A new compound, (6R,7S,2E,4E)-6,7-dihydroxy-4,6-dimethylocta-2,4-dienoic acid (1), together with eight known compounds were isolated from the co-culture of Saccharicola sp. and Botryosphaeria parva, an endophytic fungi associated with Eugenia jambolana Lam. (Myrtaceae) plant species. The structures were elucidated by spectroscopic analysis of the one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry (MS) data as well as by comparison with literature data. The bioactivity (antioxidant and antifungal) of the crude EtOAc was evaluated. All crude extracts presented antioxidant activity and only the crude extract from the co-culture was active on the fungus Cladosporium sphaerospermum. This investigation contributed to the knowledge about the metabolic production of two endophytic fungi Saccharicola sp. and Botryosphaeria parva in co-culture, once, until the present date, there are no studies in the literature that report the understanding of the chemical interaction of both grown in the same environment.

The upscaling of Xylaria cubensis, an endophyte of Eugenia brasiliensis (Myrtaceae), in PDB medium led to the isolation of known compounds including cytochalasin D (7) and cytochalasin C (8), which exhibited relatively higher phytotoxic activity in all the concentrations tested compared to the commercial herbicide GOAL®. Besides the aforementioned metabolites, one diketopiperazine (DKP) and two isocoumarins were isolated and two DKPs were also identified in the mixture. The structures were determined by 1D and 2D 1H NMR, MS analyses and were compared with the literature.

A new compound named methyl (6S,7S,2E,4E)-6,7-dihydroxy-4,6-dimethyl octanoate was isolated from Saccharicola sp. using high performance liquid chromatography-solid phase extraction-transfer tube (HPLC-SPE-TT), together with four known compounds, fusaric acid, trans-4-hydroxymellein, thymidine and adenosine. Saccharicola sp. was isolated from the stems of Eugenia jambolana Lam. (Myrtaceae) as endophytic fungus. The structure of this novel substance was established based on its spectroscopic data, including 1H and 13C nuclear magnetic resonance (NMR), 2D NMR techniques and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). This paper deals with the first report of its kind on this compound in Saccharicola sp.

One new natural product, 1-phenylethyl-O-a-L-rhamnopyranoside, together with eight known diketopiperazines and two benzene derivatives were isolated from the endophytic fungus Colletotrichum crassipes, whereas six known compounds including two griseofulvins, three cytochalasins and one dihydroisocoumarin were produced from the endophyte Xylaria sp., both endophytic fungi are associated with leaves of Casearia sylvestris. Cyclo(D)-Pro-(D)-Phe, N-(2-phenylethyl)acetamide and 5-carboxy-6-hydroxy-3-methyl-3,4-dihydroisocoumarin exhibited potent antifungal activity against Cladosporium cladosporioides and C. sphaerospermum. The compounds cyclo(D)-Pro-(D)-Phe, griseofulvin, cytochalasin B and cytochalasin D exhibited antioxidant activity, and the compounds cyclo(D)-Pro-(D)-Phe, cytochalasin B and cytochalasin C showed potent acetylcholinesterase (AChE) inhibition. In addition, this is the first report on the isolation of secondary metabolites from two endophytic fungal strains, associated with Casearia sylvestris.

The screening for antimicrobial activity of twenty five endophytic fungi isolated from the aerial parts of Paepalanthus chiquitensis (Eriocaulaceae) was assayed against the bacteria Gram-positive Staphylococcus aureus, Gram-negative Escherichia coli and Salmonella setubal, and the yeast fluconazole-resistant Candida albicans. The ethyl acetate extract produced by Fusarium fujikuroi was the most bioactive and this fungus was chosen for the chemical study, affording the isolation of an alkaloid 2-(4-butylpicolinamide) acetic acid and three known metabolites: fusaric acid, indole acetic acid and the sesterterpene terpestacin. The minimal inhibitory concentration of the extract and of fusaric acid and indole acetic acid for all the tested microorganisms had values from 125 to 1000 µg mL-1.

Six known compounds, three peptide derivatives: cyclo-(tryptophyl-phenylalanyl) (2), diketopiperazine dimer WIN 64821 (3) and 3-hydroxy-15H-tryptophenaline (4), one adenine derivative: 2-hydroxy-6-N-isopentenyl-adenine (5), one phtalide derivative: 4-methoxyphtalide (1) and one benzoic acid derivative: 3-hydroxy-4-(1-hydroxy-1,5-dimethyl-hexyl) benzoic acid (6), were isolated from the ethyl acetate extract of the endophytic fungus Aspergillus versicolor associated with the Piper aduncum plant. Their structures were determined on the basis of detailed interpretation of 1 D and 2D NMR spectra and in comparison with works reported in the literature. This paper, in effect, deals with the first report of these compounds in A. versicolor.

Seven phenolic derivatives including p-hydroxyphenyllactic acid (1), p-hydroxybenzoic acid (2), p-hydroxybenzaldehyde (3), phenyllactic acid (4), n-butyl-3,4-dihydroxybenzoate (5), n-hexyl-3,4-dihydroxybenzoate (6) and n-octyl-3,4-dihydroxybenzoate (7) were produced using Camarops sp. via the one strain-many compounds (OSMAC) approach. Their structures were determined using 2D NMR and ESI-MS spectra and were compared with works reported in the literature. This paper deals with the first report of these compounds in Camarops sp.

In this study, fifteen endophytic fungi were isolated from Paepalanthus planifolius (Eriocaulaceae). From the capitula, seven endophytes were screened and evaluated for their metabolomic profile and radical scavenging activity (2,2-diphenyl-1-picrylhydrazyl (DPPH) assay). Chemical investigation of ethyl acetate extract of the endophytic fungus Anthostomella brabeji resulted in the isolation of one new compound, (+)-(6R*,7S*,8R*)-6,7,8-trihydroxy-2,2-dimethyl-5,6,7,8-tetrahydro-chroman-4-one, and three known compounds: 6-hydroxy-2,2-dimethyl-5,6,7,8-tetrahydro-7,8-epoxycroman-4-one, siccayne and eutypinol. All of the compound structures were elucidated using 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The antimicrobial activity of the compounds and A. brabeji extract were assayed against the microorganisms Staphylococcus aureus, Escherichia coli, Salmonella setubal and Candida albicans. Measured minimal inhibitory concentration (MIC) values ranged from 31.25 to 1000.0 µg mL-1.

Our purpose was to determine the anti-Mycobacterium tuberculosis activity of the metabolites produced by the endophitic fungus Phomopsis stipata (Lib.) B. Sutton, (Diaporthaceae), cultivated in different media. The antimycobacterial activity was assessed through the Resazurin Microtiter Assay (REMA) and the cytotoxicity test performed on macrophage cell line. The extracts derived from fungi grown on Corn Medium and Potato Dextrose Broth presented the smallest values of Minimum Inhibitory Concentration (MIC) and low cytotoxicity, which implies a high selectivity index. This is the first report on the chemical composition and antitubercular activity of metabolites of P. stipata, as well as the influence of culture medium on these properties.

SESQUITERPENES PRODUCED BY ENDOPHYTIC FUNGUS Phomopsis cassiae WITH ANTIFUNGAL AND ACETYLCHOLINESTERASE INHIBITION ACTIVITIES. Two new diastereoisomeric cadinanes sesquiterpenes 3,9-dihydroxycalamenene (1-2), along with the known 3-hydroxycalamen-8-one (3) and aristelegone-A (4), were isolated from ethyl acetate extract of Phomopsis cassiae, an endophytic fungus in Cassia spectabilis. Their structures, including relative stereochemistry, were determined on the basis of detailed interpretation of 2D NMR spectra and comparison with related known compounds. Compounds 1-4 displayed antifungal activity against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum, as well as inhibition of acetylcholinesterase.

A chemical study on the EtOAc extract produced by Xylaria sp., an endophytic fungus from Piper aduncum, resulted in the isolation of a new cytochalasin 1, along with five known 19,20-epoxycytochalasin D (2), C (3), N (4), Q (5), and R (6). The 1-6 were evaluated against the fungi C. cladosporioides and C. sphaerospermum and only 5 showed weak activity. The cytotoxicity in vitro against HeLA and CHO cells lines were investigated and the cytochalasins 2-4, and 6 showed a strong activity against HeLA. The DNAdamaging activity of 1-6 were also investigated against mutant strains of S. cerevisiae.