Styryl lactone derivatives and aristolactam alkaloids from Goniothalamus tapis Miq. and their α-glucosidase inhibitory activity

Piyaporn Phukhatmuen; Passakorn Teerapongpisan; Virayu Suthiphasilp; Tharakorn Maneerat; Thidarat Duangyod; Rawiwan Charoensup; Sarot Cheenpracha; Jin-Lin Zhu; Yan Alexander Wang; Suwanna Deachathai; Raymond J Andersen; Surat Laphookhieo

doi:10.1080/14786419.2024.2306172

Styryl lactone derivatives and aristolactam alkaloids from Goniothalamus tapis Miq. and their α-glucosidase inhibitory activity

Nat Prod Res. 2024 Jan 30:1-9. doi: 10.1080/14786419.2024.2306172. Online ahead of print.

Authors

Piyaporn Phukhatmuen¹, Passakorn Teerapongpisan², Virayu Suthiphasilp³, Tharakorn Maneerat^{2

4}, Thidarat Duangyod^{1

4}, Rawiwan Charoensup^{1

4}, Sarot Cheenpracha⁵, Jin-Lin Zhu⁶, Yan Alexander Wang⁶, Suwanna Deachathai², Raymond J Andersen^{6

7}, Surat Laphookhieo^{2

4}

Affiliations

¹ School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, Thailand.
² Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, Thailand.
³ Department of Industrial Technology and Innovation Management, Faculty of Science and Technology, Pathumwan Institute of Technology, Bangkok, Thailand.
⁴ Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, Thailand.
⁵ Division of Chemistry, School of Science, University of Phayao, Phayao, Thailand.
⁶ Department of Chemistry, University of British Columbia, Vancouver, BC, Canada.
⁷ Department of Earth, Ocean & Atmospheric Sciences, University of British Columbia, Vancouver, BC, Canada.

PMID: 38288992
DOI: 10.1080/14786419.2024.2306172

Abstract

Two new styryl lactone derivatives, goniothapic acids A (1) and B (2), and 18 known compounds, were isolated from the twig and leaf extracts of Goniothalamus tapis Miq. The structures of new compounds were characterised by spectroscopic methods and HRESITOFMS. Their absolute configuration was established by comparing the experimental and calculated ECD spectra. Eleven compounds were evaluated for their α-glucosidase inhibitory activity. Of these, (-)-goniothalamin (5) and oldhamactam (16) showed the best α-glucosidase inhibitory activity with IC₅₀ values of 54.8 and 57.9 µM, respectively.

Keywords: Annonaceae; Goniothalamus tapis; aristolactam alkaloids; styryl lactones; α-glucosidase inhibitory activity.