Literature DB >> 16526806

Tedanolide C: a potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp.

Camille Chevallier1, Tim S Bugni, Xidong Feng, Mary Kay Harper, Anita M Orendt, Chris M Ireland.   

Abstract

Cytotoxicity-guided fractionation of the crude methanol extract of a marine sponge, Ircinia sp., yielded tedanolide C (1), a new 18-membered macrolide. The structure was solved by interpreting NMR and MS data, and the relative stereochemistry was determined from a combination of homo- and heteronuclear coupling constants in conjunction with molecular modeling. Compound 1 exhibited potent cytotoxicity against HCT-116 cells in vitro. Cell cycle analysis showed that treatment of cells with compound 1 arrested cells in the S-phase.

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Year:  2006        PMID： 16526806      PMCID： PMC2533847          DOI： 10.1021/jo052285+

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

Review 1.  Marine natural products and related compounds in clinical and advanced preclinical trials.

Authors:  David J Newman; Gordon M Cragg
Journal:  J Nat Prod       Date:  2004-08       Impact factor: 4.050

Review 2.  Marine natural products.

Authors:  John W Blunt; Brent R Copp; Murray H G Munro; Peter T Northcote; Michèle R Prinsep
Journal:  Nat Prod Rep       Date:  2004-01-14       Impact factor: 13.423

3.  Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens.

Authors:  Shinichi Nishimura; Shigeki Matsunaga; Satoru Yoshida; Yoichi Nakao; Hiroshi Hirota; Nobuhiro Fusetani
Journal:  Bioorg Med Chem       Date:  2005-01-17       Impact factor: 3.641

4.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors: 
Journal:  Phys Rev B Condens Matter       Date:  1988-01-15

5.  Sensitivity- and gradient-enhanced hetero (omega1) half-filtered TOCSY experiment for measuring long-range heteronuclear coupling constants.

Authors:  D Uhrín; G Batta; V J Hruby; P N Barlow; K E Kövér
Journal:  J Magn Reson       Date:  1998-02       Impact factor: 2.229

6.  13-Deoxytedanolide, a marine sponge-derived antitumor macrolide, binds to the 60S large ribosomal subunit.

Authors:  Shinichi Nishimura; Shigeki Matsunaga; Minoru Yoshida; Hiroshi Hirota; Shigeyuki Yokoyama; Nobuhiro Fusetani
Journal:  Bioorg Med Chem       Date:  2005-01-17       Impact factor: 3.641

7.  Peloruside A: a potent cytotoxic macrolide isolated from the new zealand marine sponge Mycale sp.

Authors:  L M West; P T Northcote; C N Battershill
Journal:  J Org Chem       Date:  2000-01-28       Impact factor: 4.354

8.  Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

Authors:  Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

9.  Laulimalide and isolaulimalide, new paclitaxel-like microtubule-stabilizing agents.

Authors:  S L Mooberry; G Tien; A H Hernandez; A Plubrukarn; B S Davidson
Journal:  Cancer Res       Date:  1999-02-01       Impact factor: 12.701

10.  Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule- stabilizing activity.

Authors:  Kylie A Hood; Lyndon M West; Berber Rouwé; Peter T Northcote; Michael V Berridge; St John Wakefield; John H Miller
Journal:  Cancer Res       Date:  2002-06-15       Impact factor: 12.701
  10 in total
  18 in total

1.  Stereochemically versatile synthesis of the C1-C12 fragment of tedanolide C.

Authors:  Thomas E Smith; Sarah J Fink; Zebulon G Levine; Kerani A McClelland; Adrian A Zackheim; Mary E Daub
Journal:  Org Lett       Date:  2012-02-29       Impact factor: 6.005

2.  New candidaspongiolides, tedanolide analogues that selectively inhibit melanoma cell growth.

Authors:  Emily L Whitson; Kristen M Pluchino; Matthew D Hall; James B McMahon; Tawnya C McKee
Journal:  Org Lett       Date:  2011-06-06       Impact factor: 6.005

3.  Enantioselective synthesis of alpha-methylene-beta-hydroxy carboxylic acid derivatives via a diastereoselective aldol/beta-elimination sequence: application to the C(15)-C(21) fragment of tedanolide C.

Authors:  Roland Barth; William R Roush
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

4.  Arenicolides A-C, 26-membered ring macrolides from the marine actinomycete Salinispora arenicola.

Authors:  Philip G Williams; Eric D Miller; Ratnakar N Asolkar; Paul R Jensen; William Fenical
Journal:  J Org Chem       Date:  2007-02-01       Impact factor: 4.354

5.  Enantioselective synthesis of the C1-C11 fragment of tedanolide C.

Authors:  Julie G Geist; Roland Barth; William R Roush
Journal:  Org Lett       Date:  2012-12-18       Impact factor: 6.005

6.  Total syntheses of (+)-tedanolide and (+)-13-deoxytedanolide.

Authors:  Joshua R Dunetz; Lisa D Julian; Jason S Newcom; William R Roush
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

Review 7.  Marine pharmacology in 2005-2006: antitumour and cytotoxic compounds.

Authors:  Alejandro M S Mayer; Kirk R Gustafson
Journal:  Eur J Cancer       Date:  2008-08-11       Impact factor: 9.162

8.  Candidaspongiolides, distinctive analogues of tedanolide from sponges of the genus Candidaspongia.

Authors:  Tamara L Meragelman; Richard H Willis; Girma M Woldemichael; Andrew Heaton; Peter T Murphy; Kenneth M Snader; David J Newman; Rob van Soest; Michael R Boyd; John H Cardellina; Tawnya C McKee
Journal:  J Nat Prod       Date:  2007-06-12       Impact factor: 4.050

9.  Monitoring bacterial diversity of the marine sponge Ircinia strobilina upon transfer into aquaculture.

Authors:  Naglaa M Mohamed; Venkateswara Rao; Mark T Hamann; Michelle Kelly; Russell T Hill
Journal:  Appl Environ Microbiol       Date:  2008-05-09       Impact factor: 4.792

10.  Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.

Authors:  Tyler A Johnson; Karen Tenney; Robert H Cichewicz; Brandon I Morinaka; Kimberly N White; Taro Amagata; Balanehru Subramanian; Joseph Media; Susan L Mooberry; Frederick A Valeriote; Phillip Crews
Journal:  J Med Chem       Date:  2007-07-10       Impact factor: 7.446
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