Esteroides produzidos por Penicillium herquei, um fungo endofítico isolado dos frutos de Melia azedarach (Meliaceae)

Marinho, Andrey Moacir do Rosário; Marinho, Patrícia Santana Barbosa; Filho, Édson Rodrigues

doi:10.1590/s0100-40422009000700005

Cited by 19 publications

(9 citation statements)

References 8 publications

(9 reference statements)

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“…The compounds 5 and 6 are commonly isolated from fungi and were identified through analysis of 1 H and 13 C NMR spectra and compared to the literature data and presented total similarity to ergosterol and ergosterol peroxide (Marinho et al 2009). …”

Section: Discussionmentioning

confidence: 99%

Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides(Melanconiaceae)

et al. 2016

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Endophytic fungi are fungi that colonize internal tissues of plants. There are few studies of compounds isolated from endophytic fungi of Amazon plants. Thus, the aim this study was the isolation and structural identification of sitosterol (1), stigmasterol (2), sitostenone (3), squalene (4), ergosterol (5) and ergosterol peroxide (6) from fungus Colletotrichum gloeosporioides isolated as endophytic from Virola michelli, a typical Amazon plant, used in folk medicine against skin infection. Compounds were isolated by chromatography column on silica and identified by 1 H and 13 C NMR and MS. The presence of phytosterols in fungi is rare and this is the first report of the isolation of the phytosterols sitosterol, stigmasterol and sitostenone from the genus Colletotrichum. KEYWORDS: Sterols, secondary metabolites, Amazon fungi. Fotoesteróis isolados do fungo endofítico Colletotrichum gloeosporioides (Melanconiaceae) RESUMOFungos endofíticos são fungos que colonizam os tecidos internos das plantas. Existem poucos estudos de compostos isolados de fungos endofíticos de plantas da Amazônia. Assim, o objetivo deste estudo foi o isolamento e identificação estrutural de sitosterol (1), estigmasterol (2), sitostenona (3), esqualeno (4), ergosterol (5) e peroxido de ergosterol (6) do fungo Colletotrichum gloeosporioides isolado como endofítico de Virola michelli, uma planta típica da Amazônia, usada na medicina popular no combate a infecções de pele. Os compostos foram isolados por cromatografia em coluna de sílica e identificados por RMN 1 H e 13 C e EM. A presença de fitoesteróis em fungos é rara e este é o primeiro relato do isolamento dos fitoesteróides sitosterol, estigmasterol e sitostenona do gêreno Colletotrichum. PALAVRAS-CHAVE: Esteróides, metabolitos secundários, fungos da Amazônia. (Melanconiaceae) Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides

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Section: Discussionmentioning

confidence: 99%

Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides(Melanconiaceae)

et al. 2016

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“…Compound 1 was isolated from the apolar fractions of the ethyl acetate extract in amorphous white solid form, and its 1 H and 13 C NMR data showed the identity of the ergosterol peroxide steroid, 17 which is an steroid commonly isolated from fungi and reported to have anticancer activity. 19 Monocerin (2) 1 H NMR spectrum of 3 showed signals related hydrocarbon side chain, a methoxy group and olefinic methine unit presence.…”

Section: Resultsmentioning

confidence: 99%

“…General procedures adopted for microorganism isolation followed the methodology described by Marinho et al 17 After collection, B. guianensis healthy tissues were washed with water and their surface was sterilized by immersion in 70% aqueous ethanol (1 min), followed by 5% aqueous sodium hypochlorite (4 min), and finally with 70% aqueous ethanol (30 s). Afterwards, tissues were rinsed with sterilized water.…”

Section: Microorganism Isolationmentioning

confidence: 99%

Annularins I and J: New Metabolites Isolated from Endophytic FungusExserohilum rostratum

Pinheiro¹,

Borges²,

Pina³

et al. 2016

Journal of the Brazilian Chemical Society

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The paper describes the isolation of ergosterol peroxide, monocerin, annularin I and annularin J compounds of Exserohilum rostratum biomass extracts. Compounds were isolated by silica gel column chromatography in polarity gradient and the structures were determined by nuclear magnetic resonance (NMR) and mass spectrometry (MS) methods. Monocerin, annularin I and annularin J compounds were tested against Escherichia coli, Pseudomonas aeruginosa and Bacillus subtilis bacteria and showed moderate activity. Annularin I and annularin J compounds are new natural products. Keywords: annularins, polyketides, E. rostratum, endophytic fungi IntroductionEndophytic microorganisms live in plants internal tissues without causing apparent disease to their hosts. 1 Endophyte microbial colonization can be demonstrated by isolating plant tissues disinfected through histological cut and by DNA amplification technique. 2 In tropical and temperate forests (which cover only 1.5% of the terrestrial surface), there are approximately 300,000 (three hundred thousand) plant species analyzed so far, homing more than 60% of the world's biodiversity. 3 Extreme diversity allows for the opportunity to discover new microorganisms that may be potential bioactive compounds producers for agriculture, industry and medicine. 4 There is a great interest in the study of endophytic microorganisms, including their application in pest biocontrol. Fungi are good secondary metabolite producers, and many have the same biological activity, 5-8 especially polyketides. For example, the polyketide citrinin isolated from Penicillium janthinellum completely inhibited the growth of Leishmania braziliensis.9 Some fungi species of Penicillium and Pestalotiopsis genera produce high diversity of polyketides with antimicrobial activity. 10,11In another study with a variety of endophytes isolated from Vigueira arenaria and Tithonia diversifolia fungal extracts, important antiparasitic and antimicrobial activities were observed in fungal extracts. 12 In the Nodulisporium sp. (Xylariaceae) fungus extract, which was isolated from the woody plant species Erica arborea (Ericaceae), nodulisporina D, E and F compounds were obtained, having antifungal, antibacterial and algaecide activity.13 From the endophytic fungus Ampelomyces sp., isolated from the medicinal plant Urospermum picroides (Asteraceae), 6-O-methylalaternina and altersolanol A compounds were isolated, which showed antimicrobial activity against Gram-positive pathogens Staphylococcus aureus, S. epidermidis and Enteorococcus faecalis.14 Brazil is estimated to be home of about 20% of the world's biodiversity and is considered the country in the world with the largest number of endemic species.15 About 270,000 plant species on this planet are estimated to harbor about 13.6 million unique endophytic fungal species, in addition to approximately 100,000 fungi species already known to date. Therefore, there are great chances of finding Pinheiro et al. 1433 Vol. 27, No. 8, 2016 new substances produced by endophytic fun...

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“…These data together with 13 C NMR data to the compounds allowed identify them as the steroids ergosterol (5), ergosterol peroxide (6) and cerevisterol (7) (Marinho et al 2009). The steroid ergosterol and ergosterol peroxide have signifi cant anticancer activity (Kawagishi et al 1988).…”

Section: Constituents Isolatedmentioning

confidence: 99%

(4S)-4,8-dihydroxy-1-tetralone and other chemical constituents from Pestalotiopsis sp. EJC07, endophytic fromBauhinia guianensis

Souza

Silva

Marinho

et al. 2016

An. Acad. Bras. Ciênc.

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The present work reports the isolation of eight compounds from Pestalotiopsis sp. EJC07 isolated as endophytic from Bauhinia guianensis, a tipical plant of the Amazon. The compounds (4S)-4,8-dihydroxy-1-tetralone (1), uracil (2), uridin (3), p-hydroxybenzoic acid (4), ergosterol (5), ergosterol peroxide (6), cerevisterol (7) and ducitol (8) were isolated by chromatographic procedures and identifi ed by spectral methods of 1D and 2D NMR and MS. The compound 1 is being reported for the fi rst time in the genus Pestalotiopsis.

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Esteroides produzidos por Penicillium herquei, um fungo endofítico isolado dos frutos de Melia azedarach (Meliaceae)

Cited by 19 publications

References 8 publications

Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides(Melanconiaceae)

Phytosterols isolated from endophytic fungus Colletotrichum gloeosporioides(Melanconiaceae)

Annularins I and J: New Metabolites Isolated from Endophytic FungusExserohilum rostratum

(4S)-4,8-dihydroxy-1-tetralone and other chemical constituents from Pestalotiopsis sp. EJC07, endophytic fromBauhinia guianensis

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