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LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt

Coccinia grandis or ivy gourd is an edible plant. Its leaves and fruits are used as vegetable in many countries. Many works on antidiabetic activity of a crude extract of C. grandis, i.e., in vitro, in vivo, and clinical trials studies, have been reported. Profiles of the antidiabetic compounds were...

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Autores principales: Astiti, Maharani A., Jittmittraphap, Akanitt, Leaungwutiwong, Pornsawan, Chutiwitoonchai, Nopporn, Pripdeevech, Patcharee, Mahidol, Chulabhorn, Ruchirawat, Somsak, Kittakoop, Prasat
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8701318/
https://www.ncbi.nlm.nih.gov/pubmed/34945591
http://dx.doi.org/10.3390/foods10123041
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author Astiti, Maharani A.
Jittmittraphap, Akanitt
Leaungwutiwong, Pornsawan
Chutiwitoonchai, Nopporn
Pripdeevech, Patcharee
Mahidol, Chulabhorn
Ruchirawat, Somsak
Kittakoop, Prasat
author_facet Astiti, Maharani A.
Jittmittraphap, Akanitt
Leaungwutiwong, Pornsawan
Chutiwitoonchai, Nopporn
Pripdeevech, Patcharee
Mahidol, Chulabhorn
Ruchirawat, Somsak
Kittakoop, Prasat
author_sort Astiti, Maharani A.
collection PubMed
description Coccinia grandis or ivy gourd is an edible plant. Its leaves and fruits are used as vegetable in many countries. Many works on antidiabetic activity of a crude extract of C. grandis, i.e., in vitro, in vivo, and clinical trials studies, have been reported. Profiles of the antidiabetic compounds were previously proposed by using LC-MS or GC-MS. However, the compounds responsible for antidiabetic activity have rarely been isolated and characterized by analysis of 1D and 2D NMR data. In the present work, UHPLC-ESI-QTOF-MS/MS analysis and GNPS molecular networking were used to guide the isolation of α-glucosidase inhibitors from an extract of C. grandis leaves. Seven flavonoid glycosides including rutin (1), kaempferol 3-O-rutinoside (2) or nicotiflorin, kaempferol 3-O-robinobioside (3), quercetin 3-O-robinobioside (4), quercetin 3-O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (5) or CTN-986, kaempferol 3-O-β-D-api-furanosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (6), and kaempferol 3-O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranoside (7) were isolated from C. grandis leaves. This is the first report of glycosides containing apiose sugar in the genus Coccinia. These glycosides exhibited remarkable α-glucosidase inhibitory activity, being 4.4–10.3 times more potent than acarbose. Moreover, they also displayed virucidal activity against influenza A virus H1N1, as revealed by the ASTM E1053-20 method.
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spelling pubmed-87013182021-12-24 LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt Astiti, Maharani A. Jittmittraphap, Akanitt Leaungwutiwong, Pornsawan Chutiwitoonchai, Nopporn Pripdeevech, Patcharee Mahidol, Chulabhorn Ruchirawat, Somsak Kittakoop, Prasat Foods Article Coccinia grandis or ivy gourd is an edible plant. Its leaves and fruits are used as vegetable in many countries. Many works on antidiabetic activity of a crude extract of C. grandis, i.e., in vitro, in vivo, and clinical trials studies, have been reported. Profiles of the antidiabetic compounds were previously proposed by using LC-MS or GC-MS. However, the compounds responsible for antidiabetic activity have rarely been isolated and characterized by analysis of 1D and 2D NMR data. In the present work, UHPLC-ESI-QTOF-MS/MS analysis and GNPS molecular networking were used to guide the isolation of α-glucosidase inhibitors from an extract of C. grandis leaves. Seven flavonoid glycosides including rutin (1), kaempferol 3-O-rutinoside (2) or nicotiflorin, kaempferol 3-O-robinobioside (3), quercetin 3-O-robinobioside (4), quercetin 3-O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (5) or CTN-986, kaempferol 3-O-β-D-api-furanosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (6), and kaempferol 3-O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranoside (7) were isolated from C. grandis leaves. This is the first report of glycosides containing apiose sugar in the genus Coccinia. These glycosides exhibited remarkable α-glucosidase inhibitory activity, being 4.4–10.3 times more potent than acarbose. Moreover, they also displayed virucidal activity against influenza A virus H1N1, as revealed by the ASTM E1053-20 method. MDPI 2021-12-07 /pmc/articles/PMC8701318/ /pubmed/34945591 http://dx.doi.org/10.3390/foods10123041 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Astiti, Maharani A.
Jittmittraphap, Akanitt
Leaungwutiwong, Pornsawan
Chutiwitoonchai, Nopporn
Pripdeevech, Patcharee
Mahidol, Chulabhorn
Ruchirawat, Somsak
Kittakoop, Prasat
LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt
title LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt
title_full LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt
title_fullStr LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt
title_full_unstemmed LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt
title_short LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt
title_sort lc-qtof-ms/ms based molecular networking approach for the isolation of α-glucosidase inhibitors and virucidal agents from coccinia grandis (l.) voigt
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8701318/
https://www.ncbi.nlm.nih.gov/pubmed/34945591
http://dx.doi.org/10.3390/foods10123041
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