Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa

Six bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Aiolochroia crassa: 3-bromo-5-hydroxy-O-methyltyrosine (1), 3-bromo-N,N,N-trimethyltyrosinium (2), 3-bromo-N,N,N,O-tetramethyltyrosinium (3), 3,5-dibromo-N,N,N-trimethyltyrosinium (4), 3,5-dibromo-N,N,N,O-tetramethyltyrosinium (5), and aeroplysinin-1 (6). Structural determination was performed using NMR, MS and comparison with literature data. All isolated compounds were screened for their in vitro activity against Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compound 4 showed selective antiparasitic activity against Leishmania and Plasmodium parasites. This is the first report of compounds 1, 4 and 5 in the sponge A. crassa and the first biological activity reports for compounds 2-4. This work shows that bromotyrosines are potential antiparasitic agents.

Neolignans from Licaria chrysophylla and Licaria aurea with DNA topoisomerase II-α inhibitory activity

Seven natural neolignans isolated from Licaria chrysophylla and Licaria aurea along with five semisynthetic derivatives were tested for their inhibitory action on DNA-topoisomerase by relaxation assays on pBR322 plasmid DNA. All compounds tested showed strong inhibition at a concentration of 100 µM, while none showed activity between 5 and 70 µM. These results indicate that no obvious correlation can be derived between the structure of these compounds and their inhibitory effect on the DNA relaxation activity of topoisomerase II. This is the first report on DNA topoisomerase II inhibitors from Licaria chrysophylla and Licaria aurea leading to the identification of lignoids as topoisomerase II-α inhibitors.

Volatile and non-volatile compounds and antimicrobial activity of Mansoa difficilis (Cham.) Bureau & K. Schum: (Bignoniaceae)

Essential oil from the leaves of Mansoa difficilis was analyzed by GC/MS. Oct-1-en-3-ol (49.65%) was the major compound, but diallyl di- and trisulfide were also present (0.85 and 0.37%, respectively), justifying the garlic-like odor of the crushed leaves. The hexane and methanol extracts of the leaves and stems afforded as main constituents a mixture of linear hydrocarbons, spinasterol, stigmasterol, ursolic and oleanolic acids, two apigenin derivatives and verbascoside. The hexane and methanol extracts of leaves were tested for antimicrobial activity against ten microorganisms. The hexane extract was active against both Psedomonas aeruginosa and Staphylococcus aureus.

Chemical characterization by GC-MS and phytotoxic potential of non-polar and polar fractions of seeds of Dioteryx odorata (Aubl.) Willd. from Venezuelan regions

Dipteryx odorata (Aubl.) Willd. is a tall arboreal species native to Central and Northern South America. This paper describes the chemical characterization and phytotoxic potential of polar and non-polar extracts from D. odorata seeds. Structural determinations were accomplished by chemical derivatization and analyzed by GC/MS. The chemical composition of the non-polar fraction (hexane and dichloromethane) presented fatty acids as major constituent. Medium polar and polar fractions (ethyl acetate and ethanol: water) contained carboxylic acid and high 6,7-Dyhidroxycoumarin-β-D-glucopyranoside content, not previously reported for seeds of D. odorata. Extracts showed a significant level of phytotoxic activity, correlated to the content of coumarin derivatives, predominantly in the polar fraction.

Dft theoretical study of energetic nitrogen-rich C4N6H8-n(NO2)n derivatives

Density functional theory (DFT) calculations at the B3LYP/6-31G** theoretical level were performed for a series of guanidine-fused bicyclic skeleton derivatives C4N6H8-n(NO2)n (n = 1 - 6). The heats of formation (HOFs) were calculated by isodesmic reactions, and the detonation properties were evaluated using the Kamlet - Jacobs equations. The bond dissociation energies were also analyzed to investigate the thermal stability and sensitivity of the compounds. The results show that all of the derivatives have high positive HOFs, compound G has the highest theoretical density, and compound F1 has the highest detonation velocity and detonation pressure. Considering both the detonation properties and thermal stabilities, compounds D1 and D4 (3 nitro substituents), E1 - E6 (4 nitro substituents), and G (6 nitro substituents) can be regarded as potential candidates for high-energy density materials.

Intraspecific variability of Holostylis reniformis: concentration of lignans, as determined by maceration and supercritical fluid extraction (SFE-CO2), as a function of plant provenance and plant parts

Maceration and supercritical fluid extraction were used to prepare extracts from parts of plants (Holostylis reniformis) collected in two different regions of Brazil. ¹H NMR, HPLC-DAD-ESI/MS, HPLC-DAD, GC-MS, and chemometric techniques were used to analyse lignans in the extracts and showed that yields of SFE-CO2 were less than or equal to those of hexane maceration extracts. These analyses, in conjunction with the concentrations of aliphatic hydrocarbons, fatty acids and their methyl and ethyl derivatives in the extracts, also allowed the chemical composition of parts and provenance of the plant to be differentiated.

CHEMICAL STUDY OF Hortia superba (Rutaceae) AND INVESTIGATION OF THE ANTIMYCOBACTERIAL ACTIVITY OF CRUDE EXTRACTS AND CONSTITUENTS ISOLATED FROM Hortia SPECIES

In this paper, the chemical study of Hortia superba and antimycobacterial potential of Hortia species were investigated. Crude extracts and limonoids, alkaloids, dihydrocinnamic acid derivatives and coumarins isolated from Hortia superba, Hortia oreadica and Hortia brasiliana were evaluated against Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and Mycobacterium avium. The results obtained demonstrated an inhibitory effect of the dichloromethane extract of leaves of H. oreadica (MIC 31.25 µg mL-1), indolequinazoline (15.62 µg mL-1) and furoquinoline (31.25 µg mL-1) alkaloids, and dihydrocinnamic acid derivatives (62.50 µg mL-1), on the growth of M. tuberculosis. These results are promising in relation to the search for biologically active natural products and could be useful in the development of effective new drugs against mycobacteria.

SYNTHESIS AND BIOLOGICAL EVALUATION OF SPIRO[INDOLINE-3,4’-PYRANO[2,3-C:6,5-C’]DIPYRAZOL]- 2-ONES IN THE PRESENCE OF SBA-Pr-SO3H AS A NANOCATALYST

Sulfonic acid functionalized SBA-15 nanoporous material (SBA-Pr-SO3H) with a large pore size of 6 nm, a high surface area, high selectivity, and excellent chemical and thermal stability was applied as an efficient heterogeneous nanoporous acid catalyst in the reaction of isatin with pyrazolones under mild reaction conditions. A novel class of symmetrical spiro[indoline-3,4'-pyrano[2,3-c:6,5-c']dipyrazol]-2-one derivatives was successfully obtained in high yields. Comparison of these results with those reported in the literature shows that the current method is efficient, and results in better reaction times and yields of the desired products. Other advantages of this new method are its operational simplicity, easy work-up procedure, and the use of SBA-Pr-SO3H as a reusable and environmentally benign nanoreactor, such that the reaction proceeds easily in its nanopores. We also tested the antimicrobial activity of the prepared compounds using the disc diffusion method, and some of the synthesized compounds exhibited the best results against B. subtilis and S. aureus.

SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D

A series of six new palmitic acid-based neoglycolipids related to Papulacandin D were synthesized in five steps, resulting in good yields, and they were evaluated against Candida spp. All twelve synthetic intermediates were also evaluated. The synthesis involved the initial glycosylation of two phenols (4-hydroxy-3-methoxybenzaldehyde and 3-hydroxybenzaldehyde) via their reaction with peracetylated glucosyl bromide. This was followed by deacetylation with potassium methoxide/metanol solution and the protection of two hydroxyls (C4 and C6 positions) of the saccharide unit as benzilidene acetals (10-11). The next step involved the acylation of the acetal derivatives with palmitic acid, thereby affording a mixture of two isomers mono-acylated at the C2 and C3 positions and a di-acylated product (12-17). After being isolated, each compound was subjected to the removal of the acetal protecting group to yield the papulacandin D analogues 18-23. Three compounds showed low antifungal activity against two species: C. albicans (compounds 7 and 23) and C. tropicalis (compound 17) at 200 µg mL−1.

ANION-BINDING AND SENSING PROPERTIES OF NOVEL RECEPTORS BASED ON N-(INDOL-3-YLGLYOXYLYL)BENZYLAMINE

Indole-based receptors such as biindole, carbazole, and indolocarbazole are regarded as some of the most favorable anion receptors in molecular recognition. This is because indole groups possess N–H groups as hydrogen-bonding donors. The introduction of amide groups in the indole framework can induce strong binding properties and good water solubility. In this study, we designed and synthesized a series of N-(indol-3-ylglyoxylyl)benzylamine derivatives as novel and simple anion receptors. The receptors derived by aryl and aliphatic amines can selectively recognize F– based on a color change from colorless-to-yellow in DMSO. The receptors derived by hydrazine hydrate can recognize F–, AcO–, and H2PO4– by similar color changes in DMSO and can even enable the selective recognition of F– in a DMSO–H2O binary solution by the naked eye. Spectrographic data indicate that complexes are formed between receptors and anions through multiple hydrogen-bonding interactions in dual solutions.