Biosynthesis of the lupine alkaloids. I. Lupinine

Golebiewski, W. Marek; Spenser, Ian D.

doi:10.1139/v85-450

Cited by 33 publications

(24 citation statements)

References 13 publications

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“…In six further experiments (expts. 1-6), details of which have been reported (37), samples of the same three substrates, labelled with radioactive (expt. 6) or stable isotopes (expts.…”

Section: Methods and Resultsmentioning

confidence: 99%

“…1-5), were administered to Lupinus luteus, from which labelled samples of lupinine and sparteine were isolated. These experiments have been fully described in the first paper of this series (37), which dealt with the biosynthesis of lupinine. The incorporation of label into samples of sparteine obtained in these experiments will be discussed in the present context.…”

Section: Methods and Resultsmentioning

confidence: 99%

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Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Golebiewski¹,

Spenser²

1988

Can. J. Chem.

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Contrary to predictions based on earlier observations, it is now found that label from DL-[6-14C]lysine and from [6-14C]-Δ1-piperideine does not enter the three C5 segments of lupanine with equal efficiency. One of the C5 segments is labelled at a significantly higher level than the other two C5 segments, which show identical levels of labelling. A new biogenetic model is proposed, which is consistent with these new findings as well as with all other regio- and stereochemical evidence on the mode of incorporation of precursors that is available.

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“…In six further experiments (expts. 1-6), details of which have been reported (37), samples of the same three substrates, labelled with radioactive (expt. 6) or stable isotopes (expts.…”

Section: Methods and Resultsmentioning

confidence: 99%

Section: Methods and Resultsmentioning

confidence: 99%

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Golebiewski¹,

Spenser²

1988

Can. J. Chem.

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“…5-Aminopentanal is also spontaneously cyclized into D 1 -piperideine, which has been demonstrated as the biosynthetic intermediate for several Lys-derived alkaloids including quinolizidine, lycopodium and piperidine through isotope tracing (Braekman et al, 1972;Leeper et al, 1981;Golebiewski and Spenser, 1985) and computational chemistry-based predictions (Sato et al, 2018). Interestingly, MS/MS-based structure predictions using MS-FINDER annotated several specific metabolite features as Lys-derived alkaloids, including slaframine (HI_11.19/ 199.1442) and (R)-pelletierine (RP_5.12/142.1226 andHI_7.37/142.1228), both of which were labeled by feeding with stable isotope-labeled L-lysine (Figure 4c; Table S5).…”

Section: Cadaverine Catabolic Pathway In Arabidopsis Emerged By Ectopmentioning

confidence: 99%

“…In plants, cadaverine is catabolized by copper-containing amine oxidase (CuAO) to produce 5-aminopentanal. 5-Aminopentanal undergoes further spontaneous cyclization, resulting in D 1 -piperideine, which serves as a universal intermediate of diverse Lys-derived alkaloids (Braekman et al, 1972;Leeper et al, 1981;Golebiewski and Spenser, 1985;Sato et al, 2018). In addition, cadaverine is also known to be associated with a wide range of plant physiological phenomena, such as growth, development, stress responses and cellular signaling (Smith and Wilshire, 1975;Kuznetsov et al, 2007;Tomar et al, 2013a,b;Jancewicz et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Metabolic diversification of nitrogen‐containing metabolites by the expression of a heterologous lysine decarboxylase gene in Arabidopsis

et al. 2019

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Summary Lysine decarboxylase converts l‐lysine to cadaverine as a branching point for the biosynthesis of plant Lys‐derived alkaloids. Although cadaverine contributes towards the biosynthesis of Lys‐derived alkaloids, its catabolism, including metabolic intermediates and the enzymes involved, is not known. Here, we generated transgenic Arabidopsis lines by expressing an exogenous lysine/ornithine decarboxylase gene from Lupinus angustifolius (La‐L/ODC) and identified cadaverine‐derived metabolites as the products of the emerged biosynthetic pathway. Through untargeted metabolic profiling, we observed the upregulation of polyamine metabolism, phenylpropanoid biosynthesis and the biosynthesis of several Lys‐derived alkaloids in the transgenic lines. Moreover, we found several cadaverine‐derived metabolites specifically detected in the transgenic lines compared with the non‐transformed control. Among these, three specific metabolites were identified and confirmed as 5‐aminopentanal, 5‐aminopentanoate and δ‐valerolactam. Cadaverine catabolism in a representative transgenic line (DC29) was traced by feeding stable isotope‐labeled [α‐15N]‐ or [ε‐15N]‐l‐lysine. Our results show similar 15N incorporation ratios from both isotopomers for the specific metabolite features identified, indicating that these metabolites were synthesized via the symmetric structure of cadaverine. We propose biosynthetic pathways for the metabolites on the basis of metabolite chemistry and enzymes known or identified through catalyzing specific biochemical reactions in this study. Our study shows that this pool of enzymes with promiscuous activities is the driving force for metabolite diversification in plants. Thus, this study not only provides valuable information for understanding the catabolic mechanism of cadaverine but also demonstrates that cadaverine accumulation is one of the factors to expand plant chemodiversity, which may lead to the emergence of Lys‐derived alkaloid biosynthesis.

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“…Our interest in the synthesis of lupine and Nitraria alkaloids based on biosynthetic pathways (Wanner and Koomen [4] and [5]) and the fact that diamine oxidases play an important role in these biosynthetic pathways ( [6] and [7]) led us to examine the interaction of diamine oxidase with the recently isolated alkaloid nazlinin (1-(4-butylamino)Zl,2,3,4-tetrahydro-fl-carboline) (1) and its derivatives 1-(4-butylamino)-3,4-dihydro-/3-carboline (2) and l-(4-butylamino)-/3-carboline (3). (see Fig.…”

Section: R -Cho + H202 + Nhmentioning

confidence: 99%

Inhibition of pig kidney diamine oxidase by nazlinin and nazlinin derivatives

Cheng

Dekker

Gelder

et al. 1995

Biochimica et Biophysica Acta (BBA) - Protein Structure and Mol

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Nazlinin (1-(4-butylamino)-l,2,3,4-tetrahydro-/3-carboline) (1), an alkaloid recently isolated from Nitraria schoberi, and its two derivatives, 1-(4-butylamino)-3,4-dihydro-fl-carboline (2) and 1-(4-butylamino)-fl-carboline (3), were synthesized and their interaction with pig kidney diamine oxidase (PKDO) was studied. Nazlinin appeared to be a very poor substrate while 3 was a good substrate with an apparent K m of 9.3" 10 -5 M. The enzyme was inhibited by 1 and 2. With both compounds the mode of inhibition found was non-competitive and inhibition constants calculated from the slopes and intercepts of double-reciprocal plots show that 2 is a much more potent inhibitor than the natural product. The relationship between the structure of these compounds and the results found is discussed.

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Biosynthesis of the lupine alkaloids. I. Lupinine

Cited by 33 publications

References 13 publications

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Metabolic diversification of nitrogen‐containing metabolites by the expression of a heterologous lysine decarboxylase gene in Arabidopsis

Inhibition of pig kidney diamine oxidase by nazlinin and nazlinin derivatives

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