2009
DOI: 10.1002/ejoc.200801083
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Pseudoanguillosporin A and B: Two New Isochromans Isolated from the Endophytic Fungus Pseudoanguillospora sp.

Abstract: Two new isochromans named pseudoanguillosporin A (2a) and B (3), together with the known cephalochromin (1), were isolated from Pseudoanguillospora sp. The C‐2 absolute configuration of 2a and 3 was deduced from its CD spectrum by the isochroman helicity rule, supported by TDDFT CD calculations. The absolute configuration of the sec‐hydroxyl group of 3 was determined by the Mosher NMR method from the MPA esters of its methylated derivative. The axial chirality of 1 was assigned through exciton analysis of its … Show more

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Cited by 48 publications
(46 citation statements)
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“…Both ustilaginoidins D (20) and E (21) exhibited strong cytotoxicity on KB cells by inhibiting biosynthesis of nucleic acid and protein [2]. Ustilaginoidin A (15) also inhibited ATP synthesis in mitochondria by uncoupling oxidative phosphorylation and depressing state-3 respiration of mitochondria [55].…”
Section: Cytotoxic and Antitumor Activitymentioning
confidence: 99%
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“…Both ustilaginoidins D (20) and E (21) exhibited strong cytotoxicity on KB cells by inhibiting biosynthesis of nucleic acid and protein [2]. Ustilaginoidin A (15) also inhibited ATP synthesis in mitochondria by uncoupling oxidative phosphorylation and depressing state-3 respiration of mitochondria [55].…”
Section: Cytotoxic and Antitumor Activitymentioning
confidence: 99%
“…Isochaetochromin B 2 (6) and ustilaginoidin D (20) isolated from the sponge-derived fungus Metarhizium anisopliae mxh-99 exhibited anti-tubercular activity with MIC values of 50.0 μg/mL [16]. 8'-O-Demethylnigerone (57) and 8'-O-demethylisonigerone (58) from the marine-derived Aspergillus carbonarius also showed weak anti-tubercular activity against Mycobacterium tuberculosis H37Rv with MIC values of 43.0 and 21.5 μM, respectively [7].…”
Section: Antimicrobial Activitymentioning
confidence: 99%
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“…The first alternative is isochroman pseudoanguillosporin B, showing the strong antimicrobial activity. [20] The second option is embelin, undecylcyclohexadiene substituted by hydroxy and keto groups, showing in vivo antitumor, anti-inflammatory [21] and antioxidant activity. [22][ 23] In the same algae strain, bengazole C with antitumor, antibiotic and anthelmintic properties [24] was found in the semi-polar extract.…”
Section: U-hplc/hr-ms/ms Non-target Screening and Tentative Compoundsmentioning
confidence: 99%
“…Secalonic acid A (4) 23,24 was obtained from a culture of Setophoma terrestris (NRRL 25008) obtained as a colonist of an Aspergillus f lavus sclerotium that was buried in sandy field soil near Kilbourne, IL. Cephalochromin (5) 19,20,25,26 was obtained from a culture of Cosmospora sp. (syn.…”
mentioning
confidence: 99%