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12α-hydroxy-N-demethyl-sauroxine (1), another new Lycopodium alkaloid from the Lycodane group, was isolated from Phlegmariurus saururus (Lam.) B. Øllg. (Lycopodiaceae). Elucidation of the chemical structure and relative stereochemistry were stated by spectroscopic data and chemical correlation. In addition, the inhibitory activity on acetylcholinesterase for 1 was determined as well as for N-methyllycodine (2), a derivative with the same nucleus, previously identified in P. saururus (IC50 = 33.8 ± 0.8 μM and 547.5 ± 0.5 μM, respectively) and N-demethylsauroxine (3) whose inhibition in the actual conditions was better than the previously informed. Fil: Vallejo, Mariana Guadalupe. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina Fil: Corzo, Marcos E.. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina Fil: Ortega, María Gabriela. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina

In the first chemical investigation developed on the species Dalea elegans twenty years ago, the occurrence of two prenylated derivatives of pinocembrin was reported: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-6-prenylpinocembrin (6PP) given as a new structure in this family of compounds, and another derivative of already known structure, 6-prenylpinocembrin (6P). In the present paper, their structures were again analyzed by using spectroscopic techniques, especially 2D NMR. Based on the evidence obtained it is proposed the reassignment of both flavanones as: 2′,4′-dihydroxy-5′-(1‴,1‴-dimethylallyl)-8-prenylpinocembrin (8PP) for the first and 8-prenylpinocembrin (8P) for the last. Additionally, triangularin, demethoxymatteucinol, comptonin and 7-hydroxy-5-methoxy-6,8-dimethylflavanone were isolated from aerial parts of D. elegans and informed by the first time for this species. All of these compounds were evaluated in vitro in relation to the antityrosinase effect by using a spectrophotometric method. Compound 8PP (IC50 2.32 ± 0.01 μM) exhibited the most potency and was two times more active than Kojic acid (IC50 4.93 ± 0.01 μM) used as a positive control. Triangularin also has shown an important inhibitory activity. Kinetic studies were performed for both compounds. Hence, new tyrosinase inhibitors with potential applications in pharmacy and cosmetic industry are presented. Fil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Santi, María Daniela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia; Argentina

Achyrocline satureioides extracts were tested in vitro against the growth of Paenibacillus larvae. Four different extracts were obtained by liquid-liquid extraction from an aqueous-ethyl alcohol macerate of the aerial parts of the plant. The biological activity was tested by the broth microdilution technique. Hexane extract showed the highest activity (minimum inhibitory concentration = 0.060 ± 0.037 mg/mL). Transmission electron microscopy experiments showed that the main effect exerted by the hexane extract on the cell was at the cellular membrane level. The hexane extract was analyzed by thin-layer chromatography, and the activity of its components was tested by bioautography. Four growth inhibition zones were observed in the bioautographic experiments (using hexane-acetone (7:3) as mobile phase), with that at Rf = 0.57 showing the largest zone of inhibition. High-performance liquid chromatographic experiments, using ultraviolet and electrospray ionization coupled to tandem mass spectrometric detection, showed the presence of one compound with a m/z ratio of 442, which may be related to phloroglucinols α-pyrone compounds recently discovered. The high antibacterial activity of the hexane extract and of the isolated compound determined in this work may be useful for the development of future new alternatives for the treatment of American foulbrood. Fil: Gonzalez, Maria Juliana. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina Fil: Beoletto, Viviana Graciela. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina Fil: Audisio, Marcela Carina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; Argentina Fil: Marioli, Juan Miguel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina

The presence of thiophene derivatives in Flaveria bidentis and Flaveria bidentis var. angustifolia has been investigated to expand on the existing chemical information on both taxa. Alpha-terthienyl and 5- (3-buten-1-ynyl)- 2,2′-bithienyl were found in the roots and aerial parts of F. bidentis, whereas in F. bidentis var. angustifolia α-terthienyl was found only in the roots. These results, in conjunction with the different patterns of sulphated flavonoids present in each one of these entities, reinforce the differentiation, based on exomorphological features, of Argentinian Flaveria into two species: F. bidentis and F. haumanii (formerly F. bidentis var. angustifolia).

Studies were performed on GC-MS to assess the lipophilic composition of sixAdesmia species representing two subgenera and three series. Normal fatty acids and hydrocarbons were mainly found, as well as acetylenic compounds, dibasic acids, cyclic hydrocarbons, high molecular weight alcohols and one sterol.

Two semisynthetic acetyl derivatives of the alkaloid sauroine from Huperzia saururus, monoacetyl sauroine, and diacetyl sauroine (DAS) were obtained and their chemical structures were analyzed by NMR. While monoacetyl sauroine is the typical product of acetylation, DAS is an unexpected derivative related to the keto-enol formation of sauroine. Recordings of field excitatory post-synaptic potentials from the CA1 region of rat hippocampal slices showed that only DAS acutely applied induced chemical long-term potentiation (LTP) in a dose-dependent manner with an EC50 of 1.15 0.09 lM. This effect was blocked by 10 lM D(-)-2-amino-5-phosphonopentanoic acid (AP5), suggesting dependence on the NMDA receptor. DAS significantly increased NMDA receptor-dependent excitatory post-synaptic currents without affecting a-amino- 3-hydroxy-5-methylisoxazole-4-propionate receptor-dependent currents. Repetitive administration of DAS improved visuospatial learning in the Morris Water Maze. In slices from rats tested in the Morris Water Maze, LTP resulting from electrical synaptic stimulation was 2.5 times larger than in controls. Concentration of DAS measured in the brain after repetitive administration was 29.5 lM. We conclude that slices perfused with DAS display a robust NMDA receptor-dependent chemical LTP. During chronic treatment, DAS enhances Fil: Vallejo, Mariana Guadalupe. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina Fil: Loyola, S.. Universidad de Santiago de Chile; Chile Fil: Contreras, Darwin. Universidad de Santiago de Chile; Chile Fil: Ugarte, Gonzalo. Universidad de Santiago de Chile; Chile Fil: Cifuente, Diego Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones En Tecnología Química; Argentina Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina Fil: Zeise, Marc. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones En Tecnología Química; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química. Area de Química Orgánica; Argentina Fil: Carreño, Mario. Universidad de Santiago de Chile; Chile Fil: Delgado, Ricardo. Universidad de Santiago de Chile; Chile Fil: Morales, Bernardo. Universidad de Santiago de Chile; Chile Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Farmacología. Cátedra de Farmacognosia; Argentina

The present study describes the isolation and identification of N-demethyl-sauroxine, a novel Lycopodium alkaloid obtained from Huperzia saururus (Lam.) Trevis. (Lycopodiaceae). Its structure and relative stereochemistry were elucidated on the basis of its spectral data and chemical correlations. Additionally, acetylcholinesterase inhibitory activity was evaluated (IC50 = 209.6 ± 1.1 lM). The structure of the already identified alkaloid sauroxine was also re-validated through two dimensional NMR data. Fil: Vallejo, Mariana Guadalupe. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina Fil: Agnese, Mariel. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina

A novel Lycopodium alkaloid, sauroine (7,8-dihydroxylycopodine, 1) was isolated from the aerial parts of the medicinal species Huperzia saururus. The structure and relative stereochemistry of 1 were elucidated on the basis of its spectral data.

Sulphated esters of the flavonoids sulphated quercetin 3,7,3′,4′-tetrasulphated (QTS) and quercetin 3-acetyl-7,3,4′-trisulphate (ATS), isolated from Flaveria bidentis, have demonstrated anticoagulant and antiplatelet properties. In this study, we examined if both compounds affected the expression of the procoagulant tissue factor (TF) induced by lipopolysaccharide (LPS) on human monocyte. Monocytes were pretreated with different concentrations of each flavonoid (0.1–500 μM), followed by a 4 h incubation with LPS in order to induce TF expression. Results of the TF expression showed different behaviors for the two flavonoids studied. A slight inhibitory effect on the TF expression was detected at a QTS concentration of 0.1 μM, but from 1 μM onwards a significant inhibitory effect that remained up to 500 μM could be observed. In contrast, ATS induced a poor inhibitory effect on TF expression at all concentrations tested. These results suggest that QTS has another antithrombotic property, to be added to its already renowned ability as an anticoagulant and antiplatelet compound.

From the roots of Acmella decumbens (Sm) R.K. Jansen three compounds belonging to the alkamide family were isolated: (2E, 4E)-N-hydroxiphenylethyl-2,4-decadien-9-inamide (1); (4E, 6E)-N-isobutyl-4,6-undecen-10-inamide; (2) and (2Z)-N-phenylethyl-2-nonane-6,8-diinamide (3). The structures were determined by means of IR, MS, 1H NMR, 13C NMR, DEPT 135 and COSY. Compounds 1 and 2 are reported for the first time, while 3 was previously isolated from Spilanthes acmella L. Fil: Casado, Mariela Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina Fil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina

Flaveria bidentis is a plant species that has as major constituents sulphated flavonoids in the highest degree of sulphatation. Among them, quercetin 3,7,3′,4′-tetrasulphate (QTS) and quercetin 3-acetyl-7,3′,4′-trisulphate (ATS) are the most important constituents. Both showed anticoagulant properties. The objective of the present study was to evaluate the effects of these flavonoids on human platelet aggregation in comparison with the well-known inhibitor quercetin (Qc) by using several agonists. Platelet-rich plasma (PRP) or washed human platelets (WP) were incubated with different concentrations of the flavonoids to be tested (1 to 1000 μM, final concentration), and the platelet aggregation was induced by using adenosine 5′-diphosphate (ADP), epinephrine (EP), collagen, arachidonic acid (AA) and ristocetin as agonists. QTS (500 μM) and Qc (250 μM) markedly inhibited platelet aggregation with all the aggregant agents, except ristocetin, whereas ATS (1000 μM) showed only slight antiplatelet effects. In addition, QTS and Qc antagonized the aggregation of PRP or WP induced by U-46619, a mimetic thromboxane A2 (TxA2) receptor agonist. Challenged with collagen or arachidonic acid, the thromboxane B2 (TxB2) formation was also inhibited by the flavonoids, mainly by QTS and Qc, in WP. These results demonstrate that QTS and in minor extension ATS induce a deleterious effect on the production of TxA2, as judged by TxB2 formation, in stimulated WP and a marked interference on the TxA2 receptor according to the profile of inhibition of the agonist-induced platelet aggregation when using ADP, EP, AA and collagen and confirmed with U-46619. Fil: Guglielmone, Hugo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Bioquímica Clínica; Argentina Fil: Agnese, Alicia Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina Fil: Núñez Montoya, Susana Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional del Sur. Departamento de Biología, Bioquímica y Farmacia. Cátedra de Farmacognosia; Argentina Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina

Summary Benzenic extracts from both stems and leaves of Heterophyllaea pustulata showed the most significant activity in vivo in the Brine Shrimp Lethally Test (BST), relative to others of different polarity. They were therefore selected for in vitro antimicrobial activity studies. Bacteriostatic activity against Micrococcus luteus ATCC 9341 was detected, selectively inhibiting both oxacillin-sensitive and -resistant Staphylococcus aureus, among several Gram-positive and Gram-negative bacterial species tested. Antifungal activity against important opportunist microorganisms and against those involved in superficial mycosis, all from nosocomial origin was also detected. A chemical screening revealed the presence of anthraquinones as major compounds. Among them, we identified damnacanthal, rubiadin, 2-hydroxy-3-methyl anthraquinone, soranjidiol, rubiadin-1-methyl ether, and damnacanthol in the benzenic stem extract. The benzenic leaf extract shows a similar chemical composition, except for damnacanthal, damnacanthol, soranjidiol-1-methyl ether, and 3 anthraquinones whose structures have not yet been elucidated. Acute toxicity studies revealed a low toxicity in mice for the anthraquinonic extracts, as measured in the LD50 value (123 mg/kg body wt. i.v.), and death was not observed at doses of up to 4000 mg/kg body wt. s.c.

Quercetin 3-acetyl-7,3',4'-trisulphate (ATS) and quercetin 3,7,3',4'-tetrasulphate (QTS) obtained from Flaveria bidentis (Asteraceae) were investigated in vitro for anticoagulant activity. Three different concentrations of each flavonoid were assayed at different incubation times, showing at 1 mM significant prolongation on the activated partial thromboplastin time (APTT), less on the prothrombin time (PT), and no effect on the thrombin time (TT). In order to define the action mechanism of the anticoagulant activity, all coagulation factors were evaluated and no important activity decrease was observed, indicating that another mechanism is involved. Thus, thrombin inhibition mediated by antithrombin III (ATIII) and heparin cofactor II (HCII) activation was investigated in comparison to the physiological activators, heparin and dermatan sulphate (DS), respectively. As a conclusion, no activation on ATIII for neither flavonoids was observed. On the contrary, QTS much more than ATS produced an activation on HCII comparable to the one of DS, indicating that these flavonoids act as agonists of this inhibitor. A plausible explanation of the effects of both flavonoids could be due to the different degree of sulphation of these molecules. According to the results obtained, and taking in account the high solubility of these natural products in aqueous media and the nontoxic nature of this family of compounds, further investigation on the antithrombotic effects of these flavonoids are merited.