Literature DB >> 20166736

Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge Agelas dendromorpha.

Supriya Tilvi1, Céline Moriou, Marie-Thérèse Martin, Jean-François Gallard, Jonathan Sorres, Kirti Patel, Sylvain Petek, Cécile Debitus, Ludmila Ermolenko, Ali Al-Mourabit.   

Abstract

The study of the n-butanol extract of the New Caledonian sponge Agelas dendromorpha led to the isolation and identification of three new pyrrole-2-aminoimidazole (P-2-AI) alkaloids, named agelastatins E (3) and F (4) and benzosceptrin C (5), together with 10 known metabolites, agelastatin A (1), agelastatin D (2), sceptrin (6), manzacidin A, tauroacidin A, taurodispacamide A, nortopsentin D, thymine, longamide, and 4,5-dibromopyrrole-2-carboxamide. Their structures were assigned by spectroscopic data interpretation. All the compounds were tested for cytotoxic activity.

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Year:  2010        PMID: 20166736     DOI: 10.1021/np900539j

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  20 in total

1.  Asymmetric total synthesis of ent-cyclooroidin.

Authors:  Sabuj Mukherjee; Rasapalli Sivappa; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

3.  Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis.

Authors:  Alyssa H Antropow; Kun Xu; Rachel J Buchsbaum; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2017-07-25       Impact factor: 4.354

4.  Bioinspired total synthesis of agelastatin A.

Authors:  Jeremy Chris P Reyes; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-11       Impact factor: 15.336

5.  Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.

Authors:  Sunkyu Han; Dustin S Siegel; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

6.  De novo synthesis of benzosceptrin C and nagelamide H from 7-15N-oroidin: implications for pyrrole-aminoimidazole alkaloid biosynthesis.

Authors:  E Paige Stout; Brandon I Morinaka; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2012-03-28       Impact factor: 4.050

Review 7.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

8.  Total synthesis of all (-)-Agelastatin alkaloids.

Authors:  Mohammad Movassaghi; Dustin S Siegel; Sunkyu Han
Journal:  Chem Sci       Date:  2010-01-01       Impact factor: 9.825

9.  Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe.

Authors:  Morgan Jouanneau; Brandon McClary; Jeremy Chris P Reyes; Rong Chen; Yuling Chen; William Plunkett; Xin Cheng; Andrew Z Milinichik; Earl F Albone; Jun O Liu; Daniel Romo
Journal:  Bioorg Med Chem Lett       Date:  2016-02-23       Impact factor: 2.823

10.  A biomimetic route for construction of the [4+2] and [3+2] core skeletons of dimeric pyrrole-imidazole alkaloids and asymmetric synthesis of ageliferins.

Authors:  Xiao Wang; Xiaolei Wang; Xianghui Tan; Jianming Lu; Kevin W Cormier; Zhiqiang Ma; Chuo Chen
Journal:  J Am Chem Soc       Date:  2012-11-02       Impact factor: 15.419

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