Anagyrine (Synonyms: Monolupine)

Anagyrine is an alkaloid that has been found in L. albus and has nematocidal and anticancer 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 that endogenously express high levels of the receptors.¹ Anagyrine decreases survival of B. xylophilus worms.² 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

1.Schmeller, T., Sauerwein, M., Sporer, F., et al.Binding of quinolizidine alkaloids to nicotinic and muscarinic acetylcholine receptorsJ. 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 nematodesAgr. 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 receptorsNeurotoxicol. 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 diseaseJ. Toxicol. Environ. Health1(6)899-908(1976)