Epidemiological studies have suggested that a diet rich in olive oil is associated with a reduced risk of a number of common cancers. In the last decade, significant advances have been made in the ...understanding of how virgin olive oil may work to prevent cancer. A plethora of olive oil constituents have been identified as effective agents against the initiation, promotion and progression of multistage carcinogenesis. These include minor constituents, such as the well-studied tocopherol and carotenoid antioxidants, a number of very efficient antioxidant phenolics (simple phenols-hydroxytyrosol, tyrosol- and linked phenols-secoiridoids. lignans-), the triterpene hydrocarbon squalene and the phytosterol beta-sitosterol. Provocative recent studies have revealed that the major antioxidant components of olive oil can also exert important non-antioxidant biological functions. Because the chemopreventive role of olive oil constituents is based on hypotheses and not hard data, it needs to be evaluated and verified in animal models of multistage carcinogenesis and in humans, in order to gain a better understanding of the effect of olive oil consumption on human cancer. In this review, the antioxidant activity of a number of minor olive oil components is presented and evidence of their ability to interfere with and modulate cellular pathways important in carcinogenesis is reviewed. The implications of these properties for their cancer chemopreventive potential is discussed
Studi epidemiologici hanno suggerito che una dieta ricca di olio di oliva e' associata a un minor rischio di cancro. Negli ultimi decenni sono avvenuti sensibili miglioramenti sulle conoscenze relative alle modalita' di azione preventiva dell'olio di oliva sul cancro. Numerosissimi composti presenti nell'olio d'oliva sono stati identificati come efficaci nella prevenzione dell'iniziazione, promozione e progressione della carcinogenesi. Tra questi composti minori sono elencati i tocoferoli, i carotenoidi, numerosi antiossidanti fenolici (idrossitirosolo, secoiridoidi, ecc.), lo squalene e il beta-sitosterolo. Recenti studi hanno dimostrato come i piu' rappresentativi antiossidanti dell'olio d'oliva esercitano anche un importante ruolo non-ossidante nelle funzioni biologiche. Poiche' il ruolo chemiopreventivo dell'olio d'oliva e' basato solamente su ipotesi, e' necessario testarlo e verificarlo su modelli carcinogenesi multistadio su animali e sull'uomo, al fine di migliorare le conoscenze dell'effetto dell'olio d'oliva sul cancro. In questa review e' presentata l'attivita' antiossidante di numerosi componenti minori dell'olio d'oliva, unitamente alla loro capacita' di interferire su importanti percorsi chimici della carcinogenesi. Sono infine discusse le implicazioni di queste proprieta' sulla loro potenzialita' chemiopreventiva
Squalene is the most abundant hydrocarbon in virgin olive oil and it is present in variable quantities ranging from 100 to 1,200 mg/100 g of oil. In this study the possibility of simultaneously ...determining squalene with the GLC analysis of the fatty acids, without separating the unsaponifiable fraction, was confirmed. The proposed method is rapid and is based on the methylation of the oil in alkaline solution and solubilization in isooctane before GLC analysis. The calibration curve was made using the external standard method in peanut oil. The squalene content was determined in 241 virgin olive oil samples from the Molise region, partly from industrial production and partly extracted in the laboratory from many different olive cultivars. Concentrations of squalene ranged from 90 to 870 mg/100 g of oil and varied considerably in relation to cultivar and olives ripeness
Nell'olio d'oliva vergine lo squalene e' l'idrocarburo piu' abbondante; si puo' trovare in quantita' variabili tra 100 e 1.200 mg/100 g. Nel corso di questa ricerca e' stata verificata la possibilita' di determinare lo squalene contemporaneamente all'analisi gascromatografica degli acidi grassi di un olio senza separare preliminarmente l'insaponificabile. Il metodo proposto e' molto rapido e consiste nel metilare l'olio in ambiente alcalino, previa solubilizzazione in isottano, prima di procedere all'analisi gascromatografica. La curva di taratura e' stata determinata con il metodo dello standard esterno, utilizzando un olio di arachide del commercio. E' stato dosato lo squalene in 241 campioni di olio d'oliva vergine di origine molisana, in parte di produzione industriale e in parte estratti in laboratorio da partite di olive di differenti cultivar. Le quantita' riscontrate, per la totalita' dei campioni, sono risultate comprese tra 90 e 870 mg/100 g di olio e comunque variabili in funzione della cultivar e del grado di maturazione delle olive
Triterpenoid saponins: from biological activity to biotechnological applications Cammareri, M. (Consiglio Nazionale delle Ricerche, Portici, Naples (Italy). Istituto di Genetica Vegetale)
Annali della Facoltà di Agraria della Università degli Studi di Napoli Federico II - Portici (Italy),
(2004), Letnik:
1
Journal Article
Saponins, a vast group of secondary metabolites, are ubiquitous in plants. Structurally, these compounds are complex mixtures with high molecular weight and they may be classified into two groups: ...steroidal and triterpenoid saponins, depending on the aglycone. This review focuses on the biological and pharmacological properties of triterpenoid saponins and on isolation of genes that are involved in their biosynthetic pathway. Moreover, strategies for metabolic engineering of isoprenoids are reported
Le saponine sono metaboliti secondari molto diffusi nel regno vegetale. Dal punto di vista chimico, sono molecole complesse ad alto peso molecolare, costituite da una porzione glicosidica e da un aglicone detto sapogenina, che può risultare uno sterolo (saponine steroidiche) o un triterpene (saponine triterpeniche). Questa review si focalizza sulle diverse attività biologiche e sulle proprietà farmacologiche delle saponine triterpeniche, nonché sui recenti sviluppi della ricerca rivolta all'isolamento dei geni codificanti gli enzimi che regolano il pathway biosintetico. Sono, infine, riportati alcuni esempi di ingegneria metabolica riguardo alla via biosintetica degli isoprenoidi
Transformation of Aster sedifolius via Agrobacterium rhizogenes [production of triterpenoid saponins] Cammareri, M. (Consiglio Nazionale delle Ricerche, Portici, Naples (Italy). Istituto di Genetica Vegetale); Lotti, E. (Consiglio Nazionale delle Ricerche, Portici, Naples (Italy). Istituto di Genetica Vegetale); Filippone, E. (Naples Univ., Portici (Italy). Dipartimento di Scienze del Suolo, della Pianta e dellAmbiente) ...
Annali della Facoltà di Agraria della Università degli Studi di Napoli Federico II - Portici (Italy),
(2004), Letnik:
1
Journal Article
In recent years, different strategies of metabolic engineering have been adopted to improve the production of phytochemicals useful for different purposes: pharmaceuticals, cosmetics, food additives, ...agrochemicals. In this context, the transformation of plants by Agrobacterium rhizogenes is an important achievement. This paper reports the first evidence of a stable transformation by A. rhizogenes in a member of the genus Aster naturally producing bioactive compounds (triterpenoid saponins). Root number increased in transformed explants as compared to untrasformed control. However, in Aster sedifolius we did not observe the typical traits of hairy roots as in tobacco, where extensive lateral branching of primary roots and profusion of root hairs occurred. Transformation was confirmed in the selected root lines of A. sedifolius by the presence of rolB and rolC genes. The availability of a transformation system in Aster has several implications such as the possibility of using transformed root cultures for triterpenoid saponin production
Negli ultimi anni sono state adottate strategie diverse di ingegneria metabolica per migliorare la produzione di prodotti chimici delle piante utili per utilizzazioni diverse: prodotti farmaceutici, cosmetici, additivi alimentari, prodotti chimici per l'agricoltura. In questo contesto, la trasformazione delle piante con Agrobacterium tumefaciens è un risultato importante. Questo contributo riporta la prima evidenza di una trasformazione stabile con A. rhizogenes in un membro del genere Aster che produce naturalmente composti bioattivi (saponine triterpenoidi). Il numero di radici negli espianti trasformati è aumentato rispetto al controllo non trasformato. Tuttavia, in Aster sedifolius non abbiamo osservato i caratteri tipici delle radici ricche di peli, come nel tabacco, dove si verificava una diffusa ramificazione laterale delle radici primarie e abbondanza di peli radicali. La trasformazione è stata confermata, nelle linee di cellule radicali selezionate di A. sedifolius, dalla presenza dei geni rolB e rolC. La disponibilità di un sistema di trasformazione in Aster ha numerose implicazioni, come la possibilità di utilizzare colture di radici trasformate per la produzione di saponine triterpenoidi.
In the present work the AA evaluated, by HPLC-UV, the tocopherols and squalene concentration of an extra-virgin olive oil subjected to domestic pan-frying, with an high surface/volume ratio of the ...oil. Results show that the squalene is more resistant to thermal degradation than alpha-tocopherol. The bi-dimensional fluorescence characterization (excitation-emission matrix EEM analysis) of oil samples allowed to detect, among degradation products, conjugated double bond compounds. From evolution of UV spectroscopy data, viscosity, free fatty acids, peroxide number, induction time and acidic composition, the extent of the degradation process in the olive oil was evaluated. Data revealed larger oxidation in the pan-fried oil with respect to deep-fried oil
Nel presente lavoro sono state determinate, mediante HPLC-UV, le concentrazioni di alfa-tocoferolo e di squalene di un olio extravergine di oliva fritto in padella, dove è elevato il rapporto superficie/volume dell'olio utilizzato. E' risultato che, alla degradazione termica, lo squalene è più resistente dell'alfa-tocoferolo. La caratterizzazione bidimensionale di fluorescenza (analisi delle matrici di eccitazione-emissione EEM) dei campioni di olio ha consentito di individuare, tra i prodotti di degradazione, composti aventi doppi legami coniugati. Dall'evoluzione dei dati di spettroscopia UV, viscosità, acidità libera, numero dei perossidi, tempo di induzione e composizione acidica è stato possibile stabilire l'entità della degradazione subita dall'olio di oliva esaminato. I dati rivelano la maggiore ossidazione dell'olio fritto in padella rispetto a quello soggetto a frittura profonda
La vigne (Vitis vinifera) est sensible à un grand nombre de maladies. Les politiques de limitation des traitements phytosanitaires font qu'aujourd'hui, les viticulteurs ne disposent d'aucun moyen de ...lutte contre certains bioagresseurs. C'est le cas des maladies du bois causées par des complexes fongiques nécrosant les ceps et du court noué, maladie virale transmise par des nématodes. La vigne est une espèce végétale connue pour sa production particulière de métabolites secondaires en réponse à des infections. Dans le cadre de cette thèse, nous nous sommes intéressés aux phytoanticipines, préformées dans les plantes et dont le potentiel de toxicité envers des agents pathogènes est intéressant, c’est le cas des triterpénoïdes. Les objectifs de cette thèse ont donc été dans un premier temps d'estimer la capacité de la vigne à produire de tels composés. Pour cela, la composition en triterpénoïdes de différents organes et de différents cépages a été analysée. Nous avons pu montrer que la composition générale en triterpénoïdes est caractéristique de chaque cépage et de chaque organe. Dans une deuxième partie, 9 gènes impliqués dans la synthèse de triterpènes chez la vigne ont été identifiés et leur expression a été évaluée dans différents organes, chez différents cépages et sous différentes conditions de stress biotique et abiotique. Cette étude exploratoire nous donne des pistes pour mettre en corrélation l'expression de certaines triterpène synthases avec la production différentielle de certains triterpènes à la surface des feuilles de différents cépages. Enfin, nous nous sommes intéressés aux triterpènes glycosylés, les saponines, afin d'évaluer leur potentiel dans la lutte contre certaines maladies majeures de la vigne pour lesquelles aucun traitement n'est actuellement disponible. Pour cela, l'efficacité de saponines issues de la gypsophile et du quillaja a été testée contre certains champignons associés aux maladies du bois ainsi que contre les nématodes vecteurs des virus du court noué. Nous avons pu mettre en évidence que les souches de champignons testées étaient capables de contourner la toxicité des saponines, tandis qu'un tel traitement était rapidement efficace pour lutter contre les nématodes. Afin de vérifier l'innocuité de ce traitement pour l'environnement, les doses efficaces ont été testées et n'ont pas eu d'impact significatif sur différents bioindicateurs.
Vitis vinifera is susceptible to many pathogens. These past few years, treatment policies led to the withdrawal of many pesticides. Renee, no chemical treatments are available to treat some grapevine diseases such as the grapevine trunk diseases caused by fungi complexes and the grapevine fanleaf degeneration, a viral disease transmitted from grapevine to grapevine by vector nematodes. Grapevine is known for the production of secondary metabolites as a response to pathogen infections. In this work, we focused on phytoanticipins such as triterpenoids, that are found as preformed compounds and that confer a basal resistance level to plants. First, a chemical analysis was made on the triterpenoid composition of some grapevine cultivars and organs. This study revealed that the triterpenoid composition is specific to the V. vinifera cultivar and the organ. In a genomic approach, 9 candidate genes involved in the triterpene biosynthesis were identified and their expression was studied in different organs, varieties and biotic or abiotic stress conditions. This explorative study shows correlations between gene expression and differential triterpene production at the leaf surface of the different varieties. In the last part of this study, the use of glycosylated triterpenes, also called saponins, as a substitution solution to withdrawed treattnents against major grapevine diseases was tested. Therefore, the efficiency of saponins extracted from gypsophila and quillaja was tested against fungi associated to grapevine trunk diseases and some nematodes vector of the grapevine fanleaf degeneration. These tests evidenced that the fungi were able to avoid saponins toxicity, whereas such treatment was efficient to kill nematodes. In order to evaluate the effect of the treatment on the environment, the efficient doses were tested and bad no significant impact on some bioindicators.
Ces travaux d'archéométrie concernent l’étude moléculaire par GC-MS de marqueurs lipidiques (biomarqueurs) préservés au sein de sols archéologiques et de substances végétales impliquées en tant ...qu'ingrédients dans la confection d’artefacts. Des analyses complémentaires en isotopie du carbone de composés individuels et des mesures de datation au 14C (AMS MICADAS) de la matière organique totale des sols, d'extraits lipidiques et d'un composé individuel (miliacine) ont également été effectuées. Cette approche a permis:- de montrer l’existence de la culture de millet dès l’âge du Bronze en Alsace, les sols associés à cette culture et leur contenu organique ayant été piégés et préservés dans des silos à grains enterrés datés de l’âge du Fer.- d'identifier la nature de structures archéologiques comme étant d'anciennes latrines et une aire de stabulation de bétail via l'identification de stéroïdes fécaux.- d'établir des critères chimiotaxonomiques fiables basés sur l'analyse des lipides pour l’authentification de résines de styrax et de liquidambars.- d'identifier la nature d'une résine issue de Styrax officinalis ayant été incorporée dans l’enduit organique ornant un crâne décoré (IXème millénaire av. J.-C., site de Nahal Hemar, Israël).- de mettre en évidence l’emploi de brai de bouleau comme agent collant lors de la confection d’un bijou daté du Premier âge du Fer.
In this archaeometric study, lipid biomarkers from archaeological soils and organic substances originating from plants found on artefacts were investigated by GC-MS. In addition, the stable carbon isotopic composition of individual lipids and the 14C age (AMS MICADAS) of soil organic matter, lipid extracts and one isolated compound (miliacin) were determined. Such an archaeometric approach allowed:- the existence of a millet cultivation during the Bronze Age in Alsace to be unveiled for the first time based on preserved molecular remains of this cereal in agricultural soils trapped within grain silos dated from the Iron Age.- the function of uncharacterized archaeological structures to be identified as ancient latrines and a stall area based on the identification of faecal steroidal markers.- reliable chemotaxonomic criteria for the authentication of styrax resins and liquidambar gums to be established using specific organic markers (triterpenoids, notably).- the vegetal component of an organic coating decorating a skull from the 9th millennium BC (Nahal Hemar site, Israel) to be identified as a resin from Styrax officinalis.- the use of birch bark tar as adhesive for the making of a jewellery dated from the Iron Age to be discovered.
Cette étude se propose d’évaluer les potentialités de Striga hermonthica (Del.) Benth (Scrophulariaceae) comme insecticide botanique pour la protection des récoltes de niébé Vigna unguculata (L.) ...Walp à l’encontre de Callosobruchus maculatus (Fab.) (Coleoptera : Bruchidae) lors du stockage. L’extrait à l’acétone de S. hermonthica utilisé à la dose de 0,5 % w/w (100 mg d’extrait sec pour 20 g de niébé) occasionne un effet ovicide de 48 % et donc une réduction de moitié du taux d’adultes émergeant des graines. Cet extrait exerce également une faible activité insecticide sur la forme adulte de l’insecte. La fraction éther de pétrole occasionne un effet ovicide (51 %) et larvicide (72 %) à la dose de 0,4 % (80 mg/20 g de graines) avec un taux d’adultes émergeant de seulement 9 %. Les DL50 et DL90 sont estimées à chaque étape du fractionnement de l’extrait brut (extrait acétone) afin de suivre les composés ovicides et larvicides et afin d’évaluer leur efficacité au cours du processus d’isolement. Une fraction essentiellement constituée de molécules triterpéniques a été identifiée comme responsable de l’effet ovicide constaté ; l’origine de l’activité larvicide n’a par contre pas été identifiée.
Insecticidal activities of Striga hermonthica (Del.) Benth (Scrophulariacecae) on Callobruchus maculatus (Fab.) (Coleptera Bruchidae). This paper deals with insecticidal potentialities of Striga hermonthica (Del.) (Scrophulariaceae) in protection of cowpea Vigna unguculata (L.) Walp against Callosobruchus maculatus (Fab.) (Coleoptera: Bruchidae) during storage. Crude acetone extract at 0,5% w/w (100 mg of extract for 20 g of grain) exhibits 48% of ovicidal effect and then reduces by half emergence rate of adult beetles at the first generation. This extract shows a weak insecticide activity against adults of C. maculatus. Petroleum ether fraction (0,4% w/w ) of the crude extract reveals ovicidal (51%) and larvicidal (72%) effects which reduce the emergence rate of adults to only 9%. LD50 and LD90 are monitored during crude extract fractionation to follow ovicidal and larvicidal compounds and to evaluate their efficacy during the isolation procedure. One fraction, mainly composed of two triterpenoid compounds has been identified as responsible of the ovicidal activity of S. hermonthica while the origin of the larvicidal activity hasn’t been identified.
L’intérêt des substances d’origine naturelle, potentiellement anti-tumorales nous a amené à nous intéresser aux saponines triterpéniques et stéroïdiques de plantes issues de la biodiversité africaine ...de la famille des Araliaceae et des Dracaenaceae. En effet, des études antérieures menées sur quelques plantes de ces deux familles ont conduit à l’obtention de molécules complexes et originales possédant d’excellentes propriétés cytotoxiques, immuno-modulatrices, anti-inflammatoires. Au vu de ces résultats nous avons entrepris des investigations pharmaco-chimiques sur Cussonia arborea (Araliaceae), Dracaena deisteliana et Dracaena arborea (Dracaenaceae), plantes médicinales couramment utilisées en pharmacopée traditionnelle africaine pour traiter différentes maladies. Les travaux menés ont conduit à l’isolement de 31 composés purs en utilisant les différentes techniques analytiques du laboratoire notamment les diverses techniques de chromatographie liquide successive à pression atmosphérique, moyenne pression et flash chromatographie sur silice en phase normale et en phase inverse. Les structures ont été déterminées par les méthodes de spectrométrie de masse en source FAB et de spectroscopie de RMN 1D et 2D (COSY, TOCSY, NOESY, HMBC et HSQC). Parmi les 07 composés purs obtenus des écorces de Cussonia arborea, 5 sont des nouvelles saponines triterpéniques dont un dérivé de l’acide ursolique, un dérivé de l’hédéragénine et trois dérivés de l’acide oléanolique, tous disubstitués en position 3 et 28 par des chaînes oligosaccharidiques. 13 composés purs sont obtenus à partir des feuilles de Cussonia arborea, dont 7 nouvelles saponines triterpéniques dérivés de l’acide ursolique, de l’acide 23-hydroxyursolique, de l’hédéragénine et de l’acide oléanolique dont 04 d’entre elles sont obtenues sous forme de mélanges inséparables d’isomères acide oléanolique/acide ursolique et hédéragénine/acide 23-hydroxyursolique. A partir des écorces de Dracaena arborea et des tiges de Dracaena deisteliana, nous avons isolé et caractérisé 10 saponines stéroïdiques dont 4 nouvelles et une sapogénine. Les activités de certains de ces produits purs ont été évaluées sur deux lignées de cellules cancéreuses coliques humaines HCT 116 et HT-29.
The interest of the substances from natural origin, potentially antitumor led us to interest in triterpenoid and steroidal saponins of plants from the African biodiversity belonging to the Araliaceae and Dracaenaceae families of plants. Indeed, of the former studies undertaken on some plants of these two families led to obtaining complex and original molecules having excellent cytotoxic, immuno-modulating, anti-inflammatory properties. Within sight of these results we undertook pharmaco-chemical investigations on Cussonia arborea (Araliaceae), Dracaena deisteliana, and Dracaena arborea (Dracaenaceae), medicinal plants usually used in african traditional pharmacopeia to treat various diseases. The work led to the isolation of 31 pure compounds by using the various analytical techniques in particular the various chromatography techniques (CC, MPLC, TLC, flash) on silica gel, normal and reversed phases. The structures were determined by the methods of mass spectrometry (FAB, ESI, IE) and 1D (1H and 13C) and 2D (COSY, TOCSY, NOESY, HMBC and HSQC) NMR spectroscopy. Among the 07 pure compounds obtained of the barks of Cussonia arborea, 5 are new triterpenoid saponins derivatives of ursolic acid, hederagenin and three derived from the acid oleanolic, all disubstituted in position 3 and 28 by oligosaccharidic chains. 13 pure compounds were obtained from leaves of Cussonia arborea, seven of which are new triterpenoid saponins derivatives of oleanolic acid, ursolic acid, hederagenin and 23-hydroxyursolic acid of which four were obtained as mixtures of isomers oleanolic acid/ursolic acid and hederagenin/23-hydroxyursolic acid. From the bark of Dracaena arborea and stem of Dracaena deisteliana, we isolated and characterized ten steroidal saponins including 4 new and sapogenin. The activities of some of these pure products were evaluated on two cancerous lines human colic cells HCT 116 and HT-29.
