Literature DB >> 18590311

Revisiting the sponge sources, stereostructure, and biological activity of cyclocinamide a.

Brent K Rubio1, Sarah J Robinson, Claudia E Avalos, Frederick A Valeriote, Nicole J de Voogd, Phillip Crews.   

Abstract

The dramatic biogeographical variations in the secondary metabolites from Psammocinia aff. bulbosa have complicated our efforts to reisolate the two most cytotoxic of its metabolites, (+)-psymberin and (+)-cyclocinamide A. Reported now are the results of a new study that demonstrates our ability to repeatedly isolate these two compounds through targeted collection efforts. Additional study of the new sample of (+)-cyclocinamide A has enabled finalizing its biological activity and absolute stereochemistry as 4S, 7S, 11S, 14S.

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Year:  2008        PMID: 18590311      PMCID: PMC2772108          DOI: 10.1021/np800230d

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


  16 in total

1.  Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family.

Authors:  Robert H Cichewicz; Frederick A Valeriote; Phillip Crews
Journal:  Org Lett       Date:  2004-06-10       Impact factor: 6.005

2.  Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa.

Authors:  George R Pettit; Jun-Ping Xu; Jean-Charles Chapuis; Robin K Pettit; Larry P Tackett; Dennis L Doubek; John N A Hooper; Jean M Schmidt
Journal:  J Med Chem       Date:  2004-02-26       Impact factor: 7.446

3.  Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products.

Authors:  Xin Jiang; Noelle Williams; Jef K De Brabander
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

4.  Synthesis and complete stereochemical assignment of psymberin/irciniastatin A.

Authors:  Xin Jiang; Jorge García-Fortanet; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

Review 5.  Bacterial symbionts: prospects for the sustainable production of invertebrate-derived pharmaceuticals.

Authors:  J Piel
Journal:  Curr Med Chem       Date:  2006       Impact factor: 4.530

6.  Redox inactivation of human 15-lipoxygenase by marine-derived meroditerpenes and synthetic chromanes: archetypes for a unique class of selective and recyclable inhibitors.

Authors:  Robert H Cichewicz; Victor A Kenyon; Stephanie Whitman; Nancy M Morales; Joanne F Arguello; Theodore R Holman; Phillip Crews
Journal:  J Am Chem Soc       Date:  2004-11-17       Impact factor: 15.419

7.  Highly N-methylated linear peptides produced by an atypical sponge-derived Acremonium sp.

Authors:  Claudia M Boot; Karen Tenney; Frederick A Valeriote; Phillip Crews
Journal:  J Nat Prod       Date:  2006-01       Impact factor: 4.050

8.  Halogenated cyclic peptides isolated from the sponge Corticium sp.

Authors:  Damian W Laird; Daniel V LaBarbera; Xidong Feng; Tim S Bugni; Mary Kay Harper; Chris M Ireland
Journal:  J Nat Prod       Date:  2007-03-29       Impact factor: 4.050

9.  The total synthesis of psymberin.

Authors:  Xianhai Huang; Ning Shao; Anandan Palani; Robert Aslanian; Alexei Buevich
Journal:  Org Lett       Date:  2007-05-25       Impact factor: 6.005

10.  Extending the record of meroditerpenes from Cacospongia marine sponges.

Authors:  Brent K Rubio; Rob W M van Soest; Phillip Crews
Journal:  J Nat Prod       Date:  2007-03-09       Impact factor: 4.050

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  4 in total

1.  Total Synthesis of Nominal Cyclocinamide B and Investigation into the Identity of the Cyclocinamides.

Authors:  Stephanie S Curzon; Jessica M Garcia; Joseph P Konopelski
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Total synthesis of nominal (11S)- and (11R)-cyclocinamide A.

Authors:  Jessica M Garcia; Stephanie S Curzon; Katharine R Watts; Joseph P Konopelski
Journal:  Org Lett       Date:  2012-04-05       Impact factor: 6.005

Review 3.  A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.

Authors:  Koneni V Sashidhara; Kimberly N White; Phillip Crews
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

4.  Application of the DP4 Probability Method to Flexible Cyclic Peptides with Multiple Independent Stereocenters: The True Structure of Cyclocinamide A.

Authors:  Jason K Cooper; Kelin Li; Jeffrey Aubé; David A Coppage; Joseph P Konopelski
Journal:  Org Lett       Date:  2018-07-09       Impact factor: 6.072

  4 in total

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