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      Pyran Rings Containing Polyketides from Penicillium raistrickii

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          Abstract

          Five new pyran rings containing polyketides, penicipyrans A–E ( 1– 5), together with the known pestapyrone A ( 6), were isolated from the saline soil-derived Penicillium raistrickii. Their structures were determined by interpretation of NMR and HRESIMS data. The absolute configurations of compounds 4 and 5 were established by the modified Mosher’s method and single-crystal X-ray diffraction analysis, respectively. These compounds possessed high structural diversity including two α-pyrones ( 1, 2), three isocoumarins ( 3, 4, 6), and one dihydropyran derivative ( 5). Among them, Compound 5 exhibited cytotoxicity against HL-60 and K562 cell lines with IC 50 values of 4.4 and 8.5 μM, respectively.

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          Nigerapyrones A-H, α-pyrone derivatives from the marine mangrove-derived endophytic fungus Aspergillus niger MA-132.

          Xue-Dong Liu, Peter Proksch, Shan Gao … (2011)
          Eight new α-pyrone derivatives, namely, nigerapyrones A-E (1-5) and nigerapyrones F-H (8-10), along with two known congeners, asnipyrones B (6) and A (7), were isolated from Aspergillus niger MA-132, an endophytic fungus obtained from the fresh tissue of the marine mangrove plant Avicennia marina. The structures of these compounds were elucidated on the basis of spectroscopic analysis. The undescribed geometries of the trisubstituted double bonds (C-9 and C-11) for asnipyrone B (6) have now been explicitly determined, while the incorrect placement of the methyl group at C-5 of asnipyrone A (7) has now been revised at C-3. The cytotoxic activities of the isolated α-pyrone derivatives against eight tumor cell lines as well as antimicrobial activities against two bacteria and four plant-pathogenic fungi of these compounds were evaluated. Compounds 2, 4, 5, and 7 showed weak cytotoxicity against some of the tested tumor cell lines.
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            The use of isolated natural products as scaffolds for the generation of chemically diverse screening libraries for drug discovery.

            Emma C. Barnes, Rohitesh Kumar, Rohan Davis (2016)
            A diverse range of strategies leading to natural product derived or inspired screening libraries aims to increase the number of new chemical entities emerging per year. However, the use of isolated natural products as scaffolds for the semi-synthesis of larger biological screening libraries remains rare. This particular method avoids the time-consuming and resource intensive de novo synthetic strategy for scaffold production, and has become more feasible through improvements to synthetic and isolation methodologies. This Highlight examines the increasing popularity of small- to large-sized screening libraries generated directly from isolated natural products. Several of the examples detailed herein show how this strategy can lead to improvements in not only potency but also other important (and often forgotten) drug discovery parameters such as toxicity, selectivity, lipophilicity and bioavailability. However, there are still improvements to be made to this method, particularly in the choice of the natural product scaffold and the derivatising reagents used. Avoidance of known nuisance compounds or structural alert motifs (e.g. PAINS) that interfere with bioactivity screens, and impact downstream drug development will play a significant role in the future success of this methodology. Incorporation of rational design strategies that take into account the physicochemical parameters (e.g. log P, MW, HBA, HBD) of the final semi-synthetic library analogues will also facilitate the discovery and development of leads and drugs. A multi-pronged approach to drug discovery that incorporates the use of isolated natural product scaffolds for library generation will surely be beneficial.
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              Role of Marine Natural Products in the Genesis of Antiviral Agents.

              Vedanjali Gogineni, Raymond F. Schinazi, Mark T. Hamann (2015)
              Article 0 comments Cited 29 times – based on 0 reviews     Review now
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                Author and article information

                Contributors
                Orazio Taglialatela-Scafati: Role: Academic Editor
                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): 23 December 2016
                Publication date Collection: January 2017
                Volume: 15
                Issue: 1
                Electronic Location Identifier: 2
                Affiliations
                [1 ]College of Pharmacy, Binzhou Medical College, Yantai 264003, China; maliyingbz@ 123456163.com (L.-Y.M.); desheng_liu@ 123456sina.com (D.-S.L.); huangyuling1979@ 123456163.com (Y.-L.H.); kanghuihui_1993@ 123456126.com (H.-H.K.); chhwang77@ 123456163.com (C.-H.W.)
                [2 ]The Hospital of Luzhong Mining Co., Ltd., Laiwu 271113, China; deguoli1983@ 123456sina.com
                Author notes
                [* ]Correspondence: lwz1963@ 123456163.com ; Tel.: +86-535-691-3205
                Article
                Publisher ID: marinedrugs-15-00002
                DOI: 10.3390/md15010002
                PMC ID: 5295222
                PubMed ID: 28025533
                SO-VID: 5615b28f-b00b-4ddf-9129-9f9caf26db05
                Copyright © © 2016 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                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 : 31 October 2016
                Date accepted : 15 December 2016
                Categories
                Subject: Article

                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: penicillium raistrickii,α-pyrone,isocoumarin,polyketides,saline soil-derived fungus
                Data availability:
                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: penicillium raistrickii, α-pyrone, isocoumarin, polyketides, saline soil-derived fungus

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