Cargando…
Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects
Phytochemical analysis of the Iranian plant Achillea wilhelmsii led to the isolation of 17 pure secondary metabolites belonging to the classes of sesquiterpenoids and phenolics. Two of these compounds, named wilhemsin (7) and wilhelmsolide (9), are new sesquiterpenoids, and the first shows undescrib...
Autores principales: | , , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8300625/ https://www.ncbi.nlm.nih.gov/pubmed/34209510 http://dx.doi.org/10.3390/antiox10071042 |
_version_ | 1783726492783476736 |
---|---|
author | Serino, Elena Chahardoli, Azam Badolati, Nadia Sirignano, Carmina Jalilian, Fereshteh Mojarrab, Mahdi Farhangi, Zahra Rigano, Daniela Stornaiuolo, Mariano Shokoohinia, Yalda Taglialatela-Scafati, Orazio |
author_facet | Serino, Elena Chahardoli, Azam Badolati, Nadia Sirignano, Carmina Jalilian, Fereshteh Mojarrab, Mahdi Farhangi, Zahra Rigano, Daniela Stornaiuolo, Mariano Shokoohinia, Yalda Taglialatela-Scafati, Orazio |
author_sort | Serino, Elena |
collection | PubMed |
description | Phytochemical analysis of the Iranian plant Achillea wilhelmsii led to the isolation of 17 pure secondary metabolites belonging to the classes of sesquiterpenoids and phenolics. Two of these compounds, named wilhemsin (7) and wilhelmsolide (9), are new sesquiterpenoids, and the first shows undescribed structural features. Their structures were elucidated through extensive spectroscopic analysis, mainly based on 1D and 2D NMR, and chemical derivatization. Starting from plant traditional use and previous reports on the activity of the plant extracts, all the pure compounds were evaluated on endpoints related to the treatment of metabolic syndrome. The sesquiterpene hanphyllin (8) showed a selective cholesterol-lowering activity (−12.7% at 30 µM), santoflavone (13) stimulated glucose uptake via the GLUT transporter (+16.2% at 30 µM), while the trimethoxylated flavone salvigenin (14) showed a dual activity in decreasing lipid levels (−22.5% palmitic acid biosynthesis at 30 µM) and stimulating mitochondrial functionality (+15.4% at 30 µM). This study further confirms that, in addition to the antioxidants vitexin, isovitexin, and isoschaftoside, A. wilhelmsii extracts contain molecules that can act at different levels on the metabolic syndrome symptoms. |
format | Online Article Text |
id | pubmed-8300625 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-83006252021-07-24 Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects Serino, Elena Chahardoli, Azam Badolati, Nadia Sirignano, Carmina Jalilian, Fereshteh Mojarrab, Mahdi Farhangi, Zahra Rigano, Daniela Stornaiuolo, Mariano Shokoohinia, Yalda Taglialatela-Scafati, Orazio Antioxidants (Basel) Article Phytochemical analysis of the Iranian plant Achillea wilhelmsii led to the isolation of 17 pure secondary metabolites belonging to the classes of sesquiterpenoids and phenolics. Two of these compounds, named wilhemsin (7) and wilhelmsolide (9), are new sesquiterpenoids, and the first shows undescribed structural features. Their structures were elucidated through extensive spectroscopic analysis, mainly based on 1D and 2D NMR, and chemical derivatization. Starting from plant traditional use and previous reports on the activity of the plant extracts, all the pure compounds were evaluated on endpoints related to the treatment of metabolic syndrome. The sesquiterpene hanphyllin (8) showed a selective cholesterol-lowering activity (−12.7% at 30 µM), santoflavone (13) stimulated glucose uptake via the GLUT transporter (+16.2% at 30 µM), while the trimethoxylated flavone salvigenin (14) showed a dual activity in decreasing lipid levels (−22.5% palmitic acid biosynthesis at 30 µM) and stimulating mitochondrial functionality (+15.4% at 30 µM). This study further confirms that, in addition to the antioxidants vitexin, isovitexin, and isoschaftoside, A. wilhelmsii extracts contain molecules that can act at different levels on the metabolic syndrome symptoms. MDPI 2021-06-29 /pmc/articles/PMC8300625/ /pubmed/34209510 http://dx.doi.org/10.3390/antiox10071042 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 Serino, Elena Chahardoli, Azam Badolati, Nadia Sirignano, Carmina Jalilian, Fereshteh Mojarrab, Mahdi Farhangi, Zahra Rigano, Daniela Stornaiuolo, Mariano Shokoohinia, Yalda Taglialatela-Scafati, Orazio Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects |
title | Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects |
title_full | Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects |
title_fullStr | Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects |
title_full_unstemmed | Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects |
title_short | Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects |
title_sort | salvigenin, a trimethoxylated flavone from achillea wilhelmsii c. koch, exerts combined lipid-lowering and mitochondrial stimulatory effects |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8300625/ https://www.ncbi.nlm.nih.gov/pubmed/34209510 http://dx.doi.org/10.3390/antiox10071042 |
work_keys_str_mv | AT serinoelena salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT chahardoliazam salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT badolatinadia salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT sirignanocarmina salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT jalilianfereshteh salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT mojarrabmahdi salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT farhangizahra salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT riganodaniela salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT stornaiuolomariano salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT shokoohiniayalda salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects AT taglialatelascafatiorazio salvigeninatrimethoxylatedflavonefromachilleawilhelmsiickochexertscombinedlipidloweringandmitochondrialstimulatoryeffects |