Alpha 2.0
Login Register
» Articles » PMID: 18646771

Brevisamide: an Unprecedented Monocyclic Ether Alkaloid from the Dinoflagellate Karenia Brevis That Provides a Potential Model for Ladder-frame Initiation

Overview
Journal Org Lett
Publisher American Chemical Society
Specialties Biochemistry
Chemistry
Date 2008 Jul 24
PMID 18646771
Citations 19
Authors
Masayuki Satake
Andrea J Bourdelais
Ryan M Van Wagoner
Daniel G Baden
Jeffrey L C Wright
Affiliations
Soon will be listed here.
Abstract

The dinoflagellate Karenia brevis is known for the production of brevetoxins, a family of polycyclic ether toxins, as well as their antagonist brevenal. Further examination of organic extracts of K. brevis has uncovered yet another unprecedented cyclic ether alkaloid named brevisamide. This report describes the structure elucidation of brevisamide based on detailed MS and NMR spectral analysis, and the importance of this new compound in shedding light on the biogenesis of fused polyethers is discussed.

Citing Articles

Gilman reagent toward the synthesis of natural products.

Munir R, Zahoor A, Nazeer U, Saeed M, Mansha A, Irfan A RSC Adv. 2023; 13(50):35172-35208.

PMID: 38053693 PMC: 10694855. DOI: 10.1039/d3ra07359a.

Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by spp. and Their Metabolic Products in Marine Organisms.

Hort V, Abadie E, Arnich N, Dechraoui Bottein M, Amzil Z Mar Drugs. 2021; 19(12).

PMID: 34940655 PMC: 8709462. DOI: 10.3390/md19120656.

Molecular Determinants of Brevetoxin Binding to Voltage-Gated Sodium Channels.

Konoki K, Baden D, Scheuer T, Catterall W Toxins (Basel). 2019; 11(9).

PMID: 31484365 PMC: 6784055. DOI: 10.3390/toxins11090513.

Brevenal, a Marine Natural Product, is Anti-Inflammatory and an Immunomodulator of Macrophage and Lung Epithelial Cells.

Keeler D, Grandal M, McCall J Mar Drugs. 2019; 17(3).

PMID: 30897777 PMC: 6470468. DOI: 10.3390/md17030184.

Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Ghosh A, Brindisi M RSC Adv. 2017; 6(112):111564-111598.

PMID: 28944049 PMC: 5603243. DOI: 10.1039/C6RA22611F.

References
1.
Lee M, Repeta D, Nakanishi K, Zagorski M . Biosynthetic origins and assignments of carbon 13 NMR peaks of brevetoxin B. J Am Chem Soc. 2012; 108(24):7855-6. DOI: 10.1021/ja00284a072. View
2.
Macpherson G, Burton I, LeBlanc P, Walter J, Wright J . Studies of the biosynthesis of DTX-5a and DTX-5b by the dinoflagellate Prorocentrum maculosum: regiospecificity of the putative Baeyer-Villigerase and insertion of a single amino acid in a polyketide chain. J Org Chem. 2003; 68(5):1659-64. DOI: 10.1021/jo0204754. View
3.
Yasumoto T . The chemistry and biological function of natural marine toxins. Chem Rec. 2002; 1(3):228-42. DOI: 10.1002/tcr.1010. View
4.
Baden D, Bourdelais A, Jacocks H, Michelliza S, Naar J . Natural and derivative brevetoxins: historical background, multiplicity, and effects. Environ Health Perspect. 2005; 113(5):621-5. PMC: 1257558. DOI: 10.1289/ehp.7499. View
5.
Vilotijevic I, Jamison T . Epoxide-opening cascades promoted by water. Science. 2007; 317(5842):1189-92. PMC: 2810534. DOI: 10.1126/science.1146421. View