Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14160%2F24%3A00136964" target="_blank" >RIV/00216224:14160/24:00136964 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.acs.org/doi/10.1021/acsomega.3c09677" target="_blank" >https://pubs.acs.org/doi/10.1021/acsomega.3c09677</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acsomega.3c09677" target="_blank" >10.1021/acsomega.3c09677</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro

Popis výsledku v původním jazyce

Along with the known kaempferol-3-O-alpha-l-rhamnopyranosyl-(1 -&gt; 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (1), five new flavonoids, containing the rarely isolated aglycon tamarixetin, were isolated from a methanolic extract of the endemic Balkan species Astragalus thracicus Griseb. Three of the new compounds are substituted with 3-hydroxy-3-methylglutaryl residue (HMG), untypical for the genus Astragalus. The compounds were identified as tamarixetin-3-O-alpha-l-rhamnopyranosyl-(1 -&gt; 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (2), tamarixetin-3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-galactopyranoside (3), tamarixetin 3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-beta-d-galactopyranoside (4), tamarixetin-3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (5), and tamarixetin-3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-[alpha-l-rhamnopyranosyl-(1 -&gt; 6)]-beta-d-galactopyranoside (6). Selected compounds from A. thracicus were tested to evaluate their anticollagenase activity. The greatest effect was observed for quercetin-3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-beta-d-galactopyranoside, possibly due to the presence of an ortho-dihydroxy arrangement of flavonoid ring B. The effect on collagenase and elastase was further evaluated also by in silico study, and the test compounds showed some level of in silico interaction.

Název v anglickém jazyce

Five New Tamarixetin Glycosides from Astragalus thracicus Griseb. Including Some Substituted with the Rare 3-Hydroxy-3-methylglutaric Acid and Their Collagenase Inhibitory Effects In Vitro

Popis výsledku anglicky

Along with the known kaempferol-3-O-alpha-l-rhamnopyranosyl-(1 -&gt; 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (1), five new flavonoids, containing the rarely isolated aglycon tamarixetin, were isolated from a methanolic extract of the endemic Balkan species Astragalus thracicus Griseb. Three of the new compounds are substituted with 3-hydroxy-3-methylglutaryl residue (HMG), untypical for the genus Astragalus. The compounds were identified as tamarixetin-3-O-alpha-l-rhamnopyranosyl-(1 -&gt; 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (2), tamarixetin-3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-galactopyranoside (3), tamarixetin 3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-beta-d-galactopyranoside (4), tamarixetin-3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (5), and tamarixetin-3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-[alpha-l-rhamnopyranosyl-(1 -&gt; 6)]-beta-d-galactopyranoside (6). Selected compounds from A. thracicus were tested to evaluate their anticollagenase activity. The greatest effect was observed for quercetin-3-O-beta-d-apiofuranosyl-(1 -&gt; 2)-beta-d-galactopyranoside, possibly due to the presence of an ortho-dihydroxy arrangement of flavonoid ring B. The effect on collagenase and elastase was further evaluated also by in silico study, and the test compounds showed some level of in silico interaction.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ACS Omega

ISSN

2470-1343

e-ISSN

—

Svazek periodika

9

Číslo periodika v rámci svazku

16

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

18023-18031

Kód UT WoS článku

001200689200001

EID výsledku v databázi Scopus

2-s2.0-85190607231