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1.
Planta Med ; 78(16): 1767-76, 2012 Nov.
Article in English | MEDLINE | ID: mdl-22976482

ABSTRACT

Four known (1, 2, 3, and 6) and three new compounds including a 1,4-diacetyl-2,5-dibenzylpiperazine derivative (4), a quinazolinone-containing indole derivative (5), and a new ester of 2,4-dihydroxy-6-methylbenzoic acid (7) were isolated from the fungus Neosartorya pseudofischeri S. W. Peterson. Compound 2 displayed in vitro growth inhibitory activity that ranged between the activities of etoposide and carboplatin, chosen as reference compounds, in six distinct cancer cell lines. Compound 1 displayed less activity than 2. Computer-assisted phase-contrast microscopy-related analysis revealed that 2 displayed cytostatic, not cytotoxic, effects in human U373 glioblastoma and A549 non-small cell lung cancer apoptosis-resistant cells with marked inhibition of mitotic rates. Cancer cells in the remaining phases of the cell cycle were unchanged. Flow cytometry analysis further confirmed that 2 does not induce apoptotic features in U373 or A549 cancer cells. Thus, 2 represents a novel chemical scaffold from which derivatives for anticancer cytostatic compounds can be derived.


Subject(s)
Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Cytostatic Agents/isolation & purification , Neosartorya/chemistry , Antineoplastic Agents/chemistry , Apoptosis , Carcinoma, Non-Small-Cell Lung/pathology , Cytostatic Agents/chemistry , Cytostatic Agents/pharmacology , Dioxoles/isolation & purification , Dioxoles/pharmacology , Drug Screening Assays, Antitumor , Glioblastoma/pathology , Humans , Inhibitory Concentration 50 , MCF-7 Cells , Magnetic Resonance Spectroscopy , Microscopy, Phase-Contrast/methods , Mitosis/drug effects , Neosartorya/growth & development , Neosartorya/isolation & purification , Pyrazines/isolation & purification , Pyrazines/pharmacology , Pyridines/isolation & purification , Pyridines/pharmacology , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Soil Microbiology
2.
Nat Prod Commun ; 6(6): 807-12, 2011 Jun.
Article in English | MEDLINE | ID: mdl-21815416

ABSTRACT

Chemical investigation of a collection of the fungus Neosartorya glabra from Thailand furnished sartoryglabins A-C (1a, 1b and 2) which are analogs of the reverse prenylated indole alkaloids known as (-) ardeemins. Structures of these compounds were established by NMR spectrometry and an X-ray analysis. Sartoryglabins A-C were evaluated for their in vitro growth inhibitory activity on three human tumor cell lines: MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A375-C5 (melanoma). All the compounds exhibited strong to moderate activity against the MCF-7 cell line but weak or no activity against the NCI-H460 and A375-C5 cell lines. Sartoryglabin B was found to exhibit selectivity towards the MCF-7 cell line.


Subject(s)
Indole Alkaloids/chemistry , Indole Alkaloids/pharmacology , Neosartorya/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Humans , Models, Molecular , Molecular Structure
3.
Mycorrhiza ; 20(7): 459-71, 2010 Oct.
Article in English | MEDLINE | ID: mdl-20107843

ABSTRACT

Three orchid genera, Paphiopedilum, Cymbidium, and Dendrobium, are among the most heavily traded ornamental plants in Thailand. In this study, 27 isolates of Rhizoctonia-like fungi were isolated from root sections of mature orchids in the three orchid genera, collected from diverse horticultural settings in Chiang Mai and Chiang Rai provinces of Thailand. Fungal identification was done by the morphological characterization, the comparison of the internal transcribed spacer and 5.8S ribosomal DNA sequences, and the phylogenetic analysis. Epulorhiza repens was found to be the most common species found in the roots of various species of all three orchid genera, whereas Epulorhiza calendulina-like isolates were strictly found in the roots of Paphiopedilum species. We have also isolated and described an anamorph of Tulasnella irregularis, four new anamorphic species in the genus Tulasnella, and a new anamorphic species in the family Tulasnellaceae. Our study provides information on diversity of root-associated fungi of the orchid genera and at the sampling sites that were rarely addressed in the previous studies.


Subject(s)
Biodiversity , Orchidaceae/microbiology , Rhizoctonia/classification , Rhizoctonia/isolation & purification , DNA, Fungal/chemistry , DNA, Fungal/genetics , DNA, Ribosomal/chemistry , DNA, Ribosomal/genetics , DNA, Ribosomal Spacer/chemistry , DNA, Ribosomal Spacer/genetics , Genes, rRNA , Molecular Sequence Data , Phylogeny , Plant Roots/microbiology , RNA, Fungal/genetics , RNA, Ribosomal, 5.8S/genetics , Rhizoctonia/cytology , Rhizoctonia/genetics , Sequence Analysis, DNA , Thailand
4.
J Nat Prod ; 70(7): 1200-2, 2007 Jul.
Article in English | MEDLINE | ID: mdl-17536857

ABSTRACT

Chemical study of a previously undescribed fungus, Talaromyces thailandiasis, furnished the two new merodrimanes thailandolides A (1) and B (2), an O-methylated derivative (3) of the aromatic fragment incorporated in thailandolide B, and three known closely related 1(3H)-isobenzofuran derivatives, penisimplicissin (4a), vermistatin (4b), and hydroxydihydrovermistatin (4c). Structures were established by spectroscopic measurements and confirmed by X-ray analyses of compounds 1 and 4b. The unusual peptide analogue N-benzoylphenylalanyl-N-benzoylphenyl alaninate (5) isolated earlier from a higher plant was also found.


Subject(s)
Sesquiterpenes/isolation & purification , Talaromyces/chemistry , Crystallography, X-Ray , Molecular Conformation , Molecular Structure , Sesquiterpenes/chemistry , Thailand
5.
Planta Med ; 72(10): 957-60, 2006 Aug.
Article in English | MEDLINE | ID: mdl-16902873

ABSTRACT

The oligophenalenone dimer duclauxin and two new analogues, bacillisporins D and E, were isolated from the fungus TALAROMYCES BACILLISPORUS in addition to the previously reported bacillisporins A, B and C. Structures were established by spectroscopic studies. Duclauxin and bacillisporins A, B, C and E were evaluated for cytotoxicity against three human cancer cell lines. Bacillisporin A was strongly active against MCF-7 and NCI-H460 and moderately active against SF-268 while bacillisporins B, C and duclauxin were moderately active against all three cell lines.


Subject(s)
Cytotoxins/toxicity , Phenalenes/chemistry , Phenalenes/toxicity , Talaromyces/chemistry , Cell Line, Tumor , Chromones/chemistry , Chromones/isolation & purification , Chromones/toxicity , Cytotoxins/chemistry , Cytotoxins/isolation & purification , Dimerization , Humans , Nuclear Magnetic Resonance, Biomolecular , Phenalenes/isolation & purification
6.
Mycol Res ; 109(Pt 5): 581-9, 2005 May.
Article in English | MEDLINE | ID: mdl-16018312

ABSTRACT

Phylogenetic relationships of Paecilomyces sect. Isarioidea species were analysed using the beta-tubulin gene and ITS rDNA. Maximum parsimony analyses showed that the section does not form a natural taxonomic group and is polyphyletic within the Hypocreales. However, a group was recognized, designated as the Isaria clade, to be monophyletic comprising of the following Paecilomyces species: P. amoeneroseus, P. cateniannulatus, P. cateniobliquus, P. cicadae, P. coleopterorus, P. farinosus, P. fumosoroseus, P. ghanensis, P. javanicus and P. tenuipes. Some of these species have teleomorphs in Cordyceps.


Subject(s)
Paecilomyces/classification , Paecilomyces/genetics , Cordyceps/classification , Cordyceps/genetics , DNA Transposable Elements , DNA, Ribosomal/genetics , Genes, Fungal , Molecular Sequence Data , Phylogeny , Species Specificity , Tubulin/genetics
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