Compostos voláteis em méis florais

A review about origin, composition and importance of volatile compounds in floral honeys is presented. Hydrocarbons, aromatic components, acids, diacids, terpenoids, ketones, aldehydes, esters and alcohols have been found in honey aroma of different botanical origin. Cis-rose oxide has been proposed as an indicator for Tilia cordata honey. Citrus honeys are known to contain methyl anthranilate, a compound which other honeys virtually lack. Linalool, phenylethylalcohol, phenylacetaldehyde, p-anisaldehyde and benzaldehyde are important contributors for the aroma of different unifloral honeys. Both isovaleric acid, gama-decalactone and benzoic acid appears to be important odourants for Anarcadium occidentale and Croton sp. honeys from Brazil. The furfurylmercaptan, benzyl alcohol, delta-octalactone, eugenol, phenylethylalcohol and guaiacol appear to be only relevant compounds for Anarcadium occidentale. The vanillin was considered an important odourant only for Croton sp..

Terpenos com atividade inseticida: uma alternativa para o controle químico de insetos

Many substances from different sources have been used by men for decades to control insects. After the 2nd World War, the use of inorganic compounds have declined drastically and natural products, as well as synthetic derivatives, have been widely used instead. The search for natural alternatives have improved the development of bench top bioassays and an array of synthetic approaches for known and novel natural products that shows relevant activities as feeding supressors and deterrents. The studies concerning mode of action and environmental impact of these substances, that may be biodegradable and selective for undesired insects, had led to the evaluation and discovery of a number of molecules, mostly terpenoids and alkaloids, that are well reported as candidates for inseticidal compounds that could be an effective alternative for insects control with a lower impact on human health, household animals and the environment.

Produtos naturais para o controle da transmissão da dengue: atividade larvicida de Myroxylon balsamum (óleo vermelho) e de terpenóides e fenilpropanóides

The bioassay-guided fractionation of the hexane extract obtained from the medicinal plant Myroxylon balsamum (red oil) was conducted in preparative thin layer chromatography on silica gel. The obtained fractions and some terpenoids and phenylpropanoids were assayed as larvicidal on third instar Aedes aegypti larvae, NPPN colony. The results indicate that the sesquiterpene nerolidol was the active constituent in the extract and that the sesquiterpenes were more active than the monoterpenes and phenylpropanoids utilized in this study. Lipophilicity seems to be an important property for the activity since the compounds with hydroxyl, carbonyl and methoxyl groups were less active. The results confirm also that essential oils can be a good tool for the control of dengue.

Constituintes químicos de Ottonia corcovadensis Miq. da floresta Amazônica: atribuição dos deslocamentos químicos dos átomos de hidrogênio e carbono

In an ethanolic extract of leaves of Ottonia corcovadensis (Piperaceae) were identified sixteen terpenoids of essential oil and the three flavonoids 3',4',5,5',7-pentamethoxyflavone (1), 3',4',5,7-tetramethoxyflavone (2) and 5-hydroxy-3',4',5',7-tetramethoxyflavone (3) and cafeic acid (4). Two amides (5 and 6) were isolated from an ethanolic extract of the roots. The structures were established by spectral analysis, meanly NMR (1D and 2D) and mass spectra. Extensive NMR analysis was also used to complete ¹H and 13C chemical shift assignments of the flavonoids and amides. The components of the essential oil were identified by computer library search, retention indices and visual interpretation of mass spectra.

Constituintes químicos dos frutos de Copaifera langsdorffii Desf.

Phytochemical investigation of the hexane extract of fruit shells of Copaifera langsdorffii Desf. (Caesalpinioideae) afforded ent-kaur-16-en-19-oic acid, polyalthic acid, nivenolide and the mixture of caryophyllene oxide and ent-kaur-16-en-19-oic acid. The chloroform extract of unripe seeds led to the isolation of coumarin and the GC/MS analysis of the extract allowed the identification of 81.8% of the fatty acid composition after hydrolysis followed by methylation. The main fatty acid identified was oleic acid (33.1%). The isolation of all secondary metabolites was accomplished by modern chromatographic methods and the structure determination was accomplished by spectrometric methods (IR, MS, NMR ¹H and 13C).

Alcalóides e outros metabólitos do caule e frutos de Zanthoxylum tingoassuiba A. St. Hil

Phytochemical investigation of this species, popularly known as tinguaciba and used in traditional medicine to various diseases, resulted in the isolation of 15 substances: 2 alkaloids - norchelerythrine and arnottianamide; 1 lignan - sesamin; 4 terpenoids - citronellyl acetate, lupeol, α-bisabolol and spatulenol; 5 coumarins described for the first time - xanthotoxin, isopimpinelin, O-prenylumbelliferone, imperatorin and aurapten, 1 protoalkaloid - methyl N-methylanthranilate and 2 steroids - stigmasterol and β-sitosterol. The structures of the compounds were elucidated by spectroscopic analyses and compared with literature data.

Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae)

The essential oil of the leaves of Lippia alba chemotype linalool-1,8-cineol was extracted by hidrodistillation at different seasons and analyzed by GC/MS. Qualitative and quantitative variations in regard to the period of harvesting have been performed and the results were correlated with meteorological data. The essential oil yield varied from 0.33 to 0.67%. The chemical diversity of the constituents increased throughout the year, being 1,8-cineol and linalool the major components. Possible biosynthetic routes of mono and sesquiterpenoids present in the essential oil are discussed.

Composição molecular e origem paleobotânica de âmbares da bacia do Araripe, Formação Santana

The terpenoid composition of seven amber samples from Araripe Basin (Santana Formation, Crato Member) has been analyzed by gas chromatography-mass spectrometry to determine their botanical origin. The diterpenoids, which have been identified in the fossil resin extracts are derived primarily from the abietane class, e.g., dehydroabietane, 4-epidehydroabietol, 16,17,18-trisnorabieta-8,11,13-triene, 7-oxo-16,17,19-trisnorabieta-8,11,13-trieno, dehydroabietic acid, ferruginol, hinokiol and hinokione. Their composition is certainly typical for conifers, and angiosperms can be excluded as the botanical source, as no triterpene was identified. The terpenoid characteristics strongly support a relationship to the Araucariaceae or Podocarpaceae families. In addition, the fossil record of the embedding sediments (pollen and fossil leaves) also supports the proposal of these paleobotanical origins for the ambers.

Interespecific variation in the composition of volatile oils from the leaves of Swietenia macrophylla King (Meliaceae)

The volatile oils from leaves of five Brazilian specimens of Swietenia macrophylla King (Meliaceae) collected in three different Amazon Rainforest Conservation Areas in the States of Mato Grosso, Pará, and Rondônia were extracted and analyzed by GC and GC/MS. The oils showed to be composed by terpenoids, majority hydrocarbon sesquiterpenes, being germacrene D (20.5-46.8%) and bicyclogermacrene (8.3-11.1%) the main components. Besides these derivatives, only α-cubebene, β-caryophyllene, β-gurjunene and γ-cadinene were detected in all of the analyzed samples. This analysis indicated a great diversity of constituents in the oils obtained from specimens collected in these regions, which could be associated to the different susceptibility in the attack of H. grandella in S. macrophylla cultures.

The contributions of Henri Victor Regnault in the context of organic chemistry of the first half of the nineteenth century

A very little known aspect of the scientific career of Regnault is his contribution to the emerging organic chemistry in the first half of the nineteenth century. The purpose of this article is not only to describe two of his most important researches in this field, as were the discovery of two series of halogenated derivates of certain organic compounds and the precise identification of some of the then recently discovered alkaloids, but also the main features that identified his research method. With the involvement in these subjects, Regnault unintentionally positioned himself in the midst of some of the polemics about the classification of organic compounds that characterized this age of science.

Implicações químicas na sistemática e filogenia de Bignoniaceae

Our solemn homage to the great Master Otto R. Gottlieb who knew how to teach the mystery of evolutionary relationships between chemistry and its natural sources. The micromolecular chemical study of the family Bignoniaceae shows a profile predominantly characterized by the occurrence of metabolites derived from acetic acid biosynthetic pathways such as terpenoids, quinones, flavonoids and special aromatic derivatives. Analysis of different chemosystematic parameters for the metabolite data collected, provided valuable information for the systematic characterization of the Bignoniaceae family within the Angiosperm derived taxa.

Chemotaxonomy of three genera of the annonaceae family using self-organizing maps and 13C NMR data of diterpenes

The Annonaceae family is distributed throughout Neotropical regions of the world. In Brazil, it covers nearly all natural formations particularly Annona, Xylopia and Polyalthia and is characterized chemically by the production of sources of terpenoids (mainly diterpenes), alkaloids, steroids, polyphenols and, flavonoids. Studies from 13C NMR data of diterpenes related with their botanical occurrence were used to generate self-organizing maps (SOM). Results corroborate those in the literature obtained from morphological and molecular data for three genera and the model can be used to project other diterpenes. Therefore, the model produced can predict which genera are likely to contain a compound.

Flavonoides e terpenoides de Croton muscicarpa (Euphorbiaceae)

A new sesquiterpene and twelve known compounds comprising eight flavonoids and four terpenoids, were isolated from the leaves, stems, roots and exudate of Croton muscicarpa Müll. Arg.. Their structures were identified as the terpenoids 6α-methoxy-cyperene, dammaradienol, squalene, acetyl aleuritolic acid and spathulenol, and as the flavonoids retusin, 3,7,4'-trimethoxy kaempferol, ombuine, pachipodol, kaempferol, casticin, 5-hydroxy-3,6,7,4'-tetramethoxyflavone and artemetin. All isolated compounds were characterized based on IR, MS, ¹H and 13C NMR, including 2D analyses (COSY, HSQC, HMBC, NOESY) and comparison with data from the literature.

Constituintes químicos de Solanum buddleifolium Sendtn

The chemical investigation of the stem EtOH extract of S. buddleifolium resulted in the isolation of terpenoids, amides, lignans and a steroidal alkaloid. Based on HRMS, IR and ¹H and 13C NMR data analysis, the structures of the isolated compounds were identified as: 13-hydroxysolavetivone, betulinic acid, N-trans-caffeoyltyramine, N-trans-feruloyldopamine, N-trans-p-cumaroyltyramine, N-trans-feruloyltyramine, N-trans-feruloyl3'-O-methoxydopamine, alangilignoside C, isolariciresinol, polistachiol, (+)-(8R,7'S,8'S)-3α-O-(β-D-glucopiranosyl)-lioniresinol, (-)-(8S,7'R,8'R)-3α-O-(β-D-glucopiranosyl)-lioniresinol and solamargine. The occurrence of terpenoids and amides is common in Solanum, unlike lignans which are rare. The isolated lignans described in this work are reported for the first time in the genus Solanum.

Biomolecules produced in liquid-state fermentation by a marine-derived fungus, Penicillium roqueforti

Screening of biomass of a new marine-derived strain of Penicillium roqueforti, as produced by liquid-state fermentation, led to the identification of several volatile organic compounds active in the fatty acid pathway as well as fragments produced by their catabolism, terpenoids, and metabolites from the shikimic acid pathway. In addition, five non-volatile organic compounds, triolein, ergosterol peroxide, 9(11)-dehydroergosterol peroxide, 4-hydroxybenzaldehyde, and d-mannitol, were isolated and identified by spectroscopy. The results showed that this fungal strain did not produce any mycotoxin in the culture conditions applied, and thus is useful for industrial applications, where high value-added biomolecules are generated.