Alkaloids and Styryl lactones from <i>Goniothalamus ridleyi</i> King and Their <i>α</i>-Glucosidase Inhibitory Activity
Isaraporn Polbuppha,
Passakorn Teerapongpisan,
Piyaporn Phukhatmuen,
Virayu Suthiphasilp,
Tharakorn Maneerat,
Rawiwan Charoensup,
Raymond J. Andersen,
Surat Laphookhieo
Affiliations
Isaraporn Polbuppha
Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand
Passakorn Teerapongpisan
Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand
Piyaporn Phukhatmuen
Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand
Virayu Suthiphasilp
Department of Industrial Technology and Innovation Management, Faculty of Science and Technology, Pathumwan Institute of Technology, Bangkok 10330, Thailand
Tharakorn Maneerat
Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand
Rawiwan Charoensup
Medicinal Plant Innovation Center, Mae Fah Luang University, Chiang Rai 57100, Thailand
Raymond J. Andersen
Department of Chemistry and Department of Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036, Main Mall, Vancouver, BC V6T 1Z1, Canada
Surat Laphookhieo
Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand
Gonioridleylactam (1), a new compound, is a unique dimeric aristolactam isolated from the EtOAc extract of the twigs of Goniothalamus ridleyi King. The structure of gonioridleylactam (1) consists of two different aristolactams linked together with two methylenedioxy bridges at C–3/C–3′ and C–4/C–4′, generating a ten-membered ring of [1,3,6,8]tetraoxecine. A new natural product, gonioridleyindole (3-hydroxymethyl-1-methyl-1H-benz[f]indole-4,9-dione, 2), together with eight known compounds (3–10) were also isolated from this plant. Their structures were extensively characterized by spectroscopic methods and comparisons were made with the literature. Compounds 1–4, 7, and 9 were evaluated for their α-glucosidase inhibitory activity. Of these, 3,5-demethoxypiperolide (7) displayed the highest α-glucosidase inhibitory activity, with an IC50 value of 1.25 µM.
