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...

Descripción completa

Detalles Bibliográficos
Autores principales: Serino, Elena, Chahardoli, Azam, Badolati, Nadia, Sirignano, Carmina, Jalilian, Fereshteh, Mojarrab, Mahdi, Farhangi, Zahra, Rigano, Daniela, Stornaiuolo, Mariano, Shokoohinia, Yalda, Taglialatela-Scafati, Orazio
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