Aspernolides A and B, butenolides from a marine-derived fungus Aspergillus terreus

Parvatkar, Rajesh Ramnath; D’Souza, Celina; Tripathi, Ashootosh; Naik, C.G.

doi:10.1016/j.phytochem.2008.10.017

Cited by 117 publications

(79 citation statements)

References 17 publications

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“…The structures of 1-6 were shown in Figure 1, and the 1 H and 13 C NMR data of the compounds 1 and 2 were listed in Table 1. By comparing with the literature, the known compounds were identified as aspernolide E (3), 15 4-(4-hydroxyphenyl)-5-(4-hydroxyphenylmethyl)-2-hydroxyfurane-2-one (4), 16 aspernolide B (5), 14 and butyrolactone I (6).…”

Section: Resultsmentioning

confidence: 99%

Butyrolactones Derivatives from the Fermentation Products of an Endophytic Fungus Aspergillus versicolor

Ye¹,

Xia²,

Yang³

et al. 2014

Bulletin of the Korean Chemical Society

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Two new butyrolactones, asperphenol A (1) and B (2), together with four known butyrolactones (3-6) were isolated from the fermentation products of an endophytic fungus Aspergillus versicolor. Their structures were elucidated by spectroscopic methods including extensive 1D-and 2D-NMR techniques. Compounds 1-6 were also tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compound 2 exhibited high anti-TMV activity with inhibition rate of 46.7%. The other compounds also exhibited potential anti-TMV activities with inhibition rates in the range of 21.8-28.4%.

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Section: Resultsmentioning

confidence: 99%

Butyrolactones Derivatives from the Fermentation Products of an Endophytic Fungus Aspergillus versicolor

Ye¹,

Xia²,

Yang³

et al. 2014

Bulletin of the Korean Chemical Society

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“…Because of the structural similarity of furandiones 1 and 2 with butenolides such as butyrolactone I-IV, 15,16) aspernolides A and B, 17) which were also isolated form A. terreus, the biosynthetic pathway for the two furandiones was probably similar with those of butenolides. The reported feeding experiments on the biosynthesis of xenofuranones A and B 18) and butyrolactone I 19) have shown that these butenolide derivatives were produced via condensation of α-ketocarboxylic acids such as phenylpyruvic acid and p-hydroxyphenylpyruvic acid.…”

Section: Resultsmentioning

confidence: 99%

Furandiones from an Endophytic <i>Aspergillus terreus</i> Residing in <i>Malus halliana</i>

Qiao

2012

Chem. Pharm. Bull.

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Two new furandiones named asperterone B (1) and C (2) together with four known metabolites (3-6) were isolated from the liquid culture of the endophytic fungus Aspergillus terreus MHL-P22 residing in the fresh leaves of Malus halliana. The structures of the new compounds were elucidated by analysis of their MS, IR, 1D-and 2D-NMR spectra. 1 and 2 showed moderate cytotoxic activities against human colorectal carcinoma SW1116 cells with IC 50 values of 57.5 and 71.0 µM, respectively. The biosynthetic pathway for 1, 2 and their analogues was also postulated and briefly discussed.

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“…On marine Aspergillus alone, there have been a large number of documents about producer strains of antitumor compounds with highly diverse structural types such as polyketides, peptides, alkaloids, terpenoids and lipids [20][21][22][23][24]. The reported producers include Asp.…”

Section: Relationship Between Systematics and Biological Potentialmentioning

confidence: 99%

Biological and chemical diversity of cytotoxin-producing symbiotic marine fungi in intertidal zone of Dalian

Zhang

Feng

et al. 2012

Chin. Sci. Bull.

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In this study, the biological and chemical diversity of 8 symbiotic marine fungal strains, with strong cytotoxicity against brine shrimp larvae, were investigated by nucleotide sequencing, morphology and cluster analysis of HPTLC fingerprint. These strains were identified by ITS rDNA sequencing, phylogenic analysis, and morphology to be Hypocrea lixii, Chaetomium globosum, Aspergillus fumigatus, Asp. clavatus and Alternaria sp. Their differences in secondary metabolites were shown by cluster analysis of digitalized colors of HPTLC spots, a newly developed method, which produced a similar dendrogram with that of ITS cluster analysis. Furthermore, this method can fully display intraspecific differences and even the remarkable difference in Aspergillus strains which goes beyond the boundary between genera. Their biological-chemical diversity may be the basis of their potent cytotoxicity and implies their potential in producing diversified antitumor or pesticidal constituents. Symbiotic fungi live on the surface or in the inner tissue of their hosts. Some terrestrial symbiotic fungi have been found to produce toxins or anti-feedants to protect their hosts from predators and grazers [1]. Some of these compounds can be used as antitumor or pesticidal agents. Symbiotic marine fungi have been isolated from seaweeds, sponges, corals, mangroves and sea grasses, also showing taxonomicall diversity and producing numerous active compounds [2]. The intertidal coastline of Dalian possesses diversified natural and artificial habitats and also high biodiversity of marine plants, invertebrates, and microorganisms. In our screening for useful cytotoxins from local symbiotic marine fungi using brine shrimp lethality test, a widely used bifunctional preliminary screening model to discover antitumor drugs and pesticides from the sea [3][4][5], eight strains with potent activities were discovered. Herein, we report the study on the biological and chemical diversity of these bioactive strains by ITS rDNA sequence analysis, morphology, and metabolite fingerprinting using a new cluster method.

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Aspernolides A and B, butenolides from a marine-derived fungus Aspergillus terreus

Cited by 117 publications

References 17 publications

Butyrolactones Derivatives from the Fermentation Products of an Endophytic Fungus Aspergillus versicolor

Butyrolactones Derivatives from the Fermentation Products of an Endophytic Fungus Aspergillus versicolor

Furandiones from an Endophytic <i>Aspergillus terreus</i> Residing in <i>Malus halliana</i>

Biological and chemical diversity of cytotoxin-producing symbiotic marine fungi in intertidal zone of Dalian

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