Polyphenolic compounds from flowers of Ficaria verna Huds.

Article (PDF Available)inActa poloniae pharmaceutica 56(6):475-476 · July 1999with 58 Reads
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Abstract
Four known crystalline, chromatographically homogeneous flavonoid compounds: kaempferol, kaempferol 3-O-β-D-glucopyranoside, quercetin 3-O-β-D-glucopyranoside and quercetin 3-0-β-D-(6''-α-L-rhamnopyranosyl)-glucopyranoside have been isolated from flowers of Ficaria verna. Their structures were established by chemical means and spectroscopic methods (UV, 1H NMR, 13C NMR, MS). Chromatographic analysis confirmed the presence of phenolic acids: vanillic, synapic, ferulic, p-coumaric, caffeic, p-hydroxybenzoic, protocatechuic and p-hydroxyphenylacetic.
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    Obtaining new pharmaceutical materials with enhanced properties by using natural compounds and environment-friendly methods is a continuous goal for scientists. Ficaria verna Huds. is a widespread perennial plant with applications in the treat of haemorrhoids and to cure piles; it has also anti-inflammatory, astringent, and antibiotic properties. The goal of the present study is the obtaining and characterization of new F. verna extract/β-cyclodextrin complexes by using only natural compounds, solvents, and environment-friendly methods in order to increase the quality and acceptability versus toxicity indicator. Thus, the flavonoid content (as quercetin) of Ficaria verna Huds. flowers and leaves from the West side of Romania was determined and correlated with their antioxidant activity. Further, the possibility of obtaining β-cyclodextrin supramolecular systems was studied. F. verna flowers and leaves extracts were obtained by semi-continuous solid-liquid extraction. The raw concentrated extract was spectrophotometrically analyzed in order to quantify the flavonoids from plant parts and to evaluate the antioxidant activity of these extracts. The F. verna extracts were used for obtaining β-cyclodextrin complexes; these were analyzed by scanning electron microscopy and Karl Fischer water titration; spectrophotometry was used in order to quantifying the flavonoids and evaluates the antioxidant activity. A higher concentration of flavonoids of 0.5% was determined in complexes obtained by crystallisation method, while only a half of this value was calculated for kneading method. The antioxidant activity of these complexes was correlated with the flavonoid content and this parameter reveals possible controlled release properties. The flavonoid content of F. verna Huds. from the West side of Romania (Banat county) is approximately the same in flowers and leaves, being situated at a medium value among other studies. β-Cyclodextrin complexes of F. verna extracts are obtained with lower yields by crystallisation than kneading methods, but the flavonoids (as quercetin) are better encapsulated in the first case most probably due to the possibility to attain the host-guest equilibrium in the slower crystallisation process. F. verna extracts and their β-cyclodextrin complexes have antioxidant activity even at very low concentrations and could be used in proper and valuable pharmaceutical formulations with enhanced bioactivity.
  • Article
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    A phytochemical investigation of the flowers and leaves of Ficaria verna Huds. (Ranunculaceae) yielded four additional known flavonoid compounds including: kaempferol 3-O-beta-D-(6"-a-L-rhamnopyranosyl)-glucopyranoside (nicotiflorin), apigenin 8-C-beta-D-glucopyranoside (vitexin), luteolin 8-C-beta-D-glucopyranoside (orientin) and apigenin 8-C-beta-D-(2"-O-beta-D-glucopyranosyl)-glucopyranoside (flavosativaside). The characterisation of these compounds was achieved by various chromatographic and spectroscopic methods (UV, 1H NMR, 13C NMR and MS).
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    This perennial herb of the MALVACEAE family is a 60–120 cm high hardy, velvety plant that has an erect root up to 50 cm long and a few cm thick with secondary roots. The succulent stem is usually woody at the base and unbranched. The leaves are short-petioled with an ovate, acute leafblade. The secondary leaves are narrow and drooping. The lower leaves are 5-lobed, the upper cauline leaves are often triangular, more wide than long. The reddish-white flowers are usually in axillary or terminal clusters; the 6–9 sepals of the epicalyx are fused at the base, and are 8–10 mm long and pointed; 5 sepals, 5 heart-shaped petals and numerous stamens are fused together with the anthers to a column. The ovaries in a ring, numerous styles; mericarps smooth and downy.
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    From the flowers of Ficaria verna Huds. (Ranunculaceae), two flavonol triglycosides were isolated and their structures were elucidated by means of spectroscopic analysis (UV, NMR, MS) as 3-O-[alfa-L-rhamnopyranosyl-(1-6)-beta-D-glucopyranosyl]-7-O-(beta-D-glucopyranosyl) - quercetin (1) and 3-O-[alfa-L-rhamnopyranosyl-(1-6)-beta-D-glucopyranosyl]-7-O-(beta-D-glucopyranosyl) - kaempferol (2). In addition, the structure of 1 was determined using homo- and heteronuclear 2D NMR techniques.
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    The quantitative determination of flavonoid compounds in flowers and leaves of Ficaria verna Huds. (Ranunculaceae) was carried out in different growing seasons of the plant, using Christ-Müller's method (Polish Pharmacopoeia, 1999) and high performance liquid chromatography (HPLC) analysis after acid hydrolysis. The flavonoid content was much higher in flowers than in leaves.