Along with the known kaempferol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-β-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-α-l-rhamnopyranosyl-(1 → 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-β-d-galactopyranoside (2), tamarixetin-3-O-(2,6-di-O-α-l-rhamnopyranosyl)-β-d-galactopyranoside (3), tamarixetin 3-O-β-d-apiofuranosyl-(1 → 2)-β-d-galactopyranoside (4), tamarixetin-3-O-β-d-apiofuranosyl-(1 → 2)-[6-O-(3-hydroxy-3-methylglutaryl)]-β-d-galactopyranoside (5), and tamarixetin-3-O-β-d-apiofuranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-galactopyranoside (6). Selected compounds from A. thracicus were tested to evaluate their anticollagenase activity. The greatest effect was observed for quercetin-3-O-β-d-apiofuranosyl-(1 → 2)-β-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.
- Publikační typ
- časopisecké články MeSH
ETHNOPHARMACOLOGICAL RELEVANCE: Morus alba L. is used in traditional Chinese medicine for the treatment of various diseases, including bacterial infections and inflammation. As a rich source of phenolic compounds, the plant is an object of many phytochemical and pharmacological studies. AIM OF THE STUDY: The aim of the study was to isolate and evaluate possible parallel antiviral, antibacterial, and anti-inflammatory activities of phenolic mulberry compounds. MATERIALS AND METHODS: Extensive chromatographic separation of mulberry root bark extract and in vitro biological screening of 26 constituents identified promising candidates for further pharmacological research. Selected compounds were screened for anti-infective and anti-inflammatory activities. Antiviral activity was determined by the plaque number reduction assay and by the titer reduction assay, antibacterial using broth microdilution method, and anti-inflammatory activity using COX Colorimetric inhibitor screening assay kit. One compound was evaluated in vivo in carrageenan-induced paw-edema in mice. RESULTS: Five prenylated compounds 1, 2, 8, 9, and 11, together with a simple phenolic ester 13, exhibited inhibitory activity against the replication of herpes simplex virus 1 (HSV-1) or herpes simplex virus 2 (HSV-2), with IC50 values ranging from 0.64 to 1.93 μg/mL, and EC50 values 0.93 and 1.61 μg/mL. Molecular docking studies demonstrated the effects of the active compounds by targeting HSV-1 DNA polymerase and HSV-2 protease. In antibacterial assay, compounds 1, 4, 11, and 17 diminished the growth of all of the Gram-positive strains tested, with MIC values of 1-16 μg/mL. The anti-inflammatory ability of several compounds to inhibit cyclooxygenase 2 (COX-2) was tested in vitro, and compound 16 displayed greater activity than the indomethacin, positive control. Mulberrofuran B (11) showed anti-inflammatory activity in vivo against carrageenan-induced paw-edema in mice. CONCLUSIONS: Experimental investigation showed promising antiviral, antibacterial, and/or anti-inflammatory activities of the phenolic mulberry constituents, often with multiple inhibitory effects that might be used as a potential source of new medicine.
- MeSH
- buněčné linie MeSH
- diabetes mellitus farmakoterapie metabolismus MeSH
- glukosa metabolismus MeSH
- glykogen metabolismus MeSH
- hypoglykemika farmakologie terapeutické užití MeSH
- inzulinová rezistence MeSH
- játra účinky léků metabolismus MeSH
- kosterní svaly účinky léků metabolismus MeSH
- krysa rodu rattus MeSH
- listy rostlin MeSH
- membránový potenciál mitochondrií účinky léků MeSH
- Morus * MeSH
- myši MeSH
- proteinkinasy aktivované AMP metabolismus MeSH
- reaktivní formy kyslíku metabolismus MeSH
- rostlinné extrakty farmakologie terapeutické užití MeSH
- zvířata MeSH
- Check Tag
- krysa rodu rattus MeSH
- mužské pohlaví MeSH
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
Astragalus is a very interesting plant genus, well-known for its content of flavonoids, triterpenes and polysaccharides. Its secondary metabolites are described as biologically active compounds showing several activities, e.g., immunomodulating, antibacterial, antiviral and hepatoprotective. This inspired us to analyze the Bulgarian endemic A. aitosensis (Ivanisch.) to obtain deeper information about its phenolic components. We used extensive chromatographic separation of A. aitosensis extract to obtain seven phenolic compounds (1-7), which were identified using combined LC-MS and NMR spectral studies. The 1D and 2D NMR analyses and HR-MS allowed us to resolve the structures of known compounds 5-7 as isorhamnetin-3-O-robinobioside, isorhamnetin-3-O-(2,6-di-O-α-rhamno-pyranosyl-β-galactopyranoside), and alangiflavoside, respectively, and further comparison of these spectral data with available literature helped us with structural analysis of newly described flavonoid glycosides 1-4. These were described in plant source for the first time.
- MeSH
- Astragalus chemie MeSH
- chromatografie kapalinová MeSH
- fenoly chemie izolace a purifikace MeSH
- flavonoidy chemie izolace a purifikace MeSH
- glykosidy chemie klasifikace izolace a purifikace MeSH
- hmotnostní spektrometrie MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární struktura MeSH
- triterpeny chemie MeSH
- Publikační typ
- časopisecké články MeSH
