Literature DB >> 16009558

Symbioimine and neosymbioimine, amphoteric iminium metabolites from the symbiotic marine dinoflagellate Symbiodinium sp.

Masaki Kita1, Nao Ohishi, Kazuto Washida, Mikiko Kondo, Tomoyuki Koyama, Kaoru Yamada, Daisuke Uemura.   

Abstract

Two amphoteric iminium metabolites, symbioimine (1) and neosymbioimine (2), were isolated from a cultivated symbiotic marine dinoflagellate Symbiodinium sp. Compounds 1 and 2 have a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. The plausible biogenetic pathway of 1 and 2 can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization. Symbioimine (1) inhibited the differentiation of RAW264 cells into osteoclasts (EC50 = 44 microM), and significantly inhibited cyclooxygenase-2 activity at 10 microM. Thus, symbioimine is a potent anti-resorptive and anti-inflammatory drug.

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Year:  2005        PMID: 16009558     DOI: 10.1016/j.bmc.2005.05.064

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  9 in total

1.  The Marine Dinoflagellate Alexandrium andersoni Induces Cell Death in Lung and Colorectal Tumor Cell Lines.

Authors:  Clementina Sansone; Genoveffa Nuzzo; Christian Galasso; Raffaella Casotti; Angelo Fontana; Giovanna Romano; Adrianna Ianora
Journal:  Mar Biotechnol (NY)       Date:  2018-04-20       Impact factor: 3.619

2.  Total synthesis of (+/-)-symbioimine.

Authors:  Yefen Zou; Qinglin Che; Barry B Snider
Journal:  Org Lett       Date:  2006-11-23       Impact factor: 6.005

Review 3.  Marine pharmacology in 2005-6: Marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune and nervous systems, and other miscellaneous mechanisms of action.

Authors:  Alejandro M S Mayer; Abimael D Rodríguez; Roberto G S Berlinck; Mark T Hamann
Journal:  Biochim Biophys Acta       Date:  2009-03-19

4.  Exploratory research on bioactive natural products with a focus on biological phenomena.

Authors:  Daisuke Uemura
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2010       Impact factor: 3.493

5.  Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine.

Authors:  Rie Fujita; Kengo Hanaya; Takeshi Sugai; Shuhei Higashibayashi
Journal:  Sci Rep       Date:  2021-12-15       Impact factor: 4.379

6.  Multifunctional polyketide synthase genes identified by genomic survey of the symbiotic dinoflagellate, Symbiodinium minutum.

Authors:  Girish Beedessee; Kanako Hisata; Michael C Roy; Noriyuki Satoh; Eiichi Shoguchi
Journal:  BMC Genomics       Date:  2015-11-14       Impact factor: 3.969

7.  Confirmation of pinnatoxins and spirolides in shellfish and passive samplers from Catalonia (Spain) by liquid chromatography coupled with triple quadrupole and high-resolution hybrid tandem mass spectrometry.

Authors:  María García-Altares; Alexis Casanova; Vaishali Bane; Jorge Diogène; Ambrose Furey; Pablo de la Iglesia
Journal:  Mar Drugs       Date:  2014-06-23       Impact factor: 5.118

8.  Cyclic Imines (CIs) in Mussels from North-Central Adriatic Sea: First Evidence of Gymnodimine A in Italy.

Authors:  Simone Bacchiocchi; Melania Siracusa; Debora Campacci; Martina Ciriaci; Alessandra Dubbini; Tamara Tavoloni; Arianna Stramenga; Stefania Gorbi; Arianna Piersanti
Journal:  Toxins (Basel)       Date:  2020-06-04       Impact factor: 4.546

9.  Bioactivity and Biotechnological Overview of Naturally Occurring Compounds from the Dinoflagellate Family Symbiodiniaceae: A Systematic Review.

Authors:  Jeysson Sánchez-Suárez; Mariana Garnica-Agudelo; Luisa Villamil; Luis Díaz; Ericsson Coy-Barrera
Journal:  ScientificWorldJournal       Date:  2021-12-17
  9 in total

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