One strain-many compounds (OSMAC) method for production of phenolic compounds using Camarops sp., an endophytic fungus from Alibertia macrophylla (Rubiaceae)

ONE STRAIN-MANY COMPOUNDS (OSMAC) METHOD FOR PRODUCTION OF PHENOLIC COMPOUNDS USING Camarops sp., AN ENDOPHYTIC FUNGUS FROM Alibertia macrophylla (RUBIACEAE). 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

ONE STRAIN-MANY COMPOUNDS (OSMAC) METHOD FOR PRODUCTION OF PHENOLIC COMPOUNDS USING Camarops sp., AN ENDOPHYTIC FUNGUS FROM Alibertia macrophylla (Rubiaceae)

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

Cyclo-(trp-phe) diketopiperazines from the endophytic fungus Aspergillus versicolor isolated from Piper aduncum

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

Cyclo-(trp-phe) diketopiperazines from the endophytic fungus Aspergillus versicolor isolated from Piper aduncum

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

Biologically Active Eremophilane-Type Sesquiterpenes from Camarops sp., an Endophytic Fungus Isolated from Alibertia macrophylla

Two new eremophilane-type sesquiterpenes, xylarenones F (3) and G (4), have been isolated from solid substrate cultures of a Camarops sp. endophytic fungus isolated from Alibertia macrophylla, together with the known compounds xylarenones C (1) and D (2). The structures and relative configurations of 1-4 were elucidated by extensive NMR and HRESIMS spectroscopic analysis. Due to their effects on the respiratory burst of neutrophils, which included inhibition of the reactive oxygen species production, these sesquiterpenes exhibited potential anti-inflammatory and antioxidant properties.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES

Biologically Active Eremophilane-Type Sesquiterpenes from <i>Camarops</i> sp., an Endophytic Fungus Isolated from <i>Alibertia macrophylla</i>

Two new eremophilane-type sesquiterpenes, xylarenones F (<b>3</b>) and G (<b>4</b>), have been isolated from solid substrate cultures of a <i>Camarops</i> sp. endophytic fungus isolated from <i>Alibertia macrophylla</i>, together with the known compounds xylarenones C (<b>1</b>) and D (<b>2</b>). The structures and relative configurations of <b>1</b>–<b>4</b> were elucidated by extensive NMR and HRESIMS spectroscopic analysis. Due to their effects on the respiratory burst of neutrophils, which included inhibition of the reactive oxygen species production, these sesquiterpenes exhibited potential anti-inflammatory and antioxidant properties

Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63

Prenyl indole alkaloids constitute a diverse class of natural products with complex chemical structures and potent biological activities. Investigation of the growth medium EtOAc extract produced by the endophytic fungus Aspergillus terreus P63 collected from roots of the grass Axonopus leptostachyus, yielded the prenylated indole alkaloid, giluterrin, bearing an unprecedented carbon skeleton. The structure of giluterrin was established by analysis of spectroscopic data and HRMS. The absolute configuration of giluterrin was determined by combination of electronic and vibrational circular dichroism analyses. Giluterrin presented antiproliferative profile for prostate (PC-3) and kidney (786-0) cancer cell lines32162167CONSELHO NACIONAL DE DESENVOLVIMENTO CIENTÍFICO E TECNOLÓGICO - CNPQFUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE SÃO PAULO - FAPESPsem informação2013/50228-8; 2014/25222-9National Council for Scientific and Technological Development (CNPq)National Council for Scientific and Technological Development (CNPq); National Institute of Science and Technology (INCT BioNat), Brazil [465637/2014-0]; National Institute of Science and Technology (INCT Areas Umidas), Brazil [421733/2017-9]; Sao Paulo State Research Foundation (FAPESP)Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [2013/50228-8, 2014/25222-9]; Centre for Scientific Computing (NCC/GridUNESP) of Sao Paulo State University (UNESP); FAPESPFundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP

Rearranged Terpenoids from the Marine Sponge <i>Darwinella</i> cf. <i>oxeata</i> and Its Predator, the Nudibranch <i>Felimida grahami</i>

Marine sponges are a rich source of terpenoids with rearranged spongian carbon skeletons. Investigation of extracts from the sponge <i>Darwinella</i> cf. <i>oxeata</i> yielded four new rearranged diterpenoids, oxeatine (<b>2</b>) and oxeatamides H–J (<b>3</b>-<b>5</b>), as well as the known metabolites oxeatamide A (<b>6</b>), oxeatamide A methyl ester (<b>7</b>), and membranolide (<b>1</b>). Oxeatine (<b>2</b>) has a new heterocyclic skeleton, while oxeatamide J (<b>5</b>) has an <i>N</i>-methyl urea group included in a γ-lactam moiety. UPLC-QTOF analysis of the extract obtained from the mantle of the nudibranch <i>Felimida grahami</i> indicated the presence of <b>1</b> and <b>4</b>