Phenolics: from chemistry to biology

In recent years, few classes of natural products have received as much attention as phenolics and polyphenols. This special issue of Molecules, “Phenolics and Polyphenolics”, is a remarkable confirmation of this trend. Several aspects related to phenolics chemistry, comprising the several classes, will be discussed. In addition, the increasing interest in phenolics’ biological activities is covered, and several works addressing this matter are referred

Phenolic compounds, organic acids profiles and antioxidative properties of beefsteak fungus (Fistulina hepatica)

The phenolic compounds and the organic acids composition of the edible beefsteak fungus Fistulina hepatica was determined by HPLC/DAD and HPLC/UV, respectively. The results showed a profile composed by five phenolic compounds (caffeic, p-coumaric and ellagic acids, hyperoside and quercetin) and six organic acids (oxalic, aconitic, citric, malic, ascorbic and fumaric acids). The quantification of the identified compounds revealed that ellagic acid (ca. 49.7%) and malic acid (ca. 57.9%) are the main compounds in this species. In a general way the phenolic profile revealed to be more constant than the organic acids one and could be more useful for the quality control of the species. Beefsteak fungus was also investigated for its capacity to act as a scavenger of DPPH- radical and reactive oxygen species (superoxide radical, hydroxyl radical and hypochlorous acid). Good results were obtained against DPPH in a concentration-dependent manner. Beefsteak fungus also displayed good activity against superoxide radical, achieved by its capacity to act as both scavenger and xanthine oxidase inhibitor. A prooxidant effect was noticed for hydroxyl radical, which may be due to its capacity for iron ions reduction. Little ability for iron chelation was also observed. Beefsteak fungus showed a weak protective effect against hypochlorous acid

Fatty acid composition of wild edible mushrooms species: a comparative study

A comparative study was developed on the total fatty acids composition of twelve wild edible mushroom species (Suillus bellini, Suillus luteus, Suillus granulatus, Hygrophorus agathosmus, Amanita rubescens, Russula cyanoxantha, Boletus edulis, Tricholoma equestre, Fistulina hepatica, Cantharellus cibarius, Amanita caesarea and Hydnum rufescens). In order to define qualitative and quantitative profiles, combined fatty acids were hydrolyzed with potassium hydroxide/methanol and all free compounds were derived to their methyl ester forms with methanolic boron trifluoride, followed by analysis by GC-MS. Thirty fatty acids were determined. As far as we know, the fatty acid profiles of A. caesarea and H. rufescens are described for the first time. As for the remaining species, a high number of new compounds were identified, which much improved the knowledge about their fatty acids profiles. In general, oleic, linoleic, palmitic and stearic acids were present in highest contents. Polyunsaturated and monounsaturated fatty acids, valuable healthy compounds for humans, predominated over saturated fatty acids for all the studied mushroom species. R. cyanoxantha presented the highest fatty acids amounts, while B. edulis was the poorest species. By Agglomerative Hierarchic Cluster Analysis the studied species were gathered in 5 groups, based in their fatty acid patternsFundação para a Ciência e a Tecnologia (FCT) for a grant (SFRH/BD/22108/2005)

Investigação Química da Marthasterias Glacialis da Costa Portuguesa, como Fonte de Compostos com Actividade Farmacêutica

Marine organisms are increasingly regarded as a promising source of bioactive molecules for human pharmacotherapy, being used in conditions such as cancer, inflammation, infection and pain.Marthasterias glacialis, also known as the spiny sea-star, is an echinoderm common in the Portuguese coast, however little information is available regarding its chemical constituents.In this work, the chemistry of this organism is reviewed taking into account the latest reports on several classes of natural products, namely carotenoids, sterols, fatty acids and amino acids.Os organismos marinhos tem sido considerados como uma fonte promissora de moléculas com actividade farmacoterapêutica para os humanos, sendo utilizadas em distintas patologias como neoplásicas, inflamatórias, infecciosas ou álgicas. A Marthasterias glacialis, também conhecida como estrela do mar espinhosa, é um equinodermo muito comum na costa portuguesa, existindo, contudo, pouca informação sobre a sua composição quimica.Pretende-se rever a quimica deste organismo tendo em conta os ultimos dados sobre as diferentes classes de produtos, nomeadamente carotenoides, esteróides, ácidos gordos e aminoácidos

Phenolic profile of Cydonia oblonga Miller leaves

Cydonia oblonga Miller leaves phenolic compounds were analyzed by reversed-phase HPLC/DAD and HPLC/UV. Qualitative and quantitative analysis of phenolics were carried out in a total of 36 samples of quince leaves from three different geographical origins of Northern (Bragança and Carrazeda de Ansiães) and Central Portugal (Covilhã) and three collection months (June, August, and October of 2006). These leaves presented a common phenolic profile composed by nine compounds: 3-O-, 4-O- and 5-O-caffeoylquinic acids, 3,5-O-dicaffeoylquinic acid, quercetin-3-Ogalactoside, quercetin-3-O-rutinoside, kaempferol-3-O-glycoside, kaempferol-3-O-glucoside, and kaempferol-3-O-rutinoside. 5-O-caffeoylquinic acid was the major phenolic compound (36.2%), followed by quercetin 3-O-rutinoside (21.1%). Quince leaves are characterized by higher relative contents of kaempferol derivatives than fruits (pulps, peels, and seeds), especially in what concerns kaempferol-3-O-rutinoside (12.5%). C. oblonga leaves total phenolic content was very high, varying from 4.9 to 16.5 g/kg dry matter (mean value of 10.3 g/kg dry matter), indicating that these leaves can be used as a good and cheap source of bioactive constituents. Significantly differences were observed in 3-O-caffeoylquinic and 3,5-O-dicaffeoylquinic acids contents, according to geographical provenance and harvesting month, suggesting a possible use of these compounds as geographical origin and/or maturity markers

Organic acids composition of Cydonia oblonga Miller leaf

Organic acid profiles of 36 Cydonia oblonga Miller leaf samples, from three different geographical origins of northern (Bragança and Carrazeda de Ansiães) and central Portugal (Covilhã), harvested in three collection months (June, August and October of 2006), were determined by HPLC/UV (214 nm). Quince leaves presented a common organic acid profile, composed of six constituents: oxalic, citric, malic, quinic, shikimic and fumaric acids. C. oblonga leaves total organic acid content varied from 1.6 to 25.8 g/kg dry matter (mean value of 10.5 g/kg dry matter). Quinic acid was the major compound (72.2%), followed by citric acid (13.6%). Significant differences were found in malic and quinic acids relative abundances and total organic acid contents according to collection time, which indicates a possible use of these compounds as maturity markers. Between June and August seems to be the best period to harvest quince leaves for preparation of decoctions or infusions, since organic acids total content is higher in this season

Composição química e actividade antioxidante das folhas internas da couve tronchuda

A couve tronchuda (Brassica oleracea L. var. costata DC) é uma das couves mais consumidas pelos portugueses, especialmente durante o Inverno, apresentando as folhas (internas e externas) diferenças organolépticas marcadas. No presente trabalho procedeu-se à caracterização química das folhas internas de couve tronchuda, através da identificação e quantificação dos compostos fenólicos e dos ácidos orgânicos que as compõem e avaliou-se o seu potencial antioxidante. Foram identificados e quantificados, por HPLC-DAD-ESI-MS e HPLC/DAD, respectivamente, 17 compostos fenólicos: quercetina 3-O-soforósido-7-O-glucósido, ácido 3-p-cumaroilquínico, campferol 3-O-soforósido-7-O-glucósido, campferol 3-O-(cafeoil)-soforósido-7-O-glucósido, ácido sinapoilglucósido, campferol 3-O-(sinapoil)-soforósido-7-O-glucósido, campferol 3-O-(feruloil)-soforósido-7-O-glucósido, campferol 3-O-(p-cumaroil)-soforósido-7-O-glucósido, ácido 4-p-cumaroilquínico, ácido sinápico, campferol 3-O-soforósido, 3 isómeros de 1,2-di-sinapoilgentiobiose, 1-sinapoil-2-feruloilgentiobiose, 1,2,2-tri-sinapoilgentiobiose e 1,2’-di-sinapoil-2-feruloilgentiobiose. Foram também identificados e quantificados, por HPLC/UV, sete ácidos orgânicos (ácidos aconítico, cítrico, ascórbico, málico, quínico, chiquímico e fumárico). A actividade antioxidante do extracto aquoso foi aferida pela capacidade para interceptar o radical DPPH e espécies reactivas de oxigénio (radicais superóxido e hidroxilo e ácido hipocloroso), tendo revelado grande efeito protector

Contents of carboxylic acids and two phenolics and antioxidant activity of dried Portuguese wild edible mushrooms

The organic acids and phenolics compositions of nine wild edible mushrooms species ( Suillus bellini, Tricholomopsis rutilans, Hygrophorus agathosmus, Amanita rubescens, Russula cyanoxantha, Boletus edulis, Tricholoma equestre, Suillus luteus, and Suillus granulatus) were determined by HPLC-UV and HPLC-DAD, respectively. The antioxidant potential of these species was also assessed by using the DPPH¥ scavenging assay. The results showed that all of the species presented a profile composed of at least five organic acids: oxalic, citric, malic, quinic, and fumaric acids. In a general way, the pair of malic plus quinic acids were the major compounds. Only very small amounts of two phenolic compounds were found in some of the analyzed species: p-hydroxybenzoic acid (in A. rubescens, R. cyanoxantha, and T. equestre) and quercetin (in S. luteusand S. granulatus). All of the species exhibited a concentration-dependent scavenging ability against DPPH¥. T. rutilansrevealed the highest antioxidant capacity

Chemical and antioxidative assessment of dietary turnip (Brassica rapa var. rapa L.)

The phenolic compounds and organic acids of turnip (Brassica rapa var. rapa L.) edible parts (leaves and stems, flower buds and roots) were determined by HPLC–DAD and HPLC–UV, respectively. The results revealed a profile composed of 14 phenolics (3-p-coumaroylquinic, caffeic, ferulic and sinapic acids, kaempferol 3-O-sophoroside-7-O-glucoside, kaempferol 3-O-sophoroside-7-O-sophoroside, kaempferol 3-O-(feruloyl/caffeoyl)-sophoroside-7-O-glucoside, kaempferol 3,7-O-diglucoside, isorhamnetin 3,7-O-diglucoside, kaempferol 3-O-sophoroside, 1,2-disinapoylgentiobiose, 1,20-disinapoyl-2-feruloylgentiobiose, kaempferol 3-O-glucoside and isorhamnetin 3-O-glucoside) and six organic acids (aconitic, citric, ketoglutaric, malic, shikimic and fumaric acids). The quantification of the identified compounds showed kaempferol 3-O-sophoroside-7-O-glucoside, kaempferol 3-O-(feruloyl/caffeoyl)-sophoroside-7-O-glucoside, isorhamnetin 3,7-O-diglucoside and isorhamnetin 3-O-glucoside as the main phenolics, and malic acid as the organic acid present in highest amounts. A screening of the antioxidative potential was also performed by means of the DPPH radical scavenging assay. Turnip flower buds exhibited the strongest antioxidant capacity

Tronchuda cabbage flavonoids uptake by Pieris brassicae

The flavonoid pattern of larvae of cabbage white butterfly (Pieris brassicae L.; Lepidoptera: Pieridae) reared on the leaves of tronchuda cabbage was analysed by HPLC-DAD-MS/MS-ESI. Twenty flavonoids were identified or characterised, namely 16 kaempferol and four quercetin derivatives. Kaempferol 3-O-sophoroside, a minor component of tronchuda cabbage, was found to be the main component in P. brassicae (15.8%). Apart from this, only two other flavonoids present in significant amounts in tronchuda cabbage (kaempferol 3-O-sophoroside-7-O-glucoside and kaempferol 3-O-sophoroside-7-O-sophoroside) were found in the larvae. The larvae have high amounts of quercetin derivatives (18.5%), which were present only in trace amounts in tronchuda cabbage extracts, suggesting that P. brassicae is able to selectively sequester these flavonoids. The occurrence of a high content of flavonoids not detectable in tronchuda cabbage extracts indicates that P. brassicae larvae are able to metabolize dietary flavonoids