Cytotoxic guanidine alkaloids from a French Polynesian Monanchora n. sp. sponge

Amr El-Demerdash; Céline Moriou; Marie Thérèse Martin; Alice De Souza Rodrigues-Stien; Sylvain Petek; Marina Demoy-Schneider; Kathryn Hall; John N. A. Hooper; Cécile Debitus; Ali Al-Mourabit

doi:10.1021/acs.jnatprod.6b00168

Cytotoxic guanidine alkaloids from a French Polynesian Monanchora n. sp. sponge

Amr El-Demerdash, Céline Moriou, Marie Thérèse Martin, Alice De Souza Rodrigues-Stien, Sylvain Petek, Marina Demoy-Schneider, Kathryn Hall, John N. A. Hooper, Cécile Debitus, Ali Al-Mourabit

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

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Abstract

Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of ¹H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC₅₀ values ranging from 4 nM to 10 μM.

Original language	English
Pages (from-to)	1929-1937
Number of pages	9
Journal	Journal of Natural Products
Volume	79
Issue number	8
DOIs	https://doi.org/10.1021/acs.jnatprod.6b00168
Publication status	Published - 26 Aug 2016

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title = "Cytotoxic guanidine alkaloids from a French Polynesian Monanchora n. sp. sponge",

abstract = "Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of 1H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.",

author = "Amr El-Demerdash and C{\'e}line Moriou and Martin, {Marie Th{\'e}r{\`e}se} and Rodrigues-Stien, {Alice De Souza} and Sylvain Petek and Marina Demoy-Schneider and Kathryn Hall and Hooper, {John N. A.} and C{\'e}cile Debitus and Ali Al-Mourabit",

note = "Publisher Copyright: {\textcopyright} 2016 The American Chemical Society and American Society of Pharmacognosy.",

year = "2016",

month = aug,

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doi = "10.1021/acs.jnatprod.6b00168",

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T1 - Cytotoxic guanidine alkaloids from a French Polynesian Monanchora n. sp. sponge

AU - El-Demerdash, Amr

AU - Moriou, Céline

AU - Martin, Marie Thérèse

AU - Rodrigues-Stien, Alice De Souza

AU - Petek, Sylvain

AU - Demoy-Schneider, Marina

AU - Hall, Kathryn

AU - Hooper, John N. A.

AU - Debitus, Cécile

AU - Al-Mourabit, Ali

PY - 2016/8/26

Y1 - 2016/8/26

N2 - Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of 1H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.

AB - Four bicyclic and three pentacyclic guanidine alkaloids (1-7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9-11 of known natural product crambescins, and the known crambescidins 12-15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of 1H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.

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JF - Journal of Natural Products

SN - 0163-3864

IS - 8

ER -

Cytotoxic guanidine alkaloids from a French Polynesian Monanchora n. sp. sponge

Abstract

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