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Manadodioxans A−E: polyketide endoperoxides from the marine sponge Plakortis bergquistae

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Abstract

Five new polyketide endoperoxides, manadodioxans A−E, were isolated from the marine sponge Plakortis bergquistae. Manadodioxan E showed antimicrobial activity against Escherichia coli at 10 μg/disk, while its oxo congener, manadodioxan D, was inactive.

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References

  1. Higgs MD, Faulkner D (1978) Plakortin, an antibiotic from Plakortis halichondrioides. J Org Chem 43:3454–3457

    Article  CAS  Google Scholar 

  2. Davidson BS (1991) Plakortolide, a cytotoxic peroxylactone from a Plakortis sponge. Tetrahedron Lett 32:7167–7170

    Article  CAS  Google Scholar 

  3. Varoglu M, Peters BM, Crews P (1995) The structures and cytotoxic properties of polyketide peroxides from a Plakortis sponge. J Nat Prod 58:27–36

    Article  CAS  PubMed  Google Scholar 

  4. Kossuga MH, Nascimento AM, Reimão JQ, Tempone AG, Taniwaki NN, Veloso K, Ferreira AG, Cavalcanti BC, Pessoa C, Moraes MO, Mayer AMS, Hajdu E, Berlinck RGS (2008) Antiparasitic, antineuroinflammatory, and cytotoxic polyketides from the marine sponge Plakortis angulospiculatus collected in Brazil. J Nat Prod 71:334–339

    Article  CAS  PubMed  Google Scholar 

  5. Takada N, Watanabe M, Yamada A, Suenaga K, Yamada K, Ueda K, Uemura D (2001) Isolation and structures of haterumadioxins A and B, cytotoxic endoperoxides from the Okinawan sponge Plakortis lita. J Nat Prod 64:356–359

    Article  CAS  PubMed  Google Scholar 

  6. Fattorusso C, Persico M, Calcinai B, Cerrano C, Parapini S, Taramelli D, Novellino E, Romano A, Scala F, Fattorusso E, Taglialatela-Scafati O (2010) Manadoperoxides A−D from the Indonesian sponge Plakortis cfr. simplex. Further insights on the structure−activity relationships of simple 1,2-dioxane antimalarials. J Nat Prod 73:1138–1145

    Article  CAS  PubMed  Google Scholar 

  7. Patil AD, Freyer AJ, Carte B, Johnson RK, Lahouratate P (1996) Plakortides, novel cyclic peroxides from the sponge Plakortis halichondrioides: activators of cardiac SR-Ca2+-pumping ATPase. J Nat Prod 59:219–223

    Article  CAS  PubMed  Google Scholar 

  8. Chianese G, Persico M, Yang F, Lin HW, Guo YW, Basilico N, Parapini S, Taramelli D, Taglialatela-Scafati O, Fattorusso C (2014) Endoperoxide polyketides from a Chinese Plakortis simplex: further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes. Bioorg Med Chem 22:4572–4580

    Article  CAS  PubMed  Google Scholar 

  9. Lim CW, Cha YJ, Kim JS (2005) New cyclic peroxides from a sponge, Plakortis sp. J Fish Sci Technol 8:6–9

    CAS  Google Scholar 

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Acknowledgments

We thank Dr. H. Kobayashi of the University of Tokyo and Dr. H. Rotinsulu of Universitas Pembangunan for collecting the sponges. This work was supported by Grants-in-Aid for Scientific Research (nos. 18406002, 25293025, and 26305005 to S.T.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan.

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Kumamoto University, Kumamoto, 862-0973, Japan

    Masaki Gushiken, Ippei Kagiyama, Hikaru Kato, Toshiyuki Kuwana & Sachiko Tsukamoto

  2. Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado, 95115, Indonesia

    Fitje Losung & Remy E. P. Mangindaan

  3. Naturalis Biodiversity Center, P.O. Box 9517, 2300 RA, Leiden, The Netherlands

    Nicole J. de Voogd

Authors
  1. Masaki Gushiken
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  2. Ippei Kagiyama
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  3. Hikaru Kato
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  4. Toshiyuki Kuwana
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  5. Fitje Losung
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  6. Remy E. P. Mangindaan
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  7. Nicole J. de Voogd
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  8. Sachiko Tsukamoto
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Correspondence to Sachiko Tsukamoto.

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Gushiken, M., Kagiyama, I., Kato, H. et al. Manadodioxans A−E: polyketide endoperoxides from the marine sponge Plakortis bergquistae . J Nat Med 69, 595–600 (2015). https://doi.org/10.1007/s11418-015-0920-x

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  • DOI: https://doi.org/10.1007/s11418-015-0920-x

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