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.

Abstract Alzheimer's disease affects nearly 36.5 million people worldwide, and acetylcholinesterase inhibition is currently considered the main therapeutic strategy against it. Seaweed biodiversity in Brazil represents one of the most important sources of biologically active compounds for applications in phytotherapy. Accordingly, this study aimed to carry out a quantitative and qualitative assessment of Hypnea musciformis (Wulfen) J.V. Lamouroux, Ochtodes secundiramea (Montagne) M.A. Howe, and Pterocladiella capillacea (S.G. Gmelin) Santelices & Hommersand (Rhodophyta) in order to determine the AChE effects from their extracts. As a matter of fact, the O. secundiramea extract showed 48% acetylcholinesterase inhibition at 400 μg/ml. The chemical composition of the bioactive fraction was determined by gas chromatography–mass spectrometry (GC–MS); this fraction is solely composed of halogenated monoterpenes, therefore allowing assignment of acetylcholinesterase inhibition activity to them.

Abstract Marine environment is one of the most important sources regarding natural products research. Besides, marine microorganisms have been denominated as a talented natural source for discovery of new leads. Although the association of macroalgae and fungi has been described regarding ecological issues, there is a lack of studies about marine seaweed endophytic fungi. In this context, the goal of this study was to evaluate cytotoxic, antifungal and antibacterial activities of endophytic fungi isolated from the Brazilian marine seaweed Bostrychia tenella (J.V. Lamouroux) J. Agardh (Ceramiales, Rhodophyta). Forty-five endophytic microorganism strains were isolated from B. tenella. Crude extracts and organic fractions of ten selected strains were obtained after growth in rice medium. Samples were evaluated for cytotoxicity, antifungal and antibacterial assays. Penicillium strains showed positive results in a diversity of assays, and other five strains were active in at least one test. In addition, cytochalasin D was isolated from Xylaria sp. This alga is composed of a microbiological potential, since its endophytic strains exhibited remarkable biological properties. Moreover, cytochalasin D isolation has confirmed chemical potential of marine endophytic strains. This is the first study in which cultured fungi isolates from the Brazilian macroalga B. tenella were evaluated concerning biological properties. Results corroborated that this species could be a pharmaceutical source from marine environment. Furthermore, Acremonium implicatum is being firstly described as marine endophyte and Xylaria sp., Trichoderma atroviride and Nigrospora oryzae as marine seaweed endophytes. Thus, this work reports the first study relating detailed isolation, cultivation and biological evaluation (cytotoxic, antifungal and antibacterial) of endophytes Penicillium decaturense and P. waksmanii from the Brazilian marine red alga B. tenella. We are also reporting the isolation of cytochalasin D, a known antitumor and antibiotic compound, from Xylaria sp. strain. Despite widespread prevalence in terrestrial and marine habitats, this present work describes the first occurrence of cytochalasin D as a metabolite from marine seaweed endophyte.

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 composição química dos óleos voláteis de duas espécies de Myrtaceae, Myrceugenia myrcioidese Eugenia riedeliana, ambas nativas da Mata Atlântica, foi analisada por CG-EM. A atividade inibidora de acetilcolinesterase foi determinada colorimetricamente para estes óleos. Em M. myrcioides, hidrocarbonetos monoterpênicos representaram a classe majoritária de compostos presentes no óleo volátil, sendo α-pineno o componente mais abundante e a atividade inibidora de acetilcolinesterase foi baixa, enquanto para E. riedelianaos sesquiterpenos foram observados em maiores concentrações, sendo o valerianol o componente majoritário, e este óleo apresentou uma forte atividade inibidora da enzima.

The chemical composition of volatile oils from two Myrtaceae species, Myrceugenia myrcioidesand Eugenia riedeliana, both native from the Brazilian Atlantic Rain Forest, was analyzed by GC-MS. Acetylcholinesterase inhibitory activity was colorimetrically evaluated for these oils. For M. myrcioides, monoterpene hydrocarbons represented the major class in the volatile oil, with α-pinene as the most abundant component and a weak inhibitory activity was observed, whilst for E. riedeliana sesquiterpenes were found in higher amounts, being valerianol the major compound, and this oil presented a strong acetylcholinesterase inhibition.

A utilização de parâmetros apenas morfológicos para posicionar taxonomicamente diversas espécies em sub-famílias e tribos na família Rubiaceae é bastante problemática devido à falta de informações sobre a distribuição geográfica e de características morfoanatômicas nos níveis hierárquicos mais baixos, como por exemplo, o gênero Chimarrhis. O perfil micromolecular de diferentes espécies pode auxiliar na delimitação de tribos indicando tendências filogenéticas mais completas entre as tribos das sub-famílias, já que os metabólitos secundários são expressões de adaptação, regulação e evolução de um determinado táxon. Nesse contexto, os alcalóides indólicos monoterpênicos isolados de Chimarrhis turbinata foram bastante úteis para embasar a classificação taxonômica feita por Robbrecht, em que posiciona Chimarrhis como um gênero da tribo Condamineae e subfamília Cinchonoideae.

The morphological parameters used to establish close connections among species taxonomically different into the Rubiaceae family is complex, mainly due to the lack of information on habitat and morphoanatomical characters in the lower hierarchic groups, for example, Chimarrhis genus. The micromolecular profile of delimited species into determined taxa can be useful to establish the boundaries among close taxonomic groups, and to indicate evolutionary phylogenetic trends into the taxa. Several indole alkaloids isolated from C. turbinata showed to be a valuable tool to support the taxonomic classification performed by Robbrecht, who established the most recent taxonomy for Rubiaceae, based on morphological characters, and concluded that Chimarrhis belong to Condamineae, and subfamily Cinchonoideae.

Five compounds, 2-hexyl-3-methyl-butanodioic acid (1), cytochalasin D (2), 7-dechlorogriseofulvin (3), cytochalasin B (4) and griseofulvin (5), have been isolated from the endophytic fungus Xylaria sp., and their structures were elucidated on the basis of spectroscopic data. In the bioautography assay against Cladosporium cladosporioides and Cladosporium sphaerospermum, compounds 1 and 2 were found to be active while compounds 3, 4 and 5 did not show antifungal activity.

Um flavonol inédito, 4'-metoxikaempferol-7-(acetiloxi)-3,5-O-alfa-L-ramnosídeo (1), três flavonóides conhecidos, apigenina, 7-O-metoxiquercetrina e quercetrina e quatro triterpenos, alfa-amirina, beta-amirina, ácido oleanólico e ácido ursólico foram isolados das folhas de Chiococca braquiata. As estruturas dessas substâncias foram elucidadas com base em seus dados espectroscópicos.

A new flavonol 4'-methoxykaempferol-7-(acetyloxy)-3,5-O-alpha-L-rhamnoside (1), was isolated from the leaves of Chiococca braquiata, along with three known flavonoids apigenin, 7-O-methoxyquercetrin and quercetrin and four triterpenes alpha-amirin, beta-amirin, ursolic and oleanolic acids . Their structures were established on the basis of spectroscopic methods.

Um novo sesquiterpeno, aromadendrano-4b,10a,15-triol, foi isolado das folhas de Xylopia brasiliensis Spreng (Annonaceae), juntamente com quatro derivados de esqueleto aromadendrano e três esteróides. As estruturas dos metabólitos foram definidas por meio da análise dos respectivos espectros de RMN, incluindo experimentos bidimensionais, além de espectrometria de massas. Os sesquiterpenos aromadendranos diidroxilados apresentaram atividade antifúngica frente a Cladosporium cladosporioides.

A new sesquiterpenoid, aromadendrane-4b,10a,15-triol, was isolated from the leaves of Xylopia brasiliensis Spreng (Annonaceae), together with four known aromadendrane derivatives and three steroids. The structures of these compounds were defined by analysis of their NMR spectral data, including bidimensional analysis, and mass spectrometry. The isolated aromadendranediol derivatives showed antifungal activity against Cladosporium cladosporioides.