Flavonoids are the phenolic compounds that are predominant in the Fabaceae family, and isoflavonoids are especially recognized for their contribution to the natural resistance of wood from species of this family. Herein, we investigated the phenolic compounds from extracts of wood residues from the Fabaceae species Dipteryx polyphylla Huber and Acacia mangium Willd. A phytochemical study of D. polyphylla led to isolation and identification of isoflavans such as 3’,7-dihydroxy-4'-methoxy-isoflavan (1), 2’,8-dihydroxy-4’,7-dimethoxy-isoflavan (2), 2’,7-dihydroxy-4’-methoxyisoflavan (3) and 3’,8-dihydroxy-4’,7-dimethoxy isoflavan (4). Compounds 1 and 4 are new findings. A. mangium gave monocyclic phenolics, such as ferulic acid (6), methylparaben (7) and 4-hydroxybenzaldehyde (8); flavonol melatoxetin (9) as well as fatty acid esters of spinasterol (5). The phenolic compounds that were identified contribute to the knowledge regarding the natural resistance of its woods, thus aggregating value for solid residues and plantation species recommended for reforestation
The Adolpho Ducke Forest Reserve is a fragment of the Amazon Rainforest that has the highest density of collections deposited in the INPA herbarium, and this characterized, vascular flora has been an important basis for chemical studies. This paper describes the chemical composition of the volatiles of aerial parts of the four species of Protium that occurr in the Ducke Reserve. The essential oils obtained by hydrodistillation were analyzed using GC-FID and GC-MS. P. altsonii showed high percentages of the monoterpenes α-pinene (22.05%) and limonene (17.76%) in the leaves, and linear long-chain fatty alcohols, such as n-tetradecanol (19.93%) and hexadecanol (32.56%), in the branches. The essential oil from leaves of P. laxiflorum provided sesquiterpenes α-copaene (18.98%), epi-α-cadinol (9.17%) and β-caryophyllene (9.04%) as the main compounds. In P. pallidum, the sesquiterpenes caryophyllene oxide (29.72%), α-cadinol (28.82%) and epi-α-cadinol (13.96%) were predominant in the leaves, and α-cadinol (25.50%), α-eudesmol (22.29%) and caryophyllene oxide (12.81%) predominated in the branches. β-Caryophyllene (30.59%) and caryophyllene oxide (20.63%) were the main compounds in the leaves of P. paniculatum var. riedelianum. The results presented herein contribute to the knowledge of the aromatic flora of the Ducke Reserve.
Handroanthus serratifolius (Vahl) S. Grose [Tabebuia serratifolia (Vahl) G. Nicholson] popularly known in Brazil "ipê-amarelo" is a woody species with potential of sustainable use belonging to a genus known for being as a promising naphthoquinones source which has aroused interest in search for new biological activities. In this paper, the methanolic extract fractionation from H. serratifolius sawdust using different chromatogramphic techniques yielded naphthoquinones dehydro-α-lapachone, dehydro-iso-α-lapachone and αlapachone, along with lignans paulownin and cycloolivil. The three naphthoquinones presented antiplasmodial activity against Plasmodium falciparum where the dehydro-iso-α-lapachone was more active (IC50 of 7.53 μg/mL). This same compound also exhibited significant antifungal activity against Cryptococcus neoformans.
Protium is the most frequent genus of Burseraceae in the Adolpho Ducke Forest Reserve (Manaus, Amazonas), which is where its species were previously identified and mapped and this has favored various studies of this central Amazon forest. A number of P. divaricatum Engl., P. opacum Swart and P. strumosum Daly trees were selected with the objective of providing information about their chemical and biological aspects. Resin exudation was stimulated with the use of ethephon and the essential oils from the aerial parts and the resin were evaluated using GC. The occurrence of galls was also registered. The hydrocarbon sesquiterpene ß-caryophyllene was detected in high percentages in the essential oils of leaves and twigs of P. divaricatum (52.75% and 14.74%) and P. opacum (39.55% and 17.86%), respectively. The predominant oxygenated sesquiterpenes were spathulenol in the leaves (19.52%) and twigs (31.29%) of P. divaricatum, in addition to khusimone (32.36%) in the twigs of P. opacum. Monoterpenes were identified in the essential oils of the P. strumosum resin, with p-cymene (58.97%) predominating in the naturally exuded resin, limonene (61.45%) and p-cimen-8-ol (53.92%) in the resin of the first and second extraction with ethephon, respectively. On the trees, galls were identified that will help in the identification of the three species.
The odoriferous resins produced by the trees of Protium spp (Burseraceae) are known in the Amazonian region as “breus” where they have been used to caulk canoes, as a mosquito repellent, and also have potential use in perfumery. Most species in this region have had the essential oils of their resins characterized, thus, the objective of this study was to evaluate for the first time the volatile constituents from the resin of Protium gallosum Daly, P. paniculatum Engl., P. pillosum (Cuatrec.) Daly and P. paniculatum var. riedelianum (Engl.) Daly. The samples from the individuals that had been previously identified were collected at the Adolpho Ducke Forest Reserve and subjected to hydrodistillation in a Clevenger apparatus, and the essential oils obtained were analyzed using GC-FID and GC-MS. The essential oil of P. gallosum showed high percentages of oxygenated monoterpenes (43.61%) with a predominance of terpin-4-ol (25.15%), and P. paniculatum consisted exclusively of monoterpenes that were predominantly p-cymene (43.52%; hydrocarbon monoterpene) and the 1,8-cineole (16.83%; oxygenated monoterpene). Most of the monoterpenes identified from P. pillosum and P. paniculatum var. riedelianum were hydrocarbons with a predominance of α-pinene, with 37.74% and 50.93%, respectively. 1,8-Cineole (21.89%) was also identified in the essential oil of P. pillosum. The results obtained this study add chemical knowledge to Burseraceae resins from a biological reserve of the Central Amazon.
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