Dictyosphaeric Acids A and B:  New Decalactones from an Undescribed Penicillium sp. Obtained from the Alga Dictyosphaeria versluyii

Bugni, Tim S.; Janso, Jeffrey E.; Williamson, R. Thomas; Feng, Xun; Bernan, Valerie S.; Greenstein, Michael; Carter, Guy T.; Maiese, William M.; Ireland, Chris M.

doi:10.1021/np049973t

Cited by 42 publications

(39 citation statements)

References 11 publications

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“…However, the subject of marine fungi is of much debate as most marine isolates have been found in mangrove and intertidal zones [4,10,11], rather than in true marine habitats; thus, no strict definition of “true marine fungi” currently exists [12]. Nonetheless, marine-derived fungal strains have yielded a plethora of biologically active compounds [5,13], with isolates of Penicillium and Aspergillus as the most common sources. These have mainly been isolated from substrates such as driftwood [14] and macroalgae [15], but also in deep-sediments [3,16,17].…”

Section: Introductionmentioning

confidence: 99%

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

et al. 2014

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In drug discovery, reliable and fast dereplication of known compounds is essential for identification of novel bioactive compounds. Here, we show an integrated approach using ultra-high performance liquid chromatography-diode array detection-quadrupole time of flight mass spectrometry (UHPLC-DAD-QTOFMS) providing both accurate mass full-scan mass spectrometry (MS) and tandem high resolution MS (MS/HRMS) data. The methodology was demonstrated on compounds from bioactive marine-derived strains of Aspergillus, Penicillium, and Emericellopsis, including small polyketides, non-ribosomal peptides, terpenes, and meroterpenoids. The MS/HRMS data were then searched against an in-house MS/HRMS library of ~1300 compounds for unambiguous identification. The full scan MS data was used for dereplication of compounds not in the MS/HRMS library, combined with ultraviolet/visual (UV/Vis) and MS/HRMS data for faster exclusion of database search results. This led to the identification of four novel isomers of the known anticancer compound, asperphenamate. Except for very low intensity peaks, no false negatives were found using the MS/HRMS approach, which proved to be robust against poor data quality caused by system overload or loss of lock-mass. Only for small polyketides, like patulin, were both retention time and UV/Vis spectra necessary for unambiguous identification. For the ophiobolin family with many structurally similar analogues partly co-eluting, the peaks could be assigned correctly by combining MS/HRMS data and m/z of the [M + Na]+ ions.

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Section: Introductionmentioning

confidence: 99%

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

et al. 2014

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“…; Penicillium canescens Fungus [12][13][14] Unnamed nonanolides 10-12 Cordyceps militaris (BCC 2816) Entomopathogenic fungus [29] Dictyosphaeric acids A, B (59, 60) Penicillium sp. (F01V25) Fungus [30] 8-O-Acetylmultiplolide A (13) 8-O-Acetyl-5,6-dihydro-5,6-epoxy-multiplolide A (14) 5,6-Dihydro-5,6-epoxymultiplolide A (15) 3,4-Deoxy-3,4-didehydromultiplolide A (16) Phomopsis sp. (NXZ-05) Endophytic fungus [31] Stagonolides A-I (44, 45, 17-23) Stagonospora cirsii Fungal pathogen [32][33][34] Curvulides A, B1, B2 (24)(25)(26) Unnamed nonanolide 27…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…The relative configuration at C-7 of 27 remained unresolved because it is not possible to predict the mode of the nucleophilic attack, i.e., S N 1 or S N 2 [56]. Botryolides A-D (28,29,58,30), and a known compound decarestrictine D [53] were isolated from culture of a fungicolous isolate of Botryotrichum sp. (NRRL 38180).…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…(isolate F01V25), which was in turn obtained from the green alga Dictyosphaeria versluyii. The relative stereochemistry was determined using the J-based configuration method in conjunction with molecular modelling and analyses of NOE and ROE correlations [30]. Chemical investigation of Phomopsis sp.…”

Section: Structurally Complex Nonanolides With Additional Ringsmentioning

confidence: 99%

“…Compound 57 is thought to provide an alternative treatment for infectious diseases [6]. Dictyosphaeric acid A (59) showed weak antibacterial activity towards Gram positive bacteria, including methicillinsensitive Staphylococcus aureus, MRSA, vancomycin-resistant Enterococcus faecium and Candida albicans, while dictyosphaeric acid B (60) showed no antimicrobial activity at 50 μg well -1 [30].…”

Section: Antibacterial Activitymentioning

confidence: 99%

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Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

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Fungi

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: The Fungal Kingdom: The Concept of Marine Fungi Mastigomycetes and Eumycetes (True Fungi) Elements of Classification of Eumycetes Background Information on the Structure of Chitin Fatty Acids Sterols Membrane Peptides of Fungi: Peptaibols General Comments on Secondary Metabolites of Marine Fungi Substances Isolated from Fungi Collected from the Surface of the Sea Substances Isolated from Fungi from Sediments and other Inert Substrates Substances Isolated from Fungi Associated with Cyanobacteria Algicolous Fungi: General Remarks Substances Isolated from Fungi Associated with Green Algae and Marine Spermatophyta Substances Isolated from Fungi Associated with Red Algae Substances Isolated from Fungi Associated with Brown Algae Substances Isolated from Lignicolous Fungi Substances Isolated from Fungi Associated with Sponges Substances Isolated from Fungi Associated with Cnidarians Substances Isolated from Fungi Associated with Mollusks Substances Isolated from Fungi Associated with Bryozoans Substances Isolated from Fungi Associated with Echinoderms Substances Isolated from Fungi Associated with Crustaceans Substances Isolated from Fungi Associated with Tunicates (Ascidians) Substances Isolated from Fungi Associated with Fish Summary of Marine‐Derived Fungi

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Dictyosphaeric Acids A and B: New Decalactones from an Undescribed Penicillium sp. Obtained from the Alga Dictyosphaeria versluyii

Cited by 42 publications

References 11 publications

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

Accurate Dereplication of Bioactive Secondary Metabolites from Marine-Derived Fungi by UHPLC-DAD-QTOFMS and a MS/HRMS Library

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

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