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Zeitschrift für Naturforschung C

A Journal of Biosciences

Editor-in-Chief: Seibel, Jürgen

Editorial Board: Aigner , Achim / Boland, Wilhelm / Bornscheuer, Uwe / Hoffmann, Klaus


IMPACT FACTOR 2018: 1.000

CiteScore 2018: 0.99

SCImago Journal Rank (SJR) 2018: 0.246
Source Normalized Impact per Paper (SNIP) 2018: 0.437

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1865-7125
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Volume 74, Issue 5-6

Issues

Diverse polyketides and alkaloids from Penicillium sp. KHMM: structural elucidation, biological and molecular docking studies

Abdelaaty Hamed
  • Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Universitätsstraße 25, D-33501 Bielefeld, Germany
  • Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City-Cairo 11884, Egypt
  • Other articles by this author:
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/ Mohamed Ismail
  • Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Universitätsstraße 25, D-33501 Bielefeld, Germany
  • Microbiology Department, Faculty of Science, Helwan University, Helwan-Cairo, Egypt
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/ Mohammad M. El-Metwally
  • Botany and Microbiology Department, Faculty of Science, Damanhour University, Damanhour, Egypt
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/ Marcel Frese
  • Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Universitätsstraße 25, D-33501 Bielefeld, Germany
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/ Tarek M.A. Ibrahim / Atef F. El-Haddad / Norbert Sewald
  • Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Universitätsstraße 25, D-33501 Bielefeld, Germany
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/ Mohamed ShaabanORCID iD: https://orcid.org/0000-0001-9281-2505
  • Corresponding author
  • Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Universitätsstraße 25, D-33501 Bielefeld, Germany
  • Chemistry of Natural Compounds Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, El-Behoos St. 33, Dokki-Cairo 12622, Egypt
  • orcid.org/0000-0001-9281-2505
  • Email
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Published Online: 2019-01-11 | DOI: https://doi.org/10.1515/znc-2018-0145

Abstract

As a continuation of our earlier research concerning the investigation of microbial bioactive secondary metabolites from the terrestrial Penicillium sp.KH Link 1809 isolate KHMM, the fungus was re-cultivated on a large scale to explore its bioactive compounds intensively. Fifteen compounds, including seven alkaloids (1–7), one sesquiterpene (8), an acetylenic system (9), two sterols, and sphengolipid, were identified. Their structures were established on the bases of extensive one- and two-dimensional nuclear magnetic resonance and mass measurements, and by comparison with literature data. The antimicrobial activity of the fungal extract and the corresponding compounds were studied using a panel of pathogenic microorganisms, and their in vitro cytotoxicity against the human cervix carcinoma cell line (KB-3-1) was reported as well. The molecular docking of the isolated compounds showed promising affinities for the alkaloidal compounds 46 towards α, β tubulins.

This article offers supplementary material which is provided at the end of the article.

Keywords: α, β tubulins; biological properties; mol-docking; Penicillium sp.; polyketide-alkaloides

References

  • 1.

    Blunt JW, Copp BR, Munro MH, Northcote PT, Prinsep MR. Marine natural products. Nat Prod Rep 2003;20:1–48.PubMedCrossrefGoogle Scholar

  • 2.

    Laatsch H. AntiBase 2017, a data base for rapid structural determination of microbial natural products, and annual updates. Weinheim Germany: Wiley-VCH, 2017.Google Scholar

  • 3.

    Larsen TO, Smedsgaard J, Nielsen KF, Hansen ME, Frisvad JC. Phenotypic taxonomy and metabolite profiling in microbial drug discovery. Nat Prod Rep 2005;22:672–95.PubMedCrossrefGoogle Scholar

  • 4.

    Butler MS. The role of natural product chemistry in drug discovery. J Nat Prod 2004;67:2141–53.CrossrefPubMedGoogle Scholar

  • 5.

    Rasmussen TB, Skinderso ME, Bjarnsholt T, Phipps RK, Christensen KB, Andersen JB, et al. Identity and effects of quorum-sensing inhibitors produced by Penicillium species. Microbiology 2005;151:1325–40.CrossrefPubMedGoogle Scholar

  • 6.

    Li JY, Strobel GA. Jesterone and hydroxy-jesterone antioomycete cyclohexenenone epoxides from the endophytic fungus: Pestalotiopsis jesteri. Phytochemistry 2001;57:261–5.PubMedCrossrefGoogle Scholar

  • 7.

    Brady SF, Clardy J. CR377, a new pentaketide antifungal agentisolated from an endophytic fungus. J Nat Prod 2000;63:1447–8.CrossrefPubMedGoogle Scholar

  • 8.

    Singh SB, Zink DL, Guan Z, Collado J, Pelaez F, Felock PJ, et al. Isolation, structure and HIV-1 integrase inhibitory activity of xanthoviridicatin E and F two novel fungal metabolites produced by Penicillium chrysogenum. Helv Chim Acta 2003;86:3380–5.CrossrefGoogle Scholar

  • 9.

    Zhang HW, Song YC, Tan RX. Biology and chemistry of endophytes. Nat Prod Rep 2006;23:753–71.CrossrefPubMedGoogle Scholar

  • 10.

    Song YC, Li H, Ye YH, Shan CY, Yang YM, Tan RX. Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116cell and some microbial growths. FEMS Microbiol Lett 2004;241:67–72.PubMedCrossrefGoogle Scholar

  • 11.

    Bugni TS, Ireland CM. Marine-derived fungi: a chemically and biologically diverse group of microorganisms. Nat Prod Rep 2004;21:143–63.PubMedCrossrefGoogle Scholar

  • 12.

    Grovel O, Kerzaon I, Vansteelandt M, Petit KE, Biard JF, Pouchus YF. Marine-derived Penicillium sp.: fungal diversity as a promising source of bioactive compounds. Planta Med 2008;74:SL99.Google Scholar

  • 13.

    Frisvad JC. Taxonomy, chemodiversity, and chemoconsistency of Aspergillus, Penicillium, and Talaromyces species. Front Microbiol 2014;5:773.Web of SciencePubMedGoogle Scholar

  • 14.

    Strobel G, Daisy B. Bioprospecting for microbial endophytes and their natural products. Microbiol Mol Biol Rev 2003;67:491–502.CrossrefPubMedGoogle Scholar

  • 15.

    Hassan AE. Novel natural products from endophytic fungi of Egyptian medicinal plants- chemical and biological characterization. Dissertation, Germany: University of Düsseldorf, 2007.Google Scholar

  • 16.

    Shaaban M, Sohsah GE, El-Metwally MM, Elfedawy MG, Abdel-Mogib M. Bioactive compounds produced by strain of Penicillium sp. IJSEA 2016;5:2319–7560.Google Scholar

  • 17.

    Hadfield JA, Ducki S, Hirst N, McGown AT. Tubulin and microtubules as targets for anticancer drugs. Prog Cell Cycle Res 2003;5:309–25.PubMedGoogle Scholar

  • 18.

    Mohammed YS, Luckner M. The structure of cyclopenin and cyclopenol, metabolic products from p. cyclopium westling and p. viridicatum westling. Tetrahedron Lett 1963;4:1953–8.CrossrefGoogle Scholar

  • 19.

    Wei MY, Yang RY, Shao CL, Wang CY, Deng DS, She ZG, et al. Isolation, structure elucidation, crystal structure, and biological activity of a marine natural alkaloid, viridicatol. Chem Nat Compd 2011;47:322–5.Web of ScienceCrossrefGoogle Scholar

  • 20.

    Ciegler A, Kadis S, Ajl SJ. Microbial toxins: a comprehensive treatise; fungal toxins. Metabolites of Penicillium viridicatum and closely related species. New York: Copyright by Academic press, INC 111 Fifth Avenue, 10003, Vol. VI, 1971:509.Google Scholar

  • 21.

    Luckner M, Mothes K. On the biosynthesis of 2,3-dihydroxy-4-phenyl-quinoline (viridicatin). Tetrahedron Lett 1962;3:1035.CrossrefGoogle Scholar

  • 22.

    Austin DJ, Myers MB. 3-O-methylviridicatin, a new metabolite from Penicillium puberulum. J Chem Soc 1964;1:1197–8.Google Scholar

  • 23.

    Zhang C, Ding S, Shi W, Cao F, Zhu H, Wen M. A new quinolinone from freshwater lake-derived fungus Myrothecium verrucaria. Nat Prod Res 2017;31:99–103.Web of ScienceCrossrefPubMedGoogle Scholar

  • 24.

    Bu Y, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M. Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp. J Antibiot 2016;69:57–61.Web of ScienceCrossrefGoogle Scholar

  • 25.

    Xin Z, Fang Y, Du L, Zhu T, Duan L, Chen J, et al. Aurantiomides A-C, quinazoline alkaloids from the sponge-derived fungus Penicillium aurantiogriseum SP0-19. J Nat Prod 2007;70:853–5.CrossrefPubMedWeb of ScienceGoogle Scholar

  • 26.

    Tsukamoto S, Miura S, Yamashita Y, Ohta T. Aspermytin A: a new neurotrophic polyketide isolated from a marine-derived fungus of the genus Aspergillus. Bioorg Med Chem Lett 2004;14:417–20.CrossrefPubMedGoogle Scholar

  • 27.

    Yang J, Qi X, Li W, Shao G, Yao X, Kitanaka S. WA, a new antifungal antibiotic from a soil fungus strain 38. Chin Chem Lett 1998;9:539–40.Google Scholar

  • 28.

    Li Q, Yang X, Yang Y, Zhao L, Chen G, Li X, et al. Acyclic isoprenoids of Endophytic Aspergillus sp. Y-12 from Panax notoginseng. Lett Org Chem 2017;14:14–7.CrossrefWeb of ScienceGoogle Scholar

  • 29.

    Shaaban M, Nasr H, Hassan AZ, Asker MS. Bioactive secondary metabolites from endophytic Aspergillus fumigatus: structural elucidation and bioactivity studies. Rev Latinoamer Quím 2013;41:50–60.Google Scholar

  • 30.

    Hamed A, Abdel-Razek AS, Frese M, Wibberg D, El-Haddad AF, Ibrahim TM, et al. New oxaphenalene derivative from marine-derived Streptomyces griseorubens sp. ASMR4. Z Naturforsch 2017;72:53–62.CrossrefWeb of ScienceGoogle Scholar

  • 31.

    Huang X, Chen J, Xu X, Zhang W, Zhao C. A new phenolic compound from Schizonepeta tenuifolia. Chem Nat Compd 2016;52:1005–7.CrossrefWeb of ScienceGoogle Scholar

  • 32.

    Yang T, Wang W, Wei D, Zhang T, Han B, Yu W. Synthesis of quinazolinones via radical cyclization of α-azidyl benzamides. Org Chem Front 2017;4:421–6.CrossrefWeb of ScienceGoogle Scholar

  • 33.

    Das S, Parida R, Sandeep IS, Kar B, Nayak S, Mohanty S. Chemical composition and antioxidant activity of some important betel vine landraces. Biologia 2016;71:128–32.Web of ScienceGoogle Scholar

  • 34.

    Ma Y, Qiao K, Kong Y, Li M, Guo L, Miao Z, et al. A new isoquinolone alkaloid from an endophytic fungus R22 of Nerium indicum. Nat Prod Res 2017;31:951–8.PubMedWeb of ScienceCrossrefGoogle Scholar

  • 35.

    Zhang Y, Mu J, Essmann F, Feng Y, Kramer M, Bao H, et al. A new quinolinone and its natural/artificial derivatives from a shark gill-derived fungus Penicillium crustosum AP2T1. Nat Prod Res 2017;31:985–9.Web of ScienceCrossrefGoogle Scholar

  • 36.

    Cutler HG, Crumley FG, Cox RH, Wells JM, Cole RJ. The biological properties of cyclopenin and cyclopenol. Plant Cell Physiol 1984;25:257–63.Google Scholar

  • 37.

    Cutler SJ, Cutler HG, Hamdy MK. Synthesis of cyclopenin and cyclopenol intermediates: study of analogue structures and biological activities. J Plant Growth Regul 2000;27:33–41.Google Scholar

  • 38.

    Yang J, Qi X, Li W, Shao G, Yao X, Kitanaka S. WA, a new antifungal antibiotic from a soil fungus strain 38. Chin Chem Lett 1998;9:539–40.Google Scholar

  • 39.

    Akiyama S-I, Fojo A, Hanover JA, Pastan I, Gottesman MM. Isolation and genetic characterization of human KB cell lines resistant to multiple drugs. Somat Cell Mol Genet 1985;11:117–26.CrossrefPubMedGoogle Scholar

  • 40.

    Oiso S, Takayama Y, Nakazaki R, Matsunaga N, Motooka C, Yamamura A, et al. Factors involved in the cisplatin resistance of KCP-4 human epidermoid carcinoma cells. Oncol. Rep. 2014;31:719–26.Google Scholar

  • 41.

    Bauer AW, Kirby WM, Sherris JC, Truck M. Antibiotic susceptibility testing by a standardized single disk method. Am J ClinPathol 1966;45:493–6.Google Scholar

  • 42.

    Awantu AF, Lenta BN, Bogner T, Fongang YF, Ngouela S, Wansi JD, et al. Dialiumoside, an Olean-18-ene Triterpenoid from Dialium excelsum. Z Naturforsch 2011;66:624–8.CrossrefGoogle Scholar

  • 43.

    Sammet B, Bogner T, Nahrwold M, Weiss C, Sewald N. Approaches for the synthesis of functionalized cryptophycins. J Org Chem 2010;75:6953–60.CrossrefPubMedWeb of ScienceGoogle Scholar

  • 44.

    Wolf LK. New software and websites for the chemical enter prise. Chem Eng News 2009;87:48.CrossrefGoogle Scholar

About the article

Received: 2018-09-23

Revised: 2018-11-19

Accepted: 2018-12-15

Published Online: 2019-01-11

Published in Print: 2019-05-27


Citation Information: Zeitschrift für Naturforschung C, Volume 74, Issue 5-6, Pages 131–137, ISSN (Online) 1865-7125, ISSN (Print) 0939-5075, DOI: https://doi.org/10.1515/znc-2018-0145.

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