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Alkaloids and Styryl lactones from Goniothalamus ridleyi King and Their α-Glucosidase Inhibitory Activity Polbuppha, Isaraporn; Teerapongpisan, Passakorn; Phukhatmuen, Piyaporn; Suthiphasilp, Virayu; Maneerat, Tharakorn; Charoensup, Rawiwan; Andersen, Raymond J.; Laphookhieo, Surat

Abstract

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.

Item Metadata

Title
Alkaloids and Styryl lactones from Goniothalamus ridleyi King and Their α-Glucosidase Inhibitory Activity
Creator
Polbuppha, Isaraporn; Teerapongpisan, Passakorn; Phukhatmuen, Piyaporn; Suthiphasilp, Virayu; Maneerat, Tharakorn; Charoensup, Rawiwan; Andersen, Raymond J.; Laphookhieo, Surat
Publisher
Multidisciplinary Digital Publishing Institute
Date Issued
2023-01-24
Description
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.
Subject
Goniothalamus ridleyi; dimeric aristolactam; styryl lactone; α-glucosidase inhibitory activity
Genre
Article
Type
Text
Language
eng
Date Available
2025-02-07
Provider
Vancouver : University of British Columbia Library
Rights
CC BY 4.0
DOI
10.14288/1.0448033
URI
http://hdl.handle.net/2429/90332
Affiliation
Science, Faculty of; Non UBC; Chemistry, Department of; Earth, Ocean and Atmospheric Sciences, Department of
Citation
Molecules 28 (3): 1158 (2023)
Publisher DOI
10.3390/molecules28031158
Peer Review Status
Reviewed
Scholarly Level
Faculty; Researcher
Rights URI
https://creativecommons.org/licenses/by/4.0/
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CC BY 4.0