Literature DB >> 12828469

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

Karumanchi V Rao1, Bernard D Santarsiero, Andrew D Mesecar, Raymond F Schinazi, Babu L Tekwani, Mark T Hamann.   

Abstract

Eleven manzamine type alkaloids, two beta-carbolines, and five nucleosides have been isolated from an Indonesian sponge. Among these are the previously characterized 12,34-oxamanzamine A, 12,34-oxamanzamine E, manzamine A (1), 8-hydroxymanzamine A, 6-deoxymanzamine X, manzamine E (2), manzamine X, manzamine F (4), norharman, thymine, 2',3'-didehydro-2',3'-dideoxyuridine, uracil, thymidine, and 2'-deoxyuridine. The structures for the five new compounds have been assigned as 32,33-dihydro-31-hydroxymanzamine A (3), 32,33-dihydro-6-hydroxymanzamine A-35-one (5), des-N-methylxestomanzamine A (6), 32,33-dihydro-6,31-dihydroxymanzamine A (7), and 1,2,3,4-tetrahydronorharman-1-one (8), on the basis of NMR and X-ray data. The bioactivity and SAR of the manzamines against malaria, TB, and leishmania are also presented. The structural revision of two previously reported pyrazoles as uracil and thymine is also discussed.

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Year:  2003        PMID： 12828469      PMCID： PMC4969047          DOI： 10.1021/np020592u

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


  6 in total

1.  Carbon-13 magnetic resonance. XVII. Pyrimidine and purine nucleosides.

Authors:  A J Jones; D M Grant; M W Winkley; R K Robins
Journal:  J Am Chem Soc       Date:  1970-07-01       Impact factor: 15.419

2.  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

3.  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

4.  Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica.

Authors:  R A Edrada; P Proksch; V Wray; L Witte; W E Müller; R W Van Soest
Journal:  J Nat Prod       Date:  1996-11       Impact factor: 4.050

5.  8-Hydroxymanzamine A, a beta-carboline alkaloid from a sponge, Pachypellina sp.

Authors:  T Ichiba; J M Corgiat; P J Scheuer; M Kelly-Borges
Journal:  J Nat Prod       Date:  1994-01       Impact factor: 4.050

6.  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
  6 in total
  34 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

2.  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

Review 3.  Marine pharmacology in 2003-4: marine compounds with anthelmintic antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiplatelet, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune and nervous systems, and other miscellaneous mechanisms of action.

Authors:  Alejandro M S Mayer; Abimael D Rodríguez; Roberto G S Berlinck; Mark T Hamann
Journal:  Comp Biochem Physiol C Toxicol Pharmacol       Date:  2007-02-09       Impact factor: 3.228

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.  Metabolism and resistance of Fusarium spp. to the manzamine alkaloids via a putative retro pictet-spengler reaction and utility of the rational design of antimalarial and antifungal agents.

Authors:  Noer Kasanah; Lorelei Lucas Farr; Abbas Gholipour; David E Wedge; Mark T Hamann
Journal:  Mar Biotechnol (NY)       Date:  2014-02-20       Impact factor: 3.619

6.  A beta-carboline alkaloid from the Papua New Guinea marine sponge hyrtios reticulatus.

Authors:  Wayne D Inman; Walter M Bray; Nadine C Gassner; R Scott Lokey; Karen Tenney; Young Yongchun Shen; Karen Tendyke; Ted Suh; Phillip Crews
Journal:  J Nat Prod       Date:  2010-02-26       Impact factor: 4.050

7.  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

8.  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

9.  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

Review 10.  Marine antimalarials.

Authors:  Ernesto Fattorusso; Orazio Taglialatela-Scafati
Journal:  Mar Drugs       Date:  2009-04-23       Impact factor: 5.118
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