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Pouteria lucuma Ruiz and Pav., known as the 'Gold of the Incas' or 'lucuma', is a subtropical fruit belonging to the Sapotaceae family, with a very sweet flavor, used to prepare cakes, ice creams as well as in the baking and dairy industries. To date, the content of primary metabolites is known, but little information is reported about the composition in specialized metabolites. Moreover, no study is reported on skin which represent an important agricultural waste due to the high demand for lucuma. In order to have a preliminary metabolite profile of Pouteria lucuma , the extracts of pulp and skin have been analyzed by LC-ESI/LTQOrbitrap/MS/MS in negative ion mode. The careful analysis of the accurate masses, of the molecular formulas and of the ESI/MS spectra allowed to identify specialized metabolites belonging to phenolic, flavonoid and polar lipid classes. The LC-MS/MS analysis guided the isolation of compounds occurring in the pulp extract whose structures have been characterized by spectroscopic methods including 1D- and 2D-NMR experiments and ESI-MS analysis. Furthermore, the phenolic content of the extracts along with the antioxidant activity of extracts and isolated compounds was evaluated.

Introduction: Prunus dulcis Mill. is a plant cultivated for the production of its edible seeds, known as sweet almonds. In the last decades almond demand has highly increased due to their wide use in the industrial manufacturing of almond-based foods; this has led to a huge production of waste materials, mainly corresponding to shells and husks., Objective: To achieve a deeper understanding of the chemical composition of almond husks with the aim of exploring these byproducts as a source of bioactives to be used in nutraceutical and cosmetic formulations., Methods: Methanol, ethanol and ethanol-water extracts of the almond husks were analysed by high-resolution liquid chromatography electrospray ionisation Orbitrap mass spectrometry (HR-LC-ESI-Orbitrap-MS) in negative ion mode. Tandem mass spectrometry (MS/MS) data were acquired by using the Data-Dependent Scan experiment, allowing the precursor ion to be selected as the most intense peak during LC-MS analyses. Nuclear magnetic resonance (NMR) experiments were performed on a Bruker DRX-600 spectrometer. Folin-Ciocalteu, DPPH • (2,2-diphenyl-1-picrylhydrazyl) and TEAC (Trolox equivalent antioxidant capacity) assays were employed to determine the total phenolic content and the radical scavenging activity of the extracts., Results: The LC-MS/MS analysis of the methanol extract guided the isolation of phloroglucinol derivatives, flavonoids and terpenes. Eco-friendly extraction methods showed to be selective in extracting flavonoids while the comparison of the LC-MS profiles of the Italian cultivars Toritto and Avola showed significant differences, confirming how different growing conditions may influence the metabolome of a plant species., Conclusion: This study led to a deeper insight into the chemical constituents of almond husks and showed how the eco-friendly extraction resulted in an effective method to obtain extracts rich in antioxidant sources., (© 2019 John Wiley & Sons, Ltd.)

Ziziphus jujuba Mill. leaves are receiving a great attention for their ability to improve sleep, exerting beneficial effects for both the heart and the central nervous system. With the aim to obtain a comprehensive analysis of the specialised metabolites occurring in the leaves of Z. jujuba, a LC-ESI/(HR)Orbitrap/MS profile in negative ion mode of the methanol extract was carried out. The LC-MS profile guided the isolation of 42 compounds, of which the structures were elucidated by 1D and 2D-NMR experiments. Based on this approach, 2 previously unreported dammarane-type saponins have been characterized along with flavonoid derivatives, dammarane-type saponins and triterpenic acids. Dammarane-type saponins were tested for their cytotoxic activity against A549 and HeLa cancer cell lines. None of the tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number. This work provides a deep insight on the chemistry of the leaves of Z. jujuba and could be useful for further biological studies aimed at identifying phytochemicals contributing to the health benefits attributed to this herbal drug., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

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 1 H 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., (Copyright © 2018 Elsevier B.V. All rights reserved.)

Prunus dulcis leaves have been reported to exert some biological activity, in particular potent free radical-scavenging capacity, but so far there is limited information on their chemical composition. With the aim to achieve deep insight on the chemical constituents of the leaves of P. dulcis cultivars "Toritto" and "Avola", the most appreciated in Italy, an approach based on liquid chromatography-mass spectrometry (LC-MS) combined with isolation and structure elucidation of pure compounds by Nuclear Magnetic Resonance (NMR) analysis was carried out. Results allowed to detect in cv. Toritto leaves phenolics, terpenoids and a cyanogenic glycoside. Successively, various solvent systems were chosen to afford different extracts and an approach based on principal component analysis (PCA) and partial least squares discriminant analysis (PLS-DA) from LC-MS data sets highlighted eco-friendly methods as selective in extracting phenolics and glycosides. Comparison of LC-MS profiles of the MeOH extracts of cv. Toritto and cvs. Avola (Pizzuta, Fascionello and Romana) leaves and evaluation of their phenolic contents and antioxidant activity were also carried out., (Copyright © 2018 Elsevier B.V. All rights reserved.)

Wild strawberry (Fragaria vesca) is recognized as a traditional food of Campania region (Italy). The vegetative parts have a pharmaceutical interest, being used as decoctions for hypertension treatment due their detoxifying, diuretic, stimulant and dermatological protective properties; leaves, that after collection of fruits are generally thrown away, could be an interesting byproduct, source of bioactive compounds for cosmetic and pharmaceutical industry. In the present work, the metabolite profiles of F. vesca leaves coming from populations spontaneously growing in the underwood (wild) and in crop (cultivated) and from autochthonous and non-autochthonous germplasm of Campania region (Italy) were investigated by LC-ESI/LTQOrbitrap/MS analysis. 27 metabolites mainly belonging to organic acids, flavonoids, catechin and its oligomers, and ellagitannins were putatively identified. Antioxidant activity was tested for each sample, in particular cultivated samples and wild samples with autochthonous germplasm of Campania region showed higher antioxidant activity compared to the non autochthonous ones. Moreover, in this study, it was possible to predict antioxidant metabolites, markers of this species, using LC-MS spectra and multivariate regression data analysis., (Copyright © 2017 Elsevier B.V. All rights reserved.)

Juices obtained from cold-pressed saffron (Crocus sativus L.) floral by-products were evaluated as a potential source of compounds with antioxidant and cytotoxic activities. Floral by-products were split in two batches for extraction 24 and 48h after flower harvesting, respectively. The in vitro anti-oxidant activity of these extracts was tested using the FRAP and DPPH assays, and two biological models of lipid oxidation (activity in preventing cholesterol degradation and protection against Cu(2+)-mediated degradation of the liposomal unsaturated fatty acids). The cytotoxic activity was evaluated using the MTT assay. The results show that extracts obtained 48h post-harvest contained higher levels of total polar phenols and had the highest antioxidant activity in all of the performed assays. The LC-DAD and LC-ESI-(HR)MS(n) metabolic profiles showed high levels of kaempferol derivatives and anthocyanins. This study suggests that juices from saffron floral by-products could potentially be used to develop new products for the food and health industry., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

Stevia rebaudiana is an important agricultural crop for the production of a high-potency natural sweetener, sensitive to low temperature during the developmental stage. Stimulation of chilling stress with a pre-treatment with endogenous signalling components and in particular with salicylic acid (SA), hydrogen peroxide (H2O2), 6-benzylaminopurine (BAP) and calcium chloride (CaCl2) could induce tolerance to chilling and could constitute a suitable way to maintain quality and quantity of steviol glycosides under controlled artificial environment. In the present work the effects of different putative signalling molecules on the morpho-physiological parameters were evaluated, and a specific method for the quali-quantitative analysis of steviol glycosides in S. rebaudiana plants cultivated under controlled conditions was developed, by using LC-ESI-FT (Orbitrap) MS, LC-ESI-QqQ-MS/MS and multivariate data analysis. This approach underlined that the pre-treatment has influence on the production of secondary metabolites. In particular Stevia plants characterised by higher contents of rebaudioside A and stevioside, were identified., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

Helichrysum italicum is widely used in traditional medicine, in cosmetic, in food and pharmaceutical field. In spite of this, very little is known about the chemical composition of its polar extracts. Therefore this study was addressed to the determination of the metabolite profile of the methanol extract of H. italicum flowers, by using LC-ESI(IT)MSMS. This approach oriented the isolation of 14 compounds, whose structures were unambiguously elucidated by NMR as belonging to flavonoid, phenylpropanoid and acylbenzofuran classes. In addition, one novel drimane sesquiterpene was identified. The quantitative determination of the main compounds occurring in the methanol extract of H. italicum flowers was carried out and their content was compared with that of three selected commercial food supplements based on H. italicum, by using LC-ESI(QqQ)MS. In conclusion the wide occurrence, in high amounts, of quinic acid derivatives in all the analyzed samples was highlighted, showing these compounds as chemical markers of the species for standardization procedures., (Copyright © 2014 Elsevier B.V. All rights reserved.)

Liquid chromatography electro-spray tandem mass spectrometry (LC-ESI/MS/MS) was applied to the determination of sweet glycosides (steviol glycosides), and toxic aglycon steviol in 24 samples of Stevia rebaudiana (Bertoni) aerial parts, which had been experimentally cultivated in Italy, although derived from seeds of different geographical origin. On the basis of the specific fragmentation of these compounds, an LC-MS/MS method was developed with the aim of quantifying analytes in plant material. Although toxic steviol was not detectable in all the samples, the samples with the highest levels of steviol glycosides were identified. Analysis of the different samples revealed that they were good quality samples, quality being directly linked to the presence of sweet glycosides in the plants cultivated in Italy, although there were differences in the content of these compounds according to the origin of the seeds, and in particular, a major concentration of compounds with major sweetness activity and minor toxicity was found in the population coming from Brazil (for example: sample 10, stevioside content 15.74±2.0% p/p and rebaudioside A content 3.09±0.39% p/p of dried plant). Finally, based on this metabolomic targeted approach, the results obtained for the samples were treated by Principal Component Analysis, identifying specific genotypic differences based on the geographic origin of the seeds., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

The medicinal plant Ammi visnaga is a valuable source of furanochromones and pyranocoumarins used as vasodilator agents. Its ability to germinate under unfavourable growth conditions, such as saline soil and hypoxia characterizing clay soils and marshes ecosystems, prompted us to qualitatively characterize secondary metabolites in umbels of A. visnaga plants grown under different conditions (in field, hydroponically controlled, and contrasted by salinity and/or hypoxia) by HPLC-ESI/IT/MS(n) analysis. Subsequently, the quantitative analysis of the bioactive compounds, above all furanochromones and pyranocoumarins, was carried out by HPLC-ESI/QqQ/MS/MS. The results show the influence of growing conditions on the quali-quantitative profile of A. visnaga secondary metabolites and evidence that hydroponic culture leads to increased level of A. visnaga active principles. Furthermore, two furanochromones never reported before were identified and characterized by 1D- and 2D-NMR analysis., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

The Lippia genus is used in ethnobotany as food, beverages, seasoning and antiseptic remedies, among others. The chemical compositions of fifteen extracts of six Lippia species were investigated comparatively by HPLC-PDA. To avoid data replication of previous works on this genus, Lippia lupulina Cham. root ethanol extract was selected for isolation procedures based on Principal Component Analyses (PCA) of such data. Seven compounds previously unreported in this genus were isolated from this extract (a triterpene, two furanonaphtoquinones, a furanochromone, an isoflavone, a stilbene and an iridoid). The activities of extracts, fractions and pure compounds towards Candida albicans, Candida krusei, Candida parapsilosis and Cryptococcus neoformans were investigated. Two fractions from the extract of Lippia salviaefolia leaves showed marked inhibition of fungal growth, in addition to verbascoside and asebogenin, which showed MICs lower than 15.6μg/ml and may be promising leads for the development of new antifungal agents, especially against C. neoformans., (Copyright © 2012 Elsevier Ltd. All rights reserved.)

The antispasmodic effect of 4'-methylepigallocatechin (MEC), which was isolated from Maytenus rigida Mart (Celestraceae), was investigated in vitro in guinea pig intestinal segments. In the isolated ileum, MEC (1 nM-100 μM) did not modify the ileal spontaneous tonus or the electrically elicited contractions. MEC (8 μM) significantly (p<0.01) reduced the submaximal contractions induced by histamine (2 μM), carbachol (100 μM) and BaCl₂ (0.03 M). An additive relaxing action (p<0.001) was observed by co-incubation of verapamil (10 nM) and MEC (8 μM). Although MEC (1 nM-100 μM) did not modify the contractions elicited by 60 mM KCl, it significantly reduced the CaCl₂ contractile response without changing the EC₅₀ (effective concentration of CaCl₂ causing 50% of maximum response). In brief, these results show that MEC has a potent ileal spasmolytic effect and blocks spasms induced by specific and nonspecific stimuli. Importantly, the spasmolytic effects were attained at low concentrations and might be related to the symptomatic relief of abdominal pain that is obtained from the use of the M. rigida stem bark., (Copyright © 2012 Elsevier B.V. All rights reserved.)

Nine furostanol glycosides, namely caucasicosides E-M, were isolated from the MeOH extract of the leaves of Helleborus caucasicus, along with 11 known compounds including nine furostanol glycosides, a bufadienolide and an ecdysteroid. Their structures were established by the extensive use of 1D and 2D NMR experiments along with ESIMS(n) analyses. The steroidal composition of leaves of H. caucasicus shows as particular feature the occurrence of steroidal compounds belonging to the 5β series, unusual for Helleborus species, and in particular, caucasicosides F-H are based on a 5β-polyhydroxylated steroidal aglycon never reported before., (Copyright © 2011 Elsevier Ltd. All rights reserved.)

An HPLC-ESIMS(n) method, based on high-performance liquid chromatography coupled to electrospray positive ionization multistage ion trap mass spectrometry, has been used to rapidly identify and guide the isolation of phenolic constituents from the methanol extract of the aerial parts of T. cinerea. On the basis of the results of the online screening by HPLC-ESIMS (n), 17 phenolic constituents, including two new compounds, namely demethylapollinin 7- O- β-D-glucopyranoside (1) and cineroside A (17), were isolated, and their structures were unambiguously assigned by the extensive use of 1D- and 2D-NMR experiments., (© Georg Thieme Verlag KG Stuttgart · New York.)

Phytochemical investigation of the methanolic extract of Byrsonima crassifolia's bark led to the isolation of 8 known phenolic compounds 5-O-galloylquinic acid, 3-O-galloylquinic acid, 3,4-di-O-galloylquinic acid, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid, (+)-epicatechin-3-gallate along with (+)-catechin and (+)-epicatechin. Due to their biological value, in the present study, a high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) method, working in multiple reaction monitoring (MRM) mode, has been developed to quantify these compounds. B. crassifolia bark resulted in a rich source of phenolic compounds and particularly of galloyl derivates. The proposed analytical method is promising to be applied to other galloyl derivatives to quantify these bioactive compounds in raw material and final products., (Copyright © 2011 Elsevier B.V. All rights reserved.)

Ceramides and cerebrosides are key compounds in the metabolism of sphingolipids. Produced in response to a variety of apoptotic stimuli, these metabolites mediate either mitogenic or apoptotic responses, depending on cell type and nature of stimulus. Novel strategies using these selective targets for a therapeutic intervention, e.g. in cancer, cardiovascular and neurodegenerative diseases, and HIV, have been developed, along with anticancer approaches using controlled delivery of exogenous natural ceramides from ceramide-based liposomes. Thus, great is the need to find selective and sensitive analytical methods allowing a prompt detection of ceramides and cerebrosides in natural matrices. Here we report an analytical study carried out on the Amazonian plant Dracontium loretense, resulted in a preliminary analysis a rich source of this class of natural compounds. A handy, selective, and sensitive methodology based on high-performance liquid chromatography coupled to electrospray negative ionization multistage ion trap mass spectrometry (HPLC-ESI/ITMS(n)) was developed. Analysis of fingerprint multistage mass spectra allowed the rapid identification of 3 major long-chain bases and their exact pairing with 11 different fatty acids and with carbohydrate headgroups. Thus, the structures of 21 ceramide and cerebroside species, among which 7 molecules never reported before, were unambiguously assigned. Results obtained in this study demonstrated that this analytical approach could provide a reliable and sensitive method to obtain the qualitative on-line profiling of ceramides and cerebrosides in new medicinal plant matrices., (Copyright © 2011 Elsevier B.V. All rights reserved.)

Four new bibenzyl derivatives were isolated, together with other known bibenzyls, by bioassay-guided fractionation of a CHCl₃-MeOH extract of Notholaena nivea Desv. (Pteridaceae) aerial parts. The structures were elucidated by NMR, ESIMS and other spectral analyses. Their antioxidative effects towards superoxide, lipidic peroxidation and the 2,2'-azino-bis-3-ethilbenzothiazoline-6-sulfonic acid (ABTS) radical were assayed. Results showed that the compound 3,12-dihydroxy-5-methoxybibenzyl (6) is the most active compound in the ABTS free-radical scavenging test, while in the coupled oxidation of β-carotene and linoleic acid assay the compound 5,12-dihydroxy-3-methoxydibenzyl-6-carboxylic acid (1) exerted the highest activity after 1h. A superoxide anion enzymatic test was also carried out and the results were confirmed by an inhibition of xanthine oxidase activity assay. The putative protective role played by compounds 1 and 6 on the injurious effects of reactive oxygen metabolites on the intestinal epithelium, using a Caco-2 human cell line, was investigated. H₂O₂-induced alterations were prevented by preincubating the cells with compounds 1 and 6.

Liquid chromatography electrospray mass spectrometry (LC-ESI/MS) has been applied to the full characterization of saponins and phenolics in hydroalcoholic extracts of roots of liquorice (Glycyrrhiza glabra). Relative quantitative analyses of the samples with respect to the phenolic constituents and to a group of saponins related to glycyrrhizic acid were performed using LC-ESI/MS. For the saponin constituents, full scan LC-MS/MS fragmentation of the protonated (positive ion mode) or deprotonated (negative ion mode) molecular species generated diagnostic fragment ions that provided information concerning the triterpene skeleton and the number and nature of the substituents. On the basis of the specific fragmentation of glycyrrhizic acid, an LC-MS/MS method was developed in order to quantify the analyte in the liquorice root samples. Chinese G. glabra roots contained the highest levels of glycyrrhizic acid, followed by those from Italy (Calabria)., (Copyright © 2010 Elsevier B.V. All rights reserved.)

Ethanolic extracts of Achillea ligustica All. (Asteraceae) flowering tops were evaluated. High-performance liquid chromatography-electrospray ionisation-mass spectrometry was used for the identification and quantification of phenolic compounds. 6-Hydroxykaempferol-3,6,4'-trimethyl ether, apigenin-6-C-glucoside-8-C-arabinoside, luteolin, and apigenin were the most abundant flavonoids. For the first time C-glycosylflavones were detected in A. ligustica with apigenin-6-C-glucoside-8-C-arabinoside being the most representative. The radical scavenging activity of the extracts was determined by DPPH test and ranged between 4.18 and 12.3 mM. The ability of these extracts to inhibit non-enzymatic lipid peroxidation was studied using the simple in vitro system of linoleic acid oxidation: five of the nine extracts exerted a protective effect at the lower amount tested (5 microg). Protection on CaCo-2 intestinal cells against TBH-induced toxicity was also investigated: the results showed that two of the extracts tested in this cell system had the ability to protect against oxidative stress induced by TBH starting from concentrations as low as 10 microg/ml.

Ethnopharmacological Relevance: An investigation of topical anti-inflammatory activity was undertaken on plants used in Central America traditional medicine., Aim of Study: Four herbal drugs used in the folk medicine of Central America to treat inflammatory skin affections (Acacia cornigera bark, Byrsonima crassifolia bark, Sphagneticola trilobata leaves and Sweetia panamensis bark) were evaluated for their topical anti-inflammatory activity., Materials and Methods: Petroleum ether, chloroform and methanol extracts were obtained for herbal medicines and then extracts were tested on Croton oil-induced ear dermatitis model in mice., Results: Almost all the extracts reduced the Croton oil-induced ear dermatitis in mice and the chloroform ones showed the highest activity, with ID(50) (dose giving 50% oedema inhibition) values ranging from 112 microg/cm(2) (Byrsonima crassifolia) to 183 microg/cm(2) (Sphagneticola trilobata). As reference, ID(50) of the non-steroidal anti-inflammatory drug indomethacin was 93 microg/cm(2)., Conclusions: Lipophilic extracts from these species can be regarded as potential sources of anti-inflammatory principles.

A novel triterpene glycoside, undulatoside (1), which is characterised as 3-O-(beta-D-glucopyranosyl)-29-O-(beta-D-glucopyranosyl)-2alpha,23-dihydroxyolean-12-en-28-oic acid, was isolated from Anchusa undulata subsp. hybrida and its structure was deduced by spectral data. In addition to undulatoside, seven known triterpene glycoside and a flavonoid glycoside were also isolated for the first time from this plant. The structures have been identified by spectroscopic and chemical methods. The antimicrobial activities of all extracts of the plant were investigated by disc diffusion method.

Ethanol extract of Maytenus rigida stem bark and its fractions were assessed for antinociceptive activity in tail-flick test in rats. The activity was located in the chloroform, ethyl acetate and aq.methanol fractions. Phytochemical screening revealed that catechin was the only common class of compounds present on the ethanol extract as well as on the active fractions. 4'-Methylepigallocatechin, isolated from the ethyl acetate and aq.methanol fractions, showed antinociceptive effect in the tail-flick test (75 mg/kg; p.o.), which was reversed by the opiate antagonist naloxone (3 mg/kg; i.p.).

On the basis of the biological activities exhibited by the phenolic constituents of Yucca schidigera, the antioxidant activity of the methanol extract of Yucca gloriosa roots was evaluated in the TEAC assay. The strong activity exerted by this extract prompted investigation of its phenolic constituents, yielding three new phenolic derivatives, gloriosaols C, D, and E, along with gloriosaols A and B previously isolated from Y. gloriosa roots and yuccaols C-E isolated from Y. schidigera. ESIMS and NMR data of gloriosaols C-E closely resembled those reported for gloriosaols A and B, two diasteroisomers characterized by unusual spirostructures. Careful inspection of ROESY spectra revealed that gloriosaols C-E are diastereoisomers of gloriosaols A and B. A possible assignment of the relative configuration of gloriosaols C-E, derived according to an integrated NMR-quantum mechanical (QM) approach, which was already applied to the determination of the stereostructures of gloriosaols A and B, is also proposed. Gloriosaols A-E exhibited potent antioxidant activity measured by the TEAC assay, showing the potential use of Y. gloriosa as a source of antioxidant principles.

A rapid analytical approach suitable to achieve a comprehensive characterization of the compounds present in the infusion prepared from the leaves of Byrsonima fagifolia Niedenzu (Malpighiaceae), a Brazilian plant used as an infusion to treat gastric disorders, was developed. The method was based on high-performance liquid chromatography coupled to electrospray negative ionisation multistage ion trap mass spectrometry (HPLC/ESI-ITMSn). The main ions in the ESI-ITMS spectra were attributed to a quinic acid core containing from one to five galloyl units. Quercetin derivatives containing one and two sugar moieties as well as galloyl esterification were also detected. These results indicated that HPLC/ESI-ITMSn is easily applicable to infusions of this plant and allows the rapid and direct identification of these compounds in crude plant extracts., (Copyright (c) 2007 John Wiley & Sons, Ltd.)

Uncaria tomentosa ("Uña de gato") (Rubiaceae) is widely used in South America for treatment of gastritis, arthritis, cancer and inflammatory conditions. Recent literature reports cytostatic, antiproliferative, anti-inflammatory, mutagenic and anti-mutagenic properties of extracts of the plant. The present study investigates the possible proapoptotic mechanism via the activation of caspase3, in cytostatic effects of root bark extracts of Uncaria tomentosa on three different tumoral cell lines.

Three new hopane saponins, lotoidosides A - C (1 - 3), and four new oleanane saponins, lotoidosides D - G (4 - 7), were isolated from the roots of Glinus lotoides L. (Molluginaceae). Their structures were determined by extensive 1D- and 2D-NMR spectroscopy and ESI-MS analysis. The antiproliferative activity of compounds 1 - 7 was evaluated using three continuous murine and human culture cell lines J774.A1, HEK-293, WEHI-164. Compounds 1 and 3 - 7 showed significant cytotoxicity against the three cancer cell lines with IC50 values ranging from 0.018 to 0.62 microM, while compound 2 exerted a weak activity only against the cell line HEK-293.

Tree-of-heaven (Ailanthus altissima Swingle) was evaluated for its cytotoxic and antiproliferative activities by a bioassay-oriented study. Cytotoxicity observed in HeLa cells was time-dependent; the treatment with 10 microg/mL of the root chloroform extract reduced cell viability by 56% at 24 h and 29% at 48 h of exposure, whereas no effect was recorded in the controls. Significant effects were observed also for chromatographic fractions and the pure isolated alkaloid 1-methoxy-canthin-6-one. After 72 h of incubation cell viability was less than 10% for all treatments. A possible apoptotic effect was evaluated by monitoring the presence of hypodiploid elements in HeLa cells as well as in SAOS, U87MG and U-937 tumor cell lines. The cells incubated for different times with the active extract, fraction and pure alkaloid isolated from A. altissima showed a remarkable increase in the apoptosis., (Copyright 2005 John Wiley & Sons, Ltd.)

A fast and reliable method, based on high-performance liquid chromatography coupled to electrospray ionization ion trap tandem mass spectrometry (HPLC/ESI-ITMS), was developed to investigate the infusion prepared from the leaves of Byrsonima crassa Niedenzu (Malpighiaceae), a native plant used in Brazil against gastric disorders. The use of on-line reverse-phase HPLC/ESI-ITMS allowed separation of three major classes of compounds and identification of over 20 very polar compounds characterized as galloylquinic acids, proanthocyanidins, and flavonoid glycosides, as well as the dimeric flavonoid amentoflavone and minor amounts of galloyl hexose and galloyl saccharose. This approach provided data that will allow establishment of a method for a future standardization of the infusion., (Copyright (c) 2005 John Wiley & Sons, Ltd.)

Yucca schidigera extract finds wide commercial application in foods, cosmetics and pharmaceuticals. In a previous paper we have found as the main constituents of yucca bark, yuccaol A, B and C, new and very unusual spiro-derivatives made up of a C15 unit and a stilbenic portion closely related to resveratrol. This study was performed to examine whether yuccaol A, B or C (0.01-100 microM) could affect cytosolic inducible nitric oxide synthase (iNOS) protein expression and nitric oxide (NO) generation in vitro in Escherichia coli lipopolysaccharide (LPS)-activated J774.A1 macrophage cell line. NO production, detected as NO2-, increased significantly in LPS treated J774.A1 cells from 0.05 +/- 0.03 microM to 16.64 +/- 0.58 microM (P < 0.001). Yuccaol C (0.01-100 microM), added to the culture medium 1 h before LPS-stimulation, significantly (P < 0.001) and in a concentration related manner reduced NO release (P < 0.001) and iNOS protein expression (P < 0.05). In contrast, no inhibitory effect either on iNOS protein expression or on NO release was observed when yuccaol C was added after LPS stimulation. In contrast yuccaol A inhibited significantly (P < 0.001) only NO release at the highest concentration tested (100 microM) while yuccaol B did not reduce either NO release or iNOS expression. Yuccaol C was demonstrated to reduce iNOS protein expression via the transcription factor NF-kappaB. These results indicated that the empirical use of Y. schidigera as anti-inflammatory remedy could be addressed not only to the resveratrol content but also to the presence of yuccaol C., (Copyright 2004 Elsevier Inc.)

The aqueous root extract of Ailanthus altissima showed allelopathic activity against radish (Raphanus sativus L. cv. "Saxa"), garden cress (Lepidium sativum L.), and purslane (Portulaca oleracea L.) seeds. A bioassay-oriented purification of active extracts, chromatographic fractions, and compounds demonstrated dose-dependent activity on germination and radicle growth of test seeds; radish seed was the most sensitive to allelochemicals. Active compounds have been isolated: ailanthone, ailanthinone, chaparrine, and ailanthinol B (quassinoid derivatives); the alkaloid 1-methoxycanthin-6-one is not active. The compound with greatest inhibitory activity is ailanthone. The data obtained suggest a possible use of tree-of-heaven root extracts or of its active constituents as natural herbicides.

Lepidium meyenii, known in South America as maca, has received attention worldwide as a powerful energizer that improves physical and mental conditions and increases fertility. Because of these reports, we investigated the secondary metabolites of the tuber of maca. The methanol extract of the tuber of maca contained, in addition to free sugars and amino acids, the following: uridine, malic acid and its benzoyl derivative, and the glucosinolates, glucotropaeolin and m-methoxyglucotropaeolin. Because glucosinolates and their derived products have received increasing attention due to their biological activities, the occurrence of glucosinolate degradation products in the hexane extract was also investigated, and benzylisothiocyanate and its m-methoxy derivative were isolated. The two glucosinolates were semiquantified by HPLC, and benzylisothiocyanate was semiquantified by GC/MS. The methanol extract of maca tuber also contained (1R,3S)-1-methyltetrahydro-beta-carboline-3-carboxylic acid, a molecule which is reported to exert many activities on the central nervous system.

Lepidium meyenii (Maca) is traditionally employed in the Andean region for its supposed properties in improving fertility. The aim of this study was to determine the effect of subacute oral administration of hexanic, methanolic and chloroformic extracts of Maca root on sexual performance in inexperienced male rats. The following sexual performance parameters were evaluated: 1st mount, 1st intromission, ejaculation and post-ejaculatory latencies, intercopulatory interval and copulatory efficacy. All the tested fractions significantly decreased intromission latency and intercopulatory interval and increased intromission frequency and copulatory efficacy (P < 0.05) as compared to controls. Hexanic and methanolic extracts were able to increase mount frequency (MF), while only hexanic fraction significantly improved mount latency (ML) (P=0.038). Globally, only the hexanic fraction significantly improved the majority of the sexual parameters measured. Sub-acute oral administration of hexanic Maca extract improved sexual performance parameters in sexually inexperienced male rats most effectively.

Uncaria tomentosa, also known as "Uña de gato", is a Rubiaceae species widely used in South-American folk medicine for the treatment of cancer, arthritis, gastritis and epidemic diseases. Extracts of the plant have been shown to possess cytostatic and anti-inflammatory activity as well as mutagenic and antimutagenic properties. However, to date no studies have been carried out to verify the direct antitumor activity of the extracts. The present study investigates the effects of some extracts and their chromatographic fractions from the bark of U. tomentosa on the growth of a human breast cancer cell line (MCF7). Our data indicated that, in addition to the antimutagenic activity, U. tomentosa extracts and fractions exert a direct antiproliferative activity on MCF7. The bioassay-directed fractionation from barks and leaves resulted in the isolation of two active fractions, which displayed an IC50 of 10 mg/ml and 20 mg/ml, respectively and an antiproliferative effect, with about 90% of inhibition at a concentration of 100 mg/ml.

The present study examines the effects of the extracts [petroleum ether, CHCl(3), CHCl(3)MeOH (9:1) and MeOH], partially purified fractions and pure compounds from Croton menthodorus on the electrically induced contractions of the isolated guinea-pig ileum (ECI). The results of the experiments indicate that CHCl(3)/MeOH (9:1) and MeOH extracts, tested at concentrations of 100, 50 and 25 microg/mL, dose-dependently reduced the guinea-pig ileum contractions, whereas petroleum ether and CHCl(3) extracts did not affect it. Furthermore, the partially purified fractions III-VI from the CHCl(3)/MeOH extract, each tested at concentrations of 100, 50 and 25 microg/mL also inhibited ECI. Finally, pure compound 1 (6 x 10(-6), 3 x 10(-6), 1 x 10(-6) M) isolated and purified from the most active fraction III significantly reduced, in a dose-dependent manner, the electrical contractions of the ileum. Compound 1 was identified by NMR and EI-MS data as the morphinandien-7-one, O-methylflavinantine., (Copyright 2000 John Wiley & Sons, Ltd.)

The antimicrobial activity of a methanol extract and isolated constituents of Mitracarpus scaber, a species used in folk medicine by West African native people, was evaluated against Staphylococcus aureus and Candida albicans strains. The mitracarpus methanol extract possesses both antibacterial and antimycotic activities (minimum inhibitory concentration-MIC 31.25 and 62.50 microg ml-, respectively). This extract was subsequently fractioned and monitored by bioassays leading to the isolation of seven compounds screened for antibacterial and antimycotic activities. Among these compounds, gallic acid and 3,4,5-trimethoxybenzoic acid inhibited the growth of Staph. aureus (MIC 3.90 and 0.97 microg ml-). 4-Methoxyacetophenone and 3,4,5-trimethoxyacetophenone effectively inhibited C. albicans (MIC 1.95 microg ml-). The other compounds (kaempferol-3-O-rutinoside, rutin and psoralen) which were also isolated showed low antibacterial and antimycotic activities (125-500 microg ml-).

The present study examines the effects of the extracts [petroleum ether, CHCl3, CHCl3/MeOH (9:1) and MeOH], partially purified fractions and pure compounds from Guettarda acreana on the electrically induced contractions (E.C.I.) of the isolated guinea-pig ileum. The results of the experiments indicate that CHCl3/MeOH (9:1), MeOH extract, and the MeOH soluble part from CHCl3/MeOH extract tested at concentrations of 1.2, 2.5, and 5 micrograms/ml, dose-dependently reduced the guinea-pig ileum contractions. Furthermore, some partially purified fractions I-IV from the MeOH extract, each tested at the same concentrations of the extracts, and some pure compounds (6 x 10(-6), 3 x 10(-6), 1 x 10(-6) M) isolated from the above fractions significantly reduced, in a dose-dependent manner, the electrical contractions of the ileum. The active compounds were identified as the known indole alkaloids strictosidic acid, lyalosidic acid, 5 alpha-carboxystrictosidine, strictosidine, and sickingine, as well as the known quinic acid derivatives 5-caffeoylquinic acid, 4,5-dicaffeoylquinic acid, and shikimic acid by spectral data. Two known quinovic acid glycosides and a new triterpenic glycoside, quinovic acid 3 beta-O-alpha-rhamnopyranosyl-(1-->3)-(beta-glucopyranosyl-(1-->6)-beta- glucopyranoside, were also isolated and their structures established by NMR and M5 data.

The aerial part of Werneria ciliolata afforded a series of new diterpenes: two ent-kaurane derivatives, a norkaurane, an ent-manoyloxide derivative, a dimeric diterpene, as well as a rare diterpene. Their structures were elucidated by spectroscopic methods, including the concerted application of 1D NMR techniques (DEPT and NOEDS) and 2D NMR techniques (1H-1H COSY and HETCOR). In addition, four known kauranes, four coumarins and 6-hydroxytremetone were isolated. All isolated compounds from W. ciliolata and W. dactylophylla were tested in vitro for anti-viral activity against HIV-1, but only 6-hydroxytremetone showed a significant anti-HIV-1 activity.

The CHCl3 extract of Eriobotrya japonica from an Italian source was shown to contain four new triterpene esters, namely, 23-trans-p-coumaroyltormentic acid [1], 23-cis-p-coumaroyltormentic acid [2], 3-O-trans-caffeoyltormentic acid [3], and 3-O-trans-p-coumaroylrotundic acid [4], in addition to three common ursolic acid derivatives 5, 6, and 7. An investigation of the antiviral properties of compounds 1-7 revealed that only 3 significantly reduced rhinovirus infection. The compounds were ineffective towards human immunodeficiency virus type 1 (HIV-1) and Sindbis virus replication.