Literature DB >> 14971894

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

George R Pettit1, Jun-Ping Xu, Jean-Charles Chapuis, Robin K Pettit, Larry P Tackett, Dennis L Doubek, John N A Hooper, Jean M Schmidt.   

Abstract

The Indo-Pacific marine sponge Ircinia ramosa has been found to contain two powerful (GI50 from 0.001 to <0.0001 microg/mL) murine and human cancer cell growth inhibitors. Both were isolated (10(-3)-10(-4)% yields) by cancer cell line bioassay-guided techniques and named irciniastatins A (1) and B (2). Structural elucidation by a combination of spectral analyses, primarily high resolution mass and 2D-NMR (principally APT, HMQC, HMBC, and ROESY) spectroscopy, revealed the unusual structures 1 and 2.

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Year:  2004        PMID: 14971894     DOI: 10.1021/jm030207d

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  28 in total

1.  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

2.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

3.  Irciniastatin A, a pederin-type translation inhibitor, promotes ectodomain shedding of cell-surface tumor necrosis factor receptor 1.

Authors:  Seiya Hirano; Hue Tu Quach; Tsubasa Watanabe; Naoki Kanoh; Yoshiharu Iwabuchi; Takeo Usui; Takao Kataoka
Journal:  J Antibiot (Tokyo)       Date:  2015-01-28       Impact factor: 2.649

4.  Polyketide proofreading by an acyltransferase-like enzyme.

Authors:  Katja Jensen; Holger Niederkrüger; Katrin Zimmermann; Anna L Vagstad; Jana Moldenhauer; Nicole Brendel; Sarah Frank; Petra Pöplau; Christoph Kohlhaas; Craig A Townsend; Marco Oldiges; Christian Hertweck; Jörn Piel
Journal:  Chem Biol       Date:  2012-03-23

5.  Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

Authors:  Ashutosh Pal; Zhenghong Peng; Paul T Schuber; Basvoju A Bhanu Prasad; William G Bornmann
Journal:  Tetrahedron Lett       Date:  2013-10-09       Impact factor: 2.415

6.  Total synthesis of (+)-psymberin (irciniastatin A): catalytic reagent control as the strategic cornerstone.

Authors:  Amos B Smith; Jon A Jurica; Shawn P Walsh
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

7.  Polyketide assembly lines of uncultivated sponge symbionts from structure-based gene targeting.

Authors:  Katja M Fisch; Cristian Gurgui; Nina Heycke; Sonia A van der Sar; Sally A Anderson; Victoria L Webb; Stefan Taudien; Matthias Platzer; Brent K Rubio; Sarah J Robinson; Phillip Crews; Jörn Piel
Journal:  Nat Chem Biol       Date:  2009-07       Impact factor: 15.040

8.  Progress toward the total synthesis of psymberin/irciniastatin A.

Authors:  Lauren E Brown; Yakira R Landaverry; James R Davies; Kristin A Milinkevich; Sandra Ast; Joseph S Carlson; Allen G Oliver; Joseph P Konopelski
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

9.  Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.

Authors:  Yu Feng; Xin Jiang; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2012-10-04       Impact factor: 15.419

10.  Multicomponent approach to the synthesis of oxidized amides through nitrile hydrozirconation.

Authors:  Shuangyi Wan; Michael E Green; Jung-Hyun Park; Paul E Floreancig
Journal:  Org Lett       Date:  2007-11-17       Impact factor: 6.005

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