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Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract.
Molecules. 2021 Sep 24; 26(19)M

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.

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Authors+Show Affiliations

Department of Nutritional Science, Faculty of Health and Welfare Sciences, Okayama Prefectural University, Okayama 719-1197, Japan.

Department of Nutritional Science, Faculty of Health and Welfare Sciences, Okayama Prefectural University, Okayama 719-1197, Japan.

Department of Nutritional Science, Faculty of Health and Welfare Sciences, Okayama Prefectural University, Okayama 719-1197, Japan.

Department of Nutritional Science, Faculty of Health and Welfare Sciences, Okayama Prefectural University, Okayama 719-1197, Japan.

Department of Nutritional Science, Faculty of Health and Welfare Sciences, Okayama Prefectural University, Okayama 719-1197, Japan.

Department of Nutritional Science, Faculty of Health and Welfare Sciences, Okayama Prefectural University, Okayama 719-1197, Japan.

Hayashikane Sangyo Co., Ltd., 2-4-8 Yamatomachi, Shimonoseki 750-8608, Japan.

Department of Nutritional Science, Faculty of Health and Welfare Sciences, Okayama Prefectural University, Okayama 719-1197, Japan.

MeSH

Circular DichroismEllagic AcidFood IndustryFunctional FoodGallic AcidGlucosidesGlycoside Hydrolase InhibitorsHydrolyzable TanninsLythraceaeMagnetic Resonance SpectroscopyMolecular StructurePlant ExtractsPolyphenolsSpectrometry, Mass, Electrospray Ionization

Pub Type(s)

Journal Article

Language

eng

PubMed ID

34641346

Citation

Iwaoka, Yuji, et al. "Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract." Molecules (Basel, Switzerland), vol. 26, no. 19, 2021.

Iwaoka Y, Suzuki S, Kato N, et al. Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract. Molecules. 2021;26(19).

Iwaoka, Y., Suzuki, S., Kato, N., Hayakawa, C., Kawabe, S., Ganeko, N., Uemura, T., & Ito, H. (2021). Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract. Molecules (Basel, Switzerland), 26(19). https://doi.org/10.3390/molecules26195802

Iwaoka Y, et al. Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract. Molecules. 2021 Sep 24;26(19) PubMed PMID: 34641346.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Characterization and Identification of Bioactive Polyphenols in the Trapabispinosa Roxb. Pericarp Extract. AU - Iwaoka,Yuji, AU - Suzuki,Shoichi, AU - Kato,Nana, AU - Hayakawa,Chisa, AU - Kawabe,Satoko, AU - Ganeko,Natsuki, AU - Uemura,Tomohiro, AU - Ito,Hideyuki, Y1 - 2021/09/24/ PY - 2021/08/13/received PY - 2021/09/18/revised PY - 2021/09/22/accepted PY - 2021/10/13/entrez PY - 2021/10/14/pubmed PY - 2021/11/17/medline KW - LC/UV/ESIMS analysis KW - Trapa bispinosa Roxb. KW - advanced glycation end products (AGEs) KW - antiglycation effect KW - ellagitannin KW - gallotannin KW - polyphenol KW - α-glucosidase inhibitor JF - Molecules (Basel, Switzerland) JO - Molecules VL - 26 IS - 19 N2 - 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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/34641346/Characterization_and_Identification_of_Bioactive_Polyphenols_in_the_Trapabispinosa_Roxb__Pericarp_Extract_ DB - PRIME DP - Unbound Medicine ER -