Literature DB >> 25767298

Bioconversion of 6-epi-Notoamide T Produces Metabolites of Unprecedented Structures in a Marine-derived Aspergillus sp.

Hikaru Kato1, Takashi Nakahara1, Michitaka Yamaguchi1, Ippei Kagiyama1, Jennifer M Finefield2, James D Sunderhaus2, David H Sherman3, Robert M Williams4, Sachiko Tsukamoto1.   

Abstract

We previously described the bioconversion of Notoamide T into (+)-Stephacidin A and (-)-Notoamide B, which suggested that Versicolamide B (8) is biosynthesized from 6-epi-Notoamide T (10) via 6-epi-Stephacidin A. Here we report that [13C]2-10 was incorporated into isotopically enriched 8 and seven new metabolites, which were not produced under normal culture conditions. The results suggest that the addition of excess precursor activated the expression of dormant tailoring genes giving rise to these structurally unprecedented metabolites.

Entities:  

Keywords:  Alkaloid; Aspergillus sp; Bioconversion; Notoamide

Year:  2015        PMID： 25767298      PMCID： PMC4353397          DOI： 10.1016/j.tetlet.2014.11.083

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


  16 in total

1.  Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp.

Authors:  Yousong Ding; Jeffrey R de Wet; James Cavalcoli; Shengying Li; Thomas J Greshock; Kenneth A Miller; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Sachiko Tsukamoto; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2010-09-15       Impact factor: 15.419

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.  A concise, biomimetic total synthesis of stephacidin A and notoamide B.

Authors:  Thomas J Greshock; Alan W Grubbs; Sachiko Tsukamoto; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  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

5.  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

6.  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

7.  Titration-based screening for evaluation of natural product extracts: identification of an aspulvinone family of luciferase inhibitors.

Authors:  Patricia G Cruz; Douglas S Auld; Pamela J Schultz; Scott Lovell; Kevin P Battaile; Ryan MacArthur; Min Shen; Giselle Tamayo-Castillo; James Inglese; David H Sherman
Journal:  Chem Biol       Date:  2011-11-23

8.  Biosynthetic studies of the notoamides: isotopic synthesis of stephacidin A and incorporation into notoamide B and sclerotiamide.

Authors:  Jennifer M Finefield; Hikaru Kato; Thomas J Greshock; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Org Lett       Date:  2011-06-30       Impact factor: 6.005

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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  7 in total

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

Authors:  Kayo Sugimoto; Yusaku Sadahiro; Ippei Kagiyama; Hikaru Kato; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Tetrahedron Lett       Date:  2017-05-18       Impact factor: 2.415

2.  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

3.  Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications.

Authors:  Hikaru Kato; Takashi Nakahara; Kayo Sugimoto; Kanae Matsuo; Ippei Kagiyama; Jens C Frisvad; David H Sherman; Robert M Williams; Sachiko Tsukamoto
Journal:  Org Lett       Date:  2015-01-23       Impact factor: 6.005

Review 4.  Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.

Authors:  Kimberly R Klas; Hikaru Kato; Jens C Frisvad; Fengan Yu; Sean A Newmister; Amy E Fraley; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

Review 5.  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

Review 6.  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

Review 7.  Marine Indole Alkaloids.

Authors:  Natalie Netz; Till Opatz
Journal:  Mar Drugs       Date:  2015-08-06       Impact factor: 5.118
  7 in total

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