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

doi:10.1021/np401002s

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

Chemistry

Research output: Contribution to journal › Article › peer-review

40 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 language	English
Pages (from-to)	364-369
Number of pages	6
Journal	Journal of Natural Products
Volume	77
Issue number	2
Early online date	18 Feb 2014
DOIs	https://doi.org/10.1021/np401002s
Publication status	Published - 28 Feb 2014

Bibliographical note

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.

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/np401002s

Laurent Trembleau
- School of Natural & Computing Sciences, Chemistry - Senior Lecturer
Person: Academic

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

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.",

keywords = "marine natural-products, verongida sponges, drug discovery, alkaloids, choline, constituents, chemistry, crassa, acids",

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 - Tadesse, Margey

AU - Svenson, Johan

AU - Sepicic, Kristina

AU - Trembleau, Laurent

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

U2 - 10.1021/np401002s

DO - 10.1021/np401002s

M3 - Article

SN - 0163-3864

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SP - 364

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JO - Journal of Natural Products

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IS - 2

ER -

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

Abstract

Bibliographical note

Keywords

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