Anagyrine

Anagyrine is an alkaloid that has been found in L. albus and has diverse biological activities.^1,2,3 It binds to muscarinic and nicotinic acetylcholine receptors (AChRs) with IC₅₀ values of 132 and 2,096 µM, respectively, in radioligand binding assays using pig brain membranes, which endogenously express high levels of the receptors.¹ It inhibits proliferation of TE 671 and SH-SY5Y cancer cells (EC₅₀s = 18.1 and 19.1 µM, respectively).³ Maternal ingestion of anagyrine during gestation is associated with the teratogenic condition crooked calf disease in cattle.⁴

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1. Schmeller, T., Sauerwein, M., Sporer, F., et al. Binding of quinolizidine alkaloids to nicotinic and muscarinic acetylcholine receptors. J. Nat. Prod. 57(9), 1316-1319 (1994).

2. Matsuda, K., Kimura, K., Komai, K., et al. Nematicidal activities of (–)-N-methylcytisine and (–)-anagyrine from Sophora flavescens against pine wood nematodes. Agr. BioI. Chem. 53(8), 2287-2288 (1989).

3. Green, B.T., Lee, S.T., Panter, K.E., et al. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol. Teratol. 32(3), 383-390 (2010).

4. Keeler, R.F., Cronin, E.H., and Shupe, J.L. Lupin alkaloids from teratogenic and nonteratogenic lupins. IV. Concentration of total alkaloids, individual major alkaloids, and the teratogen anagyrine as a function of plant part and stage of growth and their relationship to crooked calf disease. J. Toxicol. Environ. Health 1(6), 899-908 (1976).