Synthesis of Conjugates of the Alkaloids Cytisine and Lupinine

Mironets, R. V.; Garazd, Ya. L.; Garazd, M. M.

doi:10.1007/s10600-019-02907-0

Cited by 3 publications

(1 citation statement)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another important motivation for this effort is the desired biological activity that QAs have demonstrated in multiple studies [ 35 ]. Many QAs show beneficial and desired qualities such as antioxidant, antimicrobial, anti-carcinogenic, and anti-inflammatory activities [ 23 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 ]. However, several individual alkaloids, especially sparteine, anagyrine, and cysteine, have undesired or even toxic activity, thus their concentrations in edible lupins must be strongly regulated [ 4 , 47 ].…”

Section: Discussionmentioning

confidence: 99%

New Analytical Approach to Quinolizidine Alkaloids and Their Assumed Biosynthesis Pathways in Lupin Seeds

Namdar,

Mulder,

Ben-Simchon

et al. 2024

Toxins

View full text Add to dashboard Cite

Alkaloids play an essential role in protecting plants against herbivores. Humans can also benefit from the pharmacological effects of these compounds. Plants produce an immense variety of structurally different alkaloids, including quinolizidine alkaloids, a group of bi-, tri-, and tetracyclic compounds produced by Lupinus species. Various lupin species produce different alkaloid profiles. To study the composition of quinolizidine alkaloids in lupin seeds, we collected 31 populations of two wild species native to Israel, L. pilosus and L. palaestinus, and analyzed their quinolizidine alkaloid contents. Our goal was to study the alkaloid profiles of these two wild species to better understand the challenges and prospective uses of wild lupins. We compared their profiles with those of other commercial and wild lupin species. To this end, a straightforward method for extracting alkaloids from seeds and determining the quinolizidine alkaloid profile by LC–MS/MS was developed and validated in-house. For the quantification of quinolizidine alkaloids, 15 analytical reference standards were used. We used GC–MS to verify and cross-reference the identity of certain alkaloids for which no analytical standards were available. The results enabled further exploration of quinolizidine alkaloid biosynthesis. We reviewed and re-analyzed the suggested quinolizidine alkaloid biosynthesis pathway, including the relationship between the amino acid precursor l-lysine and the different quinolizidine alkaloids occurring in seeds of lupin species. Revealing alkaloid compositions and highlighting some aspects of their formation pathway are important steps in evaluating the use of wild lupins as a novel legume crop.

show abstract

Section: Discussionmentioning

confidence: 99%

New Analytical Approach to Quinolizidine Alkaloids and Their Assumed Biosynthesis Pathways in Lupin Seeds

Namdar,

Mulder,

Ben-Simchon

et al. 2024

Toxins

View full text Add to dashboard Cite

show abstract

Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine

Nurmaganbetov

Savelyev

Gatilov

et al. 2021

Chem Heterocycl Comp

View full text Add to dashboard Cite

A Pyridine Dearomatization Approach for the Gram Scale Synthesis of (±)-Sparteine

Lam,

Kerkovius,

Reisman

2023

Org. Lett.

View full text Add to dashboard Cite

Both enantiomers of sparteine have suffered from pricing and supply chain variability, which has inspired efforts toward efficient chemical synthesis. Here, we build upon our reported synthesis of the matrine-type lupin alkaloids in order to synthesize (±)-sparteine. Specifically, selective quenching of the cyclization between glutaryl chloride and pyridine with methanol provides a functionalized quinolizidine core that was elaborated to (±)-sparteine in six additional steps on gram scale. This synthesis provides a scalable route to sparteine from inexpensive commodity chemicals utilizing a dearomative cyclization. In addition, this route provides concise access to (±)-lupinine.

show abstract

Synthesis of Conjugates of the Alkaloids Cytisine and Lupinine

Cited by 3 publications

References 31 publications

New Analytical Approach to Quinolizidine Alkaloids and Their Assumed Biosynthesis Pathways in Lupin Seeds

New Analytical Approach to Quinolizidine Alkaloids and Their Assumed Biosynthesis Pathways in Lupin Seeds

Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine

A Pyridine Dearomatization Approach for the Gram Scale Synthesis of (±)-Sparteine

Contact Info

Product

Resources

About