Antifungal compounds produced by Colletotrichum gloeosporioides, an endophytic fungus from Michelia champaca.

In this study, eight endophytic fungi were isolated from the leaves, stems and roots of Michelia champaca. The isolates were screened and evaluated for their antifungal, anticancer and acetylcholinesterase (AChE) inhibitory activities. All of the extracts exhibited potent activity against two evaluated phytopathogenic fungi. Chemical investigation of EtOAc extracts of the endophytic fungus Colletotrichum gloeosporioides resulted in the isolation of one new compound, 2-phenylethyl 1H-indol-3-yl-acetate (1), and seven known compounds: uracil (2), cyclo-(S*-Pro-S*-Tyr) (3), cyclo-(S*-Pro-S*-Val) (4), 2(2-aminophenyl)acetic acid (5), 2(4-hydroxyphenyl)acetic acid (6), 4-hydroxy- benzamide (7) and 2(2-hydroxyphenyl)acetic acid (8). All of the compound structures were elucidated using 1D and 2D NMR and MS analyses. The antifungal and AChE inhibitory activities of compounds 1-8 were evaluated in vitro. Compound 1 exhibited promising activity against Cladosporium cladosporioides and C. sphaerospermum that was comparable to that of the positive control nystatin.

Bioactive secondary metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis.

Chemical investigation of an acetonitrile fraction from the endophytic fungus Phomopsis sp. led to the isolation of the new natural product 2-hydroxy-alternariol (7) together with the known compounds cytochalasins J (1) and H (2), 5'-epialtenuene (3) and the mycotoxins alternariol monomethyl ether (AME, 4), alternariol (AOH, 5) and cytosporone C (6). The structure of the new compound was elucidated by using 1-D and 2-D NMR (nuclear magnetic resonance) and high resolution mass spectrometry. The cytochalasins J (1) and H (2) and AOH (5) exhibited potent inhibition of the total ROS (reactive oxygen species) produced by stimulated human neutrophils and acted as potent potential anti-inflammatory agents. Moreover, cytochalasin H (2) demonstrated antifungal and acetylcholinesterase enzyme (AChE) inhibition in vitro.

Phenolic compounds and bioactive extract produced by endophytic fungus Coriolopsis rigida.

Coriolopsis rigida was isolated as an endophytic fungus from the medicinal plant Cochlospermum regium, and their production of secondary metabolites has not yet been investigated. Thus, the endophyte was cultivated on rice solid media to evaluate its ability to produce bioactive compounds and then the chloroform extract was obtained. Two phenolic compounds, tyrosol (1) and a new natural product p-hydroxyphenylacetamide (2), were isolated from the extract. The structures of the compounds were elucidated mainly by NMR. The extract showed potent antioxidant activity with an efficient concentration (EC50) value of 0.33 mg mL-1. Additionally, demonstrated allelopathic activity inhibited the seedling growth of Lactuca sativa L. and Raphanus sativus L. by 63% and 55%, respectively.

Aromatic compounds from the endophytic fungus Asordaria conoidea and their allelochemical property using OSMAC strategy.

Endophytic fungi are biodiverse and alternative source of bioactive compounds, due their different abilities of genetic expression and alteration of biosynthetic pathway when submitted to different culture conditions. The metabolic profile of three different crude extracts (A, B and C), obtained from the endophytic fungus Asordaria conoidea, were evaluated by HPLC and 1H NMR. Antioxidant and allelochemical activity were also evaluated. OSMAC diversified the metabolic production, mainly in the solid culture, where the tyrosol, 4-hydroxybenzaldehyde, 2-phenylacetamide and vanillic acid were isolated. The structures of the compounds were elucidated mainly by NMR. Extracts had antioxidant potential, however, only Extract C showed allelochemical activity, as inhibition of 65.5% in growth. This study confirms the efficiency of the OSMAC platform in producing extracts of different properties and compounds. Herein the A. conoidea was isolated for the first time as an endophytic microorganism.

Chemical, diversity and biotechnological potential of endophytic fungi isolated from Brazilian Cerrado plants / Química, diversidade e potencial biotecnológico de fungos endofíticos isolados de plantas do Cerrado Brasileiro

Abstract: This is a systematic review of scientific articles reporting the biodiversity of endophytic fungi isolated from endemic Cerrado plants in Brazil and exposes the potential applications of these microorganisms in the production of known and new metabolites. The "Portal de Periódicos" (CAPES), Science Direct, PubMed, Scielo, and Biblioteca Virtual em Saúde (BVS) databases were used. A total of 418 articles were found using the following sets of keywords: Endophytic, fungi, and Cerrado; endophytic, fungi, rupestrian, and grass lands; endophytic, fungi, Brazilian, and savanna; among these, 14 articles were selected. The articles were grouped into studies on the biodiversity of Cerrado endophytic fungi, chemical studies, and other subjects. All the articles were found to be related to the diversity present in the Cerrado of the southeastern and midwestern regions, they show high fungal biodiversity with Diaporthe genus predominant in almost all plants studied. In all the studies on the chemical diversity of endophytic fungi, new compounds or new natural products were found associated with a range of bioactivity, especially antifungal. It shows the great potential of endophytes in the production of new and bioactive secondary metabolites, as well as the unexplored chemical diversity of endophytes isolated from endemic plant species. The review shows that rare studies performed in regions where the Cerrado biome are predominant, including the central, north, and northeast regions, representing an important niche that is still unexplored.

Resumo: Esta é uma revisão sistemática de artigos científicos que relatam a biodiversidade de fungos endofíticos isolados de plantas endêmicas do Cerrado no Brasil, e expõe as possíveis aplicações desses microrganismos na produção de metabólitos novos e conhecidos. Foram utilizadas as bases de dados "Portal de Periódicos" (CAPES), Science Direct, PubMed, Scielo e Biblioteca Virtual em Saúde (BVS). Foram encontrados 418 artigos, usando os seguintes conjuntos de palavras-chave: Endophytic, fungi, and Cerrado; endophytic, fungi, rupestrian, and grasslands; endophytic, fungi, Brazilian, and savanna. Destes, 14 artigos foram selecionados. Os artigos foram agrupados em estudos sobre a biodiversidade de fungos endofíticos do Cerrado, estudos químicos e outros estudos. Todos os artigos foram relacionados à diversidade presente no Cerrado das regiões sudeste e centro-oeste, estes apresentam alta biodiversidade fúngica, com o gênero Diaporthe predominando em quase todas as plantas estudadas. Em todos os estudos sobre a diversidade química de fungos endofíticos, novos compostos ou novos produtos naturais foram identificados, associados a uma série de bioatividades, especialmente antifúngica. Isso mostra o grande potencial dos endófitos na produção de metabólitos secundários novos e bioativos, bem como a diversidade química inexplorada de endófitos isolados de espécies de plantas endêmicas. Esta revisão mostra que raros estudos foram realizados em regiões onde o bioma Cerrado é predominante, incluindo as regiões central, norte e nordeste, que representam um nicho importante ainda inexplorado.