Australine (hydrochloride)

Australine is a pyrrolizidine alkaloid originally isolated from C. australe that has enzyme inhibitory activities.^1,2,3 It is an inhibitor of glucoamylase (IC₅₀ = 5.8 µM) that also inhibits glucosidase I, sucrase, maltase, and A. niger α-glucosidase (IC₅₀s = 20, 28, 35, and 28 µM, respectively).^2,3 Australine is selective for these enzymes over glucosidase II, α- and β-mannosidase, and α- and β-galactosidase up to 500 µM, β-glucosidase, with only 5% inhibition at 66 µM, as well as isomaltase and trehalase (IC₅₀ = 97 and 160 µM, respectively). Australine (500 µg/ml) inhibits glycoprotein processing of viral glycoproteins in influenza virus-infected MDCK cells and induces the accumulation of glycoproteins.²

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1. Molyneux, R.J., Benson, M., Wong, R.Y., et al. Australine, a novel pyrrolizidine alkaloid glucosidase inhibitor from Castanospermum austral. J. Nat. Prod. 51(6), 1198-1206 (1988).

2. Tropea, J.E., Molyneux, R.J., Kaushal, G.P., et al. Australine, a pyrrolizidine alkaloid that inhibits amyloglucosidase and glycoprotein processing. Biochemistry 28(5), 2027-2034 (1989).

3. Kato, A., Kano, E., Adachi, I., et al. Australine and related alkaloids: easy structural confirmation by ¹³C NMR spectral data and biological activities. Tetrahedron Asymmetry 14(3), 325-331 (2003).