A Concise Asymmetric Total Synthesis of (+)-Epilupinine

Tsutsumi, Toshihiko; Karanjit, Sangita; Nakayama, Atsushi; Namba, Kosuke

doi:10.1021/acs.orglett.9b00607

Cited by 6 publications

(1 citation statement)

References 69 publications

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“…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

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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.

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