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

Rana, Jatinder; Robins, David J.

doi:10.1039/c39840000081

Cited by 7 publications

(5 citation statements)

References 2 publications

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“…A sample of the latter, intramolecularly doubly I3C,lSN labelled (NH2-CH2-CH2-CH~-CH~-'~CH~-'~NH~), was employed to probe the in- corporation of an intact C-N bond into lupinine (Experiment 5) (1 1). A similar experiment, with essentially identical results and conclusions, was reported in an independent investigation (14). Entry of this bond-labelled cadaverine, via 5-aminopentanal, by route Bd or Be (Scheme l), should yield a single species of intramolecularly I3C,lSN doubly labelled product in which the I3C,l5N moiety is located at the C-6,N position of lupinine.…”

Section: Figsupporting

confidence: 58%

“…The less intense set of signals shows two signals at 6 40.0 and 44.6 ppm. Signals in this spectral region are absent from the spectra of the trans fused free base (14)(15)(16)(17)(18) or the trans fused salt (15) but are present in the cis fused salt (15). The signal set of lower intensity is thus due to the cis fused salt, which is the less abundant (ca.…”

Section: Figmentioning

confidence: 95%

“…The two experiments with enantiotopically deuteriated (l-2H)cadaverine thus clarify the hidden stereochemistry of four steps in the biosynthetic sequence. The overt stereochemistry at C-1 and C-10 of lupinine is determined in the dimerization step (step b, Schemes 4 and 5) that leads from A'-piperideine (4) into tetrahydroanabasine (14).…”

Section: Figmentioning

confidence: 99%

“…This intermediate was favoured also by Robert Robinson (4). In a further variation of this theme it was suggested (5,6) that lupinine arose by rearrangement of tetrahydroanabasine (14), a dimer of A'-piperideine (4) (3, 5) (Scheme 1Be).…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of the lupine alkaloids. I. Lupinine

Golebiewski¹,

Spenser²

1985

Can. J. Chem.

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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.

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Section: Figsupporting

confidence: 58%

Section: Figmentioning

confidence: 95%

Section: Figmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of the lupine alkaloids. I. Lupinine

Golebiewski¹,

Spenser²

1985

Can. J. Chem.

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“…The most likely explanation is that an intermediate common to both sparteine and lupanine exists, which could be a dehydrosparteine (36,38). For lupinine biosynthesis see (30,31,34,94,95,99). For the biosynthesis of the cytisine-type alkaloids it has been postulated that lupanine is converted into 5,6-dehydrolupanine which is further oxidized to anagyrine, rhombifoline, cytisine and N-methylcytisine (37).…”

Section: Structural Typesmentioning

confidence: 99%

Quinolizidine Alkaloids: Biochemistry, Metabolism, and Function in Plants and Cell Suspension Cultures

Wink¹

1987

Planta Med

118

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Quinolizidine alkaloids constitute about 2% of the alkaloids that are known from plants. In this report, data on chromatography (TLC, cGLC), spectroscopy (MS, NMR), occurrence, biosynthesis (tracer studies, enzymatic experiments), accumulation, transport, degradation, biological activities (pharmacology, chemical ecology), and alkaloid formation in cell cultures are reviewed.Quinolizidine alkaloids (QA) have been studied in a number of laboratories during the last 100 years. Although of minor pharmaceutical importance (sparteine is used as an antiarrhythmic compound), interest in this group of alkaloids has increased within the last 15 years, which can be seen in the growing number of articles and reviews in this field (7,8,24,58,(91)(92)(93).It is not my intention in this review to cover the literature exhaustively, but rather to present an overview of the most significant and interesting aspects of QA biosynthesis and QA metabolism in plants and cell suspension cultures.

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Secondary Plant Substances: Ornithine-Derived Alkaloids

Schütte

1994

Progress in Botany

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

Cited by 7 publications

References 2 publications

Biosynthesis of the lupine alkaloids. I. Lupinine

Biosynthesis of the lupine alkaloids. I. Lupinine

Quinolizidine Alkaloids: Biochemistry, Metabolism, and Function in Plants and Cell Suspension Cultures

Secondary Plant Substances: Ornithine-Derived Alkaloids

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