Literature DB >> 20798789

Isolation and characterization of karlotoxin 1, a new amphipathic toxin from Karlodinium veneficum.

Ryan M Van Wagoner1, Jonathan R Deeds, Masayuki Satake, Anthony A Ribeiro, Allen R Place, Jeffrey L C Wright.   

Abstract

The karlotoxins (KmTxs) are a family of compounds produced by the dinoflagellate Karlodinium veneficum that cause membrane permeabilization. The structure of KmTx 1, determined using extensive 2D NMR spectroscopy, is very similar to the amphidinols and related compounds, though KmTx 1 features unique structural modifications of the conserved core region. The structure of KmTx 1 differs from that reported for KmTx 2, the only other reported karlotoxin to date, in lacking chlorination at its terminal alkene and possessing a hydrophobic arm that is two carbons longer.

Entities:  

Year:  2008        PMID: 20798789      PMCID: PMC2928153          DOI: 10.1016/j.tetlet.2008.08.103

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  7 in total

1.  Measurement of homonuclear proton couplings from regular 2D COSY spectra.

Authors:  F Delaglio; Z Wu; A Bax
Journal:  J Magn Reson       Date:  2001-04       Impact factor: 2.229

2.  Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities.

Authors:  Nagy Morsy; Toshihiro Houdai; Shigeru Matsuoka; Nobuaki Matsumori; Seiji Adachi; Tohru Oishi; Michio Murata; Takashi Iwashita; Tsuyoshi Fujita
Journal:  Bioorg Med Chem       Date:  2006-06-22       Impact factor: 3.641

3.  Membrane-permeabilizing activities of amphidinol 3, polyene-polyhydroxy antifungal from a marine dinoflagellate.

Authors:  Toshihiro Houdai; Shigeru Matsuoka; Nobuaki Matsumori; Michio Murata
Journal:  Biochim Biophys Acta       Date:  2004-11-17

4.  Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

Authors:  Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

5.  Lingshuiol, a novel polyhydroxyl compound with strongly cytotoxic activity from the marine dinoflagellate Amphidinium sp.

Authors:  Xiao-Chun Huang; Di Zhao; Yue-Wei Guo; Hou-Ming Wu; Li-Ping Lin; Zhong-Hua Wang; Jian Ding; Yong-Shui Lin
Journal:  Bioorg Med Chem Lett       Date:  2004-06-21       Impact factor: 2.823

6.  Effects of lipid constituents on membrane-permeabilizing activity of amphidinols.

Authors:  Nagy Morsy; Toshihiro Houdai; Keiichi Konoki; Nobuaki Matsumori; Tohru Oishi; Michio Murata
Journal:  Bioorg Med Chem       Date:  2007-12-23       Impact factor: 3.641

7.  The cytotoxicity of lingshuiol: a comparative study with amphidinol 2 on membrane permeabilizing activities.

Authors:  Xin-Ming Qi; Bo Yu; Xiao-Chun Huang; Yue-Wei Guo; Qing Zhai; Ren Jin
Journal:  Toxicon       Date:  2007-04-10       Impact factor: 3.033

  7 in total
  26 in total

1.  Acute toxicity of karlotoxins to mice.

Authors:  Allen R Place; R Munday; J S Munday
Journal:  Toxicon       Date:  2014-08-20       Impact factor: 3.033

2.  Two new karlotoxins found in Karlodinium veneficum (strain GM2) from the East China Sea.

Authors:  Pengjie Cai; Shan He; Chengxu Zhou; Allen R Place; Saddef Haq; Lijian Ding; Haimin Chen; Ying Jiang; Cheng Guo; Yaru Xu; Jinrong Zhang; Xiaojun Yan
Journal:  Harmful Algae       Date:  2016-08-27       Impact factor: 4.273

3.  Ichthyotoxic Karlodinium veneficum (Ballantine) J Larsen in the Upper Swan River Estuary (Western Australia): Ecological conditions leading to a fish kill.

Authors:  Jason E Adolf; Tsvetan R Bachvaroff; Jonathan R Deeds; Allen R Place
Journal:  Harmful Algae       Date:  2015-08-12       Impact factor: 4.273

4.  Karmitoxin: An Amine-Containing Polyhydroxy-Polyene Toxin from the Marine Dinoflagellate Karlodinium armiger.

Authors:  Silas Anselm Rasmussen; Sofie Bjørnholt Binzer; Casper Hoeck; Sebastian Meier; Livia Soman de Medeiros; Nikolaj Gedsted Andersen; Allen Place; Kristian Fog Nielsen; Per Juel Hansen; Thomas Ostenfeld Larsen
Journal:  J Nat Prod       Date:  2017-04-05       Impact factor: 4.050

5.  Structure and absolute configuration of karlotoxin-2, an ichthyotoxin from the marine dinoflagellate Karlodinium veneficum.

Authors:  Jiangnan Peng; Allen R Place; Wesley Yoshida; Clemens Anklin; Mark T Hamann
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

6.  The cytotoxic mechanism of karlotoxin 2 (KmTx 2) from Karlodinium veneficum (Dinophyceae).

Authors:  Jonathan R Deeds; Robert E Hoesch; Allen R Place; Joseph P Y Kao
Journal:  Aquat Toxicol       Date:  2014-12-15       Impact factor: 4.964

Review 7.  The expanding role of marine microbes in pharmaceutical development.

Authors:  Amanda L Waters; Russell T Hill; Allen R Place; Mark T Hamann
Journal:  Curr Opin Biotechnol       Date:  2010-10-16       Impact factor: 9.740

8.  Structure and relative potency of several karlotoxins from Karlodinium veneficum.

Authors:  Ryan M Van Wagoner; Jonathan R Deeds; Avery O Tatters; Allen R Place; Carmelo R Tomas; Jeffrey L C Wright
Journal:  J Nat Prod       Date:  2010-08-27       Impact factor: 4.050

9.  A dinoflagellate exploits toxins to immobilize prey prior to ingestion.

Authors:  Jian Sheng; Edwin Malkiel; Joseph Katz; Jason E Adolf; Allen R Place
Journal:  Proc Natl Acad Sci U S A       Date:  2010-01-19       Impact factor: 11.205

10.  Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical-Shift Analysis: Insights into their Mechanism of Action.

Authors:  Amanda L Waters; Joonseok Oh; Allen R Place; Mark T Hamann
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-16       Impact factor: 15.336

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