Marine cytotoxic jaspine B and its stereoisomers: biological activity and syntheses

Miroslava Martinková; Jozef Gonda

doi:10.1016/j.carres.2016.01.009

Marine cytotoxic jaspine B and its stereoisomers: biological activity and syntheses

Carbohydr Res. 2016 Mar 24:423:1-42. doi: 10.1016/j.carres.2016.01.009. Epub 2016 Jan 27.

Authors

Miroslava Martinková¹, Jozef Gonda²

Affiliations

¹ Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Šafárik University, Moyzesova 11, Sk-040 01 Košice, Slovak Republic. Electronic address: miroslava.martinkova@upjs.sk.
² Institute of Chemical Sciences, Department of Organic Chemistry, P. J. Šafárik University, Moyzesova 11, Sk-040 01 Košice, Slovak Republic.

PMID: 26878486
DOI: 10.1016/j.carres.2016.01.009

Abstract

Conformationally constrained sphingolipids such as anhydrophytosphingosines represented by jaspine B (also known as pachastrissamine) and its stereoisomers have become an attractive and timely target for total synthesis due to their significant biological activity as well as the unique structures. This review article describes the biological activity and chemistry of the natural jaspine B and its seven stereoisomers.

Keywords: Anhydrophytosphingosines; Asymmetric synthesis; Cytotoxic activity; Jaspine B; Sphingolipids; Stereoselective synthesis.

Publication types

Research Support, Non-U.S. Gov't
Review

MeSH terms

Animals
Aquatic Organisms / chemistry*
Chemistry Techniques, Synthetic
Cytotoxins / chemical synthesis*
Cytotoxins / chemistry
Cytotoxins / pharmacology*
Humans
Sphingosine / analogs & derivatives*
Sphingosine / chemical synthesis
Sphingosine / chemistry
Sphingosine / pharmacology
Stereoisomerism

Substances

Cytotoxins
pachastrissamine
Sphingosine