Isolation and Synthesis of Pulmonarins A and B, Acetylcholinesterase Inhibitors from the Colonial Ascidian Synoicum pulmonaria

Margey Tadesse, Johan Svenson*, Kristina Sepicic, Laurent Trembleau, Magnus Engqvist, Jeanette H. Andersen, Marcel Jaspars, Klara Stensvag, Tor Haug

*Corresponding author for this work

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Pulmonarins A and B are two new dibrominated marine acetylcholinesterase inhibitors that were isolated and characterized from the sub-Arctic ascidian Synoicum pulmonaria collected off the Norwegian coast. The structures of natural pulmonarins A and B were tentatively elucidated by spectroscopic methods and later verified by comparison with synthetically prepared material. Both pulmonarins A and B displayed reversible, noncompetitive acetylcholinesterase inhibition comparable to several known natural acetylcholinesterase inhibitiors. Pulmonarin B was the strongest inhibitor, with an inhibition constant (K-i) of 20 mu M. In addition to reversible, noncompetitive acetylcholinesterase inhibition, the compounds displayed weak antibacterial activity but no cytotoxicity or other investigated bioactivities.

Original languageEnglish
Pages (from-to)364-369
Number of pages6
JournalJournal of Natural Products
Volume77
Issue number2
Early online date18 Feb 2014
DOIs
Publication statusPublished - 28 Feb 2014

Keywords

  • marine natural-products
  • verongida sponges
  • drug discovery
  • alkaloids
  • choline
  • constituents
  • chemistry
  • crassa
  • acids

Cite this

Isolation and Synthesis of Pulmonarins A and B, Acetylcholinesterase Inhibitors from the Colonial Ascidian Synoicum pulmonaria. / Tadesse, Margey; Svenson, Johan; Sepicic, Kristina; Trembleau, Laurent; Engqvist, Magnus; Andersen, Jeanette H.; Jaspars, Marcel; Stensvag, Klara; Haug, Tor.

In: Journal of Natural Products, Vol. 77, No. 2, 28.02.2014, p. 364-369.

Research output: Contribution to journalArticle

Tadesse, Margey ; Svenson, Johan ; Sepicic, Kristina ; Trembleau, Laurent ; Engqvist, Magnus ; Andersen, Jeanette H. ; Jaspars, Marcel ; Stensvag, Klara ; Haug, Tor. / Isolation and Synthesis of Pulmonarins A and B, Acetylcholinesterase Inhibitors from the Colonial Ascidian Synoicum pulmonaria. In: Journal of Natural Products. 2014 ; Vol. 77, No. 2. pp. 364-369.
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abstract = "Pulmonarins A and B are two new dibrominated marine acetylcholinesterase inhibitors that were isolated and characterized from the sub-Arctic ascidian Synoicum pulmonaria collected off the Norwegian coast. The structures of natural pulmonarins A and B were tentatively elucidated by spectroscopic methods and later verified by comparison with synthetically prepared material. Both pulmonarins A and B displayed reversible, noncompetitive acetylcholinesterase inhibition comparable to several known natural acetylcholinesterase inhibitiors. Pulmonarin B was the strongest inhibitor, with an inhibition constant (K-i) of 20 mu M. In addition to reversible, noncompetitive acetylcholinesterase inhibition, the compounds displayed weak antibacterial activity but no cytotoxicity or other investigated bioactivities.",
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author = "Margey Tadesse and Johan Svenson and Kristina Sepicic and Laurent Trembleau and Magnus Engqvist and Andersen, {Jeanette H.} and Marcel Jaspars and Klara Stensvag and Tor Haug",
note = "ACKNOWLEDGMENTS This work was supported with grants from the Marine Biotechnology Programme in Troms{\o} (MABIT, BS0058), Norway, the Research Council of Norway (184688/S40), MabCent-SFI, and the University of Troms{\o} (UiT), Troms{\o}, Norway. The authors would like to thank Prof. B. Gulliksen (Department of Arctic and Marine Biology, UiT, Norway) for sample collection, taxonomic identification, and organism image and Dr. J. Isaksson (Department of Chemistry, UiT, Norway) for operating the 600 MHz NMR.",
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AU - Svenson, Johan

AU - Sepicic, Kristina

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AU - Engqvist, Magnus

AU - Andersen, Jeanette H.

AU - Jaspars, Marcel

AU - Stensvag, Klara

AU - Haug, Tor

N1 - ACKNOWLEDGMENTS This work was supported with grants from the Marine Biotechnology Programme in Tromsø (MABIT, BS0058), Norway, the Research Council of Norway (184688/S40), MabCent-SFI, and the University of Tromsø (UiT), Tromsø, Norway. The authors would like to thank Prof. B. Gulliksen (Department of Arctic and Marine Biology, UiT, Norway) for sample collection, taxonomic identification, and organism image and Dr. J. Isaksson (Department of Chemistry, UiT, Norway) for operating the 600 MHz NMR.

PY - 2014/2/28

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N2 - Pulmonarins A and B are two new dibrominated marine acetylcholinesterase inhibitors that were isolated and characterized from the sub-Arctic ascidian Synoicum pulmonaria collected off the Norwegian coast. The structures of natural pulmonarins A and B were tentatively elucidated by spectroscopic methods and later verified by comparison with synthetically prepared material. Both pulmonarins A and B displayed reversible, noncompetitive acetylcholinesterase inhibition comparable to several known natural acetylcholinesterase inhibitiors. Pulmonarin B was the strongest inhibitor, with an inhibition constant (K-i) of 20 mu M. In addition to reversible, noncompetitive acetylcholinesterase inhibition, the compounds displayed weak antibacterial activity but no cytotoxicity or other investigated bioactivities.

AB - Pulmonarins A and B are two new dibrominated marine acetylcholinesterase inhibitors that were isolated and characterized from the sub-Arctic ascidian Synoicum pulmonaria collected off the Norwegian coast. The structures of natural pulmonarins A and B were tentatively elucidated by spectroscopic methods and later verified by comparison with synthetically prepared material. Both pulmonarins A and B displayed reversible, noncompetitive acetylcholinesterase inhibition comparable to several known natural acetylcholinesterase inhibitiors. Pulmonarin B was the strongest inhibitor, with an inhibition constant (K-i) of 20 mu M. In addition to reversible, noncompetitive acetylcholinesterase inhibition, the compounds displayed weak antibacterial activity but no cytotoxicity or other investigated bioactivities.

KW - marine natural-products

KW - verongida sponges

KW - drug discovery

KW - alkaloids

KW - choline

KW - constituents

KW - chemistry

KW - crassa

KW - acids

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SP - 364

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