Isolation of a new secalonic acid

Howard, Colin C.; Johnstone, R. A. W.; Entwistle, Ian D.

doi:10.1039/c39730000464

Cited by 10 publications

(9 citation statements)

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“…[9] Combining all the data together suggested the absolute configuration as (5 S ,6 R ,10a S ,5′ S ,6′ R ,10a′ S ), (5 R ,6 R ,10a S ,5′ R ,6′ R ,10a′ S ), and (5 R ,6 R ,10a S ,5′ S ,6′ R ,10a′ S ) for compounds 1 – 3 , respectively. Consequently, compounds 1 – 3 were identified as secalonic acid A, [10] secalonic acid E, [11] and secalonic acid G, [12] respectively, in accordance with published data (Table S2). Most literature pertaining to these compounds dates back to the 1960s and 1970s, and therefore, the 1 H and 13 C NMR data for 1 – 3 were provided in the Supporting Information (Figures S2–S4, Table S1).…”

Section: Resultssupporting

confidence: 86%

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

et al. 2014

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Sixteen polyketides belonging to diverse structural classes, including monomeric/dimeric tetrahydroxanthones and resorcylic acid lactones, were isolated from an organic extract of a fungal culture Setophoma terrestris (MSX45109) using bioactivity-directed fractionation as part of a search for anticancer leads from filamentous fungi. Of these, six were new: penicillixanthone B (5), blennolide H (6), 11-deoxy blennolide D (7), blennolide I (9), blennolide J (10), and pyrenomycin (16). The known compounds were: secalonic acid A (1), secalonic acid E (2), secalonic acid G (3), penicillixanthone A (4), paecilin B (8), aigialomycin A (11), hypothemycin (12), dihydrohypothemycin (13), pyrenochaetic acid C (14), and nidulalin B (15). The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 1–10 were determined using ECD spectroscopy combined with time-dependent density functional theory (TDDFT) calculations, while a modified Mosher’s ester method was used for compound 16. The cytotoxic activities of compounds (1–15) were evaluated using the MDA-MB-435 (melanoma) and SW-620 (colon) cancer cell lines. Compounds 1, 4, and 12 were the most potent with IC50 values ranging from 0.16 to 2.14 μM. When tested against a panel of bacteria and fungi, compounds 3 and 5 showed promising activity against the Gram-positive bacterium Micrococcus luteus with MIC values of 5 and 15 μg/mL, respectively.

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Section: Resultssupporting

confidence: 86%

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

et al. 2014

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“…Only secalonic acid A ( 2 ) exhibited P388 cancer cell inhibitory activity (ED 50 3.5 μg/mL), and the supply was not sufficient for human cancer cell line evaluation. Secalonic acid A, isolated mainly from fungi, , was previously reported to inhibit growth of the murine L1210 lymphocytic leukemia cell line . The other six compounds were inactive against both P388 and human cancer cell lines.…”

Section: Resultsmentioning

confidence: 99%

Isolation and Structure of Ruprechstyril from Ruprechtia tangarana^†,1

et al. 2003

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Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2'-O-methylevernic acid (3), 3,3',4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3beta,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.

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“…A number of papers followed in the 1950s to 1970s, over which time more secalonic acids were isolated and structurally elucidated. In addition, various members of the family have been isolated from other fungi, including Aspergillus ochraceus (SAA = secalonic acid A), Aspergillus aculeatus (SAB, SAD, SAF), , Aspergillus japonicus (SAF), Penicillium oxalicum (SAD), Phoma terrestris (SAA, SAE), , Pyrenochaeta terrestris (SAA, SAE, SAG), Paecilomyces sp. (SAD), and, of course, C. purpurea (SAA, SAB, SAC). − Secalonic acids have also been found in lichens, including Diploicia canescens (SAB, SAD, SAF), Physiconia distorta (SAA), Parmelia entotheichochroa (SAA), Pseudoparmelia hypomiltha (SAA), Cetraria ornate (SAA), Gliocladium sp.…”

Section: Dimers and Heterodimersmentioning

confidence: 99%

Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

2012

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The majority of xanthones reported from fungi, bacteria, and lichens, and particularly those reported relatively early on, have a monomeric and fully aromatized structure. These include arthothelin, asemone, asperxanthone, austocystins, bikaverin, chaetoxanthones, chodatin, conioxanthone A, erythrommone, emericellin, globosuxanthones C and D, griseoxanthone C, lichexanthones and norlichexanthones, Microsphaeropsis xanthones, mycoxanthone, Phoma and Phomopsis xanthones, pinselin and pinselic acid, sterigmatocystins, tajixanthone, thiomelin, thiophanic acid, thiophaninic acid, thuringione, umbilicaxanthones, vinetorin, varixanthone, vertixanthone, and Wardomyces and Xylaria xanthones.Arthothelin. Santesson reported observing this compound in the mass-spectral analysis of the lichen Leconora reuteri. 65 Arthothelin (2,4,5-trichloronorlichexanthone, 19, Figure 2) has

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Isolation of a new secalonic acid

Cited by 10 publications

References 0 publications

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

Isolation and Structure of Ruprechstyril from Ruprechtia tangarana^†,1

Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

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Isolation of a new secalonic acid

Cited by 10 publications

References 0 publications

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

Isolation and Structure of Ruprechstyril from Ruprechtia tangarana†,1

Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

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Isolation and Structure of Ruprechstyril from Ruprechtia tangarana^†,1