Literature DB >> 29622844

Isolation of amoenamide A and five antipodal prenylated alkaloids from Aspergillus amoenus NRRL 35600.

Kayo Sugimoto1, Yusaku Sadahiro1, Ippei Kagiyama1, Hikaru Kato1, David H Sherman2, Robert M Williams3,4, Sachiko Tsukamoto1.   

Abstract

A new prenylated alkaloid, Amoenamide A (6), was isolated from the fungus Aspergillus amoenus NRRL 35600. Previously, 6 was postulated to be a precursor of Notoamide E4 (21) converted from Notoamide E (16), which was a key precursor of the prenylated indole alkaloids in the fungi of the genus Aspergillus. We previously succeeded in the isolation of two pairs of antipodes, Stephacidin A (1) and Notoamide B (2), from A. amoenus and A. protuberus MF297-2 and expected the presence of other antipodes in the culture of A. amoenus. We here report five new antipodes (7-11) along with a new metabolite (12), which was isolated as a natural compound for the first time, from A. amoenus.

Entities:  

Keywords:  Alkaloid; Antipode; Aspergillus; Fungus

Year:  2017        PMID: 29622844      PMCID: PMC5881583          DOI: 10.1016/j.tetlet.2017.05.057

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  22 in total

1.  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

2.  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

3.  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

4.  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

5.  Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.

Authors:  Shengying Li; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2011-12-28       Impact factor: 15.419

6.  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

7.  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

8.  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

9.  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

10.  Isolation of antipodal (-)-versicolamide B and notoamides L-N from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Tetsuro Kawabata; Hikaru Kato; Thomas J Greshock; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

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  5 in total

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

Authors:  Hikaru Kato; Aika Kai; Tetsuro Kawabata; James D Sunderhaus; Timothy J McAfoos; Jennifer M Finefield; Yukihiko Sugimoto; Robert M Williams; Sachiko Tsukamoto
Journal:  Bioorg Med Chem Lett       Date:  2017-10-09       Impact factor: 2.823

Review 2.  Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi.

Authors:  Xiaohan Wang; Yuying Li; Xuping Zhang; Daowan Lai; Ligang Zhou
Journal:  Molecules       Date:  2017-11-23       Impact factor: 4.411

3.  Unified total synthesis of the brevianamide alkaloids enabled by chemical investigations into their biosynthesis.

Authors:  Robert C Godfrey; Helen E Jones; Nicholas J Green; Andrew L Lawrence
Journal:  Chem Sci       Date:  2021-12-29       Impact factor: 9.825

Review 4.  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

5.  Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021.

Authors:  Jin Yang; Lizhi Gong; Miaomiao Guo; Yu Jiang; Yi Ding; Zhijie Wang; Xiujuan Xin; Faliang An
Journal:  Mar Drugs       Date:  2021-03-17       Impact factor: 5.118

  5 in total

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