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Chemical Compound Review:

Cyclophellitol (1R,2R,3R,4S,5R,6S)-2- (hydroxymethyl)-7...

Synonyms: Cylcophellitol, Epi-cpl, CHEMBL35576, AG-K-76798, KST-1A1535, ...

Atsumi, S. et al., Atsumi, S. et al., Withers, S.G. et al., Gloster, T.M. et al., Atsumi, S. et al.

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of Cyclophellitol

Inhibition of experimental metastasis by an alpha-glucosidase inhibitor, 1,6-epi-cyclophellitol [1].
Daily administration of cyclophellitol induces a severe abnormality of the nervous system in mice while it has no toxicity in various cultured cells [2].
The high specificity of this inactivator is evidenced by the fact that even at very high (12 mM) concentrations of cyclophellitol, no inactivation of yeast alpha-glucosidase was observed, and only extremely slow (t1/2 greater than 5 hours) inactivation of E. coli beta-galactosidase could be detected [3].

High impact information on Cyclophellitol

After a single administration of cyclophellitol the maximal inhibition of glucocerebrosidase was observed within 30 min in brain and liver, and the inhibition lasted for 2-4 days [2].
Cyclophellitol was inactive against yeast alpha-glucosidase, beta-galactosidase, beta-glucuronidase, alpha-L-fucosidase, end-beta-N-acetyl glucosaminidase, alpha-mannosidase, and cellulase [4].
The structural basis for beta-glucosidase inhibition by cyclophellitol is demonstrated using X-ray crystallography, enzyme kinetics and mass spectrometry [5].

References

Inhibition of experimental metastasis by an alpha-glucosidase inhibitor, 1,6-epi-cyclophellitol. Atsumi, S., Nosaka, C., Ochi, Y., Iinuma, H., Umezawa, K. Cancer Res. (1993) [Pubmed]
Inhibition of glucocerebrosidase and induction of neural abnormality by cyclophellitol in mice. Atsumi, S., Nosaka, C., Iinuma, H., Umezawa, K. Arch. Biochem. Biophys. (1992) [Pubmed]
Cyclophellitol: a naturally occurring mechanism-based inactivator of beta-glucosidases. Withers, S.G., Umezawa, K. Biochem. Biophys. Res. Commun. (1991) [Pubmed]
Biological activities of cyclophellitol. Atsumi, S., Iinuma, H., Nosaka, C., Umezawa, K. J. Antibiot. (1990) [Pubmed]
Structural basis for cyclophellitol inhibition of a beta-glucosidase. Gloster, T.M., Madsen, R., Davies, G.J. Org. Biomol. Chem. (2007) [Pubmed]

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