Structure and biosynthesis of amphidinol 17, a hemolytic compound from Amphidinium carterae

Journal of Natural Products
Yanhui MengJeffrey L C Wright

Abstract

Amphidinol 17 (AM17; 1), a novel amphidinol, has been isolated from a Bahamas strain of Amphidinium carterae. This new congener contains the signature hairpin region and a Delta(6) polyene arm, whereas the polyol arm is distinct from those of other amphidinols. The pattern of acetate incorporation in 1 was directly determined by feeding a single labeled substrate, [2-(13)C]acetate. While the highly conserved regions within the amphidinol family of AM17 have exhibited identical occurrences of cleaved acetates to other amphidinols for which the biosynthesis has been explored, the polyol arm for AM17 displays a higher degree of nascent chain processing that shows similarities to amphidinolide biosynthesis. AM17 exhibited an EC(50) of 4.9 microM in a hemolytic assay using human red blood cells but displayed no detectable antifungal activity.

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Citations

Aug 28, 2010·Journal of Natural Products·Ryan M Van WagonerJeffrey L C Wright
Sep 3, 2010·Journal of Natural Products·Lilibeth A SalvadorHendrik Luesch
Nov 8, 2012·Journal of Natural Products·Yoshiyuki ManabeTohru Oishi
Apr 14, 2016·Organic Letters·Yusuke OguraShigefumi Kuwahara
Jul 5, 2016·Chemical & Pharmaceutical Bulletin·Takaaki KubotaJun'ichi Kobayashi
Aug 24, 2016·Journal of Natural Products·Silas Anselm RasmussenThomas Ostenfeld Larsen
Apr 6, 2017·Journal of Natural Products·Silas Anselm RasmussenThomas Ostenfeld Larsen
Sep 1, 2017·Marine Drugs·Aaron John Christian AndersenThomas Ostenfeld Larsen
Apr 11, 2018·Angewandte Chemie·Yuma WakamiyaTohru Oishi
Dec 24, 2011·Natural Product Reports·John W BluntMichèle R Prinsep
Nov 1, 2013·Organic & Biomolecular Chemistry·Nicolas RivalFrançoise Colobert
Feb 6, 2020·Natural Product Reports·Shinichi Nishimura, Nobuaki Matsumori
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Oct 31, 2012·Organic & Biomolecular Chemistry·Nicolas RivalFrançoise Colobert
Jun 17, 2014·Natural Product Reports·Ryan M Van WagonerJeffrey L C Wright
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Jun 14, 2014·Journal of Natural Products·Genoveffa NuzzoAngelo Fontana
Sep 9, 2021·The Journal of Antibiotics·Shinichi Nishimura

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