RESUMEN
Investigation of the endophytic fungi Nigrospora sphaerica, Nigrospora oryzae, and Pseudofusicoccum stromaticum MeOH fractions isolated from the leaves of Vochysia divergens, a medicinal species from the Brazilian Pantanal, led to the identification of five compounds, namely a new compound (1E,8Z)-10,11-dihydroxy-5,5,8-trimethyl-4-oxocycloundeca-1,8-diene-1-carbaldehyde (1) and four known compounds: 5-methylmellein (2), sclerone (3), daldinone A (4), and lasiodiplodin (5). All compounds were identified using spectroscopic methods, and 1 was corroborated with mass spectrometry, while the known compounds were compared with data in the literature. The relative configuration of compound 1 was determined based on theoretical conformational studies as well as the J experimental values between the hydroxymethyne hydrogens. The antimicrobial activity of the compounds was evaluated. Promising results were obtained for compounds 2, 4, and 5 since they inhibited the bacterium Pseudomonas aeruginosa, an opportunistic pathogen, suggesting the potential of these microorganisms as a source of new antibacterial agents.
Asunto(s)
Antiinfecciosos , Antiinfecciosos/química , Hongos/metabolismo , Antibacterianos/farmacología , Antibacterianos/metabolismo , Hojas de la Planta/microbiología , Brasil , Endófitos/metabolismoRESUMEN
A chemical study of the EtOAc extract of Nemania bipapillata (AT-05), an endophytic fungus isolated from the marine red alga Asparagopsis taxiformis - Falkenbergia stage, led to the isolation of five new botryane sesquiterpenes, including the diastereomeric pair (+)-(2R,4S,5R,8S)-(1) and (+)-(2R,4R,5R,8S)-4-deacetyl-5-hydroxy-botryenalol (2), (+)-(2R,4S,5R,8R)-4-deacetyl-botryenalol (3), one pair of diastereomeric botryane norsesquiterpenes bearing an unprecedented degraded carbon skeleton, (+)-(2R,4R,8R)-(4) and (+)-(2R,4S,8S)-(5), which were named nemenonediol A and nemenonediol B, respectively, in addition to the known 4ß-acetoxy-9ß,10ß,15α-trihydroxyprobotrydial (6). Their structures were elucidated using 1D and 2D NMR, HRESIMS and comparison with literature data of similar known compounds. The absolute configurations of 2, 3 and 4 were deduced by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, while those of 1 and 5 were assigned from vibrational circular dichroism (VCD) data. Compound 4 weakly inhibited acetylcholinesterase, whereas compound 1 inhibited both acetylcholinesterase and butyrylcholinesterase. Compounds 1, 3, 5 and 6 were tested against two carcinoma cell lines (MCF-7 and HCT-116), but showed no significant citotoxicity at tested concentrations (IC50 > 50 µM).
Asunto(s)
Endófitos/aislamiento & purificación , Rhodophyta/microbiología , Terpenos/metabolismo , Xylariales/aislamiento & purificación , Acetilcolinesterasa/metabolismo , Espectroscopía de Resonancia Magnética con Carbono-13 , Inhibidores de la Colinesterasa/farmacología , Células HCT116 , Humanos , Células MCF-7 , Espectroscopía de Protones por Resonancia Magnética , Terpenos/química , Terpenos/aislamiento & purificaciónRESUMEN
Three new benzaldehyde derivatives, sporulosaldeins Aâ-âC (1: -3: ), and 3 new benzopyran derivatives, sporulosaldeins Dâ-âF (4: -6: ), were discovered from an endophytic fungus, Paraphaeosphaeria sp. F03, which was isolated from Paepalanthus planifolius leaves. Compounds 1: -6: were elucidated by 1- and 2-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry analysis. The absolute configuration of compound 5: was determined through the comparison of experimental and calculated electronic circular dichroism data. Compounds 1: -6: were found to exhibit antifungal activity with minimum inhibitory concentration (MIC) values of 7.8â-â250 µg/mL and racemic mixture of compound 6: exhibited weak cytotoxicity against MCF-7 and LM3 with IC50 values of 34.4 and 39.2 µM, respectively.
Asunto(s)
Antibacterianos/farmacología , Antifúngicos/farmacología , Ascomicetos/química , Benzaldehídos/farmacología , Benzopiranos/farmacología , Citotoxinas/farmacología , Animales , Antibacterianos/química , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Benzaldehídos/química , Benzaldehídos/aislamiento & purificación , Benzopiranos/química , Benzopiranos/aislamiento & purificación , Línea Celular Tumoral , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Endófitos , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ratones , Pruebas de Sensibilidad Microbiana , Estructura MolecularRESUMEN
Endophytic fungi were isolated from red alga Asparagopsis taxiformis - Falkenbergia stage, collected from the Brazilian coast, and were identified as Annulohypoxylon stygium (AT-03) and A. yungensis (AT-06) based on their macro/micromorphological and molecular features. Bioassay-guided fractionation of the EtOAc extract from laboratory cultures of both strains yielded known compounds pyrogallol from A. stygium, (3 R)-scytalone and (3 R,4 R)-4-hydroxy-scytalone from A. yungensis. Pyrogallol was active against methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli strains. An inactive fraction from A. stygium afforded two additional compounds, (3 R,4 R)-3,4,5-trihydroxy-1-tetralone and tyrosol. Optically active compounds had their stereochemistry determined by circular dichroism (CD) spectroscopy.
Asunto(s)
Endófitos/química , Hongos/química , Hidrocarburos Aromáticos/aislamiento & purificación , Pirogalol/farmacología , Rhodophyta/microbiología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Brasil , Escherichia coli/efectos de los fármacos , Hidrocarburos Aromáticos/química , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Naftoles/aislamiento & purificación , Naftoles/farmacología , Pirogalol/aislamiento & purificación , EstereoisomerismoRESUMEN
Three new isoaigialones, A, B, and C (1-3), along with aigialone (4), were isolated from the crude EtOAc extract of a Phaeoacremonium sp., an endophytic fungus obtained from the leaves of Senna spectabilis. The structures of these compounds were elucidated based on the analysis of spectroscopic data. Compounds 2 and 4 were active against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum. This is the first report of metabolites produced by an Phaeoacremonium sp., associated with S. spectabilis.
Asunto(s)
Acetales/aislamiento & purificación , Acetales/farmacología , Antifúngicos/aislamiento & purificación , Antifúngicos/farmacología , Ascomicetos/química , Cladosporium/química , Cetonas/aislamiento & purificación , Cetonas/farmacología , Lactonas/aislamiento & purificación , Hojas de la Planta/química , Senna/química , Acetales/química , Antifúngicos/química , Cetonas/química , Lactonas/química , Lactonas/metabolismo , Lactonas/farmacología , Estructura MolecularRESUMEN
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.
Asunto(s)
Antiinflamatorios no Esteroideos/aislamiento & purificación , Antiinflamatorios no Esteroideos/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Ascomicetos/química , Rubiaceae/microbiología , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Antiinflamatorios no Esteroideos/química , Antioxidantes/química , Brasil , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Especies Reactivas de Oxígeno/antagonistas & inhibidores , Sesquiterpenos/química , Azul de TripanoRESUMEN
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.
Asunto(s)
Antifúngicos/metabolismo , Técnicas In Vitro , Infecciones por Mycobacterium , Macrófagos Alveolares/metabolismo , Mycobacterium tuberculosis/aislamiento & purificación , Mycobacterium tuberculosis/metabolismo , Técnicas y Procedimientos Diagnósticos , Metodología como un TemaRESUMEN
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.
RESUMEN
A lignan with a new skeleton named chimarrhinin (1) was isolated from an extract of the leaves of Chimarrhis turbinata, a Rubiaceae plant species. (13)C NMR spectrometric techniques including 1D and 2D experiments and HRESIMS provided unequivocal structural confirmation of this new C(6).C(3) skeleton type. The relative configuration of 1 was established by 2D (1)H-H analysis and J couplings, while its conformation was evaluated through molecular modeling using the RM1 semiempirical method, with the aid of coupling constants obtained by NMR analysis. The antioxidant activity of the new derivative 1 and two known and previously isolated phenolic derivatives (2 and 3) was investigated. An IC(50) value of 7.50 ± 0.5 µmol L(-1) was obtained for the new derivative 1, while 2 and 3 showed IC(50) values of 18.60 ± 0.4 and 18.50 ± 0.6 µmol, respectively.
Asunto(s)
Antioxidantes/aislamiento & purificación , Lignanos/aislamiento & purificación , Rubiaceae/química , Antioxidantes/química , Antioxidantes/farmacología , Brasil , Lignanos/química , Lignanos/farmacología , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/químicaRESUMEN
In the course of our continuous search for bioactive metabolites from endophytic fungi living in plants from the Brazilian flora, leaves of Alibertia macrophylla (Rubiaceae) were submitted to isolation of endophytes, and two species of Penicillium were isolated. The acetonitrile fraction obtained in corn from a culture of Penicillium sp. 1 afforded orcinol (1). On the other hand, Penicillium sp. 1 cultivated in potato-dextrose-broth furnished two different compounds, cyclo-(L-Pro-L-Val) (2) and uracil (3). The chromatographic fractionation of the acetonitrile fraction obtained from Penicillium sp. 2 led to three dihydroisocoumarins, 4-hydroxymellein (4), 8-methoxymellein (5) and 5-hydroxymellein (6). Compounds 5 and 6 were obtained from the Penicillium genus for the first time. Additionally, metabolites 1-6 were evaluated for their antifungal and acetylcholinesterase (AChE) inhibitory activities. The most active compounds 1 and 4 exhibited detection limits of 5.00 and 10.0 microg against Cladosporium cladosporioides and C. sphaerospermum, respectively. Compound 2 showed a detection limit of 10.0 microg, displaying potent AChE inhibitory activity.
Asunto(s)
Penicillium/química , Penicillium/metabolismo , Rubiaceae/química , Antifúngicos/aislamiento & purificación , Antifúngicos/farmacología , Brasil , Inhibidores de la Colinesterasa/aislamiento & purificación , Inhibidores de la Colinesterasa/farmacología , Espectroscopía de Resonancia Magnética/métodos , Modelos Moleculares , Ocratoxinas/química , Ocratoxinas/aislamiento & purificación , Penicillium/efectos de los fármacos , Penicillium/aislamiento & purificación , Rubiaceae/microbiología , Solanum tuberosum/microbiología , Espectrofotometría , Zea mays/microbiologíaRESUMEN
The Styracaceae contains 11 genera and approximately 160 species consisting of small trees and shrubs, mostly native to tropical and subtropical regions. This family is well-known by the genus Styrax, which is notorious due to the production of resinous material, a pathological product, harvested by making incisions into the trees bark. The gum is used in perfumes, as antiseptic, expectorant, incense, and fumigating material. This paper reviews the phytochemical and biological studies carried out on 11 species of this family. A total of 92 papers were consulted, and 130 compounds were described, thus these data indicate that Styrax is by far the largest genus in the family, and the only which has been extensively investigated.
Styracaceae possui 11 gêneros e aproximadamente 160 espécies, sendo árvores e arbustos, distribuídos nas regiões tropicais e subtropicais. Esta família é conhecida principalmente devido ao gênero Styrax, que é notório pela produção de um material resinoso, produto patológico, coletado a partir de incisões realizadas no caule. Esta goma é usada em perfumes, como anti-séptico, expectorante, incenso e material fumegante. Este artigo reúne os estudos fitoquímicos e biológicos realizados em 11 espécies desta família. Foram consultados 92 artigos e levantadas 130 substâncias, que indicaram que Styrax é o maior gênero desta família e o único que foi extensivamente investigado.
RESUMEN
Communiols E-H (1-4), four new polyketide-derived natural products containing furanocyclopentane, furanocyclopentene, cyclopentene, or gamma-lactone moieties, have been isolated from two geographically distinct isolates of the coprophilous fungus Podospora communis. The structures of these compounds were determined by analysis of NMR and MS data.