Literature DB >> 16797998

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

Nagy Morsy1, Toshihiro Houdai, Shigeru Matsuoka, Nobuaki Matsumori, Seiji Adachi, Tohru Oishi, Michio Murata, Takashi Iwashita, Tsuyoshi Fujita.   

Abstract

Two new homologues of amphidinols (AM14 and AM15) were isolated from the cultured dinoflagellate Amphidinium klebsii. The structures were elucidated on the basis of 2D NMR and collision-induced dissociation MS/MS and turned out to be closely related homologues of AM7. Their weak membrane-disrupting activity indicates that the hydrophobic polyene chain is essential for the potent biological activities. Structure-activity relationship for the polyhydroxyl part was then examined with use of AM homologues possessing various chain lengths, indicating that the pore size of the channel/lesion formed by AMs was not greatly affected by the length of the polyhydroxyl chain.

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Year:  2006        PMID: 16797998     DOI: 10.1016/j.bmc.2006.06.012

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


  14 in total

1.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

Review 2.  The continuing saga of the marine polyether biotoxins.

Authors:  K C Nicolaou; Michael O Frederick; Robert J Aversa
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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

Authors:  Ryan M Van Wagoner; Jonathan R Deeds; Masayuki Satake; Anthony A Ribeiro; Allen R Place; Jeffrey L C Wright
Journal:  Tetrahedron Lett       Date:  2008-11-03       Impact factor: 2.415

4.  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

Review 5.  Marine natural products targeting the eukaryotic cell membrane.

Authors:  Shinichi Nishimura
Journal:  J Antibiot (Tokyo)       Date:  2021-09-07       Impact factor: 2.649

6.  Rapid Screening of Polyol Polyketides from Marine Dinoflagellates.

Authors:  Adrián Morales-Amador; María L Souto; Christian Hertweck; José J Fernández; María García-Altares
Journal:  Anal Chem       Date:  2022-10-03       Impact factor: 8.008

7.  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

8.  Genetic diversity, morphological uniformity and polyketide production in dinoflagellates (Amphidinium, Dinoflagellata).

Authors:  Shauna A Murray; Tamsyn Garby; Mona Hoppenrath; Brett A Neilan
Journal:  PLoS One       Date:  2012-06-04       Impact factor: 3.240

9.  A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.

Authors:  Aleksandr Grisin; P Andrew Evans
Journal:  Chem Sci       Date:  2015-08-06       Impact factor: 9.825

10.  HPLC-HRMS Quantification of the Ichthyotoxin Karmitoxin from Karlodinium armiger.

Authors:  Aaron John Christian Andersen; Lívia Soman de Medeiros; Sofie Bjørnholt Binzer; Silas Anselm Rasmussen; Per Juel Hansen; Kristian Fog Nielsen; Kevin Jørgensen; Thomas Ostenfeld Larsen
Journal:  Mar Drugs       Date:  2017-08-31       Impact factor: 5.118

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