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1.
J Asian Nat Prod Res ; 20(4): 328-336, 2018 Apr.
Article in English | MEDLINE | ID: mdl-28631515

ABSTRACT

One pair of new cyclopentaisochromenone derivatives, (+)-(S)-6-hydroxy-1,8-dimethoxy-3a-methyl-3,3a-dihydrocyclopenta[c]isochromene-2,5-dione (1a) and (-)-(R)-6-hydroxy-1,8-dimethoxy-3a-methyl-3,3a-dihydrocyclopenta[c]isochromene-2,5-dione (1b), together with seven known analog 2‒8, were isolated from a rice solid culture of the endophytic fungus Alternaria sp. TNXY-P-1, obtained from fresh leaf of Arisaema heterophyllum. Their structures were elucidated on the basis of detailed 1D, 2D NMR, and HRESIMS analysis. Among them, compounds 1a and 1b were enantiomers separated from 1 by chiral HPLC. The absolute configurations of 1a and 1b were assigned by quantum chemical calculations of the electronic circular dichroic spectra. All isolated compounds were evaluated for cytotoxic activities. Interestingly, enantiomers (+)-1a and (-)-1b showed distinct selective antitumor activities against HL-60 cell lines with IC50 values of >200, 75.3 µM, respectively.


Subject(s)
Alternaria/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Benzopyrans/isolation & purification , Benzopyrans/pharmacology , Antineoplastic Agents/chemistry , Arisaema/microbiology , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Lactones/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Stereoisomerism
2.
Appl Microbiol Biotechnol ; 93(3): 1231-9, 2012 Feb.
Article in English | MEDLINE | ID: mdl-21814808

ABSTRACT

Through bioassay-guided fractionation, the EtOAc extract of a culture broth of the endophytic fungus Phoma species ZJWCF006 in Arisaema erubescens afforded a new α-tetralone derivative, (3S)-3,6,7-trihydroxy-α-tetralone (1), together with cercosporamide (2), ß-sitosterol (3), and trichodermin (4). The structures of compounds were established on the basis of spectroscopic analyses. Compounds 1, 2, and 3 were obtained from Phoma species for the first time. Additionally, the compounds were subjected to bioactivity assays, including antimicrobial activity, against four plant pathogenic fungi (Fusarium oxysporium, Rhizoctonia solani, Colletotrichum gloeosporioides, and Magnaporthe oryzae) and two plant pathogenic bacteria (Xanthomonas campestris and Xanthomonas oryzae), as well as in vitro antitumor activities against HT-29, SMMC-772, MCF-7, HL-60, MGC80-3, and P388 cell lines. Compound 1 showed growth inhibition against F. oxysporium and R. solani with EC50 values of 413.22 and 48.5 µg/mL, respectively. Additionally, compound 1 showed no cytotoxicity, whereas compound 2 exhibited cytotoxic activity against the six tumor cell lines tested, with IC50 values of 9.3 ± 2.8, 27.87 ± 1.78, 48.79 ± 2.56, 37.57 ± 1.65, 27.83 ± 0.48, and 30.37 ± 0.28 µM, respectively. We conclude that endophytic Phoma are promising sources of natural bioactive and novel metabolites.


Subject(s)
Anti-Bacterial Agents/metabolism , Antifungal Agents/metabolism , Antineoplastic Agents/metabolism , Arisaema/microbiology , Ascomycota/metabolism , Endophytes/metabolism , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Ascomycota/growth & development , Ascomycota/isolation & purification , Benzofurans/chemistry , Benzofurans/metabolism , Benzofurans/pharmacology , Cell Line, Tumor/drug effects , Culture Media, Conditioned/chemistry , Endophytes/growth & development , Endophytes/isolation & purification , Fungi/drug effects , HL-60 Cells/drug effects , HT29 Cells/drug effects , Humans , Medicine, Chinese Traditional , Plant Diseases/microbiology , Sitosterols/chemistry , Sitosterols/metabolism , Sitosterols/pharmacology , Species Specificity , Tetralones/chemistry , Tetralones/metabolism , Tetralones/pharmacology , Trichodermin/chemistry , Trichodermin/metabolism , Trichodermin/pharmacology , Xanthomonas/drug effects
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