Calystegine B4, a novel trehalase inhibitor from Scopolia japonica

Carbohydrate Research
N AsanoR J Nash

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 A3, A5, B1, B2, B3, and C1. We gave this new alkaloid the trivial name calystegine B4. The structure of calystegine B4 was determined as 1 alpha, 2 beta, 3 alpha, 4 alpha-tetrahydroxy-nor-tropane from a variety of NMR spectral data. Calystegines B1, B2, and C1 are potent competitive inhibitors with Ki values ranging from 10(-6) to 10(-7) M for almond beta-glucosidase, while calystegine B4 inhibited this enzyme in a competitive manner, with a Ki value of 7.3 microM. Calystegine B2 is also a potent inhibitor of green coffee bean alpha-galactosidase, whereas calystegine B4 exhibited no significant activity for this enzyme. Among rat intestinal glycosidases, only trehalase was potently inhibited by calystegine B4, with an IC50 value of 9.8 microM. Furthermore, calystegine B4 potently inhibited pig kidney trehalase in a competitive manner, with a Ki value of 1.2 microM, but it was almost inactive against yeast and fungal trehalases.

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Citations

Sep 15, 2001·Phytochemistry·K BekkoucheP Christen
Sep 19, 2002·Molecular Plant-microbe Interactions : MPMI·Michael A SavkaSilvia Rossbach
Nov 26, 2010·Plant Physiology·Duncan StanleyAlison M Smith
Mar 5, 2016·Toxins·Szymon ChowańskiSabino A Bufo
Mar 26, 2004·Natural Product Reports·Birgit Dräger
May 11, 2016·Organic & Biomolecular Chemistry·Hong-Yao WangChu-Yi Yu
May 2, 2012·Organic & Biomolecular Chemistry·Akio KamimuraHidemitsu Uno
Jul 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Camilla MatassiniFrancesca Cardona
Mar 15, 2003·The Journal of Organic Chemistry·Philip R Skaanderup, Robert Madsen
Nov 10, 2001·The Journal of Organic Chemistry·M I García-MorenoJ M García Fernández

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