Abstract

In this study, we present the isolation and characterization of the structure of six gallotannins (1–6), three ellagitannins (7–9), a neolignan glucoside (10), and three related polyphenolic compounds (gallic acid, 11 and 12) from Trapa bispinosa Roxb. pericarp extract (TBE). Among the isolates, the structure of compound 10 possessing a previously unclear absolute configuration was unambiguously determined through nuclear magnetic resonance and circular dichroism analyses. The α-glucosidase activity and glycation inhibitory effects of the isolates were evaluated. Decarboxylated rugosin A (8) showed an α-glucosidase inhibitory activity, while hydrolyzable tannins revealed stronger antiglycation activity than that of the positive control. Furthermore, the identification and quantification of the TBE polyphenols were investigated by high-performance liquid chromatography coupled to ultraviolet detection and electrospray ionization mass spectrometry analysis, indicating the predominance of gallic acid, ellagic acid, and galloyl glucoses showing marked antiglycation properties. These findings suggest that there is a potential food industry application of polyphenols in TBE as a functional food with antidiabetic and antiglycation activities.

Highlights

  • Water chestnut (Trapa bispinosa Roxb.)—belonging to the family Lythraceae—is a floating annual aquatic plant originally distributed in Southeast Asia, and its cultivation is widely extended to Southern Europe, Africa, and Asia

  • Among the isolated polyphenols, decarboxylated rugosin A (8) and 1,2,3,4,6-penta-O-galloyl-β-Dglucose showed α-glucosidase inhibitory activities

  • A total of 30 Trapa bispinosa Roxb. pericarp extract (TBE) polyphenols were comprehensively identified by LC/UV/ESIMS analysis

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Summary

Introduction

Water chestnut (Trapa bispinosa Roxb.)—belonging to the family Lythraceae—is a floating annual aquatic plant originally distributed in Southeast Asia, and its cultivation is widely extended to Southern Europe, Africa, and Asia. The fruit and leaf extracts reportedly exhibit diverse biological, such as antioxidant [3] and anticancer [4] activities. The removal effect of industrial pollutant by this plant was reported as a sorbent [5]. The phytochemical studies on this plant revealed the presence of tannins, flavonoids, and saponins, while its detailed components remain elusive. The phytochemical and biological studies of Trapa japonica Flerov.—a species closely related to Trapa bispinosa.

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