Abstract
GLC-MS analysis has been developed for screening plants of the family Solanaceae for new calystegines. GLC-MS analyses of the extract of Scopolia japonica showed the presence of a new tetrahydroxy- nor-tropane alkaloid in addition to the known calystegines A 3, A 5, B 1, B 2, B 3, and C 1. We gave this new alkaloid the trivial name calystegine B 4. The structure of calystegine B 4 was determined as 1α,2β,3α,4α-tetrahydroxy- nor-tropane from a variety of NMR spectral data. Calystegines B 1, B 2, and C 1 are potent competitive inhibitors with K i values ranging from 10 −6 to 10 −7 M for almond β-glucosidase, while calystegine B 4 inhibited this enzyme in a competitive manner, with a K i value of 7.3 μM. Calystegine B 2 is also a potent inhibitor of green coffee bean α-galactosidase, whereas calystegine B 4 exhibited no significant activity for this enzyme. Among rat intestinal glycosidases, only trehalase was potently inhibited by calystegine B 4, with an IC 50 value of 9.8 μM. Furthermore, calystegine B 4 potently inhibited pig kidney trehalase in a competitive manner, with a K i value of 1.2 μM, but it was almost inactive against yeast and fungal trehalases.
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