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Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities

Journal Article


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Abstract


  • A concise synthesis of (−)-steviamine is reported along with the synthesis of its analogues 10-nor-steviamine, 10-nor-ent-steviamine and 5-epi-ent-steviamine. These compounds were tested against twelve glycosidases (at 143 μg mL−1 concentrations) and were found to have in general poor inhibitory activity against most enzymes. The 10-nor analogues however, showed 50–54% inhibition of α-L-rhamnosidase from Penicillium decumbens while one of these, 10-nor-steviamine, showed 51% inhibition of N-acetyl-β-D-glucosaminidase (from Jack bean) at the same concentration (760 μM).

UOW Authors


  •   Jiangseubchatveera, Nadechanok (external author)
  •   Bouillon, Marc E. (external author)
  •   Liawruangrath, Boonsom (external author)
  •   Liawruangrath, Saisunee (external author)
  •   Nash, Robert J. (external author)
  •   Pyne, Stephen

Publication Date


  • 2013

Citation


  • Jiangseubchatveera, N., Bouillon, M. E., Liawruangrath, B., Liawruangrath, S., Nash, R. J. & Pyne, S. G. (2013). Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities. Organic and Biomolecular Chemistry, 11 (23), 3826-3833.

Scopus Eid


  • 2-s2.0-84884564713

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1879&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/866

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 3826

End Page


  • 3833

Volume


  • 11

Issue


  • 23

Place Of Publication


  • United Kingdom

Abstract


  • A concise synthesis of (−)-steviamine is reported along with the synthesis of its analogues 10-nor-steviamine, 10-nor-ent-steviamine and 5-epi-ent-steviamine. These compounds were tested against twelve glycosidases (at 143 μg mL−1 concentrations) and were found to have in general poor inhibitory activity against most enzymes. The 10-nor analogues however, showed 50–54% inhibition of α-L-rhamnosidase from Penicillium decumbens while one of these, 10-nor-steviamine, showed 51% inhibition of N-acetyl-β-D-glucosaminidase (from Jack bean) at the same concentration (760 μM).

UOW Authors


  •   Jiangseubchatveera, Nadechanok (external author)
  •   Bouillon, Marc E. (external author)
  •   Liawruangrath, Boonsom (external author)
  •   Liawruangrath, Saisunee (external author)
  •   Nash, Robert J. (external author)
  •   Pyne, Stephen

Publication Date


  • 2013

Citation


  • Jiangseubchatveera, N., Bouillon, M. E., Liawruangrath, B., Liawruangrath, S., Nash, R. J. & Pyne, S. G. (2013). Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities. Organic and Biomolecular Chemistry, 11 (23), 3826-3833.

Scopus Eid


  • 2-s2.0-84884564713

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=1879&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/866

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 3826

End Page


  • 3833

Volume


  • 11

Issue


  • 23

Place Of Publication


  • United Kingdom