Anita Jocelyne Marsaioli

Polyisoprenylated benzophenones from Clusia floral resins.

From the floral resins of various Clusia species, seven polyisoprenylated benzophenones were isolated. HPLC allowed their quantification in all resins, revealing a distribution of benzophenone derivatives distinct from each other. In some species the staminal oils were collected and oleic, stearic and palmitic acids were the main constituents.

Floral resins of clusia spp.: Chemical composition and biological function

Abstract The floral resins of five species of Clusia belonging to two taxonomic sections of the genus were investigated. These resins are used by pollinating bees for nest construction. The major components of these reins are polyisoprenylated benzophenones, a class of biologically active compounds. We found clusianone and three hitherto unknown compounds, grandone, nemorosone and hydroxy-nemorosone.

The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae).

The chemical composition of floral volatiles of sixteen species of Clusia (Guttiferae) belonging to four different taxonomic sections of the genus was investigated. The volatiles were extracted from fresh petals by microhydrodistillation and analysed by GC/MS. The composition of the volatiles was in part, but not always, related to the taxonomic position of the species, and to a minor extent to the type of pollinator observed on the flowers as revealed by clustering analysis. The composition of the volatile components of female and male flowers belonging to the same species (C. grandiflora, C. lanceolata, C. paralicola, C. parviflora and C. spiritu-sanctensis) was found to be almost identical. Field bioassays showed the petal extracts to be attractive to pollinating bees.

Essential Oils of Seven Brazilian Baccharis Species

ABSTRACT A description of the habitat and areas where seven Baccharis species (B. caprariaefolia female and male, B. dracunculifolia female and male, B. erioclada female and male, B. myriocephala, B. platipoda, B. tridentata, B. vincaefolia) are grown, is presented. The essential oils of the aerial parts were obtained by hydrodistillation and examined by GC and GC/MS. The major constituents were: B. caprariaefolia (female/male): β -caryophyllene (17.09%/15.73%); B. dracunculifolia (female/male): β-selinene (9.90%/11.00%); (E)-nerolidol (20.80%/12.02%); B. erioclada (female/male): β-pinene (21.44%/1.16%), limonene (15.16%/2.68%), β-caryophyllene (4.21%/10.70%), spathulenol (6.61%/12.57%); B. myriocephala: δ-cadinene (9.44%), (E)-nerolidol (9.01%/12.57%); B. myriocephala: δ-cadinene (9.44%), (E)-nerolidol (9.01%) and spathulenol (9.44%); B. platipoda: spathulenol (8.76%); B. tridentata: spathulenol (21.20%) and B. vincaefolia: δ-caryophyllene (8.66%), δ-cadinene (8.88%). An oil composition variation between...

Antimycobacterial and cytotoxicity activity of synthetic and natural compounds

Antimycobacterial and cytotoxicity activity of synthetic and natural compounds. Secondary metabolites from Curvularia eragrostidis and Drechslera dematioidea, Clusia sp. floral resin, alkaloids from Pilocarpus alatus, salicylideneanilines, piperidine amides, the amine 1-cinnamylpiperazine and chiral pyridinium salts were assayed on Mycobacterium tuberculosis H37Rv. N-(salicylidene)-2-hydroxyaniline was the most effective compound with a minimal inhibitory concentration (MIC) of 8 µmol/L. Dihydrocurvularin was moderately effective with a MIC of 40 µmol/L. Clusia sp. floral resin and a gallocatechin-epigallocatechin mixture showed MIC of 0.02 g/L and 38 µmol/L, respectively. The cytotoxicity was evaluated for N-(salicylidene)-2-hydroxyaniline, curvularin, dihydrocurvularin and Clusia sp. floral resin, and the selectivity indexes were > 125, 0.47, 0.75 and 5, respectively.

Acidic biomarkers from Albacora oils, Campos Basin, Brazil

Abstract Acidic biomarkers of 8 different oil samples from Albacora oil field, Campos Basin, Brazil, were analyzed in order to obtain additional information about biodegradation and thermal evolution. For this purpose, we selected oils (lacustrine saline origin) showing different biodegradation levels and at different distances from the fault that acted as migration pathway in the area. Previous analyses using hydrocarbon biomarkers suggested a mix of oil charges, characterizing two distinct oil cycles interrupted by meteoric water circulation in these reservoirs. Analyses of the naphthenic acid biomarkers revealed a parallelism between the hydrocarbon and the acidic biomarkers. Notwithstanding, there is evidence that the carboxylic acid biomarkers, more resistent to biodegradation, can provide information on past reservoir history when most important neutral biomarkers have been biodegraded. The limitations to the use of these biomarkers are their “de novo” synthesis in the biodegradation process and the complexity of the sample manipulation prior to the analysis.

Two polyisoprenylated benzophenones from the floral resins of three Clusia species

Abstract From the floral resins of Clusia nemorosa male, C. nemorosa hermaphrodite, Clusia rosea female, Clusia grandiflora male, C. grandiflora female, Clusia insignis male (all section Chlamydoclusia ). C. renggerioides male (with pistillodium), C. renggerioides male (without pistillodium), C. renggerioides female (all section Cordylandra ) belonging to the family Clusiaceae, we have isolated two novel polyisoprenylated benzophenones, nemorosone II and 6- epi -nemorosone, and a xanthone. The latter is the first member of this class of compounds ever isolated from the genus Clusia . HPLC allowed the quantification of these and other methylated benzophenones in the methylated resins revealing that indeed these are the major constituents of Clusia floral resins. Oleic, stearic and some unusual long chain esters and acids are the main constituents of the stamen oils.

Clerodane-type diterpenes from the seed pods of Hymenaea courbaril var. stilbocarpa

Three known and two new diterpenes were isolated from the ethyl acetate extract of Hymenaea courbaril var. stilbocarpa seed pods. One of the compounds was elucidated as (5R*,8S*,9S*,10R*)-cleroda-3,13E-dien-15-oic acid and the other was elucidated, after treatment with diazomethane, as methyl (5S*,8S*,9S*,10R*)-cleroda-3,13E-dien-15-oate. The known diterpenes were identified as (-)-ozic acid, (-)-isoozic acid and (-)-kovalenic acid which were characterized as their methyl ester derivatives.

A simple solid injection device for the analyses of Bulbophyllum (Orchidaceae) volatiles

Abstract The volatile components of three orchid species ( Bulbophyllum weddellii , B. ipanemense and B. involutum ) were detected using GC/MS. Due to the minute dimension and amount of flowers, special traps and extraction methods were applied and the analyses were finally successful using a special solid sample injector which was constructed in our own laboratory. The chemical composition comparison revealed the high similarity between the volatiles present in B. weddellii and B. involutum , which is coherent with the pollinator sharing. On the other hand, the volatiles of B. ipanemense , a species pollinated by other pollinator species, are different from the two previous species.

Naphthenic acids from crude oils of Campos Basin

Abstract Previous work based on chemical evidence and information from the hydrocarbon fractions of Marlim and Albacora, giant oil fields of Campos Basin (offshore Brazil), in connection with other geochemical parameters, led to conclusions on the oil accumulation, migration and biodegradation. The acidic components, as carboxylic acids of Marlim and Albacora were never investigated before and this work revealed a significant correlation between both fractions (neutral and acidic) therefore opening new horizons for the use of these naphthenic acids as additional geochemical parameters to enrich and enlarge previous geological conclusions on Marlim and Albacora. A naphthenic acid of 16 carbon atoms was detected and based on its mass spectrum and that of its corresponding deuterated hydrocarbon an 8-carboxy-9-ethyl-drimane structure was proposed.