scholarly journals Bioactive Aromatic Derivatives from Endophytic Fungus, Cytospora sp

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.

Author(s):  
Kai-Liang Ma ◽  
Shi-Hui Dong ◽  
Hang-Ying Li ◽  
Wen-Jun Wei ◽  
Yong-Qiang Tu ◽  
...  

Abstract Three previously undescribed cytochalasins, named xylariasins A‒C (1‒3), together with six known ones (4‒9) were isolated from Xylaria sp. CFL5, an endophytic fungus of Cephalotaxus fortunei. The chemical structures of all new compounds were elucidated on the basis of extensive spectroscopic data analyses and electronic circular dichroism calculation, as well as optical rotation calculation. Biological activities of compounds 1, 4‒9 were evaluated, including cytotoxic, LAG3/MHC II binding inhibition and LAG3/FGL1 binding inhibition activities. Compounds 6 and 9 possessed cytotoxicity against AGS cells at 5 μM, with inhibition rates of 94% and 64%, respectively. In addition, all tested isolates, except compound 6, exhibited obvious inhibitory activity against the interaction of both LAG3/MHC II and LAG3/FGL1. Compounds 1, 5, 7, and 8 inhibited LAG3/MHC II with IC50 values ranging from 2.37 to 4.74 μM. Meanwhile, the IC50 values of compounds 1, 7, and 8 against LAG3/FGL1 were 11.78, 4.39, and 7.45 μM, respectively. Graphic Abstract


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.


2014 ◽  
Vol 14 (3) ◽  
pp. 290-296 ◽  
Author(s):  
Muharni Muharni ◽  
Fitrya Fitrya ◽  
Milanti Okta Ruliza ◽  
Dwi Anjar Susanti ◽  
Elfita Elfita

Two compounds from cultivation of the endophytic fungi Penicillium sp of leaves of kunyit putih (Curcuma zedoaria have been isolated. The endophytic fungus was cultivated on 5 L of Potatos Dextrose Broth (PDB) medium at room temperature (no shaking) for 3 weeks. The cultures were extracted with ethyl acetate to afford 3.0 g of residue after removal of the solvent under reduced pressure. The extract was separated and purified by silica gel column chromatography (CC) and afforded two pure compounds as colorless oily liquid (compound 1) and yellow crystal (compound 2). The structure of these compounds were characterized by detailed UV, IR, and NMR spectroscopic analysis and compound 1 as well as comparison with the reported data. Base on spectra analysis the compound 1 was determined as Di-(2-ethylhexyl)phthalate and compound 2 as 5-(4’-ethoxy-2’-hydroxy-5’-methyl-2’,3’-dihydrofuran-3’-il (hydroxy) methyl-4-isopropyl-3-methyl-2-pyran-2-on). Compound 1 is not new compound, but it is new for endophytic fungus from C. zeodoria and compound 2 is new compound.


2012 ◽  
Vol 7 (3) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Hidayat Hussain ◽  
Karsten Krohn ◽  
Barbara Schulz ◽  
Siegfried Draeger ◽  
Mamona Nazir ◽  
...  

Two new acaranoic acids, named seimatoporic acid A and B (1, and 2), together with six known compounds, R-(-)-mellein (3), cis-4-hydroxymellein (4), trans-4-hydroxymellein (5), 4R-hydroxy-5-methylmellein (6), (-)-5-hydroxymethylmellein (7), and ergosterol (8) were isolated from an endophytic fungus, Seimatosporium sp, by a bioassay-guided procedure. The structures of the new compounds have been assigned from analysis of the 1H and 13C NMR spectra, DEPT, and by 2D COSY, HMQC, HMBC and NOESY experiments. A mixture of compounds 1 and 2 showed strong antifungal activity against Botrytis cinerea, Septoria tritici, and Pyricularia oryzae.


Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1828
Author(s):  
Zhi-Bin Zhang ◽  
Si-Yao Du ◽  
Bo Ji ◽  
Chang-Jiu Ji ◽  
Yi-Wen Xiao ◽  
...  

Three new helvolic acid derivatives (named sarocladilactone A (1), sarocladilactone B (2) and sarocladic acid A (3a)), together with five known compounds (6,16-diacetoxy-25-hy- droxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (3b), helvolic acid (4), helvolinic acid (5), 6-desacetoxy-helvolic acid (6) and 1,2-dihydrohelvolic acid (7)), were isolated from the endophytic fungus DX-THL3, obtained from the leaf of Dongxiang wild rice (Oryza rufipogon Griff.). The structures of the new compounds were elucidated via HR-MS, extensive 1D and 2D NMR analysis and comparison with reported data. Compounds 1, 2, 4, 5, 6 and 7 exhibited potent antibacterial activities. In particular, sarocladilactone B (2), helvolinic acid (5) and 6-desacetoxy-helvolic acid (6) exhibited strongly Staphylococcus aureus inhibitory activity with minimum inhibitory concentration (MIC) values of 4, 1 and 4 μg/mL, respectively. The structure–activity relationship (SAR) of these compounds was primarily summarized.


2020 ◽  
Vol 15 (12) ◽  
pp. 1934578X2098522
Author(s):  
Xian Zhang ◽  
Fa-Lei Zhang ◽  
Xing Wu ◽  
Ke Ye ◽  
Xiao Lv ◽  
...  

A previously undescribed polyketide (1) and 3 known analogs (2-4) were obtained from cultures of the potato endophytic fungus Aspergillus carneus. The structures were elucidated on the basis of extensive nuclear magnetic resonance spectroscopic data. The absolute configuration of 1 was further determined by electronic circular dichroism and optical rotation calculations. Compounds 1-4 showed moderate antifungal activity against plant pathogens. Compounds 1, 2, and 4 inhibited nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells, with half-maximal inhibitory concentration values of 13.36, 30.16, and 51.47 µM, respectively. Compound 4 showed effective antioxidant activity.


Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2448
Author(s):  
Jun Wang ◽  
Hongshuai Yang ◽  
Yang Liu ◽  
Kelsang Norbo ◽  
Kewu Zeng ◽  
...  

Eight azukisapogenol triterpene glycosides, including five new compounds, oxychiliotriterpenosides A–E (1–5), two new methyl glucuronide derivatives that proved to be artifacts, oxychiliotriterpenoside E-glucuronic acid methyl ester (6) and myrioside B-glucuronic acid methyl ester (7), and a known one, myrioside B (8), was isolated from the aerial part of Oxytropis chiliophylla Royle. Their structures were elucidated based on extensive spectroscopic analyses and chemical methods. Triterpene glycosides were first obtained from O. chiliophylla, and those containing a galactose unit (1, 2, 5 and 6) and diglucosidic or triglucosidic linkage at C-29 (1–4), were reported from Oxytropis species for the first time, which might be recognized as a chemotaxonomic feature of O. chiliophylla. All isolated compounds were evaluated for their anti-inflammatory activities against NO production using lipopolysaccharide (LPS)-induced RAW 264.7 cells, but no compounds showed potent inhibition on NO production.


RSC Advances ◽  
2019 ◽  
Vol 9 (49) ◽  
pp. 28754-28763 ◽  
Author(s):  
Fei Peng ◽  
Shao-Yang Hou ◽  
Tian-Yuan Zhang ◽  
Ying-Ying Wu ◽  
Meng-Yue Zhang ◽  
...  

Two new compounds chetoseminudin F (1) and G (2) together with eleven known compounds were isolated from the solid fermentation products of the endophytic fungus Chaetomium sp. SYP-F7950.


2017 ◽  
Vol 55 (2) ◽  
pp. 188
Author(s):  
Nguyen Thi Mai

From the methanol extract of Bischofia javanica leaves, five compounds including 5'-b-D-glucopyranosyloxyjasmonic acid methyl ester (1), 2-(4-hydroxy-3-methoxyphenyl)ethyl-O-β-D-glucopyranoside (2), hexyl-O-β-D-glucopyranoside (3), friedelan-3-one (4), and gallic acid (5) were isolated. Their structures were elucidated by NMR spectra as well as in comparison with previous reported data. This is the first report of 1 and 2 from Bischofia javanica.


2015 ◽  
Vol 10 (10) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Fang Lv ◽  
Georgios Daletos ◽  
Wenhan Lin ◽  
Peter Proksch

Two new cyclic depsipeptides, W493 C (1) and D (2), along with two known derivatives W493 A (3) and B (4) were obtained from the endophytic fungus Fusarium sp. isolated from the Mangrove plant Ceriops tagal. The structures of the new compounds were determined on the basis of one- and two dimensional NMR and high-resolution mass spectroscopic data. The absolute configurations of the amino acid residues of 1 and 2 were confirmed by application of Marfey's method. W493 A (3) and B (4) exhibited moderate activity against the fungus Cladosporium cladosporiodes and weak antitumor activity against the human ovarian cancer cell line A2780.


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