scholarly journals Phenolic Compounds of Propolis from the Boreal Coniferous Zone

2012 ◽  
Vol 56 (1) ◽  
pp. 13-22 ◽  
Author(s):  
Anneli Salonen ◽  
Sanna Saarnio ◽  
Riitta Julkunen-Tiitto

Phenolic Compounds of Propolis from the Boreal Coniferous ZoneThe profile of phenolic compounds in 19 propolis samples from different provinces in Finland were analysed for the first time using HPLC-DAD. Nine individual flavonoids (comprising 26% of the identified phenolics), eleven cinnamic acid derivatives (36%), two caffeic acid derivatives (14%), three chlorogenic acid derivatives (14%), and three other phenolic acids (10%) were found in the propolis samples. The compounds found in the largest quantities were methyl-naringenin and caffeic acid phenethyl ester (CAPE). The phenolic profiles of Finnish propolis show marked differences when compared withP. nigraandP. tremuloidespropolis of Central European and Canadian origins. The phenolic compounds found in propolis samples are commonly found in the tree species growing in Finland. Non-metric multidimensional scaling showed that samples were scattered and they did not form clear groups according to the geographical origin or age of the sample.

Author(s):  
O. K. Karimov ◽  
G. Y. Kolchina ◽  
G. A. Teptereva ◽  
I. A. Chetvertneva ◽  
E. K. Karimov ◽  
...  

Objectives. Cinnamic acid derivatives belong to a large class of phenolic compounds, which are widely distributed in plants and have high potential for use in the medical and industrial fields. They have various useful practical properties, e.g., antioxidant, anti-inflammatory, antiplatelet, and anti-melanogenic properties. Hydroxycinnamic acids are of particular interest as phenylpropanoids, which are the starting compounds of lignin. The aim of this work was to study the electronic structure and analyze the reactivity of the simplest representatives of phenylpropanoids formed during the biosynthesis of the coumaric (p-hydroxycinnamic), caffeic (3,4-dihydroxycinnamic), ferulic (3-methoxy-4-hydroxycinnamic), sinapic (3,5-dimethoxy-4- hydroxycinnamic), and 3,4-dimethoxycinnamic acids. These acids are the biogenetic precursors of most other phenolic compounds (coumarins, melanins, lignins, and flavonoids) and are found in almost all higher plants.Methods. Calculations with full optimization of the geometric parameters were performed using the original Hartree–Fock theory and hybrid density functional method. All calculations were performed using the Firefly program. Results. A comparative quantum chemical calculation of the geometric parameters of hydroxycinnamic acid molecules was conducted via two methods, and the values of the charges on atoms according to Mulliken were determined. It was found that with the addition of hydroxyl and methoxy substituents at the meta and para positions relative to the carboxyl fragment, the electron density shifts toward the benzene ring, and the symmetry of the molecule decreases. Additionally, in these structures, there is π,π-conjugation of the carboxyl fragment of the –СН=СНСООН molecule with the aromatic ring, which significantly affects the geometric configuration of the molecule. The maximum positive charge is concentrated on the C9 atom, while the maximum negative charge is on the oxygen atoms belonging to the methoxy substituents and the hydroxyl group, which confirms the role of oxygen atoms in the chemical transformations of acids. Conclusions. Two different methods were used to calculate the geometric, electronic, and energy parameters and electrophilicity indices of the studied hydroxycinnamic acids in the gas phase. The obtained values were consistent (within the limits of error) with the experimental data as well as the results described in earlier works’ calculations by other methods.


2021 ◽  
Vol 38 ◽  
pp. 00063
Author(s):  
Olga Kotsupiy ◽  
Tatyana Shemetova

For the first time, the composition and content of phenolic compounds (PC) of plant leaves of an endemic rare species of the Xiphidium Bunge section of the genus Astragalus L. of Siberia – Astragalus palibinii Polozhij was studied by HPLC. 11 compounds of phenolic nature were identified in water-ethanol extracts of A. palibinii leaves: gallic, p-hydroxybenzoic, chlorogenic, caffeic, ferulic, trans-ferulic, cinnamic acids, isoquercitrin, rutin, isoramnetin-3-O-rutinoside and L-epicatechin. The composition of PC in the leaves of plants of three cenopopulations A. palibinii from Khakassia is the same, with the exception of one hydroxycinnamic acid in trace amounts. The content (mg per 100 g DW) of flavonol glycosides in the leaves of A. palibinii plants varies in the range of 0.442–0.907, the content of hydroxycinnamic and hydroxybenzoic acids in the range of 98.5–109.7 and 32.5–83.9, respectively. The quantitative profiles of all the studied groups of PC are characterized by significant variability in the content of individual components. The variability of the content of hydroxycinnamic acids, flavonoids and hydroxybenzoic acids was determined as very low, medium and increased, respectively.


2012 ◽  
Vol 7 (10) ◽  
pp. 1934578X1200701
Author(s):  
Riaz Hussain ◽  
Bakhat Ali ◽  
Muhammad Imran ◽  
Abdul Malik

Two new cinnamic acid derivatives, thymofolinoates A (1) and B (2) have been isolated from the chloroform soluble fraction of Euphorbia thymifolia and their structures assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, HMQC and HMBC experiments. In addition, p-hydroxy cinnamic acid (3), 5-hydroxy-6,7,8,4′-tetramethoxy flavone (4), and 5-hydroxy-3′,4′,6,7,8-pentamethoxy flavone (5) have also been isolated for the first time from this species.


2012 ◽  
Vol 2012 ◽  
pp. 1-6 ◽  
Author(s):  
Belén Márquez-García ◽  
M. Ángeles Fernández-Recamales ◽  
Francisco Córdoba

We evaluated the effects of cadmium on phenolic composition of Erica andevalensis, an endemic protected heather that grows in mine affected soils. Plants cultivated under laboratory-controlled conditions were exposed to acute doses of cadmium to investigate the mechanisms this species possesses to survive in the presence of toxic metals in its natural habitat. Cadmium increased the total levels of phenolics and flavonoids compounds, and the total antioxidant capacity. Cinnamic acid derivatives, epicatechin, and rutin were increased in the presence of cadmium when applied in levels that did not alter the ratio of chlorophylls. Phenolic compounds play an important role in the metabolism of E. andevalensis to survive in heavy metal polluted soils.


2020 ◽  
pp. 149-155
Author(s):  
Anastasiya Petrovna Belanova ◽  
Vera Andreyevna Kostikova ◽  
Galina Ivanovna Vysochina

The expansion of alien plant species in natural communities is now taking a global scale. Since most invasive plants have economically valuable properties, many researchers agree that these plants must be used as new sources of biological resources. The composition and content of biologically active compounds were studied in the leaves of potentially invasive species of Novosibirsk – Physocarpus opulifolius (L.) Maxim. and its ornamental cultivars Ph. opulifolius ‘Diabolo’, Ph. opulifolius ‘Luteus’ by the method of High-Performance Liquid Chromatography. For the first time an analysis of phenolic profiles of introduced, self-sown and cultivated Ph. opulifolius plants has been performed. Presence of 22 phenolic compounds represented by several groups of substances with predominating flavanols (hyperoside, rutin, astragalin and quercetin) has been established. Avicularin has been only revealed in the leaves of cultivars. The sum of identified flavonols greatly varies in different samples, the highest content is in the cultivar Ph. opulifolius ‘Diabolo’ (14.68 mg/g) and self-sown plants of Ph. opulifolius (14.22 mg/g). The content of the sum of identified flavons (vitexin, isovitexin, baicalin) and phenolic acid (сhlorogenic and caffeic acids) is almost the same in all Ph. opulifolius samples under study. The data obtained will allow to widen the idea of the resource potential of the aggressive invasive species and its ornamental cultivars in the secondary areal.


Author(s):  
Rima Boukhary ◽  
Maha Aboul-ElA ◽  
Othman Al-Hanbali ◽  
Abdalla El-Lakany

Centaurea horrida has been used in folk medicine for many purposes as diuretic, antiinflammatory, hypotensive, antidiarrhetic, mild astringent, bitter tonic, stomachic, digestive, and emmenagogue and in cosmetics. An infusion of this plant is used to treat diabetes and digestive problems Also it is used as a wash for tired eyes and in conjunctivitis. C.horrida grown in Lebanon is widely used in the treatment of diarrhea, as antihypertensive and as hypoglycemic. Phytochemical investigation of the species grown in Lebanon led to the isolation and identification of five phenolic compounds isolated from methanol, ethyl acetate and butanol fractions of Centaurea extracts. Their structures were determined by NMR, MS, UV and IR methods. It is important to mention that the isolated flavonoids fisetin, hispidulin, quercetin, quercetin -3-D- galactoside and caffeic acid were isolated for the first time from Centaurea horrida. L growing in the Middle East.


2017 ◽  
Vol 2017 ◽  
pp. 1-10 ◽  
Author(s):  
Arkadiusz Dziedzic ◽  
Robert Kubina ◽  
Agata Kabała-Dzik ◽  
Marta Tanasiewicz

Natural polyphenols have been observed to possess antiproliferative properties. The effects, including apoptotic potential of bioactive phenolic compounds, caffeic acid (CA) and its derivative caffeic acid phenethyl ester (CAPE), on cell proliferation and apoptosis in human head and neck squamous carcinoma cells (HNSCC) line (Detroit 562) were investigated and compared. Cancer cells apoptosis rates and cell cycle arrests were analysed by flow cytometry. Exposure to CA and CAPE was found to result in a dose-dependent decrease in the viability of Detroit 562 cells at different levels. CA/CAPE treatment did significantly affect the viability of Detroit 562 cells (MTT results). CAPE-mediated loss of viability occurred at lower doses and was more pronounced, with the concentrations which inhibit the growth of cells by 50% estimated at 201.43 μM (CA) and 83.25 μM (CAPE). Dead Cell Assay with Annexin V labelling demonstrated that CA and CAPE treatment of Detroit 562 cells resulted in an induction of apoptosis at 50 μM and 100 μM doses. The rise of mainly late apoptosis was observed for 100 μM dose and CA/CAPE treatment did affect the distribution of cells in G0/G1 phase. A combination of different phenolic compounds, potentially with chemotherapeutics, could be considered as an anticancer drug.


1997 ◽  
Vol 52 (5-6) ◽  
pp. 308-312 ◽  
Author(s):  
Christine A. Kraus ◽  
Gerhard Spiteller

Abstract The influence of ageing on the amount and composition of phenolic compounds and their glucosides was studied in one to five-year-old shoots of Picea abies. The total content of phenolics increased remarkably within the first two years of growth. In this period cinnamic acid derivatives were dominating, but beginning with the end of the first vegetation period a dramatic increase of acetophenones was observed. Obviously at the end of the first vegetation period the cinnamic acid derivatives are subjected to oxidation resulting in an increase of acetophenones.


2018 ◽  
Vol 44 (3) ◽  
pp. 299-306
Author(s):  
Gülin Renda ◽  
Arzu Özel ◽  
Emine Akyüz Turumtay ◽  
Burak Barut ◽  
Büşra Korkmaz ◽  
...  

Abstract Background Aboveground parts and bulbs of Ornithogalum species are consumed as food and used in traditional medicine in worldwide. Objective It is aimed to report the antioxidant capacity and phenolic compounds content of Ornithogalum sigmoideum, Ornithogalum orthophyllum and Ornithogalum oligophyllum for the first time. Materials and methods Antioxidant activity of the crude methanol extracts of the aerial parts and the bulbs of the species were determined with 1,1-diphenyl-2-picryl-hydrazyl, superoxide radical scavenging, ferrous ion-chelating effect, phosphomolybdenum-reducing antioxidant power and ferric-reducing antioxidant power assay. The ethylacetate, diethylether and water subextracts from leaf and flower were analyzed to quantify selected phenolic compounds by HPLC-UV. Results Among the six extracts, the methanol extract of the aerial parts of O. orthophyllum contained the highest amount of phenolic compounds (GAE, 11.0 mg/g extract). The aerial parts of O. orthophyllum showed higher DPPH and SOD activities than the other extracts with the SC50 values of 0.39±0.05 mg/mL and 0.44±0.08 mg/mL, respectively. Protocatechuic acid, p-hydroxybenzoic acid, vanillic acid and p-coumaric acid were the most abundant compounds at all the subextracts. Conclusion The antioxidant activity is found to be in accordance with the levels of phenolic content in the extracts.


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