New bioactive cyclic peroxides from the Caribbean marine sponge Plakortis zyggompha

Fabrice Berrué; Olivier P. Thomas; Corinne Funel Le Bon; Fernando Reyes; Philippe Amade

doi:10.1016/j.tet.2005.09.077

New bioactive cyclic peroxides from the Caribbean marine sponge Plakortis zyggompha

Fabrice Berrué, Olivier P. Thomas, Corinne Funel Le Bon, Fernando Reyes, Philippe Amade

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

25 Citations (Scopus)

Abstract

The new plakortide Q (1) has been isolated from the little studied marine sponge Plakortis zyggompha, together with the six new cyclic peroxide analogues 2-7 in their methyl ester forms 2a-7a. Their structure was fully elucidated through NMR and MS analyses and the relative stereochemistry of the 1,2-dioxane ring was established after interpretation of the coupling constant values and the NOESY data. The carboxylic acid function of these compounds was proved to be very reactive and methylation was found to take place during the purification process. The non-esterified peroxides exhibited more cytotoxic activity against human tumor cell lines than their corresponding methyl esters.

Original language	English
Pages (from-to)	11843-11849
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2005.09.077
Publication status	Published - 12 Dec 2005
Externally published	Yes

Keywords

Antitumoral
Marine sponge
Peroxides
Plakortis

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10.1016/j.tet.2005.09.077

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title = "New bioactive cyclic peroxides from the Caribbean marine sponge Plakortis zyggompha",

abstract = "The new plakortide Q (1) has been isolated from the little studied marine sponge Plakortis zyggompha, together with the six new cyclic peroxide analogues 2-7 in their methyl ester forms 2a-7a. Their structure was fully elucidated through NMR and MS analyses and the relative stereochemistry of the 1,2-dioxane ring was established after interpretation of the coupling constant values and the NOESY data. The carboxylic acid function of these compounds was proved to be very reactive and methylation was found to take place during the purification process. The non-esterified peroxides exhibited more cytotoxic activity against human tumor cell lines than their corresponding methyl esters.",

keywords = "Antitumoral, Marine sponge, Peroxides, Plakortis",

author = "Fabrice Berru{\'e} and Thomas, \{Olivier P.\} and Bon, \{Corinne Funel Le\} and Fernando Reyes and Philippe Amade",

year = "2005",

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doi = "10.1016/j.tet.2005.09.077",

language = "English",

volume = "61",

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T1 - New bioactive cyclic peroxides from the Caribbean marine sponge Plakortis zyggompha

AU - Berrué, Fabrice

AU - Thomas, Olivier P.

AU - Bon, Corinne Funel Le

AU - Reyes, Fernando

AU - Amade, Philippe

PY - 2005/12/12

Y1 - 2005/12/12

N2 - The new plakortide Q (1) has been isolated from the little studied marine sponge Plakortis zyggompha, together with the six new cyclic peroxide analogues 2-7 in their methyl ester forms 2a-7a. Their structure was fully elucidated through NMR and MS analyses and the relative stereochemistry of the 1,2-dioxane ring was established after interpretation of the coupling constant values and the NOESY data. The carboxylic acid function of these compounds was proved to be very reactive and methylation was found to take place during the purification process. The non-esterified peroxides exhibited more cytotoxic activity against human tumor cell lines than their corresponding methyl esters.

AB - The new plakortide Q (1) has been isolated from the little studied marine sponge Plakortis zyggompha, together with the six new cyclic peroxide analogues 2-7 in their methyl ester forms 2a-7a. Their structure was fully elucidated through NMR and MS analyses and the relative stereochemistry of the 1,2-dioxane ring was established after interpretation of the coupling constant values and the NOESY data. The carboxylic acid function of these compounds was proved to be very reactive and methylation was found to take place during the purification process. The non-esterified peroxides exhibited more cytotoxic activity against human tumor cell lines than their corresponding methyl esters.

KW - Antitumoral

KW - Marine sponge

KW - Peroxides

KW - Plakortis

UR - https://www.scopus.com/pages/publications/27744604716

U2 - 10.1016/j.tet.2005.09.077

DO - 10.1016/j.tet.2005.09.077

M3 - Article

AN - SCOPUS:27744604716

SN - 0040-4020

VL - 61

SP - 11843

EP - 11849

JO - Tetrahedron

JF - Tetrahedron

IS - 50

ER -

New bioactive cyclic peroxides from the Caribbean marine sponge Plakortis zyggompha

Abstract

Keywords

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