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      Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae

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          Abstract

          Five new ( 1– 5) and two known xanthones ( 6 and 7), one of the latter ( 6) obtained for the first time as a natural product, together with three known anthraquinones, questin, penipurdin A, and questinol, were isolated from the coastal saline soil-derived Aspergillus iizukae by application of an OSMAC (one strain many compounds) approach. Their structures were determined by interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, as well as comparison of these data with those of related known compounds. Antiviral activity of xanthones 1− 7 was evaluated through the cytopathic effect (CPE) inhibition assay, and compound 2 exhibited distinctly strong activity towards influenza virus (H1N1), herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) with IC 50 values of 44.6, 21.4, and 76.7 μM, respectively, which indicated that it was worth to further investigate it as a potential lead compound. The preliminary structure-activity relationship of the xanthones is discussed.

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          Revision of Aspergillus section Flavipedes: seven new species and proposal of section Jani sect. nov.

          Vit Hubka, Alena Novakova, Miroslav Kolařík … (2024)
          Aspergillus section Flavipedes contains species found worldwide in soils and rhizospheres, indoor and cave environments, as endophytes, food contaminants and occasionally as human pathogens. They produce many extensively studied bioactive secondary metabolites and biotechnologically relevant enzymes. The taxa were revised based on phylogenetic analysis of sequences from four loci (β-tubulin, calmodulin, RPB2, ITS rDNA), two PCR fingerprinting methods, micro- and macromorphology and physiology. Section Flavipedes includes three known and seven new species: A. ardalensis, A. frequens, A. luppii, A. mangaliensis, A. movilensis, A. polyporicola and A. spelaeus. The name A. neoflavipes was proposed for Fennellia flavipes a distinct species from its supposed asexual state A. flavipes. Aspergillus iizukae, A. frequens and A. mangaliensis are the most common and widely distributed species, whereas A. flavipes s. str. is rare. A dichotomous key based on the combination of morphology and physiology is provided for all recognized species. Aspergillus section Jani is established to contain A. janus and A. brevijanus, species previously classified as members of sect. Versicolores, Terrei or Flavipedes. This new section is strongly supported by phylogenetic data and morphology. Section Jani species produce three types of conidiophores and conidia, and colonies have green and white sectors making them distinctive. Accessory conidia found in pathogenic A. terreus were found in all members of sects. Flavipedes and Jani. Our data indicated that A. frequens is a clinically relevant and produces accessory conidia during infection.
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            Sorbicatechols A and B, antiviral sorbicillinoids from the marine-derived fungus Penicillium chrysogenum PJX-17.

            Jixing Peng, Xiaomin Zhang, Lin Du … (2014)
            Two novel sorbicillinoids combining a bicyclo[2.2.2]octane with a 2-methoxyphenol moiety, named sorbicatechols A (1) and B (2), were isolated from the culture of the marine sediment-derived fungus Penicillium chrysogenum PJX-17, together with the known protocatechuic acid methyl ester and caffeic acid methyl ester (3). Their structures, including absolute configurations, were assigned by analysis of NMR, MS data, and TDDFT ECD calculations. Compounds 1 and 2 exhibited activities against influenza virus A (H1N1), with IC50 values of 85 and 113 μ M, respectively.
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              Flavonolignans from Aspergillus iizukae, a fungal endophyte of milk thistle (Silybum marianum).

              Tamam El-Elimat, Huzefa Raja, Tyler N. Graf … (2014)
              Silybin A (1), silybin B (2), and isosilybin A (3), three of the seven flavonolignans that constitute silymarin, an extract of the fruits of milk thistle (Silybum marianum), were detected for the first time from a fungal endophyte, Aspergillus iizukae, isolated from the surface-sterilized leaves of S. marianum. The flavonolignans were identified using a UPLC-PDA-HRMS-MS/MS method by matching retention times, HRMS, and MS/MS data with authentic reference compounds. Attenuation of flavonolignan production was observed following successive subculturing of the original flavonolignan-producing culture, as is often the case with endophytes that produce plant-based secondary metabolites. However, production of 1 and 2 resumed when attenuated spores were harvested from cultures grown on a medium to which autoclaved leaves of S. marianum were added. The cycle of attenuation followed by resumed biosynthesis of these flavonolignans was replicated in triplicate.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Mar Drugs
                Journal ID (iso-abbrev): Mar Drugs
                Journal ID (publisher-id): marinedrugs
                Title: Marine Drugs
                Publisher: MDPI
                ISSN (Electronic): 1660-3397
                Publication date (Electronic): 15 November 2018
                Publication date Collection: November 2018
                Volume: 16
                Issue: 11
                Electronic Location Identifier: 449
                Affiliations
                [1 ]College of Pharmacy, Binzhou Medical University, Yantai 264003, China; kanghuihui_1993@ 123456126.com (H.-H.K.); zhanghuaibinhua@ 123456163.com (H.-B.Z.); 18660627015@ 123456163.com (M.-J.Z.); maliyingbz@ 123456163.com (L.-Y.M.)
                [2 ]Beijing Higher Institution Engineering Research Center of Food Additives and Ingredients, Beijing Key Laboratory of Flavor Chemistry, Beijing Laboratory for Food Quality and Safety, Beijing Technology and Business University, Beijing 100048, China; renhong@ 123456th.btbu.edu.cn
                Author notes
                [* ]Correspondence: desheng_liu@ 123456sina.com or deshengliu@ 123456bzmc.edu.cn (D.-S.L.); lwz1963@ 123456163.com or lwz1963@ 123456bzmc.edu.cn (W.-Z.L.); Tel.: +86-535-691-3205 (W.-Z.L.)
                Article
                Publisher ID: marinedrugs-16-00449
                DOI: 10.3390/md16110449
                PMC ID: 6265927
                PubMed ID: 30445748
                SO-VID: 814b9d36-ff8e-4770-ae31-70e3a0171c88
                Copyright © © 2018 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 27 October 2018
                Date accepted : 14 November 2018
                Categories
                Subject: Article

                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: aspergillus iizukae,xanthones,antiviral activity,structure-activity relationship
                Data availability:
                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: aspergillus iizukae, xanthones, antiviral activity, structure-activity relationship

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