Literature DB >> 14583033

Manadomanzamines A and B: a novel alkaloid ring system with potent activity against mycobacteria and HIV-1.

Jiangnan Peng1, Jin-Feng Hu, Abul B Kazi, Ze Li, Mitchell Avery, Olivier Peraud, Russell T Hill, Scott G Franzblau, Fangqiu Zhang, Raymond F Schinazi, Susan S Wirtz, Phillip Tharnish, Michelle Kelly, Subagus Wahyuono, Mark T Hamann.   

Abstract

Two novel alkaloids, named manadomanzamines A (1) and B (2), were isolated from an Indonesian sponge Acanthostrongylophora sp. (Haplosclerida: Petrosiidae). Their structures were elucidated and shown to be a novel organic skeleton related to the manzamine type alkaloids. Their absolute configuration and conformation were determined by CD, NOESY, and molecular modeling analysis. The microbial community analysis for the sponge that produces these unprecedented alkaloids has also been completed. Manadomanzamines A (1) and B (2) exhibited strong activity against Mycobacterium tuberculosis (Mtb) with MIC values of 1.9 and 1.5 mug/mL, respectively. Manadomanzamines A and B also exhibit activities against human immunodeficiency virus (HIV-1) and AIDS opportunistic fungal infections.

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Year:  2003        PMID: 14583033      PMCID: PMC4928190          DOI: 10.1021/ja030087z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

Review 1.  The manzamine alkaloids.

Authors:  Jin-Feng Hu; Mark T Hamann; Russell Hill; Michelle Kelly
Journal:  Alkaloids Chem Biol       Date:  2003

2.  Activities of 3'-azido-3'-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1.

Authors:  R F Schinazi; J P Sommadossi; V Saalmann; D L Cannon; M Y Xie; G C Hart; G A Smith; E F Hahn
Journal:  Antimicrob Agents Chemother       Date:  1990-06       Impact factor: 5.191

3.  Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.

Authors:  L Collins; S G Franzblau
Journal:  Antimicrob Agents Chemother       Date:  1997-05       Impact factor: 5.191

4.  Phylogenetic diversity of bacteria associated with the marine sponge Rhopaloeides odorabile.

Authors:  N S Webster; K J Wilson; L L Blackall; R T Hill
Journal:  Appl Environ Microbiol       Date:  2001-01       Impact factor: 4.792

5.  New manzamine alkaloids with potent activity against infectious diseases.

Authors:  K A El Sayed; M Kelly; U A Kara; K K Ang; I Katsuyama; D C Dunbar; A A Khan; M T Hamann
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

6.  In vivo antimalarial activity of the beta-carboline alkaloid manzamine A.

Authors:  K K Ang; M J Holmes; T Higa; M T Hamann; U A Kara
Journal:  Antimicrob Agents Chemother       Date:  2000-06       Impact factor: 5.191

7.  New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea.

Authors:  Jin-Feng Hu; John A Schetz; Michelle Kelly; Jiang-Nan Peng; Kenny K H Ang; Horst Flotow; Chung Yan Leong; Siew Bee Ng; Antony D Buss; Scott P Wilkins; Mark T Hamann
Journal:  J Nat Prod       Date:  2002-04       Impact factor: 4.050

8.  Selective inhibition of human immunodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine.

Authors:  R F Schinazi; A McMillan; D Cannon; R Mathis; R M Lloyd; A Peck; J P Sommadossi; M St Clair; J Wilson; P A Furman
Journal:  Antimicrob Agents Chemother       Date:  1992-11       Impact factor: 5.191

9.  New manzamine alkaloids with activity against infectious and tropical parasitic diseases from an Indonesian sponge.

Authors:  Karumanchi V Rao; Bernard D Santarsiero; Andrew D Mesecar; Raymond F Schinazi; Babu L Tekwani; Mark T Hamann
Journal:  J Nat Prod       Date:  2003-06       Impact factor: 4.050

  9 in total
  25 in total

1.  Manzamine A as a novel inhibitor of herpes simplex virus type-1 replication in cultured corneal cells.

Authors:  Jayavardhana R Palem; Gautam R Bedadala; Khalid A El Sayed; Shao-chung V Hsia
Journal:  Planta Med       Date:  2010-07-19       Impact factor: 3.352

Review 2.  Role of Marine Natural Products in the Genesis of Antiviral Agents.

Authors:  Vedanjali Gogineni; Raymond F Schinazi; Mark T Hamann
Journal:  Chem Rev       Date:  2015-08-28       Impact factor: 60.622

3.  Manzamine B and E and ircinal A related alkaloids from an Indonesian Acanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer's diseases.

Authors:  Karumanchi V Rao; Marwa S Donia; Jiangnan Peng; Esther Garcia-Palomero; Diana Alonso; Ana Martinez; Miguel Medina; Scott G Franzblau; Babu L Tekwani; Shabana I Khan; Subagus Wahyuono; Kristine L Willett; Mark T Hamann
Journal:  J Nat Prod       Date:  2006-07       Impact factor: 4.050

4.  Bioactive (+)-manzamine A and (+)-8-hydroxymanzamine A tertiary bases and salts from Acanthostrongylophora ingens and their preparations.

Authors:  Volodymyr Samoylenko; Shabana I Khan; Melissa R Jacoba; Babu L Tekwani; Larry A Walker; Charles D Hufford; Ilias Muhammad
Journal:  Nat Prod Commun       Date:  2009-02       Impact factor: 0.986

5.  A novel activity from an old compound: Manzamine A reduces the metastatic potential of AsPC-1 pancreatic cancer cells and sensitizes them to TRAIL-induced apoptosis.

Authors:  Esther A Guzmán; Jacob D Johnson; Patricia A Linley; Sarath E Gunasekera; Amy E Wright
Journal:  Invest New Drugs       Date:  2010-03-30       Impact factor: 3.850

6.  Structure-activity relationship and mechanism of action studies of manzamine analogues for the control of neuroinflammation and cerebral infections.

Authors:  Jiangnan Peng; Sucheta Kudrimoti; Sivaprakasam Prasanna; Srinivas Odde; Robert J Doerksen; Hari K Pennaka; Yeun-Mun Choo; Karumanchi V Rao; Babu L Tekwani; Vamsi Madgula; Shabana I Khan; Bin Wang; Alejandro M S Mayer; Melissa R Jacob; Lan Chun Tu; Jürg Gertsch; Mark T Hamann
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

7.  Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases.

Authors:  Karumanchi V Rao; Noer Kasanah; Subagus Wahyuono; Babu L Tekwani; Raymond F Schinazi; Mark T Hamann
Journal:  J Nat Prod       Date:  2004-08       Impact factor: 4.050

8.  Structure-activity relationship studies of manzamine A: amidation of positions 6 and 8 of the beta-carboline moiety.

Authors:  Amir E Wahba; Jiangnan Peng; Sucheta Kudrimoti; Babu L Tekwani; Mark T Hamann
Journal:  Bioorg Med Chem       Date:  2009-09-19       Impact factor: 3.641

9.  Acantholactone, a new manzamine related alkaloid with an unprecedented δ-lactone and ε-lactam ring system.

Authors:  Amir E Wahba; Yann Fromentin; Yike Zou; Mark T Hamann
Journal:  Tetrahedron Lett       Date:  2012-09-07       Impact factor: 2.415

10.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

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