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Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake
Ten phenolic constituents, including three new macrocyclic glycosides (1–3), a new phenolic glycoside (5), a new biphenyl glycoside (6), and five known compounds (4, 7–10), were isolated from a 70% MeOH extract of the leaves of Heliciopsis terminalis by liquid chromatography-tandem mass spectrometry...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9695999/ https://www.ncbi.nlm.nih.gov/pubmed/36355487 http://dx.doi.org/10.3390/ph15111315 |
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author | Ryu, Byeol Park, Eun-Jin Doan, Thi-Phuong Cho, Hyo-Moon An, Jin-Pyo Pham, Thi-Linh-Giang Pham, Ha-Thanh-Tung Oh, Won-Keun |
author_facet | Ryu, Byeol Park, Eun-Jin Doan, Thi-Phuong Cho, Hyo-Moon An, Jin-Pyo Pham, Thi-Linh-Giang Pham, Ha-Thanh-Tung Oh, Won-Keun |
author_sort | Ryu, Byeol |
collection | PubMed |
description | Ten phenolic constituents, including three new macrocyclic glycosides (1–3), a new phenolic glycoside (5), a new biphenyl glycoside (6), and five known compounds (4, 7–10), were isolated from a 70% MeOH extract of the leaves of Heliciopsis terminalis by liquid chromatography-tandem mass spectrometry (LC-MS/MS)-guided molecular networking. The chemical structures of new compounds 1–3, 5 and 6 were established based on comprehensive spectroscopic data analysis, including 1D and 2D NMR and HRESIMS techniques. All isolated compounds (1–10) were evaluated for their stimulation of glucose uptake in differentiated 3T3-L1 adipocytes using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-d-glucose (2-NBDG) as a fluorescent glucose analog. Compounds 3, 6 and 8 showed stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells. Among them, compounds 3 and 6 activated the AMPK signaling pathway in differentiated C2C12 myoblasts. |
format | Online Article Text |
id | pubmed-9695999 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-96959992022-11-26 Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake Ryu, Byeol Park, Eun-Jin Doan, Thi-Phuong Cho, Hyo-Moon An, Jin-Pyo Pham, Thi-Linh-Giang Pham, Ha-Thanh-Tung Oh, Won-Keun Pharmaceuticals (Basel) Article Ten phenolic constituents, including three new macrocyclic glycosides (1–3), a new phenolic glycoside (5), a new biphenyl glycoside (6), and five known compounds (4, 7–10), were isolated from a 70% MeOH extract of the leaves of Heliciopsis terminalis by liquid chromatography-tandem mass spectrometry (LC-MS/MS)-guided molecular networking. The chemical structures of new compounds 1–3, 5 and 6 were established based on comprehensive spectroscopic data analysis, including 1D and 2D NMR and HRESIMS techniques. All isolated compounds (1–10) were evaluated for their stimulation of glucose uptake in differentiated 3T3-L1 adipocytes using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-d-glucose (2-NBDG) as a fluorescent glucose analog. Compounds 3, 6 and 8 showed stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells. Among them, compounds 3 and 6 activated the AMPK signaling pathway in differentiated C2C12 myoblasts. MDPI 2022-10-25 /pmc/articles/PMC9695999/ /pubmed/36355487 http://dx.doi.org/10.3390/ph15111315 Text en © 2022 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 Ryu, Byeol Park, Eun-Jin Doan, Thi-Phuong Cho, Hyo-Moon An, Jin-Pyo Pham, Thi-Linh-Giang Pham, Ha-Thanh-Tung Oh, Won-Keun Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake |
title | Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake |
title_full | Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake |
title_fullStr | Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake |
title_full_unstemmed | Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake |
title_short | Heliciopsides A−E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake |
title_sort | heliciopsides a−e, unusual macrocyclic and phenolic glycosides from the leaves of heliciopsis terminalis and their stimulation of glucose uptake |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9695999/ https://www.ncbi.nlm.nih.gov/pubmed/36355487 http://dx.doi.org/10.3390/ph15111315 |
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