α-Glucosidase inhibitory and nitric oxide production inhibitory activities of alkaloids isolated from a twig extract of Polyalthia cinnamomea

  • Bioorg Med Chem. 2020 May 15;28(10):115462. doi: 10.1016/j.bmc.2020.115462.
Virayu Suthiphasilp  1 ,  Wisanu Maneerat  2 ,  Narawadee Rujanapun  3 ,  Thidarat Duangyod  3 ,  Rawiwan Charoensup  3 ,  Suwanna Deachathai  1 ,  Raymond J Andersen  4 ,  Brian O Patrick  4 ,  Stephen G Pyne  5 ,  Surat Laphookhieo  6
Affiliations
  • 1. Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand.
  • 2. Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand; Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai 57100, Thailand.
  • 3. Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai 57100, Thailand; School of Integrative Medicine, Mae Fah Luang University, Chiang Rai 57100, Thailand.
  • 4. Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.
  • 5. School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales 2522, Australia.
  • 6. Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand. Electronic address: [email protected].
PMID: 32247751 DOI: 10.1016/j.bmc.2020.115462
Abstract

The first phytochemical investigation of Polyalthia cinnamomea led to the isolation and identification of two new oxoprotoberberine Alkaloids, (-)-(13aS)-polyalthiacinnamines A and B, together with eleven known compounds. The structures of the new compounds were elucidated by extensive spectroscopic methods. The absolute configuration of miliusacunine E and consanguine B was established by X-ray diffraction analysis using Cu Kα radiation and ECD spectra, whereas the absolute configurations of polyalthiacinnamines A and B were established by comparison of their ECD spectra and specific rotations with those of miliusacunine E and consanguine B. Compounds 1-4, 6, and 8 exhibited α-glucosidase inhibitory activities (IC50 values ranging from 11.3 to 57.9 µM) better than a positive control (acarbose, IC50 83.5 μM). Compound 2 also exhibited NO production inhibitory activity with an IC50 value of 24.4 μM (indomethacin, a positive control, IC50 = 32.2 μM).

Keywords
NO production inhibitory activity; Oxoprotoberberine alkaloids; Polyalthia cinnamomea; α-Glucosidase inhibitory activity.
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