Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines

Daniel Canals; David Mormeneo; Gemma Fabriàs; Amadeu Llebaria; Josefina Casas; Antonio Delgado

doi:10.1016/j.bmc.2008.11.026

Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines

Daniel Canals
, David Mormeneo
, Gemma Fabriàs
, Amadeu Llebaria
, Josefina Casas
, Antonio Delgado

Medical Oncology

Research Unit on Bioactive Molecules (RUBAM)
University of Barcelona

Research output: Contribution to journal › Article › peer-review

105 Scopus citations

Abstract

The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different configurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role in autophagy.

Original language	English
Pages (from-to)	235-241
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	1
DOIs	https://doi.org/10.1016/j.bmc.2008.11.026
State	Published - Jan 1 2009

Keywords

Ceramide
Cytotoxicity
Dihydroceramide
Phytosphingosine
Stereoisomers

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10.1016/j.bmc.2008.11.026

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AU - Canals, Daniel

AU - Mormeneo, David

AU - Fabriàs, Gemma

AU - Llebaria, Amadeu

AU - Casas, Josefina

AU - Delgado, Antonio

PY - 2009/1/1

Y1 - 2009/1/1

N2 - The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different configurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role in autophagy.

AB - The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different configurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role in autophagy.

KW - Ceramide

KW - Cytotoxicity

KW - Dihydroceramide

KW - Phytosphingosine

KW - Stereoisomers

UR - https://www.scopus.com/pages/publications/57649143954

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M3 - Article

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AN - SCOPUS:57649143954

SN - 0968-0896

VL - 17

SP - 235

EP - 241

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 1

ER -

Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines

Abstract

Keywords

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