A total of 36 ethanol extracts from different anatomical parts of 27 plant species (18 families), native to the Pantanal and Cerrado biomes in Midwest Brazil, was assessed for their effect against Aedes aegypti larvae, the vector of dengue, hemorrhagic dengue, Zika and chikungunya fevers. Only the extract obtained from seeds of Guarea kunthiana (Meliaceae) proved active (LC50 = 169.93 μg/mL). A bioassay-guided investigation of this extract led to the isolation and identification of melianodiol, a protolimonoid, as the active constituent (LC50 = 14.44 mg/mL). Meliantriol, which was also obtained from the bioactive fraction, was nevertheless devoid of any larval toxicity, even at the highest concentration tested (LC50 > 100.0 mg/mL). These results indicate that the larvicidal activity of melianodiol stems from the presence of the carbonyl moiety at C-3 in the 21,23-epoxy-21,24,25-trihydroxy-tirucall-7-ene-type skeleton. The structures of both protolimonoids were established on the basis of spectral methods (1H and 13C NMR and MS). This is the first report on the toxicity of melianodiol against Ae. aegypti larvae. Based on the results, melianodiol can be regarded as a potential candidate for use as an ecologically sound biocontrol agent for reducing the larval population of this vector.

In addition to β-sitosterol, stigmasterol, phaeophitin A, luteolin, kaempferol, quercetin, (+)-catechin, quercetin-3-O-α-L-rhamnopyranoside, rutin, and p-hydroxy-benzoic acid, six known sesquiterpenes, namely (rel)-2β,6β-epoxy-5β-hydroxy-isodaucane, oplopanone, 1β,6α-dihydroxy-4(15)-eudesmene, caryophyllene oxide, α-cadinol, and spathulenol, were isolated from the leaves of Pterodon pubescens (Leguminosae) growing in the Cerrado of Mato Grosso do Sul, Brazil. The (rel)-2β,6β-epoxy-5β-hydroxy-isodaucane corresponds to the correct structure of homalomenol D. The sesquiterpene oplopanone, which bears a modified cadinane skeleton, is being reported for the first time in this genus. The structures of the compounds were determined on the basis of spectral data (MS, IR, and NMR-1D and 2D) and subsequent comparison with data reported in the literature.

From the leaves of a specimen of Trichilia silvatica Meliaceae, eight known compounds were isolated, namely, two pregnanes, 2α,3β,4β-trihydroxypregnan-16-one (1) and 2β,3β,4β-trihydroxypregnan-16-one (2), three diterpenes, cneorubine X (3), kolavelool (4) and kolavenol (5), in addition to γ-tocopherol, 3-O-β-D-glucopyranosyl-β-sitosterol and 3-O-β-D-glucopyranosyl-stigmasterol. This is the first reported occurrence of pregnane 1, diterpenes 3-5 and µ-tocopherol in the genus Trichilia. The structures of the isolated compounds were determined on the basis of their spectral data.

Macrosiphonia petraea (A. St.-Hil.) Kuntze is a plant popularly known as "velame". Its root infusion is used in the folk medicine of Mato Grosso do Sul, Brazil, for the treatment of inflammatory diseases. Phytochemical investigation of the roots of this species led to the identification of 17 compounds belonging to four different classes: two pregnanes, 12β-hydroxypregna-4,6,16-triene-3,20-dione, neridienone A, and 12β-hydroxypregna-4,6-diene-3,20-dione, cybisterol, one hydroxylated fatty acid, 5-hydroxy-octadeca-6(E)-8(Z)dienoic acid, two lignoids, pinoresinol and 8a-hydroxypinoresinol, ten pentacyclic triterpenoids, and two steroids.

Six new eremophilane sesquiterpenes, (rel)-4β,5β,7β-eremophil-9-en-12-oic acid (1), (rel)-4β,5β,7β-eremophil-1(10)-en-12-oic acid (2), (rel)-4β,5β,7β-eremophil-1(10)-en-2-oxo-12-oic acid (3), (rel)-4β,5β,7β-eremophil-9-en-12,8α-olide (4), (rel)-4β,5β,7β-eremophil-9-en-12,8β-olide (5) and (rel)-4β,5β,7β-eremophil-9α,10α-epoxy-12-oic acid (6), were isolated from the leaves of a specimen of Ocotea lancifolia (Lauraceae). Two other known sesquiterpenes, 4β,5β,7β-eremophil-11-en- 10α-ol (7) reported for the first time in the genus Ocotea, and the aromadendrene sesquiterpene, spathulenol (8), were also isolated. Their structures were determined on the basis of spectral data (MS, IR, UV and NMR-1D and 2D) and subsequent comparisons with the literature.

Ethanol extracts from six selected species from the Cerrado of the Central-Western region of Brazil, which are used in traditional medicine for the treatment of infectious diseases and other medical conditions, namely Erythroxylum suberosum St. Hil. (Erythroxylaceae), Hyptis crenata Pohl. ex Benth. (Lamiaceae), Roupala brasiliensis Klotz. (Proteaceae), Simarouba versicolor St. Hil. (Simaroubaceae), Guazuma ulmifolia Lam. (Sterculiaceae) and Protium heptaphyllum (Aubl.) March. (Burseraceae), as well as fractions resulting from partition of these crude extracts, were screened in vitro for their antifungal and antibacterial properties. The antimicrobial activities were assessed by the broth microdilution assay against six control fungal strains, Candida albicans, C. glabrata, C. krusei, C. parapsilosis, C. tropicalis and Cryptococcus neoformans, and five control Gram-positive and negative bacterial strains, Escherichia coli, Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosa and Staphylococcus aureus. Toxicity of the extracts and fractions against Artemia salina was also evaluated in this work. All plants investigated showed antimicrobial properties against at least one microorganism and two species were also significantly toxic to brine shrimp larvae. The results tend to support the traditional use of these plants for the treatment of respiratory and gastrointestinal disorders and/or skin diseases, opening the possibility of finding new antimicrobial agents from these natural sources.Among the species investigated, Hyptis crenata, Erythroxylum suberosum and Roupala brasiliensis were considered the most promising candidates for developing of future bioactivity-guided phytochemical investigations.

Two new sesquiterpenes 6α-ethoxyeudesm-4(15)-en-1β-ol (1) and (7R*)-5-epi-opposit-4(15)-ene-1β,7-diol (7) were isolated from the seeds of a specimen of Guarea guidonia (Meliaceae). Five other known sesquiterpenes, eudesm-4(15)-ene-1β,6α-diol (2), 5-epi-eudesm-4(15)-ene-1β,6β-diol (3), eudesm-4(15)-ene-1β,5α-diol (4), eudesm-4(15),7-dien-1β-ol (5) and (7R*)-opposit-4(15)-ene-1β,7-diol (6), were also isolated in this work. Their structures were determined on the basis of spectral data (MS, IR, and NMR-1D and 2D) and subsequent comparisons with the literature. The substances 3, 4 and 6 are reported for the first time in Meliaceae and 5 for the first time in the genus Guarea.

A new salicylic acid derivative, pentacosanyl salicylate, was isolated from the leaves of the plant toxic to cattle, Riedeliella graciliflora, in addition to a digalactosyldiacylglycerol (DGDG), 1,2-di-O-α-linolenoyl-3-O-α-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-glycerol, kaempferol-3-O-β-D-glucopyranoside, kaempferol-3-O-α-L-rhamnopyranoside, quercetin-3-O-α-L-rhamnopyranoside, rutin, (+)-catechin and the dimer (+)-catechin-(4β-8)-catechin, glutinol, squalene, β-sitosterol, stigmasterol, phytol, β-carotene, α-tocopherol and ficaprenol-12. Their structures were determined using spectral techniques (MS, IR, and NMR-1D and 2D) and based on literature data.

Os efeitos de resíduos de plantas cultivadas e seus extratos sobre Sclerotinia sclerotiorum são poucos conhecidos. Três experimentos foram conduzidos, com resíduos de plantas cultivadas e seus extratos etanólicos e suas partições. Resíduos e extratos de culturas de aveia, ervilhaca, feijão, milheto, milho e trigo foram avaliados em condições controladas. Escleródios cobertos com resíduos de aveia, ervilhaca, feijão e milheto não germinaram carpogenicamente. Extratos etanólicos de resíduos de aveia e ervilhaca mostraram-se eficientes na inibição da germinação carpogênica, enquanto que do milheto e do trigo não diferiram da testemunha. Todas as partições de extratos etanólicos avaliadas reduziram a germinação carpogênica. Resíduos vegetais afetaram negativamente o número de apotécios emitidos por escleródio.

The effects of crop residues and their extracts on Sclerotinia sclerotiorum are not well documented. Three experiments were conducted with crop residues and their ethanol and partition extracts. Oat, vetch, bean, pearl millet, corn and wheat were assessed under controlled conditions. Sclerotia covered with oat, vetch, bean and pearl millet residues did not germinate carpogenically. Ethanol extracts of oat and vetch residues were efficient in inhibiting carpogenic germination whereas pearl millet and wheat did not differ from control. All partitioned ethanol extracts inhibited germination. Crop residues negatively affected the number of apothecia per sclerotium.

Dois novos seco- e di-seco-pregnanos, 2α,3β-diidrσxi-2β,19-hemicetal-16,17-seco-pregn-17-en-16-oato de metila (1) e ácido 2,3:16,17-di-seco-pregn-17-en-3-óico-16-oato de metila-19-hidróxi-2-carboxílico-2,19-lactona (2), foram isolados da casca do caule de Guarea guidonia. Suas estruturas foram determinadas com base em dados espectrais, particularmente RMN uni- e bidimensionais e massas. Os esqueletos pregnânicos incomuns seco- e di-seco destes compostos estão sendo relatados pela primeira vez em Meliaceae, assim como a ocorrência de pregnanos no gênero Guarea.

Two new seco- and di-seco-pregnanes, 2α,3β-dihydroxy-16,17-seco-pregn-17-ene-16-oic acid methyl ester 2β,19-hemiketal (1) and 2,3:16,17-di-seco-pregn-17-ene-3-oic acid-16-oic acid methyl ester-19-hydroxy-2-carboxylic acid-2,19-lactone (2), have been obtained from the trunk bark of Guarea guidonia. Their structures have been established by a combination of 1D- and 2D-NMR spectroscopic techniques and MS data. The unique seco- and di-seco-pregnane carbocyclic skeletal types as found in compounds 1 and 2 are being reported in the Meliaceae for the first time as well as the occurrence of pregnanes in the genus Guarea.

A new triterpene, 3beta,6beta,21beta-trihydroxyolean-12-ene and a new iridoid, 8alpha-methyl-8beta-hydroxy-6beta-(3',4'-dimethoxy)benzoyloxy-1 alpha,3alpha-dimethoxy-octahydro-cyclopenta[c]pyran were isolated from the trunk bark of a specimen of Tabebuia heptaphylla (Bignoniaceae) collected in the "Pantanal" of Mato Grosso do Sul, Brazil. Twelve known compounds were also obtained in this work, comprising four iridoids, 6-O-p-hydroxybenzoylajugol, 6-O-p-methoxybenzoylajugol, 6-O-3",4"-dimethoxybenzoylajugol, 8alpha-methyl-8beta-hydroxy-6beta-(4'-hydroxy)benzoyloxy-1alpha,3 alpha-dimethoxy-octahydro-cyclopenta[c]pyran, a cyclopentene dialdehyde, 2-formyl-5-(3',4'-dimethoxybenzoyloxy)-3-methyl-2-cyclopentene-1-acetaldehyde, a phenylethanoid glycoside, verbascoside and three benzoic acid derivatives, p-hydroxybenzoic, p-methoxybenzoic and 3,4-dimethoxybenzoic acids, in addition to squalene, sitostenone and sitosterol. The antioxidant properties of the isolated compounds were also evaluated in this work.