Effects of a synthetic analog of polycavernoside A on human neuroblastoma cells.

Cell Physiol Biochem

Departamento de Farmacologia. Facultad de Veterinaria. Universidad de Santiago de Compostela. Campus de Lugo. Lugo, Spain.

Published: April 2007

Background: Polycavernoside A is a glycosidic marine toxin first extracted from the red alga Polycavernosa tsudai in 1991 when 3 people died after the ingestion of this food. Polycavernoside A is an interesting molecule because of its complex macrolide structure and strong bioactivity. However, the target site of this toxin has not been characterized.

Methods: We studied the effects of a synthethic analog of polycavernoside A on human neuroblastoma cells by measuring changes in membrane potential with bis-oxonol and variations in intracellular calcium levels with fura-2. Fluorescent phalloidin was utilized for assaying activity on actin cytoskeleton.

Results: Data showed that this polycavernoside A analog induced a membrane depolarization and an increase in cytosolic calcium levels.

Conclusion: These results provide the first insight into the mode of action of polycavernoside A, suggesting that: i) this toxin triggers an initial extracellular calcium entry neither produced across L-type voltage-gated calcium channels nor activation of muscarinic receptors ii) there is a depolarization induced by the toxin and due to the extracellular calcium entry.

Download full-text PDF

Source
http://dx.doi.org/10.1159/000099206DOI Listing

Publication Analysis

Top Keywords

analog polycavernoside
8
polycavernoside human
8
human neuroblastoma
8
neuroblastoma cells
8
extracellular calcium
8
calcium entry
8
polycavernoside
6
calcium
5
effects synthetic
4
synthetic analog
4

Similar Publications

Isolation and structure determination of a new analog of polycavernosides from marine sp. cyanobacterium.

Beilstein J Org Chem

March 2024

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

Polycavernoside E (), a new polycavernoside analog, was isolated from a marine sp. cyanobacterium. The relative configuration was elucidated primarily by analyzing the two dimensional nuclear magnetism resonance (2D NMR) data.

View Article and Find Full Text PDF

Comparative cytotoxicity of gambierol versus other marine neurotoxins.

Chem Res Toxicol

June 2011

Departamento de Farmacología, Facultad de Veterinaria, Universidad de Santiago de Compostela, Campus de Lugo, 27002 Lugo, Spain.

Many microalgae produce compounds that exhibit potent biological activities. Ingestion of marine organisms contaminated with those toxins results in seafood poisonings. In many cases, the lack of toxic material turns out to be an obstacle to make the toxicological investigations needed.

View Article and Find Full Text PDF

Prins-type macrocyclizations as an efficient ring-closing strategy in natural product synthesis.

Angew Chem Int Ed Engl

November 2010

Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Silverman Hall, Northwestern University, Evanston, IL 60208, USA.

Prins-type macrocyclizations have recently emerged as a successful strategy in the synthesis of polyketide-derived natural products. This reaction provides a concise and selective means to form tetrahydropyran-containing macrocyclic rings of varying size. A high degree of functionality within the macrocycle is tolerated and the yields for these transformations are typically good to excellent.

View Article and Find Full Text PDF

Effects of a synthetic analog of polycavernoside A on human neuroblastoma cells.

Cell Physiol Biochem

April 2007

Departamento de Farmacologia. Facultad de Veterinaria. Universidad de Santiago de Compostela. Campus de Lugo. Lugo, Spain.

Background: Polycavernoside A is a glycosidic marine toxin first extracted from the red alga Polycavernosa tsudai in 1991 when 3 people died after the ingestion of this food. Polycavernoside A is an interesting molecule because of its complex macrolide structure and strong bioactivity. However, the target site of this toxin has not been characterized.

View Article and Find Full Text PDF

[structure: see text] Two approaches to the synthesis of the aglycon 120 of polycavernoside A (1) were developed, only one of which was completed. The successful "second-generation" route assembled the aglycon seco acids 102 and 106 via Nozaki-Hiyama-Kishi coupling of aldehyde 70, prepared from methyl (S)-3-hydroxy-2-methylpropionate (72) and (S)-pantolactone (73), with vinyl bromide 71. The latter was obtained from a sequence which commenced from the silyl ether 24 of 3-hydroxypropionaldehyde and entailed cyclization of (Z)-zeta-hydroxy-alpha,beta-unsaturated ester 82.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!