Corylus avellana L. (Betulaceae) leaves, consumed as infusion, are used in traditional medicine, for the treatment of hemorrhoids, varicose veins, phlebitis, and edema due to their astringent, vasoprotective, and antiedema properties. In previous works we reported from the leaves of Corylus avellana cv. "Tonda di Giffoni" diarylheptanoid derivatives, a class of plant secondary metabolites with a wide variety of bioactivities. With the aim to give an interesting and economically feasible opportunity to C. avellana leaves as source of functional ingredients for pharmaceutical and cosmetic formulations, "green" extracts were prepared by employing "eco-friendly" extraction protocols as maceration, infusion and SLDE-Naviglio extraction. Metabolite profiles of the extracts were obtained by 1H NMR experiments and data were processed by multivariate statistical analysis to highlight differences in the extracts and to evidence the extracts with the highest concentrations of bioactive metabolites. Based on the NMR data, a total of 31 compounds were identified. The metabolite variation among the extracts was evaluated using Principle Component Analysis (PCA) and Partial Least Squares-Discriminant Analysis (PLS-DA). Furthermore, the total phenolic content of the extracts was measured by Folin-Ciocalteu colorimetric assay and the antioxidant activity of extracts was assayed by the spectrophotometric tests DPPH• and ABTS and by an in vitro test based on the evaluation of cellular reactive oxygen species production stimulated by pyocyanin.
- MeSH
- fenoly analýza farmakologie MeSH
- lidé MeSH
- líska chemie metabolismus MeSH
- listy rostlin chemie MeSH
- metabolomika metody MeSH
- nukleární magnetická rezonance biomolekulární metody MeSH
- protonová magnetická rezonanční spektroskopie metody MeSH
- pyokyanin farmakologie MeSH
- reaktivní formy kyslíku metabolismus MeSH
- rostlinné extrakty analýza chemie farmakologie MeSH
- scavengery volných radikálů analýza farmakologie MeSH
- technologie zelené chemie metody MeSH
- THP-1 buňky MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
Isoquercitrin, (IQ, quercetin-3-O-β-d-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6″. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B fromCandida antarcticaimmobilized on acrylic resin). The enzymatic procedure gave no products with "hydroxyaromatic" acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case ofp-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. Reducing capacity of the cinnamate, gallate and 4-hydroxyphenylpropanoate towards Folin-Ciocalteau reagent was significantly lower than that of IQ, while other derivatives displayed slightly better or comparable capacity. Compared to isoquercitrin, most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, but they showed significantly better 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS) scavenging activity and were substantially more active in the inhibition oftert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes. The most active compounds were the hydroxyphenylpropanoates.
- MeSH
- estery * chemie MeSH
- hmotnostní spektrometrie MeSH
- molekulární struktura MeSH
- nukleární magnetická rezonance biomolekulární MeSH
- peroxidace lipidů účinky léků MeSH
- quercetin analogy a deriváty analýza chemická syntéza farmakologie MeSH
- scavengery volných radikálů analýza chemická syntéza farmakologie MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
Reversed phase liquid chromatography-atmospheric pressure chemical ionization mass spectrometry (RP-HPLC/MS-APCI) was used to identify and quantify triacylglycerols (TAGs) having odd-numbered ω-phenylalkanoic acids from seeds of the flower plant Dracunculus vulgaris, and TAGs from the bacterium Rhodococcus erythropolis prepared by precursor directed biosynthesis from phenylalanine and having the corresponding even-numbered ω-phenylalkanoic acids. Model compounds, which are not commercially available, were prepared by organic synthesis and this allowed us to extend the number of identified natural TAGs to nearly 140 molecular species. Both synthetic and natural compounds containing ω-phenylalkanoic acids were found to have antioxidant and free radical scavenging properties.
- MeSH
- Araceae chemie MeSH
- chromatografie s reverzní fází MeSH
- hmotnostní spektrometrie MeSH
- mastné kyseliny analýza chemie izolace a purifikace MeSH
- Rhodococcus chemie MeSH
- scavengery volných radikálů analýza chemie izolace a purifikace MeSH
- semena rostlinná chemie MeSH
- techniky syntetické chemie MeSH
- triglyceridy analýza chemie izolace a purifikace MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The ability of Linaria vulgaris (Scrophulariaceae) infusion to act as a scavenger of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, reactive oxygen species (superoxide radical, hydroxyl radical, hypochlorous acid (HOCl)) and nitric oxide was investigated. The obtained data indicate that the infusion has a good scavenging activity against superoxide radical and is a very potent nitric oxide and DPPH scavenger. In hydroxyl radical assay a pro-oxidant capacity was noticed, especially for concentrations higher than 31.25 microg mL(-1). No effect was found against HOCl. A phytochemical study of this extract was also performed. The HPLC/UV analysis allowed the identification and quantification of eight organic acids (oxalic, aconitic, citric, ketoglutaric, ascorbic, malic, shikimic and fumaric acids). The phenolic composition of the lyophilised infusion was also determined by HPLC/DAD and four compounds were quantified, but, despite its high content, only linarin was managed to be identified.
- MeSH
- bifenylové sloučeniny chemie MeSH
- fenoly analýza MeSH
- financování organizované MeSH
- hydraziny chemie MeSH
- hydroxylový radikál chemie MeSH
- kyselina chlorná chemie MeSH
- kyseliny karboxylové analýza MeSH
- Linaria chemie MeSH
- oxid dusnatý chemie MeSH
- pikráty MeSH
- scavengery volných radikálů analýza MeSH
- superoxidy chemie MeSH
- vysokoúčinná kapalinová chromatografie MeSH
The aim of this study was to determine the amount of phenol compounds in tinctures prepared from Ginkgo leaves, Echinacea plant, and Ginseng roots and to evaluate the antioxidative activity of these preparations. We studied the antioxidative activity using the standard 2,2-diphenyl-1-picrylhydrazyl (DPPH.) radical cation scavenging and tyrosine nitration inhibition tests. The obtained findings showed that the amount of phenol compounds in the studied tinctures differed and ranged between 114 to 340+/-29 gallic acid equivalents (GAE) mg/100 mL. We found that the amount of phenol compounds in Ginkgo tincture was statistically significantly greater than that in Echinacea or Ginseng tinctures. The effectiveness of Ginkgo tincture was by 52.7% (P<0.01) lower (from 1343+/-11 mumol catechin/100 mL solution to 637+/-64 catechin/100 mL solution), compared to Echinacea tincture. Ginseng tincture was the weakest scavenger of free radicals--only 8+/-1 micromol catechin/100 mL solution. The inhibition of tyrosine nitration was by 34% (P<0.01) greater in Echinacea tincture, compared to Ginkgo tincture (from 892+/-36 micromol catechin/100 mL solution to 588+/-17 micromol catechin/100 mL solution). Ginseng tincture was the weakest inhibitor of tyrosine nitration--only 20+/-8 micromol catechin/100 mL solution, which was by 44.6 times less, compared to Echinacea tincture. Tests on DPPH. radical cation scavenging and inhibition of nitration showed that the antioxidative activity of Echinacea tincture was statistically significantly greater compared to that of Ginkgo or Ginseng tinctures. This allows us to conclude that antioxidative activity is determined not only by phenol compounds, but also by a complex of other components of medicinal raw material.
- MeSH
- antioxidancia analýza MeSH
- Echinacea chemie MeSH
- fenoly analýza MeSH
- Ginkgo biloba chemie MeSH
- indikátory a reagencie MeSH
- interpretace statistických dat MeSH
- rostlinné přípravky chemie MeSH
- scavengery volných radikálů analýza MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- ženšen chemie MeSH
- Publikační typ
- hodnotící studie MeSH
- srovnávací studie MeSH
Oxid dusnatý je relativně stabilní, vysoce reaktivní radikál vznikající v organizmu oxidací guanidinovéhodusíku aminokyseliny L-argininu působením NO-syntasy za vzniku L-citrullinu. Účastní secelé řady fyziologických i patologických procesů. Rozdíl mezi fyziologickou a patologickou koncentracíoxidu dusnatého je velmi nepatrný, a proto hledáme vhodné metody jeho stanovení a látkyovlivňující hladinu oxidu dusnatého, a tím snižující jeho nadprodukci. Testování scavengerovéaktivity vůči NO bylo provedeno metodou podle Griesse (spektrofotometrické stanovení dusitanů,jako oxidačních produktů NO), kterou jsme porovnávali s námi vyvíjenou HPLC metodou (vysokoúčinnákapalinová chromatografie). Antiradikálový účinek testovaných látek (kyselina acetylsalicylová,piracetam, paracetamol, serotonin, stobadin dihydrochlorid, 5-hydroxy-L-tryptofan,N-acetyl-L-cystein, L-glutathion, N-acetyl-DL-penicillamin) vůči NO byl porovnán s tzv. celkovouantioxidační aktivitou – TRAP (total radical-trapping antioxidant parameter), která odpovídáschopnosti vychytávat peroxylové radikály. Na základě získaných výsledků je piracetam a kyselinaacetylsalicylová bez antioxidační aktivity, paracetamol vykazuje pravděpodobně mírné zhášecíschopnosti vůči oxidu dusnatému a ostatní testované látky (především 5-hydroxy-L-tryptofan,serotonin, stobadin) jsou silnými antioxidanty vůči NO i peroxylového radikálu.
Nitrogen oxide is a relatively stable, highly reactive radical, which develops in the organism byoxidation of the guanidine nitrogen of the amino acid L-arginine by the action of NO-synthase withthe development of L-citrulline. It participates in a number of physiological and pathologicalprocesses. The difference between the physiological and pathological concentration of nitrogen oxideis very small, and for that reason we search for suitable methods of its determination and thesubstances influencing the level of nitrogen and thus decreasing its overproduction. Testing ofscavenger activity against NO was performed by the method following Griess (spectrophotometricdetermination of nitrites as the oxidation products of NO), which was compared with the HPLC(high-performance liquid chromatography) method developed by the present authors. The antiradicaleffect of the compounds being assayed (acetylsalicylic acid, piracetam, paracetamol, serotonin,stobadin dihydrochloride, 5-hydroxy-L-tryptophan, N-acetyl-L-cysteine, L-glutathion, and N-acetyl--DL-penicillamine) against NO was compared with the so-called total antioxidant activity – TRAP(total radical-trapping antioxidant parameter), which corresponds to the capability to trap peroxylradicals. On the basis of the obtained data, piracetam and acetylsalicylic acid show no antioxidantactivity, paracetamol shows probably moderate scavenging action against nitrogen oxide, and othercompounds tested (primarily 5-hydroxy-L-tryptophan, serotonin, stobadin) are strong antioxidantsagainst both NO and peroxyl radical.
- MeSH
- antioxidancia analýza farmakologie MeSH
- gastroenteritida metabolismus mikrobiologie MeSH
- infekce vyvolané Helicobacter pylori komplikace metabolismus MeSH
- lidé MeSH
- reaktivní formy kyslíku analýza metabolismus MeSH
- scavengery volných radikálů analýza fyziologie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- srovnávací studie MeSH
- MeSH
- diabetes mellitus 1. typu etiologie metabolismus patologie MeSH
- diabetes mellitus 2. typu etiologie metabolismus patologie MeSH
- diabetes mellitus MeSH
- diabetické angiopatie patofyziologie MeSH
- endotel fyziologie patologie MeSH
- glykosylace MeSH
- hyperglykemie metabolismus patologie MeSH
- inzulin fyziologie metabolismus MeSH
- lidé MeSH
- lipidy biosyntéza MeSH
- lipoproteiny biosyntéza MeSH
- oxidační stres fyziologie MeSH
- scavengery volných radikálů analýza MeSH
- Check Tag
- lidé MeSH
Závěrečná zpráva o řešení grantu Interní grantové agentury MZ ČR
71 s. : il. ; 30 cm
Problematika včasné diagnostiky a prevence diabet. cévních komplikací jako následku porušené rovnováhy mezi nadměrnou tvorbou vysokoreaktivních forem kyslíku a sníženou antioxidační kapacitu krve, možnosti terapeutického ovlivnění.
- MeSH
- diabetické angiopatie prevence a kontrola diagnóza etiologie MeSH
- glutathionperoxidasa krev MeSH
- lipidové peroxidy analýza MeSH
- scavengery volných radikálů analýza MeSH
- selen farmakologie aplikace a dávkování MeSH
- superoxiddismutasa krev MeSH
- vitaminy farmakologie aplikace a dávkování MeSH
- Konspekt
- Fyziologie člověka a srovnávací fyziologie
- NLK Obory
- vnitřní lékařství
- NLK Publikační typ
- závěrečné zprávy o řešení grantu IGA MZ ČR