Literature DB >> 19159277

The marine sponge Diacarnus bismarckensis as a source of peroxiterpene inhibitors of Trypanosoma brucei, the causative agent of sleeping sickness.

Brent K Rubio1, Karen Tenney, Kean-Hooi Ang, Maha Abdulla, Michelle Arkin, James H McKerrow, Phillip Crews.   

Abstract

Human African trypanosomiasis, also known as African sleeping sickness, is a neglected tropical disease with inadequate therapeutic options. We have launched a collaborative new lead discovery venture using our repository of extracts and natural product compounds as input into our growth inhibition primary screen against Trypanosoma brucei. Careful evaluation of the spectral data of the natural products and derivatives allowed for the elucidation of the absolute configuration (using the modified Mosher's method) of two new peroxiterpenes: (+)-muqubilone B (1a) and (-)-ent-muqubilone (3a). Five known compounds were also isolated: (+)-sigmosceptrellin A (4a), (+)-sigmosceptrellin A methyl ester (4b), (-)-sigmosceptrellin B (5), (+)-epi-muqubillin A (6), and (-)-epi-nuapapuin B methyl ester (7). The isolated peroxiterpenes demonstrated activities in the range IC(50) = 0.2-2 mug/mL.

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Year:  2009        PMID: 19159277      PMCID: PMC2880650          DOI: 10.1021/np800711a

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


  18 in total

1.  Antimalarial, antiviral, and antitoxoplasmosis norsesterterpene peroxide acids from the Red Sea sponge Diacarnus erythraeanus.

Authors:  K A El Sayed; M T Hamann; N E Hashish; W T Shier; M Kelly; A A Khan
Journal:  J Nat Prod       Date:  2001-04       Impact factor: 4.050

2.  Mechanism of methyl esterification of carboxylic acids by trimethylsilyldiazomethane.

Authors:  Erik Kühnel; David D P Laffan; Guy C Lloyd-Jones; Teresa Martínez Del Campo; Ian R Shepperson; Jennifer L Slaughter
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Identification of novel inhibitors of UDP-Glc 4'-epimerase, a validated drug target for african sleeping sickness.

Authors:  Michael D Urbaniak; Jioji N Tabudravu; Aichi Msaki; Kathy Mansfield Matera; Ruth Brenk; Marcel Jaspars; Michael A J Ferguson
Journal:  Bioorg Med Chem Lett       Date:  2006-09-07       Impact factor: 2.823

4.  Cytotoxic cyclic norterpene peroxides from a Red Sea sponge Diacarnus erythraenus.

Authors:  D T Youssef; W Y Yoshida; M Kelly; P J Scheuer
Journal:  J Nat Prod       Date:  2001-10       Impact factor: 4.050

5.  Mycaperoxide H, a new cytotoxic norsesterterpene peroxide from a Thai marine sponge Mycale sp.

Authors:  Preecha Phuwapraisirisan; Shigeki Matsunaga; Nobuhiro Fusetani; Nilnaj Chaitanawisuti; Sirusa Kritsanapuntu; Piamsak Menasveta
Journal:  J Nat Prod       Date:  2003-02       Impact factor: 4.050

6.  Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa.

Authors:  Sabrin R M Ibrahim; Rainer Ebel; Victor Wray; Werner E G Müller; RuAngelie Edrada-Ebel; Peter Proksch
Journal:  J Nat Prod       Date:  2008-08-02       Impact factor: 4.050

7.  Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB.

Authors:  Jeremy P Mallari; Anang Shelat; Aaron Kosinski; Conor R Caffrey; Michele Connelly; Fangyi Zhu; James H McKerrow; R Kiplin Guy
Journal:  Bioorg Med Chem Lett       Date:  2008-04-08       Impact factor: 2.823

8.  Peroxide bond-dependent antiplasmodial specificity of artemisinin and OZ277 (RBx11160).

Authors:  Marcel Kaiser; Sergio Wittlin; Angela Nehrbass-Stuedli; Yuxiang Dong; Xiaofang Wang; Andrew Hemphill; Hugues Matile; Reto Brun; Jonathan L Vennerstrom
Journal:  Antimicrob Agents Chemother       Date:  2007-06-11       Impact factor: 5.191

Review 9.  Human African trypanosomiasis: pharmacological re-engagement with a neglected disease.

Authors:  M P Barrett; D W Boykin; R Brun; R R Tidwell
Journal:  Br J Pharmacol       Date:  2007-07-09       Impact factor: 8.739

Review 10.  The continuing problem of human African trypanosomiasis (sleeping sickness).

Authors:  Peter G E Kennedy
Journal:  Ann Neurol       Date:  2008-08       Impact factor: 10.422

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  12 in total

1.  Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi.

Authors:  Katharine R Watts; Joseline Ratnam; Kean-Hooi Ang; Karen Tenney; Jennifer E Compton; James McKerrow; Phillip Crews
Journal:  Bioorg Med Chem       Date:  2010-03-01       Impact factor: 3.641

Review 2.  The structural diversity and promise of antiparasitic marine invertebrate-derived small molecules.

Authors:  Katharine R Watts; Karen Tenney; Phillip Crews
Journal:  Curr Opin Biotechnol       Date:  2010-10-16       Impact factor: 9.740

Review 3.  Recent Advances of Marine Sponge-Associated Microorganisms as a Source of Commercially Viable Natural Products.

Authors:  Tan Suet May Amelia; Ferr Angelus C Suaberon; Johanne Vad; Afiq Durrani Mohd Fahmi; Jonel P Saludes; Kesaven Bhubalan
Journal:  Mar Biotechnol (NY)       Date:  2022-05-14       Impact factor: 3.619

4.  Inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells by the norsesterterpene peroxide, epimuqubilin A.

Authors:  Sarot Cheenpracha; Eun-Jung Park; Bahman Rostama; John M Pezzuto; Leng Chee Chang
Journal:  Mar Drugs       Date:  2010-03-01       Impact factor: 5.118

5.  Additional insights on the bastadins: isolation of analogues from the sponge Ianthella cf. reticulata and exploration of the oxime configurations.

Authors:  Laurent Calcul; Wayne D Inman; Alexi A Morris; Karen Tenney; Joseline Ratnam; James H McKerrow; Frederick A Valeriote; Phillip Crews
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

6.  Hit-to-lead development of the chamigrane endoperoxide merulin A for the treatment of African sleeping sickness.

Authors:  Gabriel Navarro; Supchar Chokpaiboon; Geraldine De Muylder; Walter M Bray; Sean C Nisam; James H McKerrow; Khanitha Pudhom; Roger G Linington
Journal:  PLoS One       Date:  2012-09-27       Impact factor: 3.240

Review 7.  Marine pharmacology in 2009-2011: marine compounds with antibacterial, antidiabetic, antifungal, anti-inflammatory, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous systems, and other miscellaneous mechanisms of action.

Authors:  Alejandro M S Mayer; Abimael D Rodríguez; Orazio Taglialatela-Scafati; Nobuhiro Fusetani
Journal:  Mar Drugs       Date:  2013-07-16       Impact factor: 5.118

8.  Relative and absolute stereochemistry of diacarperoxides: antimalarial norditerpene endoperoxides from marine sponge Diacarnus megaspinorhabdosa.

Authors:  Fan Yang; Yike Zou; Ru-Ping Wang; Mark T Hamann; Hong-Jun Zhang; Wei-Hua Jiao; Bing-Nan Han; Shao-Jiang Song; Hou-Wen Lin
Journal:  Mar Drugs       Date:  2014-08-08       Impact factor: 5.118

Review 9.  Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions.

Authors:  Vera A Vil'; Ivan A Yaremenko; Alexey I Ilovaisky; Alexander O Terent'ev
Journal:  Molecules       Date:  2017-11-02       Impact factor: 4.411

10.  Chemoinformatic analysis as a tool for prioritization of trypanocidal marine derived lead compounds.

Authors:  Yunjiang Feng; Marc Campitelli; Rohan A Davis; Ronald J Quinn
Journal:  Mar Drugs       Date:  2014-03-04       Impact factor: 5.118

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