FLAVONOIDS AND PHENOLIC ACIDS ISOLATED FROM Macrolobium acaciifolium (FABACEAE) LEAVES AND BRANCHES METHANOLIC EXTRACTS. The phytochemical study of Macrolobium acaciifolium extracts allowed the isolation and identification of 18 substances, 15 of which are reported for the first time in this species. From the methanolic extract of the leaves, the flavonoids luteolin-3’-O-α-L-rhamnoside (1), neoastilbin (2), astilbin (3), neoisoastilbin (4), isoastilbin (5), quercetin-3-O-α-L-rhamnoside (6), quercetin-3-O-rutinoside (7), kaempferol-3-O-rutinoside (8), quercetin-3-O-glicoside (9) and kaempferol-7-O-rutinoside (10) were isolated. From the methanolic extract of branches, the flavonoids chrysoeriol (13), apigenin (14), 7,4’-dihydroxyflavone (16), eriodictyol (17) and luteolin (18), in addition to the phenolic acids 3,4-dihydroxybenzoic acid (11), 3-methoxy,4-hydroxybenzoate (12) and methyl 3,4-dihydroxybenzoate (15) were isolated. The structural identification of the compounds was established by proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC) and correlated spectroscopy (COSY) analyses. In this paper, we also discuss about the anisotropic effects on H-1”, H-2”, H-5” and H-6” rhamnose of isomers dihydroflavonoids. FABACEAE (FABACEAE EXTRACTS 1 substances species leaves luteolin3OαLrhamnoside luteolinOαLrhamnoside 3 O α L rhamnoside 1, , (1) 2, 2 (2) 3, (3) 4, 4 (4) 5, 5 (5) quercetin3OαLrhamnoside quercetinOαLrhamnoside quercetin 6, 6 (6) quercetin3Orutinoside quercetinOrutinoside rutinoside 7, 7 (7) kaempferol3Orutinoside kaempferolOrutinoside kaempferol 8, 8 (8) quercetin3Oglicoside quercetinOglicoside glicoside 9 (9 kaempferol7Orutinoside 10 (10 isolated branches 13, 13 (13) 14, 14 (14) 7,4dihydroxyflavone 74dihydroxyflavone dihydroxyflavone 7,4 16, 16 (16) 17 (17 18, (18) 3,4dihydroxybenzoic 34dihydroxybenzoic dihydroxybenzoic 3,4 11, 11 (11) 3methoxy,4hydroxybenzoate 3methoxy4hydroxybenzoate methoxyhydroxybenzoate methoxy,4 hydroxybenzoate methoxy 12 (12 3,4dihydroxybenzoate 34dihydroxybenzoate dihydroxybenzoate (15 1H H NMR, NMR NMR) carbon13 carbon carbon-1 13C C HSQC, HSQC (HSQC) HMBC (HMBC COSY (COSY analyses paper H1, H1 H-1” H2, H2 H-2” H5 H-5 H6 H-6 dihydroflavonoids OαLrhamnoside (1 (2 (3 (4 (5 (6 Orutinoside (7 (8 Oglicoside ( (13 (14 4dihydroxyflavone 74 (16 (18 4dihydroxybenzoic 34 (11 3methoxy 4hydroxybenzoate methoxy4 methoxy, 4dihydroxybenzoate carbon1 carbon- (HSQC H-1 H-2 H-

Abstract Vismia japurensis Reichardt is a plant of ecological and chemical importance from which a variety of bioactive substances have been isolated. The current study aimed to establish in vitro cultures of this species as a source of secondary metabolites. Appropriate decontamination treatments and germination tests were performed and, after in vitro culture establishment, the propagated plants were multiplied in a sterile environment to increase the biomass of available experimental material. Seeds showed low contamination and a high germination percentage on Woody Plant Medium (WPM) supplemented with gibberellic acid (both at concentrations of 5 and 10 mg/L). V. japurensis nodal segments rapidly regenerated when first grown in WPM and then transplanted to Murashige and Skoog medium (MS). After 60 days in MS medium, the propagated plants were removed, lyophilized, and extracted with hexane and methanol. The hexane extract was fractionated via open column chromatography, and the substance isolated was purified by high performance liquid chromatography. Structural determination of the isolated substance was carried out using one and two-dimensional nuclear magnetic resonance and mass spectrometry. The isolated substance was identified as 1,8,10-trihydroxy-3,10-dimethyl-9(10H)-anthracenone, which, based on the conducted literature search, is reported for the first time. metabolites establishment material (WPM both 1 mg/L. mgL mg/L . mg L mg/L) V MS. (MS) 6 removed lyophilized methanol chromatography twodimensional two dimensional spectrometry 1,8,10trihydroxy3,10dimethyl910Hanthracenone, 1810trihydroxy310dimethyl910Hanthracenone trihydroxydimethylHanthracenone 1,8,10 trihydroxy 3,10 dimethyl 9 10H anthracenone, 8 3 anthracenone H 1,8,10-trihydroxy-3,10-dimethyl-9(10H)-anthracenone search time (MS 10trihydroxy3 10dimethyl910Hanthracenone Hanthracenone 1,8,10trihydroxy3,10dimethyl910Hanthracenone 1810 1,8,1 310 3,1 10trihydroxy dimethylHanthracenone 181 1,8, 31 3, 18 1,8 1,

The inorganic composition of the bark and leaf of a plant from the Amazon rainforest, Andira surinamensis, was determined using two non-destructive, multi-element techniques: X-ray fluorescence (XRF) and Rutherford backscattering spectrometry (RBS). XRF measurements were made using both a conventional X-ray source and synchrotron radiation. It was observed that although magnesium, aluminum, silicon, phosphorus, sulfur, chlorine, and potassium are present in higher concentrations in the leaf, calcium is about three times more concentrated in the bark. Manganese, iron, copper, zinc, strontium and barium were also detected, with barium showing a concentration above the minimum toxicity level for plants. Chemical speciation of sulfur, performed using the X-ray absorption near edge structure (XANES) technique, showed that sulfur is present in several oxidation states, with a much larger contribution from the inorganic sulfate in the leaves. The article evidences that the combined use of synchrotron radiation and non-destructive multi-element techniques allows for an efficient and accurate determination of the inorganic composition and chemical speciation in plants.

An alternative spectrophotometric ferric reducing activity power (FRAP) method for quantification of total reducing capacity (TRC) was developed. The method is based on the reduction of FeIII to FeII by antioxidant compounds containing 2,2’-bipyridine (bipy) in aqueous solution. Absorbance values recorded at 521 nm, characteristic of the Fe(bipy)32+ complex formed, were used to determine the TRC of some plants-derived beverages. For the teas samples, the TRC values obtained with the proposed method and cupric reducing antioxidant capacity (CUPRAC) reagent had an excellent agreement (adjusted correlation coefficient (r2) = 0.951). Concerning herbs samples, the TRC values obtained with the proposed FRAP method correlated very well with values obtained using the 2,2’-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS•+) method (adjusted r2 = 0.975). It can be inferred from these results that other beverages derived from plants (e.g., beers, wines, and fruits juices) could also be analyzed with this new FRAP assay. In addition, the reducing capacity of 21 phenolic derivatives was determined with the proposed method in order to elucidate their structure-reactivity relationship. As expected, the phenolic derivative structure changes greatly the TRC values obtained with this proposed FRAP assay.

ABSTRACT Candida spp. is associated with almost 80% of all nosocomial fungal infections and is considered a major cause of blood stream infections. In humans, Cryptococcosis is a disease of the lungs caused by the fungi Cryptococcus gattii and Cryptococcus neoformans. It can be potentially fatal, especially in immune-compromised patients. In a search for antifungal drugs, Deguelia duckeana extracts were assayed against these two fungi and also against Candida albicans, which causes candidiasis. Hexane branches and CH2Cl2 root extracts as well as the substances 4-hydroxylonchocarpine, 3,5,4′-trimethoxy-4-prenylstilbene and 3′,4′-methylenedioxy-7-methoxyflavone were assayed to determine the minimal inhibitory concentration. Phytochemical study of CH2Cl2 root and hexane branch extracts from D. duckeana A.M.G. Azevedo, Fabaceae, resulted in the isolation and characterization of nine phenolic compounds: 4-hydroxyderricine, 4-hydroxylonchocarpine, 3′,4′,7-trimethoxy-flavonol, 5,4′-dihydroxy-isolonchocarpine, 4-hydroxyderricidine, derricidine, 3,5,4′-trimethoxy-stilbene, 3′,4′,7-trimethoxyflavone and yangambin. The only active extract was a CH2Cl2 root showing minimal inhibitory concentration 800 µg/ml against C. gattii, and the investigation of compounds obtained from this extract showed that 4-hydroxylonchocarpine was active against all three fungi (C. neoformans, C. gattii and C. albicans). These results suggest that D. duckeana extracts have potential therapeutic value for the treatment of pathogenic fungi.