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      Sorbicillinoid-Based Metabolites from a Sponge-Derived Fungus Trichoderma saturnisporum

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          Abstract

          Antibacterial activity assessment and high performance liquid chromatography associated with nuclear magnetic resonance (HPLC/NMR) data revealed that the EtOAc extract of the fermented endophytic fungus Trichoderma saturnisporum DI-IA, obtained from the marine sponge Dictyonella incisa, contained conjugated olefinic metabolites with antibacterial activity. Chemical examination of the fungal strain resulted in the isolation of eight new sorbicillinoid-based compounds, namely saturnispols A–H ( 1– 8). Their structures were determined on the basis of extensive spectroscopic analysis, including the experimental and calculated electronic circular dichroism (ECD) data for the configurational assignments. Saturnispol F exerted significant inhibition against a panel of bacteria strains including vancomycin-resistant enterococci (VRE) with a minimum inhibitory concentrations (MIC) ranging from 1.63 to 12.9 μg/mL, while saturnispol H showed selective effects against VRE and B. subtilis.

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          Vancomycin-resistant enterococcal infections.

          Douglas B. Murray (2000)
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            The sorbicillinoid family of natural products: isolation, biosynthesis, and synthetic studies.

            Andrew M Harned, Kelly Volp (2011)
            The sorbicillinoids are a family of hexaketide metabolites that have been isolated from a variety of fungal sources, collected from both marine and terrestrial sources. Since 1948, the family has grown in size to include over 50 members, many of which have complex, highly oxygenated, bicyclic and tricyclic frameworks. In conjunction with their biological activity, the structural complexity of these structures has inspired several synthetic campaigns and has also led to controversy surrounding the biosynthetic pathway responsible for the natural production of these compounds. Through this review, we aim to give a historical perspective to each of these areas and hope to inspire new avenues of research for addressing the knowledge gaps that still exist.
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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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                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): 04 July 2018
                Publication date Collection: July 2018
                Volume: 16
                Issue: 7
                Electronic Location Identifier: 226
                Affiliations
                [1 ]State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China; 13683042952@ 123456163.com (J.M.); chengwei@ 123456bjmu.edu.cn (W.C.)
                [2 ]Food and Medicine College, Zhejiang Ocean University, Zhoushan 316022, China; wangbin@ 123456zjou.edu.cn
                [3 ]Department of Pharmacoguosy, Faculty of Pharmacy, Ankara University, Tandogan, Ankara 06100, Turkiye; hajar.heydari@ 123456yahoo.com (H.H.); belma.konuklugil@ 123456gmail.com (B.K.)
                [4 ]College of Veterinary Medicine, China Agricultural University, Beijing 100193, China; zhukcau@ 123456gmail.com
                Author notes
                [* ]Correspondence: whlin@ 123456bjmu.edu.cn ; Tel.: +86-10-82806188
                [†]

                These authors contributed equal to this work.

                Author information
                https://orcid.org/0000-0001-8242-3952
                https://orcid.org/0000-0002-4978-4083
                Article
                Publisher ID: marinedrugs-16-00226
                DOI: 10.3390/md16070226
                PMC ID: 6071017
                PubMed ID: 29973484
                SO-VID: b0e82136-23ed-43e6-adce-b89cd803337b
                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 : 08 June 2018
                Date accepted : 27 June 2018
                Categories
                Subject: Article

                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: marine fungus,trichoderma saturnisporum,saturnispols a–h,structural elucidation,antibacterial effects
                Data availability:
                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: marine fungus, trichoderma saturnisporum, saturnispols a–h, structural elucidation, antibacterial effects

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