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 and 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, vol. 9, No 16, p. 18023-18031. ISSN 2470-1343. Available from: https://dx.doi.org/10.1021/acsomega.3c09677.

Basic information

• Original name: 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
• Authors: VASILEV, Hristo (100 Bulgaria, belonging to the institution), Karel ŠMEJKAL (203 Czech Republic, belonging to the institution), Sabína JUSKOVÁ (703 Slovakia, belonging to the institution), Jiří VÁCLAVÍK (203 Czech Republic, belonging to the institution) and Jakub TREML (203 Czech Republic, belonging to the institution).
• Edition: ACS Omega, WASHINGTON, American Chemical Society, 2024, 2470-1343.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10400 1.4 Chemical sciences
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 4.100 in 2022
• Organization unit: Faculty of Pharmacy
• Doi: http://dx.doi.org/10.1021/acsomega.3c09677
• UT WoS: 001200689200001
• Keywords in English: FLAVONOL GLYCOSIDESANTIOXIDANTEXPRESSIONSAPONINSPARTS
• Tags: rivok, ÚPL
• Tags: Reviewed

Abstract

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.