Jaspines A and B: Two New Cytotoxic Sphingosine Derivatives from the Marine Sponge Jaspis sp.

Ledroit, Veronique; Debitus, Cécile; Lavaud, Catherine; Massiot, Georges

doi:10.1002/chin.200314195

Cited by 3 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The cytotoxicity found for this natural product in several cell lines (Kuroda et al, 2002;Ledroit et al, 2003) has been associated to its activity as sphingomyelin synthase inhibitor (Salma et al, 2012(Salma et al, , 2009). However, Jaspine B, its diasteroisomers (Yoshimitsu et al, 2011) and some derivatives thereof have also been evaluated as SK inhibitors showing a moderate inhibition of both isoforms in the low µM range (Byun et al, 2013).…”

Section: Sphingolipid Analogs As Sk Inhibitorsmentioning

confidence: 97%

Inhibitors of sphingosine-1-phosphate metabolism (sphingosine kinases and sphingosine-1-phosphate lyase)

Sanllehí

Abad

Casas

et al. 2016

Chemistry and Physics of Lipids

View full text Add to dashboard Cite

Section: Sphingolipid Analogs As Sk Inhibitorsmentioning

confidence: 97%

Inhibitors of sphingosine-1-phosphate metabolism (sphingosine kinases and sphingosine-1-phosphate lyase)

Sanllehí

Abad

Casas

et al. 2016

Chemistry and Physics of Lipids

View full text Add to dashboard Cite

“…[17] and Jaspis sp. [18] led to the isolation of a cyclic anhydrophytosphingosine, named pachastrissamine or Jaspine B, which was reported to exhibit strong cytotoxicity against different human solid tumor cell lines [17,18]. However, its mechanism of action remains to be clarified.…”

Section: Introductionmentioning

confidence: 99%

The natural marine anhydrophytosphingosine, Jaspine B, induces apoptosis in melanoma cells by interfering with ceramide metabolism

Salma

Lafont

Therville

et al. 2009

Biochemical Pharmacology

View full text Add to dashboard Cite

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. A c c e p t e d M a n u s c r i p t 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 AbstractMarine environment has frequently afforded a variety of biologically active compounds with strong anticancer and cytotoxic properties. In the present study, the mechanism of action of Jaspine B, an anhydrophytosphingosine derivative isolated from the marine sponge Jaspis sp., was investigated. Jaspine B was able to doseand time-dependently decrease the viability of murine B16 and human SK-Mel28 melanoma cells. On these cells, Jaspine B treatment triggered cell death by typical apoptosis as illustrated by phosphatidylserine externalization, the release of cytochrome c and caspase processing. These effects were associated with increased intracellular ceramide levels owing to perturbed ceramide metabolism. Indeed, Jaspine B exposure strongly inhibited the activity of sphingomyelin synthase (SMS), an enzyme that converts de novo ceramide into the membrane lipid sphingomyelin.Moreover, whereas Jaspine B-induced cell death was enhanced in SMS1-depleted cells, it was strongly inhibited in cells that stably overexpress human SMS1. Finally, the cytotoxic effects of Jaspine B truncated analogs were also shown to be dependent on SMS activity.Altogether, Jaspine B is able to kill melanoma cells by acting on SMS activity and consequently on ceramide formation, and may represent a new class of cytotoxic compounds with potential applications in anticancer melanoma therapy.

show abstract

“…The Debitus research group reported isolation of the same natural product from a different marine sponge Jaspis sp. (Ledroit et al, 2003). In anti-cancer assays, this novel sphingosine derivative proved to be the most potent compound against the A549 human lung carcinoma cell line isolated from the Jaspis genus.…”

Section: Introductionmentioning

confidence: 98%

Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks

et al. 2013

View full text Add to dashboard Cite

Dedicated to Professor Štefan Toma on the occasion of his 75th birthdayAminohydroxylation of prochiral divinylcarbinol and subsequent Pd(II)-catalysed oxy-/amidocarbonylation of aminopentenediols is reported. The method was applied to the preparation of useful building blocks for syntheses of cytotoxic jaspines and glycosidase inhibitor DLX-homologues. The key intermediates, tetrahydrofuranolactones (l-arabino-II) and pyrrolidinolactones (l-arabino-IX and l-xylo-IX), were prepared in a short 2-step sequence from divinylcarbinol.

show abstract

Jaspines A and B: Two New Cytotoxic Sphingosine Derivatives from the Marine Sponge Jaspis sp.

Cited by 3 publications

References 1 publication

Inhibitors of sphingosine-1-phosphate metabolism (sphingosine kinases and sphingosine-1-phosphate lyase)

Inhibitors of sphingosine-1-phosphate metabolism (sphingosine kinases and sphingosine-1-phosphate lyase)

The natural marine anhydrophytosphingosine, Jaspine B, induces apoptosis in melanoma cells by interfering with ceramide metabolism

Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks

Contact Info

Product

Resources

About