Withaphysalin Derivatives from Iochroma arborescens Induce Antiproliferative and Antimigratory Activities in vitro.

Withanolides are steroidal lactones commonly found in plants of the Solanaceae family that have significant medicinal value. In this study, three withanolides extracted from Iochroma arborescens leaves were isolated and characterized. These included withaphysalin F (3: ) and two newly identified epimeric compounds: 18R- and 18S-O-methyl-withaphysalin F (1: and 2: ). Their structures were elucidated by NMR, IR, MS, CD, and X-ray diffraction analysis, and their potential against cell proliferation and migration was investigated. The cytotoxic assay revealed activity against different tumor and non-tumor cell lines. (18S)-O-methyl-withaphysalin F (2: ) presented cell death effects after at least 6 hours of exposure. MDA-MB-231 cells were exposed to 0.06 and 0.6 µM of (18S)-O-methyl-withaphysalin F (2: ), and reductions in cell adhesion, migration, and clonogenicity were observed. Morphological analysis revealed negative regulation in filopodia, salience, and roughness, as well as alterations in cellular microarchitecture. These results provide clues as to the effects of (18S)-O-methyl-withaphysalin F (2: ), allowing new molecular modifications to improve potency and selectivity and increase our antineoplastic arsenal.

Withanolide Profile and Acetylcholinesterase Inhibitory Activity of Two Argentinean Jaborosa Species.

Acetylcholinesterase (AChE) inhibitors are still an important option for managing symptoms of mild to moderate Alzheimer's disease. In this study, we aimed to evaluate the potential in vitro AChE inhibitory activity of two Argentinian endemic Solanaceae species, Jaborosa bergii and J. runcinata. UHPLC-DAD-HRMS metabolite profiling revealed the presence of withanolides in the active CH2Cl2 subextracts. Their fractionation led to the isolation and identification of two known spiranoid withanolides from J. runcinata and three new withanolides with a skeleton similar to that of trechonolide-type withanolides from J. bergii. The known compounds showed moderate AChE inhibitory activity, while the new ones were inactive.

Antibacterial activity of withanolides and their structure-activity relationship.

Two new withanolides, (17R,20S,22R)-4ß-acetoxy-5ß,6ß-epoxy-19,27-dihydroxy-1-oxo-witha-2,24-dienolide (withalongolide A 4-acetate (5) and (17R,20S,22R)-5ß,6ß-epoxy-27-hydroxy-1,4-dioxo-witha-24-enolide (9), and seven known withanolides with normal structure (1-4, 6-8) were isolated from aerial parts of Cuatresia colombiana. Several semisynthetic derivatives were prepared from the natural metabolites withaferin A and jaborosalactone 38. The compounds were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS). The compounds isolated from C. colombiana, sixteen withanolides previously isolated from different Solanaceae species with different skeletons and semisynthetic derivatives were evaluated for their antibacterial activity against a selected panel of Gram-positive and Gram-negative bacteria. According to the bioactivity against S. aureus and E. faecalis, the compounds evaluated were divided into three groups: compounds with high activity (MIC 0.063 mM), compounds with moderate activity (0.5 mM > MIC > 0.125 mM) and non-active compounds (MIC ≥1 mM); in addition, some structure-activity relationship keys could be inferred.

Anti-inflammatory withajardins from the leaves of Athenaea velutina.

Withajardins, uncommon modified withanolide-type steroids, have been isolated exclusively from plants of the Solanaceae family so far. Two undescribed withajardins and the known tuboanosigenin were isolated from the hexane/EtOAc 1:1 extract from Athenaea velutina leaves. Their structures were established by an extensive analysis of 1D and 2D-NMR and HRMS data. The absolute configuration was determined by X-ray diffraction (withajardin L and tuboanosigenin) and circular dichroism (CD) analyses (withajardin M). The anti-inflammatory activity of compounds was evaluated through the inhibition of the lipopolysaccharide (LPS)-induced nitric oxide (NO), TNF-α, and IL-6 release in RAW264.7 cells. The cell viability effects to RAW 264.7 cells showed IC50 values of 74.4-354.4 µM. The compounds attenuated LPS-induced release of NO and decreased pro-inflammatory cytokines TNF-α and IL-6 in RAW264.7 cells.

Smoke of Capsicum baccatum L. var. baccatum (Solanaceae) repels nymphs of triatoma infestans (Klug) (Hemiptera: Reduviidae) / Humo de capsicum baccatum L. var. baccatum (Solanaceae) repele las ninfas de Triatoma infestans (Klug) (Hemiptera: Reduviidae)

Control of the Chagas disease vector, Triatoma infestans (Klug) (Hemiptera: Reduviidae) with synthetic pesticides in Bolivia has become increasingly inefficient due to the development of resistance in the insects. In the Chaco region of Bolivia, guaraní populations have approached the problem by fumigating their houses with the smoke of native plants. Through interviews and field work with local guides, the main plant used by the guaraníes was collected and later identified as Capsicum baccatumL. var. baccatum (Solanaceae). In choice bioassays, filter papers exposed to the smoke of the plant repelled nymphs of T. infestans. Activity remained significant after storing the exposed filter papers for 9 days. Chemical analysis of smoke and literature data suggested that capsaicinoids present in the smoke were responsible for the repellent effect. The data presented provide a rationale for the use of C. baccatumvar. baccatumto control the Chagas vector bythe guaraní populations.

El control del vector de la enfermedad de Chagas, Triatoma infestans (Klug) (Hemiptera: Reduviidae) con plaguicidas sintéticos en Bolivia se ha vuelto cada vez más ineficiente debido al desarrollo de resistencias en los insectos. En la región del Chaco de Bolivia, las poblaciones guaraníes han abordado el problema fumigando sus casas con el humo de las plantas nativas. A través de entrevistas y trabajo de campo con guías locales, se recogió la principal planta utilizada por los guaraníes y posteriormente se identificó como Capsicum baccatumL. var. baccatum (Solanaceae). En bioensayos selectos, los papeles de filtro expuestos al humo de la planta repelieron a las ninfas de T. infestans. La actividad siguió siendo significativa después de almacenar los papeles de filtro expuestos durante 9 días. El análisis químico del humo y los datos de la literatura sugieren que los capsaicinoides presentes en el humo eran responsables del efecto repelente. Los datos presentados proporcionan una justificación para el uso de C. baccatum var. baccatum para el control del vector Chagas por las poblaciones guaraníes.

Withalutin, a new cytotoxic withanolide from Athenaea velutina (Sendtn.) D'Arcy.

Bioassay-guided fractionation of dichloromethane extract from Athenaea velutina leaves led to the isolation of three withanolides, all being reported for the first time in this species. They were identified as withacnistin (1), withacnistin acetate (2) and a new withanolide, designated as withalutin (3). The structures were established by spectral data analysis, including MS, 1D and 2D NMR. In addition, in silico ADMET studies were employed to understand the pharmacokinetic properties of these withanolides. The withanolides isolated from A. velutina reduced cancer cell viability with IC50 values ranging from 1.52 to 5.39 µM. In silico prediction revealed that withanolides have good gastrointestinal absorption or oral bioavailability properties; and are not likely to be mutagenic or hepatotoxic. These findings revealed that A. velutina is an important source of cytotoxic withanolides.

Milk-clotting and hydrolytic activities of an aspartic protease from Salpichroa origanifolia fruits on individual caseins.

In recent years, many attempts have been made to find new plant proteases to make artisan cheeses. The global increase in cheese consumption, together with a lower supply and increasing cost of calf rennet, religious factors (Islam and Judaism) and food choices (vegetarianism) have led to the search for suitable rennet substitutes for milk clotting. This study describes the milk-clotting and hydrolytic activities of an aspartic protease from Salpichroa origanifolia fruits (SoAP) on individual caseins to explore its potential use as an alternative to animal rennet. The milk-clotting index obtained for SoAP was 8.4 times lower than that obtained for chymosin. SoAP showed a higher degree of hydrolysis on α-casein than on the other fractions under the proposed conditions. RP-HPLC, mass spectrometry analyses and sequencing of the hydrolysates allowed identifying five peptides from α-casein, one peptide from ß-casein, and three peptides from k-casein. In silico analysis showed that the peptides identified may display a wide variety of potential biological activities. These results demonstrate the possibility of using SoAP for the manufacture of new types or artisan cheeses, with the simultaneous added value of the potential health-promoting benefits of the bioactive peptides generated during the hydrolysis.

Cyclotides from Brazilian Palicourea sessilis and Their Effects on Human Lymphocytes.

Cyclotides are plant-derived peptides found within five families of flowering plants (Violaceae, Rubiaceae, Fabaceae, Solanaceae, and Poaceae) that have a cyclic backbone and six conserved cysteine residues linked by disulfide bonds. Their presence within the Violaceae species seems ubiquitous, yet not all members of other families produce these macrocyclic peptides. The genus Palicourea Aubl. (Rubiaceae) contains hundreds of neotropical species of shrubs and small trees; however, only a few cyclotides have been discovered hitherto. Herein, five previously uncharacterized Möbius cyclotides within Palicourea sessilis and their pharmacological activities are described. Cyclotides were isolated from leaves and stems of this plant and identified as pase A-E, as well as the known peptide kalata S. Cyclotides were de novo sequenced by MALDI-TOF/TOF mass spectrometry, and their structures were solved by NMR spectroscopy. Because some cyclotides have been reported to modulate immune cells, pase A-D were assayed for cell proliferation of human primary activated T lymphocytes, and the results showed a dose-dependent antiproliferative function. The toxicity on other nonimmune cells was also assessed. This study reveals that pase cyclotides have potential for applications as immunosuppressants and in immune-related disorders.

Hybrids of Solanum corymbiflorumand S. diploconos(Solanaceae) –a hope for new commercial varieties of edible fruits / Híbridos de Solanum Corymbiflorum e S. diploconos (Solanaceae) –uma alternativa paranovas cultivares comerciais defrutas comestíveis

Solanum diploconos(Mart.) Bohs („guava tamarillo”) and Solanum corymbiflorum(Sendtn.) Bohs („hardy tamarillo”) are wild relatives to subtropical, orchard, small tree –Solanum betaceumCav. (called simply „tamarillo”). Both these species create edible fruits, but they have not been cultivated widely so far as fruit trees. However, each one of these species has valuable features. Solanum corymbiflorumis quite hardy to frost, deciduous and early blooming both in fenological year time as well as in its lifespan but has untasty fruits. Solanum diploconoshas quite good tasting fruits and it is pest and disease resistant. This work has been an attempt to connect their best features in hybrids to create new, potentially commercial cultivars to grow as fruit plants. Three types of hybrids were created: F1 hybrid type –Solanum corymbiflorum× Solanum diploconos, BC1 backrossing type -(Solanum corymbiflorum× Solanum diploconos) × Solanum corymbiflorum and the second BC1 backcrossing type –(Solanum corymbiflorum× Solanum diploconos) × Solanum diploconos. Out of the numerous variable individuals within each type, we selected three very valuable from an agronomic point of view cultivars (Solanum'Lynn', 'Pinczow Springs' and 'Iwona'). The work with crossing and selecting the next cultivars will be continued.

Solanum diploconos(Mart.) Bohs (”guava tamarillo”) e Solanum corymbiflorum(Sendtn.) Bohs (”hardy tamarillo”) são espécies silvestres de forma arbustiva –Solanum betaceumCav. (chamado simplesmente “tamarillo”). Ambas as espécies geram frutos comestíveis, mas não têm sido cultivadas como árvores frutíferas. Entretanto, cada uma destas espécies tem características valiosas. Solanum corymbiflorumé bastante resistente à geada, perde suas folhas periodicamente e possui floração precoce, tanto no ano fenológico como em sua vida útil, mas tem frutos pouco saborosos. No entanto, Solanum diploconostem frutos bastante saborosos e é resistente a pragas e doenças. Este estudo foiuma tentativa de captar as melhores características existentes em híbridos para criar novas cultivares, potencialmente comerciais, e que possam desenvolver como planta frutífera. Três tipos de híbridos foram criados: tipo híbrido F1 –(Solanum corymbiflorum× Solanum diploconos), tipo BC1 retrocruzamento -(Solanum corymbiflorum× Solanum diploconos) × Solanum corymbiflorume o segundo tipo BC1 retrocruzamento -(Solanum corymbiflorum× Solanum diploconos) × Solanum diploconos. Dos numerosos indivíduos variáveis dentro de cada tipo, foram selecionados três cultivares muito valiosas do ponto de vista agronômico (Solanum'Lynn', 'Pinczow Springs' e 'Iwona'). O trabalho de cruzamento e seleção das próximas cultivares terá continuidade e aprimoramento.

Hybrids of Solanum corymbiflorumand S. diploconos(Solanaceae) –a hope for new commercial varieties of edible fruits / Híbridos de Solanum Corymbiflorum e S. diploconos (Solanaceae) –uma alternativa paranovas cultivares comerciais defrutas comestíveis

Solanum diploconos(Mart.) Bohs („guava tamarillo”) and Solanum corymbiflorum(Sendtn.) Bohs („hardy tamarillo”) are wild relatives to subtropical, orchard, small tree –Solanum betaceumCav. (called simply „tamarillo”). Both these species create edible fruits, but they have not been cultivated widely so far as fruit trees. However, each one of these species has valuable features. Solanum corymbiflorumis quite hardy to frost, deciduous and early blooming both in fenological year time as well as in its lifespan but has untasty fruits. Solanum diploconoshas quite good tasting fruits and it is pest and disease resistant. This work has been an attempt to connect their best features in hybrids to create new, potentially commercial cultivars to grow as fruit plants. Three types of hybrids were created: F1 hybrid type –Solanum corymbiflorum× Solanum diploconos, BC1 backrossing type -(Solanum corymbiflorum× Solanum diploconos) × Solanum corymbiflorum and the second BC1 backcrossing type –(Solanum corymbiflorum× Solanum diploconos) × Solanum diploconos. Out of the numerous variable individuals within each type, we selected three very valuable from an agronomic point of view cultivars (Solanum'Lynn', 'Pinczow Springs' and 'Iwona'). The work with crossing and selecting the next cultivars will be continued.(AU)

Solanum diploconos(Mart.) Bohs (”guava tamarillo”) e Solanum corymbiflorum(Sendtn.) Bohs (”hardy tamarillo”) são espécies silvestres de forma arbustiva –Solanum betaceumCav. (chamado simplesmente “tamarillo”). Ambas as espécies geram frutos comestíveis, mas não têm sido cultivadas como árvores frutíferas. Entretanto, cada uma destas espécies tem características valiosas. Solanum corymbiflorumé bastante resistente à geada, perde suas folhas periodicamente e possui floração precoce, tanto no ano fenológico como em sua vida útil, mas tem frutos pouco saborosos. No entanto, Solanum diploconostem frutos bastante saborosos e é resistente a pragas e doenças. Este estudo foiuma tentativa de captar as melhores características existentes em híbridos para criar novas cultivares, potencialmente comerciais, e que possam desenvolver como planta frutífera. Três tipos de híbridos foram criados: tipo híbrido F1 –(Solanum corymbiflorum× Solanum diploconos), tipo BC1 retrocruzamento -(Solanum corymbiflorum× Solanum diploconos) × Solanum corymbiflorume o segundo tipo BC1 retrocruzamento -(Solanum corymbiflorum× Solanum diploconos) × Solanum diploconos. Dos numerosos indivíduos variáveis dentro de cada tipo, foram selecionados três cultivares muito valiosas do ponto de vista agronômico (Solanum'Lynn', 'Pinczow Springs' e 'Iwona'). O trabalho de cruzamento e seleção das próximas cultivares terá continuidade e aprimoramento.(AU)

Withanolides from the genus Exodeconus (Solanaceae). Chemotaxonomical considerations.

Five Exodeconus species were phytochemically analyzed. From the aerial parts of E. pusillus, the 7α,27-dihydroxy-1-oxo-22R-witha-2,5,24-trienolide and three other previously unreported normal-type withanolides were isolated. All the studied species had normal type and/or ring-D aromatic withanolides, and some had already been isolated from other Solanaceae genera, and therefore, these compounds are not chemotaxonomic markers at the generic level. The chemical composition of an undescribed Exodeconus species analyzed here supports the designation of this taxon as a new entity. The integral chemical profile of Exodeconus can be evaluated for its taxonomic implication when a more robust phylogeny of Solanaceae is available that allows the phylogenetic relationships with its closest genera to be clarified.

Screening of plants from the Brazilian Atlantic Forest led to the identification of Athenaea velutina (Solanaceae) as a novel source of antimetastatic agents.

Plant biodiversity is a source of potential natural products for the treatment of many diseases. One of the ways of discovering new drugs is through the cytotoxic screening of extract libraries. The present study evaluated 196 extracts prepared by maceration of Brazilian Atlantic Forest trees with organic solvents and distilled water for cytotoxic and antimetastatic activity. The MTT assay was used to screen the extract activity in MCF-7, HepG2 and B16F10 cancer cells. The highest cytotoxic extract had antimetastatic activity, as determined in in vitro assays and melanoma murine model. The organic extract of the leaves of Athenaea velutina (EAv) significantly inhibited migration, adhesion, invasion and cell colony formation in B16F10 cells. The phenolic compounds and flavonoids in EAv were identified for the first time, using flow injection with electrospray negative ionization-ion trap tandem mass spectrometry analysis (FIA-ESI-IT-MSn ). EAv markedly suppressed the development of pulmonary melanomas following the intravenous injection of melanoma cells to C57BL/6 mice. Stereological analysis of the spleen cross-sections showed enlargement of the red pulp area after EAv treatment, which indicated the activation of the haematopoietic system. The treatment of melanoma-bearing mice with EAv did not result in liver damage. In conclusion, these findings suggest that A velutina is a source of natural products with potent antimetastatic activity.

Fast Isolation of Flavonoids from the Endemic Species Nolana ramosissima I.M. Johnst and Its Endothelium-Independent Relaxation Effect in Rat Aorta.

The infusion of the desertic plant Nolana ramosissima I.M. Johnst showed vascular smooth muscle relaxation in rat aorta and the presence of several phenolic compounds, which were detected by high resolution UHPLC-Orbitrap-HESI-MS. In addition, five flavonoids were rapidly isolated from a methanolic extract using high-performance counter-current chromatography (HPCCC). The N. ramosissima extract showed endothelium-independent relaxation effect in rat aorta. Sixty-one compounds were detected in the infusion, mainly glycosylated flavonoids, flavanones and several oxylipins, suggesting that a synergistic effect between the compounds in the extracts could be responsible for the relaxation activity. Vascular activity experiments were done in isolated organ bath. In rat aorta, a nitric oxide inhibitor did not prevent the relaxation effects of the extract; however, a selective guanylyl cyclase inhibitor partially blunted this effect. The compound 5,3'-dihydroxy-4'7-dimethoxyflavone presented higher relaxation effect than 100 µg/mL of N. ramosissima extract. The extract and the isolated metabolites from N. ramosissima can show relaxation effects on rat aorta by a mechanism that is independent of the endothelium.

Selective Antiproliferative Withanolides from Species in the Genera Eriolarynx and Deprea.

Four new withanolides (2-5), together with 4ß,7ß,20-trihydroxy-1-oxowitha-2,5,24-trienolide (1), were isolated from the aerial parts of Eriolarynx iochromoides. The antiproliferative activity of all compounds purified from E. iochromoides together with four withaphysalins and four physangulidines isolated previously from three Deprea species were evaluated against human solid tumor cell lines. Four withanolides showed antiproliferative activity comparable in potency to cisplatin. Selectivity toward cancer cells and interaction with P-glycoprotein of the active withanolides were evaluated.

Fabiana imbricata Ruiz et Pav. (Solanaceae), a review of an important Patagonian medicinal plant.

ETHNOPHARMACOLOGICAL RELEVANCE: Fabiana imbricata (Solanaceae) is a Patagonian medicinal plant with a long tradition of use. The aim of this review is to provide an integrative overview of the traditional uses, chemistry, bioactivity and chemical profiling of the crude drug. MATERIALS AND METHODS: The information was collected from scientific databases searching with the keywords Fabiana imbricata, Fabiana species, Fabiana (Solanaceae) and includes local literature and books. RESULTS: The indications of use reported in literature show little variation from the data published as early as 1889. The chemical studies showed a rich diversity in metabolites including phenolics, coumarins, flavonoids, phenylpropanoids, terpenes, alkaloids and sugars. Bioactivity studies supported the traditional use as diuretic and also the potential of the crude drug as a gastroprotective agent. The plant can be used as a source of compounds with effect on gastric ulcers and shows enzyme inhibitory activity. While the germination rate of the plant is very low, protocols were developed for the rapid in vitro propagation of the species. The toxicity of the crude drug extracts was low and did not show clastogenic effect in human lymphocytes. Further research is needed to disclose the potential of the F. imbricata sesquiterpenes on other relevant biological targets.

Leishmanicidal Activity of Withanolides from Aureliana Fasciculata var. Fasciculata.

Leishmaniasis is the generic denomination to the neglected diseases caused by more than 20 species of protozoa belonging to the genus Leishmania. The toxic and parenteral-delivered pentavalent antimonials remain to be the first-line treatment. However, all the current used drugs have restrictions. The species Aureliana fasciculata (Vell.) Sendtner var. fasciculata is a native Brazilian species parsimoniously studied on a chemical point of view. In this study, the antileishmanial activity of A. fasciculata was evaluated. Among the evaluated samples of the leaves, the dichloromethane partition (AFfDi) showed the more pronounced activity, with IC50 1.85 µg/ml against promastigotes of L. amazonensis. From AFfDi, two active withanolides were isolated, the Aurelianolides A and B, with IC50 7.61 µM and 7.94 µM, respectively. The withanolides also proved to be active against the clinically important form, the intracellular amastigote, with IC50 2.25 µM and 6.43 µM for Aurelianolides A and B, respectively. Furthermore, withanolides showed results for in silico parameters of absorption, distribution, metabolism, excretion, and toxicity (ADMET) similar to miltefosine, the reference drug, and were predicted as good oral drugs, with the advantage of not being hepatotoxic. These results suggest that these compounds can be useful as scaffolds for planning drug design.

Antimicrobial activity of an aspartic protease from Salpichroa origanifolia fruits.

Plant proteases play a fundamental role in several processes like growth, development and in response to biotic and abiotic stress. In particular, aspartic proteases (AP) are expressed in different plant organs and have antimicrobial activity. Previously, we purified an AP from Salpichroa origanifolia fruits called salpichroin. The aim of this work was to determine the cytotoxic activity of this enzyme on selected plant and human pathogens. For this purpose, the growth of the selected pathogens was analysed after exposure to different concentrations of salpichroin. The results showed that the enzyme was capable of inhibiting Fusarium solani and Staphylococcus aureus in a dose-dependent manner. It was determined that 1·2 µmol l-1 of salpichroin was necessary to inhibit 50% of conidial germination, and the minimal bactericidal concentration was between 1·9 and 2·5 µmol l-1 . Using SYTOX Green dye we were able to demonstrate that salpichroin cause membrane permeabilization. Moreover, the enzyme treated with its specific inhibitor pepstatin A did not lose its antibacterial activity. This finding demonstrates that the cytotoxic activity of salpichroin is due to the alteration of the cell plasma membrane barrier but not due to its proteolytic activity. Antimicrobial activity of the AP could represent a potential alternative for the control of pathogens that affect humans or crops of economic interest. SIGNIFICANCE AND IMPACT OF THE STUDY: This study provides insights into the antimicrobial activity of an aspartic protease isolated from Salpichroa origanifolia fruits on plant and human pathogens. The proteinase inhibited Fusarium solani and Staphylococcus aureus in a dose-dependent manner due to the alteration of the cell plasma membrane barrier but not due to its proteolytic activity. Antimicrobial activity of salpichroin suggests its potential applications as an important tool for the control of pathogenic micro-organisms affecting humans and crops of economic interest. Therefore, it would represent a new alternative to avoid the problems of environmental pollution and antimicrobial resistance.

Athenolide A, a New Steroidal Lactone from the Leaves of Athenaea martiana (Solanaceae) Determined by Means of HPLC-HR-MS-SPE-NMR Analysis.

Athenaea (Solanaceae) is an endemic genus belonging to the Brazilian Atlantic Rainforest. Recently, botanical investigations suggested the re-evaluation of the generic status of the genus Athenaea as a synonym of Aureliana. In this study, the first investigation of the Athenaea genus performed on Athenaea martiana by means of HPLC-HR-MS-SPE-NMR combined with high-resolution radical scavenging profile led to identification of several phenolic acids as radical scavengers: protocatechuic acid (1), 4-hydroxybenzoic acid (2), caffeic acid (3), vanillic acid (4), and ferulic acid (6). Additional analysis revealed a new steroidal lactone, named athenolide A (9). Their structures were elucidated by extensive use of NMR spectroscopy as well as HR-MS. Chemotaxonomic considerations based on these results supported the chemical relationships between the Athenaea and Aureliana genera, in agreement with the recent botanical findings.

Antioxidant activity and chemical composition of oleoresin from leaves and flowers of Brunfelsia uniflora.

In this study, the temperature and pressure of supercritical CO2 extraction were evaluated to obtain oleoresin of Brunfelsia uniflora leaves and flowers. The oleoresin compounds were identified by gas chromatography-mass spectrometry. The antioxidant activity was evaluated by three different methods. The highest oleoresin yields were 3.32% at 40°C and 200 bar for the leaves, and 1.03% at 60°C and 200 bar for the flowers. The main extracted compounds from leaves were phytol varying from 11.95 to 36.42% and α-tocopherol from 15.53 to 43.10%, and from flowers were geranyl linalool from 11.05 to 21.42% and α-amyrin from 9.66 to 22.12%. Oleoresin obtained at 60°C and 150 bar from leaves presented high antioxidant activity by DPPH (IC50 1.90 mg/mL) and by FRAP (1.8 µmol Fe2+/mg). ß-carotene/linoleic acid co-oxidation oleoresin from leaves at 0.25 mg/mL presented higher antioxidant activity than Trolox. The total phenolic content of the oleoresin from leaves ranged from 66.20 to 83.33 µg/mg and from flowers it was just up to 12.46 µg/mg. The extraction conditions affected yield, chemical composition, and antioxidant activity of oleoresin from leaves and flowers. This is the first report on the antioxidant activity of B. uniflora oleoresin from leaves and flowers and provides subsidies for potential applications in chemical, pharmaceutical, and food industries.

Phytochemical Study of the Genus Salpichroa (Solanaceae), Chemotaxonomic Considerations, and Biological Evaluation in Prostate and Breast Cancer Cells.

Twelve Salpichroa taxa have been phytochemically analyzed. From the aerial parts of S. scandens, four known salpichrolides A, C, I, S, and an unreported withanolide named salpichrolide V (1), were isolated. In S. dependens, S. gayi, S. glandulosa subsp. glandulosa, S. glandulosa subps. weddellii, S. leucantha, S. micrantha, S. microloba, S. proboscidea, S. ramosissima, S. tristis var. tristis, and S. weberbauerii, no withanolides were found. The chemical content of ca. 85% of the Salpichroa taxa is in agreement with molecular studies, which suggest that Salpichroa and Jaborosa, a genus considered morphologically close to Salpichroa, are distant in the systematic of the Solanoideae subfamily. Moreover, the in vitro cytotoxic activity of a set of natural salpichrolides and derivatives was examined against two prostate carcinoma cell lines (PC3 and LNCaP) and two human breast cancer cell lines (MCF-7 and T47D). Several compounds showed moderate activity (IC50  = 64.91 - 29.97 µm).