic contaminants of agricultural products, there is limited knowledge about their biosynthesis. While the intermediates were well defined by feeding experiments, only one enzyme involved in PA biosynthesis has been characterized so far, the homospermidine synthase catalyzing the first committed step in PA biosynthesis. This review gives an overview about structural diversity of PAs, biosynthetic pathways of necine base, and necic acid formation and how PA accumulation is regulated. Furthermore, we discuss their role in plant ecology and their modes of toxicity towards humans and animals. Finally, several examples of PA-producing crop plants are discussed.

show abstract

The biosynthesis of retronecine

Cited by 28 publications

References 27 publications

Biosynthesis of the lupine alkaloids. I. Lupinine

Biosynthesis of the lupine alkaloids. I. Lupinine

Quinolizidine alkaloid biosynthesis: incorporation of [1-amino-15N, 1-13C]cadaverine into lupinine

Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants

Contact Info

Product

Resources

About