Alelopathic activity of extracts of Ocotea puberula (Rich.) Nees on the germination and initial growth of lettuce

The interest in the exploration of compounds from the secondary metabolism is seen as a strategic alternative in agriculture, even for the control of invasive plants. The objective of this work was to measure the allelopathic activity of extracts CHCl3 and AcOEt from the leaves of O. puberula on the germination of lettuce. The ethanolic extract was obtained from the dried and milled leaves. The crude extract was solubilized in ethanol and acidified (hydroalcoholic fraction). The C6H14 fraction was obtained by liquid-liquid extraction of the hydroalcoholic fraction, the same procedure was used to extract the AcOEt fraction. The hydroalcoholic fraction was basified and extracted with CHCl3. The chemical profile of the obtained fractions was analyzed by Thin Layer Chromatography using specific revelators that confirmed the presence of alkaloids as majority compounds in AcOEt and CHCl3 fractions. The fractions were evaluated for allelopathic potential on lettuce cypselas at 0.8 g mL‑1, 0.4 g mL-1 and 0.2 g mL-1. In germination tests the germination parameters analyzed were: germination percentage (% G) and germination speed index (IVG). The results indicated significant changes in the %G, IVG and root growth (CR) of the lettuce seeds and seedlings. The ethanolic extract of leaves of O. puberula showed allelopathic influence on the species L. sativa. Both the AcOEt and CHCl3 fractions reduced the germination rates evaluated, and the latter indicated a dose-response inhibition between the treatments applied

Phytotoxic Activity and Metabolism of Botrytis cinerea and Structure−Activity Relationships of Isocaryolane Derivatives

Research has been conducted on the biotransformation of (8S,9R)-isocaryolan- 9-ol (4a) and (1S,2S,5R,8S)-8 methylene-1,4,4-trimethyltricyclo[6.2.1.02,5]undecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6−9, while the biotransformation of compound 5a yielded compounds 10−13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)- Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3, 4a, and 5a, together with their biotransformation products 6−8, 10, and 14−17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7−13 are described for the first time

Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols

Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus Botrytis cinerea. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of B. cinerea. Further development of both classes of antifungal agent requires exploration of the structure-activity relationships for the antifungal effects on B. cinerea and phytotoxic effects on a model crop. In this paper, we report on the preparation of a series of alkoxy-clovane and -isocaryolane derivatives, some of them described here for the first time (2b, 2d, 2f-2h, and 4c-4e); the evaluation of their antifungal properties against B. cinerea, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of Lactuca sativa (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against B. cinerea for 2d, 2h, 4c and 4d. In general terms, while 2-alkoxyclovan-9-ols (2a-2e) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (2f-2i) and 8-alkoxyisocaryolan-9-ols (4a-4d), where stimulating effects would make them suitable candidates for application to plants.This research was supported by a grant from Ministerio de Ciencia, Innovacion y Universidades (RTI2018-097356-B-C21, MCIU/AEI/FEDER, EU). A.d.A.P.B., G.G.d.S. and J.A.T. thank Coordenacao de Aperfeicoamento de Pessoal de nivel superior (CAPES, Brazil) for research fellowships (CAPES-DGU 197/09)

Estudo do epicarpo e do mesocarpo externo do fruto de Caryocar brasiliense Camb. (pequi): síntese e biotransformação de isocariolanos e derivados para avaliação da atividade biológica

Exportado OPUSMade available in DSpace on 2019-08-13T13:16:25Z (GMT). No. of bitstreams: 1 tese_de_jociani_ascari___29_03_2011.pdf: 51195247 bytes, checksum: 898d7229410b3d6feb69d019e720e893 (MD5) Previous issue date: 29O presente trabalho consta de duas partes. Na Parte 1 é descrito o estudo fitoquímico do mesocarpo e epicarpo externo do pequi (Caryocar brasiliense Camb.), sendo a primeira vez que esta parte da planta é estudada. Foram isoladas seis substâncias puras, sendo elas, galato de etila, -hidroximetilfurfural, ácido gálico, chiquimato de metila, galato de metila e quatro misturas, ß-D-frutopiranose e ß-D-frutofuranose, a- e ß-D-glicose, lupeol e ácido oléico, ß-sitosterol e estigmasterol, contaminados com o ácido oléico. Foram avaliadas as atividades citotóxica, antioxidante, alelopática e antimicrobiana sobre o extrato bruto, frações e substâncias puras. Na Parte 2 desta tese foram feitas transformações químicas e biotransformações (pela utilização do fungo B. cinerea) de isocariolanos. Foram isolados 11 produtos de transformação química, sendo eles, 5a-hidroxicariofila- 4(12),8(13)-dieno, (8R,9R)-8-metoxi-isocariolan-9-ol, isocariolan-9-ona,(1S,2S, 5R,8S)-1,4,4-trimetiltriciclo[6.2.1.02, 5]undecano-8-carbaldeído,(8R,9R)-isocariolano -8,9-diol, isocariolan-9a-ol, (1R,2S,5R,8S)-8-hidroximetil-1,4,4-trimetil triciclo[6.2.1.02,5]undecano, (8R,9R)-8-etoxi-isocariolan-9-ol, (8R,9R)-8-propoxiisocariolan- 9-ol, (8R,9R)-8-butoxi-isocariolan-9-ol, (8R,9R)-8-pentoxi-isocariolan-9- ol e 13 novos produtos de biotransformação, sendo eles, (4R,8R,9R)-8-metoxiisocariolan- 9,15-diol, (3S,8R,9R)-isocariolan-3,8,9-triol, (4R,8R,9R)-isocariolan- 8,9,15-triol, (6R,8S,9R)-isocariolan-6,8,9-triol, (2R,5S,8R,9R)-isocariolan-5,8,9- triol, (6S,8S,9R)-isocariolan-6,8,9-triol, (2S,4R,5R)-4-hidroximetil-1,4-dimetiltriciclo [6.3.1.02,5]dodecan-9-ona, (15R,9R)-isocariolan-9,15-diol, (3S,9R)-isocariolan-9,3- diol, (1S,2S,5R,6S,8S)-1-metil-4,4,8-trimetilentriciclo[6.2.1.02,5]undeca-6ß,12-diol, (1R,2S,5R,6S,8R,9S)-1-metil-4,4,8-trimetilentriciclo [6.2.1.02,5]undeca-6ß,9ß,12- triol,(1R,2S,4R,5R,6S,8S)-1-metil-4,4,8- trimetilentriciclo [6.2.1.02,5]undeca-6ß,15,12 -triol, (1S,2S,5R,8S)-1-metil-4,4,8-trimetilentriciclo[6.2.1.02,5]undeca-12,14,15-triol. Foram realizados testes de avaliação das atividades fungistática e alelopática sobre alguns dos derivados isocariolânicos isolados.This Thesis consists of two parts. In Part 1, the phytochemical study of mesocarpe and external epicarpe of pequi (Caryocar brasiliense Camb.) and their biological activity are described. This study led to the isolation of six pure compounds, ethyl gallate, 5-hydroxymethylfurfural, gallic acid, methyl shikimate, methyl gallate and four mixtures, -D-fructopiranose and -D-fructofuranose, - and -D-glucose, lupeol and oleic acid, -sitosterol and stigmasterol, contaminated with oleic acid. Biological assays for citotoxic, antioxidant, antimicrobial and allelopathicactivities were carried out for the crude extract, fractions and pure substances. In Part 2 of this thesis we describe chemical transformations and biotransformations (by using the fungus B. cinerea) of isocariolane compounds, resulting in 11 new products of chemical transformations, 5-hidroxycaryophylla-4(12),8(13)-diene, (8R,9R)-8-methoxyisocariolan-9-ol, isocaryolan-9-one,(1S,2S,5R,8S)-1,4,4-trimetyltriciclo[6.2.1.02,5] undecane-8-carbaldehyde, (8R,9R)- isocaryolan-8,9-diol, isocaryolan-9-ol, (1R,2S,5R,8S)-8-hydroxymethyl-1,4,4- trimethyltricicle[6.2.1.02,5]undecan, (8R,9R)-8-etoxyisocariolan -9-ol, (8R,9R)-8- propoxyisocariolan-9-ol, (8R,9R)-8-butoxyisocariolan-9-ol, (8R,9R)-8- pentoxyisocariolan-9-ol and 13 new biotransformation products, (4R,8R,9R)-8-metoxyisocariolan-9,15-diol, (3S,8R,9R)-isocaryolan-3,8,9-triol, (4R,8R,9R)- isocaryolan-8,9,15-triol, (6R,8S,9R)-isocaryolan-6,8,9-triol, (2R,5S, 8R,9R)- isocaryolan-5,8,9-triol, (6S,8S,9R)-isocaryolan-6,8,9-triol, (2S,4R,5R)-4- hydroxymethyl-1,4-dimethyltricycle[6.3.1.02,5]dodecan-9-one, (15R,9R)-isocaryolan-9,15-diol, (3S,9R)- isocaryolan-9,3-diol, (1S,2S,5R,6S,8S)-1-methyl- 4,4,8-trimethylentricycle[6.2.1.02,5]undeca-6,12-diol, (1R,2S,5R,6S,8R,9S)-1- methyl-4,4,8-trimethylentricycle[6.2.1.02,5]undeca-6,9,12-triol, (1R,2S,4R,5R,6S, 8S)-1-methyl-4,4,8-trimethylentricycle[6.2.1.02,5]undeca-6,15,12-triol, (1S,2S,5R,8S)-1-methyl-4,4,8-trimethylentricycle[6.2.1.02,5]undeca-12,14,15-triol .Bioassays to evaluate fungistatic and allelophatic activities of someisoariolanes isolated were carried out

A stability-indicating high performance liquid chromatography method to determine apocynin in nanoparticles

In this study, we developed and validated a fast, specific, sensitive, precise and stability-indicating high performance liquid chromatography (HPLC) method to determine the drug apocynin in bovine serum albumin (BSA) nanoparticles. Chromatographic analyses were performed on an RP C18 column and using a photodiode array detector at a wavelength of 276 nm. Mobile phase consisted of a mixture of acetonitrile and 1% acetic acid (60:40, v/v), and it was eluted isocratically at a flow rate of 0.8 mL/min. The retention time of apocynin chromatographic peak was 1.65 min. The method was linear, precise, accurate and specific in the range of 5–100 μg/mL. The intra- and inter-day precisions presented relative standard deviation (RSD) values lower than 2%. The method was robust regarding changes in mobile phase proportion, but not for flow rate. Limits of detection and quantitation were 78 ng/mL and 238 ng/mL, respectively. Apocynin was exposed to acid and alkali hydrolysis, oxidation and visible light. The drug suffered mild degradation under acid and oxidation conditions and great degradation under alkali conditions. Light exposure did not degrade the drug. The method was successfully applied to determine the encapsulation efficiency of apocynin in BSA nanoparticles

Chemical composition, antioxidant and anti-inflammatory activities of the essential oils from male and female specimens of Baccharis punctulata (Asteraceae)

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Phytotoxic Activity and Metabolism of <i>Botrytis cinerea</i> and Structure–Activity Relationships of Isocaryolane Derivatives

Research has been conducted on the biotransformation of (8<i>S</i>,9<i>R</i>)-isocaryolan-9-ol (<b>4a</b>) and (1<i>S</i>,2<i>S</i>,5<i>R</i>,8<i>S</i>)-8-methylene-1,4,4-trimethyltricyclo­[6.2.1.0^2,5]­undecan-12-ol (<b>5a</b>) by the fungal phytopathogen <i>Botrytis cinerea</i>. The biotransformation of compound <b>4a</b> yielded compounds <b>6</b>–<b>9</b>, while the biotransformation of compound <b>5a</b> yielded compounds <b>10</b>–<b>13</b>. The activity of compounds <b>4a</b> and <b>5a</b> against <i>B. cinerea</i> has been evaluated. (8<i>R</i>,9<i>R</i>)-Isocaryolane-8,9-diol (<b>6</b>), a major metabolite of compound <b>4a</b>, shows activity compared to its parent compound <b>4a</b>, which is inactive. The effect of isocaryolanes <b>3</b>, <b>4a</b>, and <b>5a</b>, together with their biotransformation products <b>6</b>–<b>8</b>, <b>10</b>, and <b>14</b>–<b>17</b>, on the germination and radicle and shoot growth of <i>Lactuca sativa</i> (lettuce) has also been determined. Compounds <b>7</b>–<b>13</b> are described for the first time

Selina-1,3,7(11)-trien-8-one and Oxidoselina-1,3,7(11)-trien-8-one from Eugenia uniflora Leaf Essential Oil and Their Cytotoxic Effects on Human Cell Lines

The sesquiterpenes selina-1,3,7(11)-trien-8-one and oxidoselina-1,3,7(11)-trien-8-one were isolated from the essential oil of Eugenia uniflora L. leaves. The structures were elucidated using spectrometric methods (UV, GC&ndash;MS, NMR, and specific optical rotation). The relationship between antioxidant activity, as determined by DPPH assay, and the cytotoxic effect was evaluated using tumor cells, namely lung adenocarcinoma epithelial cells (A549) and human hepatoma carcinoma cells (HepG2), as well as a model of normal human lung fibroblast cells (IMR90). Both compounds did not show prominent free-radical scavenging activity according to DPPH assay, and did not inhibit lipid peroxidation in Wistar rat brain homogenate. The isolated compounds showed pro-oxidative effects and cytotoxicity in relation to the IMR90 cell line