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

J 2024

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

VASILEV, Hristo; Karel ŠMEJKAL; Sabína JUSKOVÁ; Jiří VÁCLAVÍK; Jakub TREML et al.

Základní údaje

Originální název

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

Autoři

VASILEV, Hristo; Karel ŠMEJKAL; Sabína JUSKOVÁ; Jiří VÁCLAVÍK a Jakub TREML

Vydání

ACS Omega, WASHINGTON, American Chemical Society, 2024, 2470-1343

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.300

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14160/24:00136964

Organizační jednotka

Farmaceutická fakulta

Klíčová slova anglicky

FLAVONOL GLYCOSIDESANTIOXIDANTEXPRESSIONSAPONINSPARTS

Štítky

rivok, ÚPL

Příznaky

Recenzováno

Změněno: 29. 8. 2024 08:47, Mgr. Daniela Černá

Anotace

V originále

Along with the known kaempferol-3-O-alpha-l-rhamnopyranosyl-(1 -> 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 -> 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 -> 2)-beta-d-galactopyranoside (4), tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (5), and tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[alpha-l-rhamnopyranosyl-(1 -> 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 -> 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.

Citovat

VASILEV, Hristo; Karel ŠMEJKAL; Sabína JUSKOVÁ; Jiří VÁCLAVÍK a Jakub TREML. 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. ACS Omega. WASHINGTON: American Chemical Society, 2024, roč. 9, č. 16, s. 18023-18031. ISSN 2470-1343. Dostupné z: https://doi.org/10.1021/acsomega.3c09677.

@article{2426464,
   author = {Vasilev, Hristo and Šmejkal, Karel and Jusková, Sabína and Václavík, Jiří and Treml, Jakub},
   article_location = {WASHINGTON},
   article_number = {16},
   doi = {https://doi.org/10.1021/acsomega.3c09677},
   keywords = {FLAVONOL GLYCOSIDESANTIOXIDANTEXPRESSIONSAPONINSPARTS},
   language = {eng},
   issn = {2470-1343},
   journal = {ACS Omega},
   title = {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},
   url = {https://pubs.acs.org/doi/10.1021/acsomega.3c09677},
   volume = {9},
   year = {2024}
}

TY  - JOUR
ID  - 2426464
AU  - Vasilev, Hristo - Šmejkal, Karel - Jusková, Sabína - Václavík, Jiří - Treml, Jakub
PY  - 2024
TI  - 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
JF  - ACS Omega
VL  - 9
IS  - 16
SP  - 18023-18031
EP  - 18023-18031
PB  - American Chemical Society
SN  - 24701343
KW  - FLAVONOL GLYCOSIDESANTIOXIDANTEXPRESSIONSAPONINSPARTS
UR  - https://pubs.acs.org/doi/10.1021/acsomega.3c09677
N2  - Along with the known kaempferol-3-O-alpha-l-rhamnopyranosyl-(1 -> 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 -> 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 -> 2)-beta-d-galactopyranoside (4), tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-beta-d-galactopyranoside (5), and tamarixetin-3-O-beta-d-apiofuranosyl-(1 -> 2)-[alpha-l-rhamnopyranosyl-(1 -> 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 -> 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.
ER  -

VASILEV, Hristo; Karel ŠMEJKAL; Sabína JUSKOVÁ; Jiří VÁCLAVÍK a Jakub TREML. 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. \textit{ACS Omega}. WASHINGTON: American Chemical Society, 2024, roč.~9, č.~16, s.~18023-18031. ISSN~2470-1343. Dostupné z: https://doi.org/10.1021/acsomega.3c09677.

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