New antitumour fungal metabolites from<i>Alternaria porri</i>

Phuwapraisirisan, Preecha; Rangsan, Jakaphan; Siripong, Pongpun; Tip‐pyang, Santi

doi:10.1080/14786410802265415

Cited by 38 publications

(32 citation statements)

References 10 publications

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“…[5, 23,24,37] However, their axial chirality has not yet been assigned. Regarding their biaryl chromophoric system, 6 and 7 show close similarity to 2, which also has a 5 monomeric unit but the other monomer is fully conjugated.…”

Section: Resultsmentioning

confidence: 99%

New Anthracene Derivatives – Structure Elucidation and Antimicrobial Activity

et al. 2012

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Three new anthracene derivatives, which include tetrahydroanthraquinone 1 and two tetrahydroanthraquinone heterodimers 2 and 3, were isolated from Stemphylium globuliferum, together with four known metabolites 4-7. Detailed analysis of the spectroscopic data allowed the unambiguous determination of the structures of 1 and 2 and a revision of the structure of alterporriol C and its atropisomer. Furthermore, alterporriol G, previously obtained as part of a mixture, was isolated in its pure form for the first time and its structure was also revised. The absolute configurations of 1, 2 and 3 were assigned by calculation of their CD spectra, which also allowed the configurational assignment of altersolanol A and the determination of the axial chirality of alterporriols D and E. All isolated compounds were analysed for their antimicrobial and cytotoxic activities. Compounds 1 and 5 inhibited the growth of most pathogenic microorganisms tested, whereas 2, 6 and 7 showed selective inhibition of bacteria but were inactive against fungi. Three new anthracene derivatives and four known metabolites were isolated from the extract of the endophytic Stemphylium globuliferum. The structures were determined by comprehensive NMR spectroscopy and MS, and the absolute configurations by TDDFT and ZINDO methods. All isolated compounds were tested for their cytotoxic and antimicrobial activities

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Section: Resultsmentioning

confidence: 99%

New Anthracene Derivatives – Structure Elucidation and Antimicrobial Activity

et al. 2012

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“…Eight compounds were isolated from this fungal strain, including two alterporriol-type dimers, the relative and absolute configurations of which were established by using spectral and theoretical methods. The novel compound, alterporriol S ( 1 ), was the first member of alterporriols with a unique C-10−C-2′ linkage [20,22,23,26,27,28,29,30,31,32,33]. Anthranoid dimers consisting of such a coupling type could only be found in a small population of terrestrial plants [14,15,34,35,36,37,38,39,40,41,42,43] and marine animal [44]; this was the first report of a fungus origin.…”

Section: Discussionmentioning

confidence: 99%

Alterporriol-Type Dimers from the Mangrove Endophytic Fungus, Alternaria sp. (SK11), and Their MptpB Inhibitions

Xia

et al. 2014

Marine Drugs

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A new alterporriol-type anthranoid dimer, alterporriol S (1), along with seven known anthraquinone derivatives, (+)-aS-alterporriol C (2), hydroxybostrycin (3), halorosellinia A (4), tetrahydrobostrycin (5), 9α-hydroxydihydrodesoxybostrycin (6), austrocortinin (7) and 6-methylquinizarin (8), were isolated from the culture broth of the mangrove fungus, Alternaria sp. (SK11), from the South China Sea. Their structures and the relative configurations were elucidated using comprehensive spectroscopic methods, including 1D and 2D NMR spectra. The absolute configurations of 1 and the axial configuration of 2 were defined by experimental and theoretical ECD spectroscopy. 1 was identified as the first member of alterporriols consisting of a unique C-10−C-2′ linkage. Atropisomer 2 exhibited strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with an IC50 value 8.70 μM.

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“…porri producing alterporriol F and plant endophytic Alternaria sp. producing 5 compounds against cancer cells [38,39].…”

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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New antitumour fungal metabolites fromAlternaria porri

Cited by 38 publications

References 10 publications

New Anthracene Derivatives – Structure Elucidation and Antimicrobial Activity

New Anthracene Derivatives – Structure Elucidation and Antimicrobial Activity

Alterporriol-Type Dimers from the Mangrove Endophytic Fungus, Alternaria sp. (SK11), and Their MptpB Inhibitions

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

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