Literature DB >> 29037945

Enantioselective inhibitory abilities of enantiomers of notoamides against RANKL-induced formation of multinuclear osteoclasts.

Hikaru Kato1, Aika Kai1, Tetsuro Kawabata1, James D Sunderhaus2, Timothy J McAfoos2, Jennifer M Finefield2, Yukihiko Sugimoto3, Robert M Williams4, Sachiko Tsukamoto5.   

Abstract

The marine-derived Aspergillus protuberus MF297-2 and the terrestrial A. amoenus NRRL 35600 produce enantiomeric prenylated indole alkaloids. Investigation of biological activities of the natural and synthetic derivatives revealed that (-)-enantiomers of notoamides A and B, 6-epi-notoamide T, and stephacidin A inhibited receptor activator of nuclear factor-κB (NF-κB) ligand (RANKL)-induced osteoclastogenic differentiation of murine RAW264 cells more strongly than their respective (+)-enantiomers. Among them, (-)-6-epi-notoamide T was the most potent inhibitor with an IC50 value of 1.7μM.
Copyright © 2017 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Aspergillus; Enantiomer; Fungus; Notoamide; Osteoclastogenesis

Mesh：

Substances：

Year:  2017        PMID： 29037945      PMCID： PMC5909812          DOI： 10.1016/j.bmcl.2017.10.017

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  23 in total

Review 1.  Osteoclast differentiation and activation.

Authors:  William J Boyle; W Scott Simonet; David L Lacey
Journal:  Nature       Date:  2003-05-15       Impact factor: 49.962

2.  A concise total synthesis of the notoamides C and D.

Authors:  Alan W Grubbs; Gerald D Artman; Sachiko Tsukamoto; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.

Authors:  Hikaru Kato; Takushi Yoshida; Takanori Tokue; Yuka Nojiri; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams; Sachiko Tsukamoto
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hikaru Kato; Masayuki Samizo; Yuka Nojiri; Hiroyuki Onuki; Hiroshi Hirota; Tomihisa Ohta
Journal:  J Nat Prod       Date:  2008-12       Impact factor: 4.050

5.  Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Authors:  Thomas J Greshock; Alan W Grubbs; Ping Jiao; Donald T Wicklow; James B Gloer; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 6.  Advances in the regulation of osteoclasts and osteoclast functions.

Authors:  B F Boyce
Journal:  J Dent Res       Date:  2013-08-01       Impact factor: 6.116

7.  STUDIES ON THE BIOSYNTHESIS OF THE STEPHACIDINS AND NOTOAMIDES. TOTAL SYNTHESIS OF NOTOAMIDE S.

Authors:  Timothy J McAfoos; Shengying Li; Sachiko Tsukamoto; David H Sherman; Robert M Williams
Journal:  Heterocycles       Date:  2010-12-31       Impact factor: 0.831

8.  Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.

Authors:  Jennifer M Finefield; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  J Org Chem       Date:  2011-06-28       Impact factor: 4.354

9.  Asymmetric total syntheses of (+)- and (-)-versicolamide B and biosynthetic implications.

Authors:  Kenneth A Miller; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Chem       Date:  2009-04       Impact factor: 24.427

10.  Notoamide O, a structurally unprecedented prenylated indole alkaloid, and notoamides P-R from a marine-derived fungus, Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hideharu Umaoka; Kohei Yoshikawa; Tsuyoshi Ikeda; Hiroshi Hirota
Journal:  J Nat Prod       Date:  2010-08-27       Impact factor: 4.050
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  2 in total

Review 1.  Marine natural products that inhibit osteoclastogenesis and promote osteoblast differentiation.

Authors:  Ahmed H H El-Desoky; Sachiko Tsukamoto
Journal:  J Nat Med       Date:  2022-04-10       Impact factor: 3.192

Review 2.  Structural analysis of previously unknown natural products using computational methods.

Authors:  Hikaru Kato
Journal:  J Nat Med       Date:  2022-07-18       Impact factor: 3.192
  2 in total

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