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Phytochemical studies on the polar fractions of plants belonging to the Lamiaceae family with aspects of chemotaxonomy, ethno-pharmacology, nutraceutics and phytochemical evolution
Full text linkIn this PhD thesis, a comprehensive phytochemical analysis was performed on a series of nineteen plants belonging to the Lamiaceae family. In particular, five Ajuga, three Teucrium, one Galeopsis, two Melittis, two Sideritis and six Stachys species were studied for their content in secondary metabolites in the polar fraction. One hundred and sixty-nine compounds were, respectively, isolated and identified by these species mainly by means of Column Chromatography and by means of NMR Spectroscopy and MS Spectrometry. These phytochemicals belong to thirteen different classes of natural compounds and were even evidenced in more species. Among these, three resulted to be new compounds, identified for the first time during this study. Their presence was important from the chemotaxonomic, ethnopharmacological and nutraceutical points of view. In fact, the chemotaxonomic markers of the family, of specific genera and species were evidenced thus confirming the botanical classification of the studied species under the phytochemical profile. Moreover, these compounds proved to be very useful to justify most of the ethnopharmacological and nutraceutical uses of these species and to also provide possible further ones. Lastly, some of the secondary metabolites found in some species were used to draw two Sporne diagrams correlating phytochemistry and their own evolution. In this case, some concordance between these data with those usually reported in literature in this context, was observed but also a couple of cases of great discordance, thus suggesting to use also phytochemical evolution, together with molecular data, to draw the evolutionary phylogenetic trees of the species in order to have more precise result
Analisi fitochimica di Ajuga genevensis L. e Pedicularis verticillata L., due specie caratteristiche dell’ambiente dolomitico
No full textContent Of The Polar Fraction Of An European Mushroom: Suillus bellinii (Inzenga) Watling
No full textSuillus bellinii (Inzenga) Watling is a mushroom belonging to the Botelaceae family. The fruiting bodies are characterized by an irregular cap, large pores, a short and squat stem and lastly a whitish dampish flesh with a very sweet taste. Right for these features it is considered one of the most appreciated species of Suillus group. This species, as well as several edible fungi, is often employed as component of low caloric diets. Moreover it’s widely utilized for its high tumor inhibiting and cytotoxic properties. In this work we report the composition of the methanolic fraction obtained from the fruiting bodies of this mushroom. Four major classes of compounds were isolated: fatty acids, terpenoids, amino acids and one aromatic ketone. The fatty acids are still under study to determine the specific compounds as well as the isolated terpenoid and the aromatic ketone. On the other hand it was identified suillin which is formed by a diterpenic chain linked to an aromatic ring in the position 3. This compound was found for the first time in this species although not in the genus and, togheter with isosuillin, it’s responsible for the pharmacological activity of this mushroom. For what concerns the amino acidic part, some were identified like tryptophan and threonine while further analysis is necessary to confirm the suspected presence of valine, leucine and phenylalanine. The presence of amino acids add some nutritional value to this edible fungus
Primary and secondary metabolites of an European edible mushroom and its nutraceutical value. Suillus bellinii (Inzenga) Kuntze
No full textIn this work, we report the study on the composition in primary and secondary metabolites of the polar and less-polar fractions obtained from the fruiting bodies of Suillus bellinii (Inzenga) Kuntze collected from Central Italy. Thirteen compounds were identified through a series of classical chromatographic methods and through spectroscopic techniques (nuclear magnetic resonance (NMR) and mass spectrometry (MS)), namely suillin (1), ergosterol (2), glutamic acid (3), isoleucine (4), leucine (5), threonine (6), tyrosine (7), valine (8), D-mannitol (9), sucrose (10), D-sorbitol (11), fumaric acid (12) and alanine (13). These results allowed us to make specific considerations about the possible applications of this mushroom, which vary from medicine, due to the high cytotoxic and antitumor properties of suillin (1), to nutritional values, due to the presence of essential nutrients as amino acids and pre-vitamin D2 (ergosterol), together with low-calories sweeteners, confirming the close association between the identified components and the health-promoting properties of this species
MOLECULAR PATTERN COMPARISON BETWEEN TWO PEDICULARIS SPECIES
No full textIn this work we report a comparison of the polar fraction composition between two Pedicularis species, namely P. verticillata L. and P. kerneri Dalla Torre, collected in the area of the Dolomites, Italian Alps, at an altitude comprised between 2000-2700 m a.s.l. The genus Pedicularis was traditionally comprised in Scrophulariaceae family but more recently was moved into the Orobancaceae, as well as other hemiparasitic species, on the basis of molecular data. Pedicularis species are mainly used in the Chinese folk medicine against several disorders like diuresis, exhaustion, collapse and senility. Little studies have been previously performed on P. verticillata evidencing the presence of neolignans, phenylpropanoids and iridoid glycosides while no references were available on P. kerneri, probably because of the relative inaccessibility of their habitat. The study of the polar fraction of P. verticillata led to the isolation and identification of seven compounds which were aucubin (1), euphroside (2), monomelittoside (3), mussaenosidic acid (4), D-mannitol (5) verbascoside (6) and echinacoside (7). The first four compounds are glycosidic iridoids while compound (5) is a chiral polyol frequently recognized in hemiparasitic species belonging to Orobanchaceae, i.e. P. viscosa and B. trixago and lastly compounds (6) and (7) are phenyl-propanoids. The co-occurrence of iridoid glycosides and phenylpropanoids have a chemotaxonomical importance. The composition of P. kernerii revealed the presence of iridoids like aucubin (1), euphroside (2), monomelittoside (3), mussaenosidic acid (4), plantarenaloside (8), 8-epiloganic acid (9), mannitol (5) and verbascoside (6) among phenyl-propanoids. It is interesting the presence in P. kerneri of 8-epiloganic acid (9) since it is considered a precursor of the other iridoids recognized in this species. Although in both cases we evidenced compounds already isolated from the genus, this study allowed us to show some similarities and differences between the two studied species. The first evidence is the different amount of iridoids in the two species with the major presence revealed in P. kernerii. Moreover, there are only two differences between the two phytochemical pattern: the further presence of plantarenaloside (8) and 8-epiloganic acid (9) in P. kernerii. As for the phenyl-propanoids, verbascoside was found in both Pedicularis while only P. verticillata showed also the presence of echinacoside. Moreover, we foresaw that the two studied samples presented a chemotype already recognized in species from Colorado as P. crenulata Benth; P. groenlandica Retz; P. procera Gray and P. racemosa Dougl. Ex Hook, characterized by euphroside (2) and aucubin (1) as main components. However the most interesting character was the presence of monomelittoside (2) actually never reported in this genus but previously found in species belonging to Lamiaceae family, as Melittis melissophyllum, but also in Plantaginaceae, and in Verbenaceae, Clerodendrum thomsonae Balf. f. All these families are comprised in the Lamiales order, and the co-occurrence of monomelittoside (2) is an evidence of the taxonomical affinity among these families
A rare bis-rhamnopyranosyl-aromadendrin derivative and other flavonoids from the flowers of Genista cilentina Vals. an endemic species of Southern Italy
No full textA rare bis-rhamnopyranoside of aromadendrin, besides isoflavones of chemosystematic importance and peculiar compounds never reported in the genus, was identified from the flowers of Genista cilentina, an Italian endemic species. The structure of the aromadendrin derivative was elucidated by means of 1D and 2D NMR techniques. The exclusivity of the observed molecular pattern in comparison with other Genista species was further discussed from a chemotaxonomic point of view. A huge quantity of flavonoids in aglycone form resulted selectively accumulated in flowers
Secondary metabolites from Scrophularia canina L.
No full textScrophularia canina L. is a herbaceous perennial plant belonging to Scrophulariaceae and growing abundantly in Italy. In this work we report the composition of the polar fraction of the ethanolic extract of S. canina harvested in the pre-park area of National Park of Abruzzo, Lazio and Molise (Central Italy). This study allowed the isolation and the identification of a total of six compounds: one phenyl-propanoid, verbascoside; one acyclic diterpenic alcohol called phytol; four iridoid glucosides namely aucubin, harpagide, 8-O-acetyl-harpagide and 8-epiloganic acid. Verbascoside is a quite common compound which is often identified as a constituent of species of the Asterideae subclass and has a taxonomic relevance when evidenced together with iridoids. Also phytol is a widespread compound since it’s part of the chlorophyll structure. Aucubin, harpagide and 8-O-acetyl-harpagide have already been evidenced in this species while the other three compounds were recognized for the first time in this study. From a biosynthetic point of view, it’s important to underline the presence of 8-epiloganic acid since it is considered the biogenetic precursor of a wide series of substances owning an iridoidic skeleton which are generally found in Scrophulariaceae and in other families of the Lamiales order and for this reason they are considered of chemotaxonomical relevance
Phytochemical analysis on the leaves of Agathis microstachya J.F. Bailey & C.T. White
No full textThe first phytochemical analysis on the leaves of Agathis microstachya J.F. Bailey & C.T. White collected in Rome was reported in this work. The study evidenced the presence of four compounds i.e., 7,4’’’-dimethoxy-agathisflavone (1), 7,7’’-dimethoxy-cupressuflavone (2), dactylifric acid (3) and shikimic acid (4) which were identified by means of spectroscopic techniques. Compounds (1, 2, 4) were reported in the species for the first time as well as this is the second report on the presence of dactylifric acid (3) in the whole Araucariaceae family. The absence of diterpenoids from the studied accession is also important. All these chemotaxonomic aspects were discussed
Riesame della frazione polare della Stachys alopecuros subs. divulsa del Parco Nazionale dei Monti Sibillini
No full textLa Stachys alopecuros subsp. divulsa Ten Grande (Lamiaceae), è una specie endemica del centro Italia caratteristica dell’ambiente montano che cresce su pascoli sassosi, prati aridi, rupi e boscaglie. Recentemente questa specie è stata oggetto di analisi fitochimica che ne ha messo in risalto la composizione in metaboliti secondari evidenziando la presenza di saponine (sitosterol-3-O-β-glucopiranoside), feniletanoidi glicosidici (verbascoside) e iridoidi, tra questi i markers chemotassonomici del genere (harpagide ed acetil-harpagide) ed un nuovo derivato di glicosidico del teuhircoside (4’-galattopiranosil-teuhircoside). In questo studio abbiamo riesaminato la frazione iridoidica applicando una metodica brevettata particolarmente adatta all’isolamento e frazionamento di questa classe di composti e che sfrutta l’adsorbimento su carbone attivo, seguita da desorbimento mediante soluzioni etanoliche a differente polarità, solitamente 30, 60 e 95 %. Questo permette di ottenere tre frazioni in cui i componenti iridoidi si smistano in base alla loro polarità.
I successivi frazionamenti su colonna di gel di silice, condotti sul desorbito al 60 %, hanno finora confermato la presenza dei markers chemotassonomici harpagide (1) ed il suo 8-O acetilderivato (2), insieme ad allobetonicoside (3) ed ajugoside (4) (Figura 1). Il composto (4) viene evidenziato per la prima volta in questo studio come componente di questa specie ma era già stato isolato da altre Stachys evidenziando così la loro prossimità sistematica.
Tra i composti fenolici è stato isolato l’acido clorogenico (5) un derivato caffeoilchinico già rinvenuto in altre specie appartenenti a questo genere ma non evidenziato in precedenza dalla S. alopecuros subsp. divulsa. La maggior parte dei composti isolati presenta interessanti attività biologiche, quali quella antinfiammatoria, antiossidante e antitumorale, che fanno di questa specie una potenziale fonte di composti farmacologicamente attivi.Stachys alopecuros subsp. divulsa Big Ten (Lamiaceae) is an endemic species of central Italy characteristic of the mountain environment that grows on stony pastures, dry meadows, cliffs and woods. Recently this species has been subjected to phytochemical analysis that highlighted the composition in secondary metabolites reporting the presence of saponins (sitosterol-3-O-β-glucopyranoside), phenylethanoid glycoside (verbascoside) and iridoids, including the chemotaxonomic markers of the genus (harpagide and acetyl-harpagide) and a new derivative teuhircoside biglycosidic (4'-galactopyranosyl-teuhircoside).
In this study we have reviewed the iridoidic fraction applying a patented method which is particularly suited to the isolation and the fractionation of this class of compounds and which exploits the activated carbon adsorption, followed by desorption by means of ethanolic solutions at different polarities, usually 30, 60 and 95%. This allows to obtain three fractions in which the iridoid components will be handling according to their polarity.
Subsequent fractionations on silica gel columns, conducted on the desorbed product at 60%, have so far confirmed the presence of the chemotaxonomic markers, harpagide (1) and its 8-O acetyl derivative (2), together with allobetonicoside (3) and ajugoside (4) (Figure 1). The compound (4) is reported for the first time in this study as a component of this species but has already been isolated from other Stachys thus highlighting their systematic proximity.
Among the phenolic compounds it was isolated chlorogenic acid (5) a caffeoylquinic derivative caffeoilchinico already found in other species belonging to this genus but not previously seen by S. alopecuros subsp. divulsa.
Most of the isolated compounds own interesting biological activities, such as the anti-inflammatory, antioxidant and anti-tumoral ones which make this species a potential source of pharmacologically active compound
Secondary metabolites from flowers of Genista cilentina Vals
No full textGenista cilentina Vals. is an Italian endemic species belonging to Fabaceae which is characteristic of Cilento, a territory of Campania region overlooking the Tyrrhenian Sea. The phytochemical analysis of the ethanolic extract from the flowers revealed the presence of several flavonoid and isoflavonoid yet evidenced in this genus, and resulted in accordance with the flavonoidic pattern reported by Harborne for Genisteae tribe. In particular were identified genistein (1) the main isoflavonoid, biochanin A (2), luteolin (3) and apigenin (4) as aglycones, while several glycosidated derivatives are currently under study. Is worth of mention the conspicuous presence of liquiritigenin (5) a chalcone evidenced as the only synthesized compound in Genista tinctoria hairy root cultures treated with abscissic acid. Compound (5) is also endowed with interesting biological activities, i.e. gastroprotective, antiviral and counteracting the Alzheimer disease progression
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