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
Predložená práca sa zaoberá izoláciou a identifikáciou flavonoidov prítomných v listoch pajazmínu tenkolistového (Philadelphus tenuifolius Rupr. et Maxim.). Z metanolového extraktu listov tejto rastliny bol izolovaný kvercetín-3-O-glukozid (izokvercitrín), z butanolového extraktu kempferol-3-O-glukozid-7-O-ramnozid. Izolované látky boli identifikované pomocou fyzikálno-chemických metód, porovnaním výsledkov so štandardami a literatúrou. Z rastlinného druhu Philadelphus tenuifolius Rupr. et Maxim. boli izolované prvýkrát. Kľúčové slová: Philadelphus tenuifolius • Hydrangeaceae • flavonoidové glykozidy
The paper deals with the isolation and identification of the constituents of the leaves of Philadelphus tenuifolius Rupr. et Maxim. A methanolic extract was used to isolate quercetin-3-O-glucoside (isoquercitrin), and a butanolic extract to isolate kaempferol-3-O-glucoside-7-O-rhamnoside. Isolates were identified by physical-chemical data, comparison with authentic samples and literature data. The above-mentioned compounds were isolated from Philadelphus tenuifolius Rupr. et Maxim. for the first time. Keywords: Philadelphus tenuifolius • Hydrangeaceae • flavonoid glycosides
- Klíčová slova
- flavonoidové glykosidy,
- MeSH
- chromatografie na tenké vrstvě MeSH
- flavonoidy * analýza izolace a purifikace MeSH
- glykosidy analýza izolace a purifikace MeSH
- hmotnostní spektrometrie MeSH
- Hydrangeaceae * MeSH
- kempferoly analýza chemie izolace a purifikace MeSH
- listy rostlin * chemie MeSH
- quercetin analýza chemie izolace a purifikace MeSH
- rostlinné extrakty analýza chemie MeSH
- Publikační typ
- práce podpořená grantem MeSH
Glycosides of benzodioxole-indole alkaloid 6-hydroxy-galanthindole (7-(6'-(hydroxymethyl)benzo[d][1',3']dioxol-5'-yl)-1-methyl-1H-indol-6-ol) having axial chirality were isolated from Narcissus cultivar 'Dutch Master'. The structure, including absolute configuration, was determined by means of extensive spectroscopic data such as UV, IR, CD, MS, 1D and 2D NMR spectra, and computational chiroptical methods. The aglycone has a structure containing two aromatic moieties with substituents hindering rotation about the biaryl axis and is connected to a saccharide moiety linked at C-6 and made up of one, two, or three sugars (glucose, alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranose, and trisaccharide ([beta-D-xylopyranosyl(1-->2)]-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranose).
- MeSH
- alkaloidy amarylkovitých chemie MeSH
- benzodioxoly chemie izolace a purifikace MeSH
- glykosidy chemie izolace a purifikace MeSH
- indolové alkaloidy chemie izolace a purifikace MeSH
- molekulární struktura MeSH
- Narcissus chemie MeSH
- rostlinné extrakty chemie MeSH
- sacharidy MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Three new nervogenic acid glycosides, 1-O-alpha-L-rhamnopyranosyl 3,5-bis(3-methyl-but-2-enyl)-4-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-benzoate, 3,5-bis(3-methyl-but-2-enyl)-4-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-benzoic acid, and bis{3,5-bis(3-methyl-but-2-enyl)-4-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-benzoyl} 1,2-O-beta-d-glucopyranose, which we named condobulbosides A-C, were isolated from a methanol extract of the leaves of Liparis condylobulbon together with an apigenin C-glycoside, schaftoside. Their structures were established on the basis of spectral techniques, namely, UV, IR, HR-MS spectroscopy, both 1D and 2D NMR experiments, and chemical reactions.
Hirtusneanoside, a new O-deoxyglycoside of a dimeric tetrahydroxanthone, was isolated from the lichen Usnea hirta. Its structure, including the absolute configuration, was determined by means of extensive spectroscopic data (UV, IR, MS, CD, 1D and 2D NMR) and chemical degradation. Hirtusneanoside has a unique structure comprising L-rhamnopyranoside of a tetrahydroxanthone dimer and showed growth inhibitory activities against Gram-positive bacteria.
- MeSH
- antibakteriální látky farmakologie chemie izolace a purifikace MeSH
- Bacillus subtilis účinky léků MeSH
- financování organizované MeSH
- glykosidy farmakologie chemie izolace a purifikace MeSH
- molekulární struktura MeSH
- nukleární magnetická rezonance biomolekulární MeSH
- Staphylococcus aureus účinky léků MeSH
- Usnea chemie MeSH
- xantony farmakologie chemie izolace a purifikace MeSH
- Geografické názvy
- Česká republika MeSH
Colleflaccinosides A and B, two chiral bianthraquinone glycosides from the two geographical varieties of lichen Collema flaccidum collected in Russia and Israel have been isolated as new natural products. Their structures were elucidated using UV, CD, IR, MS, 1D and 2D NMR spectral data, and chemical degradation. The colleflaccinosides B had significant antitumor activity in the crown gall tumor inhibition test.
- MeSH
- Agrobacterium tumefaciens účinky léků MeSH
- anthrachinony farmakologie chemie izolace a purifikace MeSH
- antiinfekční látky farmakologie chemie izolace a purifikace MeSH
- antitumorózní látky fytogenní farmakologie chemie izolace a purifikace MeSH
- cirkulární dichroismus MeSH
- glykosidy farmakologie chemie izolace a purifikace MeSH
- lišejníky chemie MeSH
- mikrobiální testy citlivosti MeSH
- molekulární konformace MeSH
- molekulární modely MeSH
- nádory rostlin MeSH
- nukleární magnetická rezonance biomolekulární MeSH
- spektrofotometrie infračervená MeSH
- spektrofotometrie ultrafialová MeSH
- spektrometrie hmotnostní - bombardování rychlými atomy MeSH
- Geografické názvy
- Izrael MeSH
- Rusko MeSH
Práca sa zaoberá izoláciou a identifikáciou flavonoidov prítomných v listoch Holodiscus discolor (Pursh) Maxim. (Rosaceae). Z metanolového extraktu boli izolované tri flavonoidové glykozidy flavonolového typu: kempferol–3–O–ramnozid, kvercetín–3–O–glukozid (izokvercitrín) a kvercetín–3–O–ramnozid (kvercitrín), ktoré boli identifikované pomocou fyzikálno-chemických metód, porovnaním so štandardmi a literatúrou. Z rastlinného druhu Holodiscus discolor (Pursh) Maxim. boli izolované prvýkrát.
The paper deals with the isolation and identification of constituents of the leaves of Holodiscus discolor (Pursh) Maxim. (Rosaceae). Three flavonoid glycosides of flavonol type were isolated from the methanolic extract: kaempferol–3–O–rhamnoside, quercetin–3–O–glucoside (isoquercitrin) and quercetin–3–O–rhamnoside (quercitrin). Isolates were identified by physical-chemical data, by comparison with authentic samples and literature data. The above-mentioned compounds were isolated from Holodiscus discolor (Pursh) Maxim. for the first time.
