scholarly journals Ring B Aromatic Steroids from an Endophytic Fungus, Colletotrichum sp.

2009 ◽  
Vol 4 (11) ◽  
pp. 1934578X0900401 ◽  
Author(s):  
Wen Zhang ◽  
Siegfried Draeger ◽  
Barbara Schulz ◽  
Karsten Krohn

The new (22E,24R)-3-acetoxy-19(10→6)-abeo-ergosta-5,7,9,22-tetraen-3β-ol (1) and the known (22E,24R)-19(10→6)-abeo-ergosta-5,7,9,22-tetraen-3β-ol (2), two interesting ergosteroids with rare aromatized ring B, together with seven known derivatives, namely (22E,24R)-ergosta-5,7,22-trien-3β-ol (3), (22E,24R)-ergosta-4,7,22-trien-3-one (4), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), (22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (6), (22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol (7), (22E,24R)-6-acetoxy-ergosta-7,22-dien-3β,5α,6β-triol (8), and (22E,24R)-3,6-diacetoxy-ergosta-7,22-dien-3β,5α,6β-triol (9), were isolated from Colletotrichum sp., an endophytic fungus isolated from Ilex canariensis from Gomera. The structures of these compounds were elucidated by detailed spectroscopic analysis, comparison with reported data, and chemical interconversion. The isolation of these metabolites not only displays a beautiful array of chemical diversity, but also gives insight into the biosynthetic interconnections. Preliminary studies showed antimicrobial activity of these compounds against the fungus Microbotryum violaceum, the alga Chlorella fusca, and the bacteria Escherichia coli and Bacillus megaterium.

2011 ◽  
Vol 6 (5) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Shan Lu ◽  
Siegfried Draeger ◽  
Barbara Schulz ◽  
Karsten Krohn ◽  
Ishtiaq Ahmed ◽  
...  

Two new benzyl γ-butyrolactone analogues, ( R)-5-(( S)-hydroxy(phenyl)-methyl)dihydrofuran-2(3H)-one (1) and its 6-acetate (2), and a new naphthalenone derivative (8), together with eight additional known aromatic derivatives, ( S)-5-(( S)-hydroxy(phenyl)-methyl)dihydrofuran-2(3H)-one (3), ( S)-5-benzyl-dihydrofuran-2(3H)-one (4), 5-phenyl-4-oxopentanoic acid (5), γ-oxo-benzenepentanoic acid methyl ester (6), 3-(2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-2-furyl)propionic acid (7), (3 R)-5-methylmellein (9), integracins A (10) and B (11) were isolated from Cytospora sp., an endophytic fungus isolated from Ilex canariensis from Gomera. The structures of these compounds were elucidated by detailed spectroscopic analysis, comparison with reported data, and chemical interconversion. The absolute configurations of the new compounds (1, 2, 8) were established on the basis of optical rotation or CD spectra analysis. Preliminary studies showed antimicrobial activity of these compounds against the fungi Microbotryum violaceum, Botrytis cinerea and Septoria tritici, the alga Chlorella fusca, and the bacterium Bacillus megaterium.


Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4118 ◽  
Author(s):  
Noha Fathallah ◽  
Marwa M. Raafat ◽  
Marwa Y. Issa ◽  
Marwa M. Abdel-Aziz ◽  
Mokhtar Bishr ◽  
...  

Ammi majus L.; Family Apiaceae; is a plant indigenous to Egypt. Its fruits contain bioactive compounds such as furanocoumarins and flavonoids of important biological activities. An endophytic fungus was isolated from the fruits and identified as Aspergillus amstelodami (MK215708) by morphology, microscopical characterization, and molecular identification. To our knowledge this is the first time an endophytic fungus has been isolated from the fruits. The antimicrobial activity of the Ammi majus ethanol fruits extract (AME) and fungal ethyl acetate extract (FEA) were investigated, where the FEA showed higher antimicrobial activity, against all the tested standard strains. Phytochemical investigation of the FEA extract yielded five prenylated benzaldehyde derivative compounds isolated for the first time from this species: Dihydroauroglaucin (1), tetrahydroauroglaucin (2), 2-(3,6-dihydroxyhepta-1,4-dien-1-yl)-3,6-dihydroxy-5-(dimethylallyl)benzaldehyde (3), isotetrahydroauroglaucin )4), and flavoglaucin (5). Structure elucidation was carried out using (1H- and 13C-NMR). Fractions and the major isolated compound 1 were evaluated for their antimicrobial and antibiofilm activity. Compound 1 showed high antimicrobial activity against Escherichia coli with minimum inhibitory concentration (MIC) = 1.95 µg/mL, Streptococcus mutans (MIC = 1.95 µg/mL), and Staphylococcus aureus (MIC = 3.9 µg/mL). It exhibited high antibiofilm activity with minimum biofilm inhibitory concentration (MBIC) = 7.81 µg/mL against Staphylococcus aureus and Escherichia coli biofilms and MBIC = 15.63 µg/mL against Streptococcus mutans and Candida albicans and moderate activity (MBIC = 31.25 µg/mL) against Pseudomonas aeruginosa biofilm. This reveals that dihydroauroglaucin, a prenylated benzaldehyde derivative, has a broad spectrum antimicrobial activity. In conclusion, it was observed that the MICs of the FEA are much lower than that of the AME against all susceptible strains, confirming that the antimicrobial activity of Ammi majus may be due to the ability of its endophytic fungi to produce effective secondary metabolites.


2012 ◽  
Vol 531 ◽  
pp. 346-349 ◽  
Author(s):  
Hong Chi Zhang ◽  
Yang Min Ma ◽  
Rui Liu

Within our screening program for antimicrobial materials, eight compounds (1-8) were isolated from an endophytic fungus Fusarium sp. of Eucommia ulmoides. Compound 1, 2, 5-8 were isolated for the first time from endophytic fungi. Their structures were elucidated on the basis of NMR spectroscopic analysis with the reported data in the literature. All compounds showed potent antibacterial and antifungal activities and can be use as new antimicrobial materials.


1994 ◽  
Vol 57 (1) ◽  
pp. 59-61 ◽  
Author(s):  
GERHARD J. HAAS ◽  
RAFFI BARSOUMIAN

The antimicrobial activity of hop resins against Streptococcus salivarius, Staphylococcus aureus (two strains), Bacillus megaterium, Escherichia coli B, and Bacillus subtilis was investigated. However, resistance development was carried out on Streptococcus salivarius, Staphylococcus aureus (two strains), and Bacillus megaterium. The two hop resins used were iso-alpha resin and beta resin. Prior to resistance development, S. salivarius, S. aureus, and B. megaterium were all inhibited by the iso-alpha-hop resin in the 0.01 to 0.03% range. The beta-hop resin which, according to the literature, is more active than the iso-alpha resin initially inhibited these organisms at the 0.003 to 0.01% concentrations. The ease of resistance development varied between the different microbes, B. megaterium being the least prone to develop resistance.


2009 ◽  
Vol 4 (11) ◽  
pp. 1934578X0900401 ◽  
Author(s):  
Shu-Shan Gao ◽  
Xiao-Ming Li ◽  
Bin-Gui Wang

Two new perylene derivatives, 7-epi-8-hydroxyaltertoxin I (1) and 6-epi-stemphytriol (2), along with two known compounds stemphyperylenol (3) and altertoxin I (4) were isolated from Alternaria alternata, a marine endophytic fungus derived from an unidentified algal species of the genus Laurencia. Structures of compounds 1-4 were determined on the basis of detailed spectroscopic analysis, as well as by comparison with literature reports. The antimicrobial activities of compounds 1 and 3 against Staphylococcus aureus, Escherichia coli, and Aspergillus niger were evaluated; neither showed obvious activity.


2018 ◽  
Vol 54 (2C) ◽  
pp. 465
Author(s):  
Cao Duc Tuan

Nine compounds (1-9) were isolated and characterized from the culture broth of the marinebacteria Micromonospora sp. (strain G068), which was isolated from sediment collected at CoTo – Quang Ninh. Their structures were determined by spectroscopic analysis including MS, 1DNMR and 2D NMR, as well as by comparison with reported data in the literature. Allcompounds were evaluated for their antimicrobial activities against a panel of clinicallysignificant microorganisms. Compounds 1, 6, and 9 selectively inhibited Escherichia coli withMIC values of 128, 128 and 64 μg/mL, respectively.


2002 ◽  
Vol 3 (2) ◽  
Author(s):  
R. Z. Da Silva ◽  
E. De M. RIOS ◽  
M. Z. Da SILVA ◽  
L. De F. Leal ◽  
R. A. YUNES ◽  
...  

O presente trabalho envolveu extração, isolamento, purificação e identificação dos constituintes químicos das partes aéreas da Mikania lanuginosa DC (ASTERACEAE). No processo de extração ocorreu a formação de um precipitado, no qual foi isolado e purificado um composto majoritário, que por análises espectroscópicas de IV, RMN 1H, RMN 13C e por comparação com os dados existentes na literatura, foi identificado como sendo o diterpeno ácido caurenóico. Foram realizados ensaios biológicos para avaliar a ação antimicrobiana com o precipitado, extrato etanólico bruto, as frações hexânica, diclorometano, acetato de etila, butanólica e o diterpeno ácido caurenóico contra as cepas Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228 e Bacillus cereus, pela técnica da difusão em meio sólido por cavidade e posteriormente pelo método de diluição em placa. Os resultados demonstraram que as frações hexânica, diclorometano, acetato de etila, butanólica e o ácido caurenóico obtidos da M. lanuginosa, apresentaram atividade antimicrobiana moderada frente as bactérias Gram positivas e foram inativos contra as bactérias Gram negativas. Phytochemical Investigation and Antimicrobial Activity Evaluation of the Mikania lanuginosa DC (ASTERACEAE) Abstract The present study investigated the extraction, isolation and purification the chemical compounds of the aerial parts of Mikania lanuginosa DC (ASTERACEAE). In the process of extraction it occurred the formation of a precipitate, it which was isolated and purified a ruling compound, and by spectroscopic analysis of the IR, 1H NMR, 13C NMR and comparison with reported data in the literature it was identified as being the diterpene kaurenoic acid. It were performed biological assays to estimate the antimicrobial action with the precipited, crude etanolic extract, hexane, dichoromethane, acetate ethyl, butane fractions and diterpene kaurenoic acid contrasting with strains Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228 e Bacillus cereus, by technique of the diffusion in solid mean by cavity and afterwards by the plaque dilution method. The results showed that the hexane, dichoromethane, acetate ethyl, butane fractions and the kaurenoic acid obtained from the Mikania lanuginosa DC presented a moderate antimicrobial activity face to Gram positives bacteria and got inert against the Gram negatives bacteria.


2009 ◽  
Vol 64 (5-6) ◽  
pp. 350-354 ◽  
Author(s):  
Amal H. Aly ◽  
Abdessamad Debbab ◽  
RuAngelie Edrada-Ebel ◽  
Victor Wray ◽  
Werner E. G. Müller ◽  
...  

1A hitherto unidentified endophytic strain of the genus Chaetomium, isolated from the medicinal plant Otanthus maritimus, yielded a new tetrahydrofuran derivative, aureonitolic acid (), along with 5 known natural products, 2 - 6. The structure of 1 was determined by extensive spectroscopic analysis and comparison with reported data. Extracts of the fungus, grown either in liquid culture or on solid rice media, exhibited considerable cytotoxic activity when tested in vitro against L5178Y mouse lymphoma cells. Compounds 2 and 6 showed significant growth inhibition against L5178Y cells with EC50 values of 7.0 and 2.7 μg/mL, respectively, whereas 1 was inactive


Planta Medica ◽  
2013 ◽  
Vol 79 (05) ◽  
Author(s):  
ADC Abergas ◽  
MCQ Aleria ◽  
ZJS Alimagno ◽  
KNC Batac ◽  
AFM De Lara ◽  
...  

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